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Results: 902 Rentals

  • Robbins Nest Farm a Private Retreat Offering Secluded Luxury on the James River
    From $355 per night (USD)

    VRBO

    Robbins Nest Farm a Private Retreat Offering Secluded Luxury on the James River

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Virginia's hottest destination getaway—Robbins Nest Farm. Situated on the majestic James River in historic C ...

    From $355 per night (USD)

    VRBO

    Details
  • Wintergreen Resort Retreat: Ski, Hike, Golf!
    From $584 per night (USD)

    Expedia

    Wintergreen Resort Retreat: Ski, Hike, Golf!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    From skiing at Wintergreen Resort to hiking the Appalachian Trail, this 4-bedroom, 3-bath house is perfect in any season ...

    From $584 per night (USD)

    Expedia

    Details
  • 3 hour Kayak trip for Free! The heart of Nelson, 140 acres,mile of river trails!
    From $319 per night (USD)

    VRBO

    3 hour Kayak trip for Free! The heart of Nelson, 140 acres,mile of river trails!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Only Reserved guests are allowed in the cabin. Hunting and the use of any firearm is Not permitted anywhere on the prope ...

    From $319 per night (USD)

    VRBO

    Details
  • surrounded by mountains, rivers breweries , cideries, wineries, the AT and BRP
    From $225 per night (USD)

    VRBO

    surrounded by mountains, rivers breweries , cideries, wineries, the AT and BRP

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Rockfish Valley Farm cottage Stay in the heart of the Rockfish Valley NOTE The VRBO ...

    From $225 per night (USD)

    VRBO

    Details
  • 2 minutes from the shops and activities; Cozy 1 bedroom end unit.
    From $141 per night (USD)

    VRBO

    2 minutes from the shops and activities; Cozy 1 bedroom end unit.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Charming recently updated cozy 1 bedroom, 1 bath condo with private parking. Less than 2 minute walk to ski slopes and M ...

    From $141 per night (USD)

    VRBO

    Details
  • Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
    From $212 per night (USD)

    Expedia

    Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful cabin in the woods! Welcome to our home! This beautiful mountain cabin is located on the top of Wintergreen R ...

    From $212 per night (USD)

    Expedia

    Details
  • Beautiful Wintergreen Retreat 5 min from the slopes
    From $533 per night (USD)

    VRBO

    Beautiful Wintergreen Retreat 5 min from the slopes

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Come spend your vacation in one of the best properties new to the Wintergreen market, conveniently located in the resort ...

    From $533 per night (USD)

    VRBO

    Details
  • Escape to the Blue Ridge Mountains at Wine-tergreen!
    From $150 per night (USD)

    Expedia

    Escape to the Blue Ridge Mountains at Wine-tergreen!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Your perfect escape in the beautiful Blue Ridge Mountains! Enjoy a glass of the region's famous wines in front of the w ...

    From $150 per night (USD)

    Expedia

    Details
  • Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14
    From $575 per night (USD)

    VRBO

    Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Welcome to the Mountain Treehouse! We recently renovated the home with all upgraded amenities, including a brand new hot ...

    From $575 per night (USD)

    VRBO

    Details
  • Avon Hill: Private Pool + Mountain views + Rockfish River Fun!
    From $1833 per night (USD)

    VRBO

    Avon Hill: Private Pool + Mountain views + Rockfish River Fun!

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    18

    The quote provided here is only for the Lodge. If your party is larger than 18 people or if you are looking for a place ...

    From $1833 per night (USD)

    VRBO

    Details
  • Lovingston Get Away Lovingston, VA
    From $139 per night (USD)

    VRBO

    Lovingston Get Away Lovingston, VA

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    We are located in the Village of Lovingston, VA. There are wineries, breweries, and distilleries. We have Wintergreen Sk ...

    From $139 per night (USD)

    VRBO

    Details
  • 5 Bedroom Hilltop Villa with Magnificent Views
    From $451 per night (USD)

    Expedia

    5 Bedroom Hilltop Villa with Magnificent Views

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    15

    This beautiful secluded hilltop home offers breathtaking panoramic views of the Blue Ridge Mountains and the graceful Ja ...

    From $451 per night (USD)

    Expedia

    Details
  • Breathtaking views! Beautifully decorated.
    From $308 per night (USD)

    VRBO

    Breathtaking views! Beautifully decorated.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy a Fall/Winter getaway in our lovely three bedroom condo! Enjoy breathtaking views! Spend a day relaxing at the Sp ...

    From $308 per night (USD)

    VRBO

    Details
  • Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!
    From $234 per night (USD)

    Expedia

    Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 bedroom 2 bath and a queen sofa bed. Sleeps 4-6 very comfortably. This is our second condo here as we’ve fallen so in ...

    From $234 per night (USD)

    Expedia

    Details
  • Cozy Studio Overlooking 18 Hole
    From $133 per night (USD)

    VRBO

    Cozy Studio Overlooking 18 Hole

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A slice of paradise overlooking the 18th hole and Devils Grill. Located across the street from the spa and Nature Found ...

    From $133 per night (USD)

    VRBO

    Details
  • Cozy Wintergreen Resort Condo: Walk to Ski Lifts!
    From $201 per night (USD)

    Expedia

    Cozy Wintergreen Resort Condo: Walk to Ski Lifts!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the unparalleled beauty and easy relaxation that Wintergreen Resort provides when you book this cozy 2-bedroo ...

    From $201 per night (USD)

    Expedia

    Details
  • Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
    From $275 per night (USD)

    VRBO

    Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Newly updated 2 bedroom/2 bathroom slope-side condo with amazing Mountain Views. Short walk around the building gets you ...

    From $275 per night (USD)

    VRBO

    Details
  • Large 5 Br/3 ba Lodge on Wintergreen Mountain
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    Expedia

    Large 5 Br/3 ba Lodge on Wintergreen Mountain

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Fantastic lodge-style home perfect for large groups on Wintergreen Mountain -walking distance to trails, lodge and sceni ...

    Click For Pricing

    Expedia

    Details
  • Estate in Blue Ridge Foothills - 20 min to Charlottesville
    From $1460 per night (USD)

    VRBO

    Estate in Blue Ridge Foothills - 20 min to Charlottesville

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    14

    **Outdoor Heated Pool** **Hot Tub** **Event Site** **Mountain Views** The perfect escape to the scenic Rockfish Valley ...

    From $1460 per night (USD)

    VRBO

    Details
  • Green House on the Hill - near route 151
    From $290 per night (USD)

    Expedia

    Green House on the Hill - near route 151

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Nestled at the base of the beautiful Blue Ridge Mountains, this 3 bedroom home sleeps up to 10 guests with comfort. Loc ...

    From $290 per night (USD)

    Expedia

    Details
  • Cozy chalet on Wintergreen Mountain
    From $210 per night (USD)

    VRBO

    Cozy chalet on Wintergreen Mountain

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    On a private, wooded lot, this chalet home is perfectly located in the year-round Wintergreen Resort. We’re less than a ...

    From $210 per night (USD)

    VRBO

    Details
  • 4 BR cabin mins to trails & breweries pets welcome
    From $412 per night (USD)

    Expedia

    4 BR cabin mins to trails & breweries pets welcome

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Feel right at home when you arrive at this lovely cabin at the very top of Wintergreen Resort mountain fresh ready for a ...

    From $412 per night (USD)

    Expedia

    Details
  • The Modern Mountain Condo
    From $200 per night (USD)

    VRBO

    The Modern Mountain Condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy place ...

    From $200 per night (USD)

    VRBO

    Details
  • COZY A-Frame Spacious Deck w/ Grill
    From $272 per night (USD)

    Expedia

    COZY A-Frame Spacious Deck w/ Grill

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Year-round adventure awaits just outside of this incredible A-frame cabin with 4 bedrooms and 2 baths! Featuring an idyl ...

    From $272 per night (USD)

    Expedia

    Details
  • Dog Friendly - Backs to Golf - Spacious Deck
    From $287 per night (USD)

    VRBO

    Dog Friendly - Backs to Golf - Spacious Deck

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    S'more Family Time is the perfect rental at Wintergreen Resort! The home sleeps 8 comfortably. It was designed for two f ...

    From $287 per night (USD)

    VRBO

    Details
  • Huge deck, grill, stunning mountain views. EV charging station available.
    From $303 per night (USD)

    Expedia

    Huge deck, grill, stunning mountain views. EV charging station available.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Same as Three Springs listing + additional bedroom, bath, laundry, kitchen, dining, and living area with large screen TV ...

    From $303 per night (USD)

    Expedia

    Details
  • Wintergreen Resort Home w/ Deck: Walk to Slopes
    From $543 per night (USD)

    VRBO

    Wintergreen Resort Home w/ Deck: Walk to Slopes

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Pack your gear and head out to the mountains of Virginia for a stay at this 5-bed, 4-bath vacation rental, large enough ...

    From $543 per night (USD)

    VRBO

    Details
  • Calm Creek Retreat - golf course view, spacious deck, open entertainment area!
    From $488 per night (USD)

    VRBO

    Calm Creek Retreat - golf course view, spacious deck, open entertainment area!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    The leaves are changing and Calm Creek Retreat offers a gorgeous setting for enjoying the cooler temps on the mountain! ...

    From $488 per night (USD)

    VRBO

    Details
  • Beautiful, Remodeled Cottage in the Heart of Afton
    From $186 per night (USD)

    VRBO

    Beautiful, Remodeled Cottage in the Heart of Afton

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the George Washington National Forest, Gracewood is a retreat from the mental and emotional activity of every ...

    From $186 per night (USD)

    VRBO

    Details
  • Cooler in the mountains, with hot tub.
    From $292 per night (USD)

    Expedia

    Cooler in the mountains, with hot tub.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Terrace level apartment w/ private entrance, Private deck, 2 bdrms, full kitchen, mini-frig stocked with local wine, LR ...

    From $292 per night (USD)

    Expedia

    Details
  • ....................................................
    Click For Pricing

    VRBO

    ....................................................

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    1

    ........................................................................................................................ ...

    Click For Pricing

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  • House on the slopes  Ski-in/out
    From $304 per night (USD)

    Expedia

    House on the slopes Ski-in/out

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Enjoy this charming 3-bedroom, 2-bathroom house located on the slopes of Tyro. Step outside, strap on your boards or ski ...

    From $304 per night (USD)

    Expedia

    Details
  • Charming Renovated 1930’s Soapstone Quarry Bungalow
    From $275 per night (USD)

    VRBO

    Charming Renovated 1930’s Soapstone Quarry Bungalow

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Relaxing, peaceful getaway in gorgeous Nelson County. Adjacent to a large hay field which leads down to a branch of the ...

    From $275 per night (USD)

    VRBO

    Details
  • Bright Wintergreen Resort Home; Deck & Grill!
    From $551 per night (USD)

    Expedia

    Bright Wintergreen Resort Home; Deck & Grill!

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Escape to the mountains, and stay at this spacious and welcoming vacation rental in Wintergreen Resort! The 6-bedroom, 4 ...

    From $551 per night (USD)

    Expedia

    Details
  • CritzerShop - route 151- walk to the Brewey!
    From $323 per night (USD)

    VRBO

    CritzerShop - route 151- walk to the Brewey!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Walk to Blue Mountain Brewery! Fiber Internet ( 1 Gbps ) for working stays. We are right on the main route of 151. This ...

    From $323 per night (USD)

    VRBO

    Details
  • One of the Best Views in Wintergreen!
    From $372 per night (USD)

    Expedia

    One of the Best Views in Wintergreen!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    9

    This unique property has some of the best views in Wintergreen. Make this your retreat after a day filled with hiking, ...

    From $372 per night (USD)

    Expedia

    Details
  • Event Space for Families or Groups
    From $280 per night (USD)

    VRBO

    Event Space for Families or Groups

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Welcome to HeartRock Homesite. Our cut flower farmette is stocked with modern comforts for all ages. An outdoor playgr ...

    From $280 per night (USD)

    VRBO

    Details
  • Sweet Afton | Country House in Heart of Wine Country
    From $343 per night (USD)

    Expedia

    Sweet Afton | Country House in Heart of Wine Country

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    2 bed, 1 bath country cottage in the heart of wine and beer country located in Afton "proper". This quaint cottage sits ...

    From $343 per night (USD)

    Expedia

    Details
  • Mountain Home at Wintergreen Resort...in the heart of Virginia's wine country.
    From $669 per night (USD)

    VRBO

    Mountain Home at Wintergreen Resort...in the heart of Virginia's wine country.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Ski up the mountain in the late fall, winter and early spring . Enjoy golf, visiting wineries and breweries in the valle ...

    From $669 per night (USD)

    VRBO

    Details
  • Cut Flower Farm: A Bountiful Getaway for Couples or Small Families.
    From $159 per night (USD)

    Expedia

    Cut Flower Farm: A Bountiful Getaway for Couples or Small Families.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to HeartRock! Our cut flower farmette is stocked with modern comforts for all ages. A magical outdoor playgrou ...

    From $159 per night (USD)

    Expedia

    Details
  • Modern Luxury Mountain Home within Wintergreen Retreat Collection
    From $744 per night (USD)

    VRBO

    Modern Luxury Mountain Home within Wintergreen Retreat Collection

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    18

    With gorgeous mountain views of the Blue Ridge and Blackrock Village this luxury mountain home is one of the largest in ...

    From $744 per night (USD)

    VRBO

    Details
  • RNF Virginia's hottest destination getaway!!! Robbin's Nest Farm!!!
    From $194 per night (USD)

    Expedia

    RNF Virginia's hottest destination getaway!!! Robbin's Nest Farm!!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    RNF Virginia's hottest destination getaway -- Robbins's Nest Farm -- sits nestled between the Blue Ridge Mountains and t ...

    From $194 per night (USD)

    Expedia

    Details
  • New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
    From $148 per night (USD)

    VRBO

    New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Be among the first to stay in this new construction! Fabulous condo with nice finishes and new furniture. Everything y ...

    From $148 per night (USD)

    VRBO

    Details
  • Wintergreen Resorts newest gem! Over 3800 sf!
    Click For Pricing

    Expedia

    Wintergreen Resorts newest gem! Over 3800 sf!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Capture all the beauty of Wintergreen's 4 seasons with this unique property. 4 floors (elevator & stairs), 3800 sf, 4 be ...

    Click For Pricing

    Expedia

    Details
  • Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.
    From $354 per night (USD)

    VRBO

    Spectacular Waterfront Retreat on Piney River in the Blue Ridge Mountains.

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    8

    High speed Wi-Fi added June 2023. It’s mountain viewing and festival time in the Blue Ridge Mountains! Sycamore Shade ...

    From $354 per night (USD)

    VRBO

    Details
  • Breathtaking views!! Overlooking the slopes
    From $158 per night (USD)

    VRBO

    Breathtaking views!! Overlooking the slopes

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Come enjoy beautiful year round views in this lovely two bedroom/ two bath Condo. It has a wood burning fireplace for c ...

    From $158 per night (USD)

    VRBO

    Details
  • Blue Ridge, Tye River, C-Ville, Crabtree, Wintergreen, Sweet Briar, Farm
    From $327 per night (USD)

    VRBO

    Blue Ridge, Tye River, C-Ville, Crabtree, Wintergreen, Sweet Briar, Farm

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    Experience a warm Blue Ridge Mountain welcome at the Tye River Farmhouse in Arrington, Virginia. Located in scenic Nels ...

    From $327 per night (USD)

    VRBO

    Details
  • Wintergreen Resort Condo w/ Deck; Ski, Hike, Shops
    From $334 per night (USD)

    Expedia

    Wintergreen Resort Condo w/ Deck; Ski, Hike, Shops

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Experience the quintessential four-seasons getaway at this 4-bedroom, 3.5-bathroom Wintergreen Resort Condo situated min ...

    From $334 per night (USD)

    Expedia

    Details
  • Luxe Private Getaway in the Heart of Wintergreen!
    From $557 per night (USD)

    VRBO

    Luxe Private Getaway in the Heart of Wintergreen!

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    14

    Enjoy the very best of Wintergreen! Walking distance to Appalachian Mountain trails & just minutes to the slopes at Wint ...

    From $557 per night (USD)

    VRBO

    Details
  • Cozy cabin for 2 w/ great mt views & walking trails!
    From $158 per night (USD)

    Expedia

    Cozy cabin for 2 w/ great mt views & walking trails!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Sentosa Cabin is a sanctuary for nature lovers and a perfect couple's or single's getaway or anyone wanting to enjoy a p ...

    From $158 per night (USD)

    Expedia

    Details
  • Beautiful Farmhouse On 11 Heavenly Acres
    From $249 per night (USD)

    VRBO

    Beautiful Farmhouse On 11 Heavenly Acres

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    10

    Nestled in the Rockfish gap right under Devil's Knob our farmhouse is situated perfectly in the center of everything tha ...

    From $249 per night (USD)

    VRBO

    Details
  • Mountaintop Wintergreen Resort Home w/ Deck, Views
    From $338 per night (USD)

    Expedia

    Mountaintop Wintergreen Resort Home w/ Deck, Views

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Escape to the mountains with this spacious 4-bed, 3-bath Virginia vacation rental home! Tucked into the Wintergreen Reso ...

    From $338 per night (USD)

    Expedia

    Details
  • The Wintergreen Chalet
    From $530 per night (USD)

    VRBO

    The Wintergreen Chalet

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    The Wintergreen Chalet is a sprawling 6-bedroom 4.5 bath home located at the top of Devil's Knob Mountain within the Win ...

    From $530 per night (USD)

    VRBO

    Details
  • 5 BR, Sleeps 14, Hot Tub, EV Charger, Golf Course Views
    From $524 per night (USD)

    VRBO

    5 BR, Sleeps 14, Hot Tub, EV Charger, Golf Course Views

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Blue Ridge Rose is a three level home in Wintergreen Resort overlooking the sixth green and fairway of the Devils Knob’s ...

    From $524 per night (USD)

    VRBO

    Details
  • Creek Front Property! Spicewood Cabin Near Wintergreen and Crabtree Falls
    From $193 per night (USD)

    VRBO

    Creek Front Property! Spicewood Cabin Near Wintergreen and Crabtree Falls

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spicewood cabin is located in the heart of scenic Nelson County. Our family owned property is nestled in the Blue Ridge ...

    From $193 per night (USD)

    VRBO

    Details
  • Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK
    From $295 per night (USD)

    Expedia

    Amazing Mountain views - Ski In Ski Out - Wifi - fireplace - Pets OK

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We are Slope-side with a full view to the North/East, Dobie Mountain Condominium, 2 Bedroom, 2 Bath, and recently instal ...

    From $295 per night (USD)

    Expedia

    Details
  • Cozy 'Hillside Hideaway' in Wintergreen Resort!
    From $270 per night (USD)

    VRBO

    Cozy 'Hillside Hideaway' in Wintergreen Resort!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A peaceful mountain Wintergreen stay awaits at this 3-bedroom, 2-bath vacation rental! Just a short walk from the ski li ...

    From $270 per night (USD)

    VRBO

    Details
  • Dog friendly. No stairs! New to VRBO
    From $578 per night (USD)

    Expedia

    Dog friendly. No stairs! New to VRBO

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Come relax in the tastefully decorated cozy two bedroom two bath condo. Relax by the wood burning fireplace or take a hi ...

    From $578 per night (USD)

    Expedia

    Details
  • The Fairway Chalet Wintergreen
    From $398 per night (USD)

    VRBO

    The Fairway Chalet Wintergreen

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to The Fairway Chalet, your perfect mountain retreat nestled in the heart of Wintergreen Resort. Perched alongsi ...

    From $398 per night (USD)

    VRBO

    Details
  • Ski In & Out Mountain & Firework Views Studio
    From $160 per night (USD)

    Expedia

    Ski In & Out Mountain & Firework Views Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy a stylish experience at this centrally-located studio next to the Mountain Inn. Our spacious deck overlooks the s ...

    From $160 per night (USD)

    Expedia

    Details
  • Pizza, Brews & Views!
    From $282 per night (USD)

    VRBO

    Pizza, Brews & Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This unit is perfectly situated at The Ledges, just a quick five-minute drive to the Mountain Inn. Mountain Dreams is a ...

    From $282 per night (USD)

    VRBO

    Details
  • Misty Mountain Cabin w/spa
    From $582 per night (USD)

    Expedia

    Misty Mountain Cabin w/spa

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    15

    Misty Mountain cabin w/spa and mountain views (Sleeps 14) This unique home 4 bedroom/ 3 bath home has stunning views of ...

    From $582 per night (USD)

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  • Zero step entry- EV charger- 2 King suites
    From $382 per night (USD)

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    Zero step entry- EV charger- 2 King suites

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Our home offers a comfortable, modern, and tranquil space for families & friends to gather & enjoy all that Wintergreen ...

    From $382 per night (USD)

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  • Hot Tub DogsOK Grill Fireplace Pac Man Pool Tennis
    From $242 per night (USD)

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    Hot Tub DogsOK Grill Fireplace Pac Man Pool Tennis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Activities are endless: apple picking, breweries/wineries, hiking, lake, horseback riding, golf, tennis, skiing... Take ...

    From $242 per night (USD)

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  • ‘Bear Haven’ - Third-Floor Escape w/ Pool Access!
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    ‘Bear Haven’ - Third-Floor Escape w/ Pool Access!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Pack your bags for a trip to the famous Wintergreen Resort when you stay at this 2-bed, 2-bath vacation rental! ‘Bear Ha ...

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  • Updated! Cozy and clean two bedroom condo.
    From $196 per night (USD)

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    Updated! Cozy and clean two bedroom condo.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    It's cooler in the mountains! Come relax at this clean and cozy two bedroom condo. We are on the top floor but there ar ...

    From $196 per night (USD)

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  • Gorgeous Rustic Mountain Cabin with Scenic Views! Welcome to Green Oak Cabin
    From $341 per night (USD)

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    Gorgeous Rustic Mountain Cabin with Scenic Views! Welcome to Green Oak Cabin

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Instantly escape when you walk through the front door. The calmness of the cabin and the serenity of the mountains offer ...

    From $341 per night (USD)

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  • Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort
    From $331 per night (USD)

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    Fully renovated house, tons of upgrades & beautiful views in Wintergreen Resort

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Located on a quiet street with fantastic views, this Wintergreen home is fully renovated and available for rent. Just a ...

    From $331 per night (USD)

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  • Cub Creek Mt Getaway Near Wintergreen and the Blue Ridge Parkway
    From $95 per night (USD)

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    Cub Creek Mt Getaway Near Wintergreen and the Blue Ridge Parkway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Come and enjoy all that the Blue Ridge Mountains have to offer - ski, snowboard or golf at the Wintergreen Resort, swim ...

    From $95 per night (USD)

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  • Large and Luxurious Exec 5BR Chalet
    From $504 per night (USD)

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    Large and Luxurious Exec 5BR Chalet

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    House, 5 Bedrooms, 4.5 Baths, (Sleeps/Max occupancy 10 people) Important notes for prospective renters: 1) Our house get ...

    From $504 per night (USD)

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  • Golf Course Views Golden Tee Pool Tennis Golf Hike
    From $219 per night (USD)

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    Golf Course Views Golden Tee Pool Tennis Golf Hike

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    5min to ski slopes! Nestled in middle of Devils Knob Golf Course, unique 2,229sqft home features primary suite on first ...

    From $219 per night (USD)

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  • Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
    From $257 per night (USD)

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    Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to our mountain home at Wintergreen Resort! We fell in love with this house for the same reasons that we know yo ...

    From $257 per night (USD)

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  • 30+ Days Luxury Mountain Villa in Virginia Wine Country, 25mins from C'ville
    From $326 per night (USD)

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    30+ Days Luxury Mountain Villa in Virginia Wine Country, 25mins from C'ville

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Relaxation, nature, and vino await you! Located in the heart of Virginia wine country, Three Vines Villa is the perfect ...

    From $326 per night (USD)

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  • Mntn View Hot Tub Pool Table Pool Tennis Golf
    From $707 per night (USD)

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    Mntn View Hot Tub Pool Table Pool Tennis Golf

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or adventurous getaways. Cl ...

    From $707 per night (USD)

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  • Spectacular mountain home perfect for multiple families! Just added '80s arcade!
    From $329 per night (USD)

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    Spectacular mountain home perfect for multiple families! Just added '80s arcade!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This is a true Post & Beam home built by quality craftsman Tim Behler in a spectacular natural setting. The home shows b ...

    From $329 per night (USD)

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  • Country escape in the heart of the Blue Ridge Mountains
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    Country escape in the heart of the Blue Ridge Mountains

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    2-story 1904 Farmhouse on 2 acres just off of the brew ridge trail • Patio w grill • Fireplace • Fully equipped kitch ...

    Click For Pricing

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  • View from the Top
    From $241 per night (USD)

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    View from the Top

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy breathtaking panoramic mountain and valley views from this beautiful 2 bedroom, 3rd floor condo. The building's el ...

    From $241 per night (USD)

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  • 2br/2ba:  Million Dollar View from Luxury Condo on the Ridge.
    From $145 per night (USD)

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    2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    FALL SPECIAL!!! $99 WEEKNIGHTS (Sunday-Thursday) The most comfortable, elegant condo on the Ridge. Five Star Gold. Rece ...

    From $145 per night (USD)

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  • WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
    From $216 per night (USD)

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    WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want ...

    From $216 per night (USD)

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  • Couples Mountain Retreat
    From $177 per night (USD)

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    Couples Mountain Retreat

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to North Fork Cabin Rental's Hawks View! We are family owned cabins nestled in the Blue Ridge Mountains. Our ca ...

    From $177 per night (USD)

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  • Deer Run - Mountain Getaway
    From $192 per night (USD)

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    Deer Run - Mountain Getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to North Fork Cabin Rental's Deer Run! We are family owned cabins nestled in the Blue Ridge Mountains. our cabi ...

    From $192 per night (USD)

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  • Rustic Mountain Retreat-Bear Paw
    From $167 per night (USD)

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    Rustic Mountain Retreat-Bear Paw

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to North Fork Cabin Rental's Bear Paw! We are family owned cabins nestled in the Blue Ridge Mountains. Our cabi ...

    From $167 per night (USD)

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    Details
  • Marley's Cabin - a five star getaway on Wintergreen mountain
    From $716 per night (USD)

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    Marley's Cabin - a five star getaway on Wintergreen mountain

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy dramatic views of the Blue Ridge Mountains from Marley’s Cabin on Wintergreen Mountain, located in the heart of Ce ...

    From $716 per night (USD)

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  • Fantastic Post & Beam 5br Valley location near All Pool, Lake, Beach, Sleep 16
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    Fantastic Post & Beam 5br Valley location near All Pool, Lake, Beach, Sleep 16

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    15

    ***Take Advantage of this early listing pricing! The home is being prepared for vacation rentals with some upgrades, so ...

    Click For Pricing

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  • Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
    From $409 per night (USD)

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    Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    13

    Spacious 3 level home with room to spread out. 5 bedrooms, 2 living rooms, and a rec room. 2 propane fireplaces and hi ...

    From $409 per night (USD)

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  • Relaxing House in the mountain/Fireplace/Pet Friendly/Close to slopes
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    Relaxing House in the mountain/Fireplace/Pet Friendly/Close to slopes

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Pet friendly, 5 bedrooms 3.5 bathroom charming house close to the top of the mountain. Huge open space on first level wi ...

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  • ❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
    From $423 per night (USD)

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    ❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Nestled in the heart of Virginia’s wine country on a golf course! Just 5 mins from Bold Rock Cidery and Devil's Backbone ...

    From $423 per night (USD)

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  • Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit
    From $293 per night (USD)

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    Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    The perfect outdoor adventure is waiting for you at this charming home in Nellysford. This 2-bedroom, 1-bathroom vacatio ...

    From $293 per night (USD)

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  • Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub
    From $562 per night (USD)

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    Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    Perched atop Wintergreen Resort, our luxurious retreat offers 2800 sq ft of space that comfortably sleeps 12 guests. Boa ...

    From $562 per night (USD)

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  • Classic Ski Chalet with Hot Tub, EV Charger. Views-skiing-tennis-hiking-golf!
    From $526 per night (USD)

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    Classic Ski Chalet with Hot Tub, EV Charger. Views-skiing-tennis-hiking-golf!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Bring your family to enjoy Three Timbers, our family's beautifully decorated and updated home, a classic timber-frame mo ...

    From $526 per night (USD)

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  • Find peace at Dove's Landing at Wintergreen resort - \nfamily- and pet-friendly!
    From $426 per night (USD)

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    Find peace at Dove's Landing at Wintergreen resort - \nfamily- and pet-friendly!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    13

    Located in the heart of Wintergreen Resort with all the family-friendly activities that make the Mountain famous - great ...

    From $426 per night (USD)

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  • Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski
    From $474 per night (USD)

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    Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    13

    Welcome to AFTON CABIN HOME. This modern rustic home nestled in the mountains of Afton is sure to deliver the vacation ...

    From $474 per night (USD)

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  • Cozy Cottage with beautiful Mountain View’s - close to wineries
    From $476 per night (USD)

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    Cozy Cottage with beautiful Mountain View’s - close to wineries

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The Cozy Cottage offers plenty of room to relax, with over 1,600 square feet of space divided amongst two floors. Define ...

    From $476 per night (USD)

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  • Gorgeous, spacious 4 bedroom home in Wintergreen Resort
    From $336 per night (USD)

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    Gorgeous, spacious 4 bedroom home in Wintergreen Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to our oasis in the mountains! This comfortable, spacious, and airy 4 bedroom/3 bathroom (approx 2600 square fe ...

    From $336 per night (USD)

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  • First-Floor Wintergreen Resort Condo w/ Balcony
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    First-Floor Wintergreen Resort Condo w/ Balcony

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy the world-class skiing and resort amenities from the comfort of this cozy Wintergreen Resort condo. With its conve ...

    Click For Pricing

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  • Wintergreen Resort Studio w/ Deck & Ski-Out Access
    From $142 per night (USD)

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    Wintergreen Resort Studio w/ Deck & Ski-Out Access

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Whisk away a loved one and enjoy an all-season retreat at this Wintergreen Resort vacation rental! This lovely studio of ...

    From $142 per night (USD)

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  • Newly Updated Cozy Condo in the Heart of Wintergreen!  Pet friendly.
    From $183 per night (USD)

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    Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Location, location, location- our cozy condo is short walk to everything! Park your car for the weekend and walk everyw ...

    From $183 per night (USD)

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  • Hiker’s paradise!  Come relax this summer!!!
    From $500 per night (USD)

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    Hiker’s paradise! Come relax this summer!!!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Wintergreen mountain house located yards from the Blue Ridge Parkway and Appalachian Trail! Whether you are skiing in th ...

    From $500 per night (USD)

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  • You deserve it all! Awesome Views, Comfy Condo & Elevator!
    From $211 per night (USD)

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    You deserve it all! Awesome Views, Comfy Condo & Elevator!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Looking for an all inclusive family vacation? Look no further! We have your total four seasons get away solution with ...

    From $211 per night (USD)

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  • Pine Cottage: Hot Tub, 2 mins to Bold Rock!
    From $387 per night (USD)

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    Pine Cottage: Hot Tub, 2 mins to Bold Rock!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Looking for a fun space to celebrate with friends, a small bachelorette party space, or a getaway with a funky vibe and ...

    From $387 per night (USD)

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