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Results: 560 Rentals

  •  Spacious Home, Private Pool, Tennis Court, Lake, Minutes From Town and Shopping
    From $1251 per night (USD)

    VRBO

    Spacious Home, Private Pool, Tennis Court, Lake, Minutes From Town and Shopping

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    15

    There's a lot to love about this casually elegant home. Biking, kayaking, fishing, hiking, lakeside cocktails, chil ...

    From $1251 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
  • Wintergreen Resort Condo w/ Deck; Ski, Hike, Shops
    From $334 per night (USD)

    VRBO

    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)

    VRBO

    Details
  • The Summit on 1Tribe Farm
    Click For Pricing

    Expedia

    The Summit on 1Tribe Farm

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This 5,000 square foot home sits atop a knoll on a 192 acre farm. Enjoy the serene sounds of nature and the expansive vi ...

    Click For Pricing

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • ‘Bear Haven’ - Third-Floor Escape w/ Pool Access!
    Click For Pricing

    Expedia

    ‘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 ...

    Click For Pricing

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Close to Wineries & Skyline Drive, Wintergreen, Enjoy Basic City location!
    From $166 per night (USD)

    VRBO

    Close to Wineries & Skyline Drive, Wintergreen, Enjoy Basic City location!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy this private bungalow. The space is ideal for couples or groups looking for an affordable and convenient spot to e ...

    From $166 per night (USD)

    VRBO

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

    VRBO

    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)

    VRBO

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

    VRBO

    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)

    VRBO

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

    VRBO

    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)

    VRBO

    Details
  • Stylish 2 Bedroom Unit-Convenient Downtown walkable location, Close to 151, Blue Ridge Parkway, Brew
    From $137 per night (USD)

    VRBO

    Stylish 2 Bedroom Unit-Convenient Downtown walkable location, Close to 151, Blue Ridge Parkway, Brew

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Unwind in this charming urban hideaway that offers an affordable and convenient spot to enjoy the sites! Conveniently l ...

    From $137 per night (USD)

    VRBO

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Valley Extended Suites
    From $106 per night (USD)

    VRBO

    Valley Extended Suites

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>While you're here, you can enjoy all the comforts of home and more, including a full-sized refrigerator/freezer and a ...

    From $106 per night (USD)

    VRBO

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

    VRBO

    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)

    VRBO

    Details
  • Relaxing House in the mountain/Fireplace/Pet Friendly/Close to slopes
    Click For Pricing

    VRBO

    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 ...

    Click For Pricing

    VRBO

    Details
  • Find out why this property is Almost Heaven
    From $145 per night (USD)

    Expedia

    Find out why this property is Almost Heaven

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Relax in a fully furnished apartment, with private, wheel chair accessible entrance. Sleeps two on a king bed with priva ...

    From $145 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

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

    VRBO

    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)

    VRBO

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite
    From $223 per night (USD)

    Expedia

    Bed&Breakfast in a 1795 Log Cabin on working farm, Margaret Baylor-Swoope suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    We are a family run bed and breakfast in a restored circa 1795 hand-hewn log cabin decorated with period antiques. The ...

    From $223 per night (USD)

    Expedia

    Details
  • Reconnect with family & friends at our large, private, stylish Wintergreen home
    From $921 per night (USD)

    VRBO

    Reconnect with family & friends at our large, private, stylish Wintergreen home

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    16

    No need to leave the things you love about your home behind when you vacation! Our home features floor to ceiling windo ...

    From $921 per night (USD)

    VRBO

    Details
  •  Wintergreen Resort Post & Beam Home Beauty
    From $446 per night (USD)

    VRBO

    Wintergreen Resort Post & Beam Home Beauty

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This special place on the Blue Ridge Mountain pwky is close to everything. Plan to ski, snow tube, hike & explore parks ...

    From $446 per night (USD)

    VRBO

    Details
  • The Hideaway Suite: Sauna & Lux Amenities
    From $279 per night (USD)

    VRBO

    The Hideaway Suite: Sauna & Lux Amenities

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Hideaway is a private unit on the garden level of the owner's home, with off-street parking available throughout you ...

    From $279 per night (USD)

    VRBO

    Details
  • Family Friendly, Cozy Home on the Mountain Golf Course. All Necessities Included
    From $226 per night (USD)

    Expedia

    Family Friendly, Cozy Home on the Mountain Golf Course. All Necessities Included

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We take extra cleaning precautions with covid 19. Newer listing to VRBO, super hosts on Airbnb with many reviews for yo ...

    From $226 per night (USD)

    Expedia

    Details
  • Recent improvements, walk to events, trails and slopes
    From $314 per night (USD)

    VRBO

    Recent improvements, walk to events, trails and slopes

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Clean, Comfortable and Convenient! Free Internet (FireFly Fiber Optic Broadband, 1Gbps) Walk to slopes and skip the shu ...

    From $314 per night (USD)

    VRBO

    Details
  • Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite
    From $223 per night (USD)

    Expedia

    Stay in a 1795 Log Cabin on a working farm, George Washington Swoope, Jr Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    We are a family run bed and breakfast in a restored circa 1795 hand-hewn log cabin decorated with period antiques. The ...

    From $223 per night (USD)

    Expedia

    Details
  • Bed & Breakfast in a 1795 Log Cabin on working farm, Eliza Trent Swoope Suite
    From $266 per night (USD)

    VRBO

    Bed & Breakfast in a 1795 Log Cabin on working farm, Eliza Trent Swoope Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Inn at Meadowcroft is a bed and breakfast in a fully restored circa 1795 log cabin. The room is a beautiful grand su ...

    From $266 per night (USD)

    VRBO

    Details
  • Bed&Breakfast in a 1795 Log Cabin on working farm, Honorable Jacob Swoope Suite
    From $477 per night (USD)

    Expedia

    Bed&Breakfast in a 1795 Log Cabin on working farm, Honorable Jacob Swoope Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Inn at Meadowcroft is located in a fully restored 1795 log cabin. The Honorable Jacob Swoope Suite has a large livi ...

    From $477 per night (USD)

    Expedia

    Details
  • Second-Floor Condo w/ Community Pool Access!
    From $179 per night (USD)

    VRBO

    Second-Floor Condo w/ Community Pool Access!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Relish incredible amenities and a variety of activities during your stay at this 1-bedroom, 2-bathroom Wintergreen Resor ...

    From $179 per night (USD)

    VRBO

    Details
  • Solon Serenity: A Beautiful, Serene Setting with Mtn Views, Weekly and Monthly Discounts!
    From $338 per night (USD)

    Expedia

    Solon Serenity: A Beautiful, Serene Setting with Mtn Views, Weekly and Monthly Discounts!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Solon Serenity: A Beautiful, Serene Setting with Mtn Views, Fire Pit, Grill Experience the peacefulness of country livi ...

    From $338 per night (USD)

    Expedia

    Details
  • Cozy 5-bedroom home for large gatherings.
    From $743 per night (USD)

    VRBO

    Cozy 5-bedroom home for large gatherings.

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    13

    Within the Wintergreen Resort, this 4-season mountain home is perfect for a large gathering with friends and family. A g ...

    From $743 per night (USD)

    VRBO

    Details
  • Oak Tree Cottage: Beautiful farm with mountain views.
    From $301 per night (USD)

    Expedia

    Oak Tree Cottage: Beautiful farm with mountain views.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Our four bedroom cottage is located in Waynesboro, VA at the foot of the Blue Ridge Mountains. The Skyline Drive and the ...

    From $301 per night (USD)

    Expedia

    Details
  • NEW! Cheerful 2 bd bungalow with hot tub. Must see!
    From $163 per night (USD)

    VRBO

    NEW! Cheerful 2 bd bungalow with hot tub. Must see!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub u ...

    From $163 per night (USD)

    VRBO

    Details
  • Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
    From $244 per night (USD)

    Expedia

    Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Fresh air, cooler temps and Mountain View’s is like food for the soul. Our Dobie condo is situated just steps from the W ...

    From $244 per night (USD)

    Expedia

    Details
  • Pet-Friendly VA Home ~ 30 Mi to Shenandoah NP
    From $243 per night (USD)

    VRBO

    Pet-Friendly VA Home ~ 30 Mi to Shenandoah NP

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    100

    Make your retreat to Weyers Cave to revel in the beauty of nature, relax with loved ones, and escape the hustle and bust ...

    From $243 per night (USD)

    VRBO

    Details
  • Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub
    From $701 per night (USD)

    Expedia

    Opulent Retreat Amidst Blue Ridge's Serenity * Dog Friendly * Hot Tub

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    18

    Welcome to Whiskey Ridge Retreat, a cozy mountain getaway located within minutes of the ski lodge at Wintergreen Resort. ...

    From $701 per night (USD)

    Expedia

    Details
  • The Hawksbill Haus (w/ hot tub)
    From $236 per night (USD)

    VRBO

    The Hawksbill Haus (w/ hot tub)

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Hello!! Nestled perfectly between the North Terminus of the Blue Ridge Parkway, the entrance to Skyline Drive, all of t ...

    From $236 per night (USD)

    VRBO

    Details
  • Wintergreen Resort Escape ~ Walk to Ski Lift!
    From $159 per night (USD)

    Expedia

    Wintergreen Resort Escape ~ Walk to Ski Lift!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Breathe in the fresh mountain air and experience the forested surroundings when you book and stay at this cozy Roseland ...

    From $159 per night (USD)

    Expedia

    Details
  • 3 master bedroom condo in mountain resort
    From $245 per night (USD)

    VRBO

    3 master bedroom condo in mountain resort

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful 1350 sqft condo with balcony views of trees and winter mountain views. Wood burning fireplace with free wood! ...

    From $245 per night (USD)

    VRBO

    Details
  • Wintergreen Home w/ Deck - Near Skiing & Hiking!
    Click For Pricing

    Expedia

    Wintergreen Home w/ Deck - Near Skiing & Hiking!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    This updated 3-bedroom, 2-bath vacation rental home is located at Virginia's premier Blue Ridge Mountain resort: Winterg ...

    Click For Pricing

    Expedia

    Details
  • Hilltop Escape >1 mile from North River
    From $448 per night (USD)

    VRBO

    Hilltop Escape >1 mile from North River

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Hilltop Escape Situated on 7.5 acres, Close to North River, Bridgewater College, Hone Quarry This beautifully appointed ...

    From $448 per night (USD)

    VRBO

    Details
  • 7th Hole Chalet - New 7-person Hot Tub / Sauna / 3 Fireplaces / New VRBO!
    From $494 per night (USD)

    Expedia

    7th Hole Chalet - New 7-person Hot Tub / Sauna / 3 Fireplaces / New VRBO!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    A one-of-a-kind experience for both Skiing, Hiking & Golfing at the 7th Hole Chalet. Enjoy spectacular views off the gre ...

    From $494 per night (USD)

    Expedia

    Details
  •  New rental ! Fairy Tale Cottage
    From $483 per night (USD)

    VRBO

    New rental ! Fairy Tale Cottage

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    *Please note: House does not have AC* Come and relax by the cozy gas fireplace, enjoy a hot chocolate after hiking one o ...

    From $483 per night (USD)

    VRBO

    Details
  • Welcome to The Sanctuary! Gorgeous Church Revival
    From $495 per night (USD)

    Expedia

    Welcome to The Sanctuary! Gorgeous Church Revival

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Experience a truly unique and romantic getaway at The Sanctuary, nestled in Downtown Staunton! This charming home featur ...

    From $495 per night (USD)

    Expedia

    Details
  • Newly renovated 2BR in downtown Staunton.  Apt A
    From $210 per night (USD)

    VRBO

    Newly renovated 2BR in downtown Staunton. Apt A

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    3

    The apartment is a newly renovated 2BR/2 bath on the second floor in an 1880 Beaux Arts building downtown, above Réunio ...

    From $210 per night (USD)

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  • Bed & Breakfast in a 1795 Log Cabin on working farm, George Washington, Sr Suite
    From $375 per night (USD)

    Expedia

    Bed & Breakfast in a 1795 Log Cabin on working farm, George Washington, Sr Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    We are a family run bed and breakfast in a restored circa 1795 hand-hewn log cabin decorated with period antiques. The ...

    From $375 per night (USD)

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    Details
  • Cozy Wintergreen Resort Escape Near Leaf Peeping!
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    Cozy Wintergreen Resort Escape Near Leaf Peeping!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Spend your days shredding the Wintergreen slopes, snow tubing at The Plunge, or hiking a segment of the Appalachian Trai ...

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  • Convenient downtown location Urban Oasis Near Hiking, Wineries, Breweries
    From $134 per night (USD)

    VRBO

    Convenient downtown location Urban Oasis Near Hiking, Wineries, Breweries

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy this cozy abode, ideal for couples or groups looking for an affordable and convenient spot to enjoy the sites! Lo ...

    From $134 per night (USD)

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    Details
  • The Revival Room in The Sanctuary! Two Bed Oasis!
    From $652 per night (USD)

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    The Revival Room in The Sanctuary! Two Bed Oasis!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    It's rare to find a place that's both historic and one-of-a-kind! The Revival Room, located on the first floor of "The S ...

    From $652 per night (USD)

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    Details
  • Torry Ridge--hot tub, mountain views, fireplace
    From $486 per night (USD)

    Expedia

    Torry Ridge--hot tub, mountain views, fireplace

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Torry Ridge takes its name from the high ridge above Sherando Lake. Spacious with large windows and mountain views of Wi ...

    From $486 per night (USD)

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    Details
  • Blue Ridge Parkway cabin--2BR, hot tub, fireplace
    From $326 per night (USD)

    VRBO

    Blue Ridge Parkway cabin--2BR, hot tub, fireplace

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Part of Love Ridge Mountain Lodging. Spy Rock cabin is named for an overlook with a panoramic vista of the Blue Ridge. S ...

    From $326 per night (USD)

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    Details
  • White Rock Cabin--1BR, ADA, kitchenette, fireplace
    From $234 per night (USD)

    Expedia

    White Rock Cabin--1BR, ADA, kitchenette, fireplace

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Part of Love Ridge Mountain Lodging. Named for a popular nearby hiking and mountain biking trail, White Rock is a stand ...

    From $234 per night (USD)

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    Details
  • Sherando Cabin--hot tub, kitchen, fireplace
    From $383 per night (USD)

    VRBO

    Sherando Cabin--hot tub, kitchen, fireplace

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Part of Love Ridge Mountain Lodging. Bring the whole family to this mountain retreat. Sherando cabin sleeps up to 10 peo ...

    From $383 per night (USD)

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    Details
  • Three Ridges Cabin--kitchen, fireplace, jacuzzi
    From $250 per night (USD)

    Expedia

    Three Ridges Cabin--kitchen, fireplace, jacuzzi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Part of Love Ridge Mountain Lodging. Named for the closest of the three adjacent National Wilderness Areas, Three Ridges ...

    From $250 per night (USD)

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    Details
  • High Meadows--King BR, fireplace, jacuzzi, kitchen
    From $270 per night (USD)

    VRBO

    High Meadows--King BR, fireplace, jacuzzi, kitchen

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Superhosts are experienced, highly rated hosts who are committed to providing great stays for guests. Part of Love Rid ...

    From $270 per night (USD)

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    Details
  • Bee Mountain Cabin fireplace, kitchen, jacuzzi
    From $242 per night (USD)

    Expedia

    Bee Mountain Cabin fireplace, kitchen, jacuzzi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Part of Love Ridge Mountain Lodging. Named for the mountain summit next to Three Ridges, Bee Mountain is an open floor p ...

    From $242 per night (USD)

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    Details
  • Ravens Roost--mountain views, hot tub, fireplace
    From $421 per night (USD)

    VRBO

    Ravens Roost--mountain views, hot tub, fireplace

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Part of Love Ridge Mountain Lodging, Ravens Roost takes its name from the stunning nearby overlook on the Blue Ridge Par ...

    From $421 per night (USD)

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    Details
  • Kennedy Ridge Cabin--1BR, jacuzzi, kitchenette
    From $219 per night (USD)

    Expedia

    Kennedy Ridge Cabin--1BR, jacuzzi, kitchenette

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Part of Love Ridge Mountain Lodging. Named for a mountain biking and off-road double track that skirts the Saint Mary’s ...

    From $219 per night (USD)

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    Details
  • Dripping Rock--1 King BR, Jacuzzi, Kitchenette
    From $237 per night (USD)

    VRBO

    Dripping Rock--1 King BR, Jacuzzi, Kitchenette

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Part of Love Ridge Mountain Lodging. Named for the trail next to Wintergreen Resort, Dripping Rock is a one bedroom cabi ...

    From $237 per night (USD)

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    Details
  • Meadow Mountain Cabin at Love Ridge Mountain Lodging
    From $283 per night (USD)

    Expedia

    Meadow Mountain Cabin at Love Ridge Mountain Lodging

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Named for a nearby mountain, Meadow Mountain is a stand alone, one bedroom, dog-friendly cabin with a jacuzzi tub and a ...

    From $283 per night (USD)

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    Details
  • \The Sparrow\ at Historic Downtown Staunton
    From $280 per night (USD)

    VRBO

    \"The Sparrow\" at Historic Downtown Staunton

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Perched on top of the famous Sears Hill, "The Sparrow" is a homey cottage located in Historic Downtown Staunton. Newly r ...

    From $280 per night (USD)

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    Details
  • Recently updated - breathtaking view of the Blue Ridge Mountains
    From $292 per night (USD)

    Expedia

    Recently updated - breathtaking view of the Blue Ridge Mountains

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Little Bear Lookout. Come for the view, experience the location, & enjoy the comfort! Updated in May 2022! ...

    From $292 per night (USD)

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    Details
  • Luxury Mountain House on Golf Course- Book for Summer/Fall
    From $409 per night (USD)

    VRBO

    Luxury Mountain House on Golf Course- Book for Summer/Fall

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Wintergreen Luxury Property on Mountain Golf Course. Summer weeks/weekends are nearly sold out. Some June dates availabl ...

    From $409 per night (USD)

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    Details
  • Luxe Wintergreen Resort Escape w/ Hot Tub!
    From $570 per night (USD)

    Expedia

    Luxe Wintergreen Resort Escape w/ Hot Tub!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Treat your family to a mountainside retreat and book this 4-bedroom, 3-bath Roseland vacation rental! This amenity-packe ...

    From $570 per night (USD)

    Expedia

    Details
  • Wintergreen Resort Condo < 1 Mi to Ski Resort
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    Wintergreen Resort Condo < 1 Mi to Ski Resort

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    An exhilarating getaway awaits at this Wintergreen Resort vacation rental! Nestled in the Blue Ridge Mountains, this 1-b ...

    Click For Pricing

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    Details
  • The Bungalow at Afton Mountain Retreat
    From $425 per night (USD)

    Expedia

    The Bungalow at Afton Mountain Retreat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foot ...

    From $425 per night (USD)

    Expedia

    Details
  • Idyllic Wintergreen Condo w/ Resort Amenities
    From $177 per night (USD)

    VRBO

    Idyllic Wintergreen Condo w/ Resort Amenities

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    With easy access to resort amenities and the great outdoors, this Wintergreen Resort vacation rental is the perfect spot ...

    From $177 per night (USD)

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  • Grand Chalet w/ Hot Tub -  Near Wintergreen Resort
    From $752 per night (USD)

    VRBO

    Grand Chalet w/ Hot Tub - Near Wintergreen Resort

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Adventure and leisure combine at this luxurious 4-bedroom, 3-bathroom vacation rental home in Roseland, Virginia. Locate ...

    From $752 per night (USD)

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  • Cozy Mountain Retreat with Heated Floors
    From $177 per night (USD)

    VRBO

    Cozy Mountain Retreat with Heated Floors

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Step into a beautifully crafted retreat where a stunning live-edge oak breakfast bar with leather stools awaits. Enjoy t ...

    From $177 per night (USD)

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    Details
  • HOT TUB! 4BR Spacious Townhome 1 Mi to Wintergreen Slopes + Shuffleboard Table
    Click For Pricing

    Expedia

    HOT TUB! 4BR Spacious Townhome 1 Mi to Wintergreen Slopes + Shuffleboard Table

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Come enjoy the beautiful Blue Ridge/Wintergreen area in a spacious 2,445 sqft, 3 level townhome, 2 min. drive to lodge a ...

    Click For Pricing

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    Details
  • Cabin on Penmerryl Farm - (2-Night Minimum Stay)
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    Cabin on Penmerryl Farm - (2-Night Minimum Stay)

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    ***2-Night Minimum Stay*** Penmerryl's 2 log cabins face our swimming pool and offer guests a private and rustic experi ...

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  • Log Home Retreat On Picturesque Private Farm
    From $226 per night (USD)

    Expedia

    Log Home Retreat On Picturesque Private Farm

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    7

    Get away from it all at this log cabin home in beautiful West Augusta. Enjoy the private setting surrounded by a 900+ a ...

    From $226 per night (USD)

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    Details
  • Private One Bedroom by Mountain Stream
    From $188 per night (USD)

    VRBO

    Private One Bedroom by Mountain Stream

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Cabin Barnwood is a very private one bedroom, with a nice patio and creek. The bedroom has a queen pencil poster bed, a ...

    From $188 per night (USD)

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  • Logwood Cabin Pre Civil War
    From $192 per night (USD)

    VRBO

    Logwood Cabin Pre Civil War

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Pre-Civil War Log cabin Cabin Creekwood is a family-owned business providing relaxing getaways in the Blue Ridge Mountai ...

    From $192 per night (USD)

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    Details
  • Pet Friendly Three Bedroom in Blue Ridge Mountains
    From $252 per night (USD)

    VRBO

    Pet Friendly Three Bedroom in Blue Ridge Mountains

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Oakwood is a large three bedroom, two bath cabin, all on one level. The master bedroom contains a queen bed, plus a s ...

    From $252 per night (USD)

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    Details
  • Pet Friendly Two Bedroom in Blue Ridge Mtns
    From $208 per night (USD)

    VRBO

    Pet Friendly Two Bedroom in Blue Ridge Mtns

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    A very comfortable two bedroom, Mountainwood gives plenty of room to spread out. The main room is nice and open, includ ...

    From $208 per night (USD)

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    Details
  •  HOT TUB + Pet Friendly + visit 80 acres to let your dogs run off-leash!
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    VRBO

    HOT TUB + Pet Friendly + visit 80 acres to let your dogs run off-leash!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    We are dog lovers with Australian Shepherds! Before we moved to the mountains full-time and would visit, we would alway ...

    Click For Pricing

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    Details
  • WILDBRIAR LODGE • 6BR/6BA • MASTER SUITES • HOT TUB • GAME ROOM • MOUNTAIN VIEWS
    From $2347 per night (USD)

    Expedia

    WILDBRIAR LODGE • 6BR/6BA • MASTER SUITES • HOT TUB • GAME ROOM • MOUNTAIN VIEWS

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    20

    This property is undergoing a complete remodel, expected to be finished by June 2025. Updates include a new 12-seater th ...

    From $2347 per night (USD)

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    Details
  • Downtown Waynesboro Location, Walk to Dining/Bars/Brewery Stylish NEW decor! Washer/Dryer in unit
    From $106 per night (USD)

    VRBO

    Downtown Waynesboro Location, Walk to Dining/Bars/Brewery Stylish NEW decor! Washer/Dryer in unit

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Enjoy this cozy abode, ideal for singles or a couple looking for an affordable and convenient spot to enjoy the sites! L ...

    From $106 per night (USD)

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    Details
  • Affordable Suites of America Waynesboro
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    Affordable Suites of America Waynesboro

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>A short distance from snowboarding, downhill skiing, and more, this smoke-free apartment lets you experience it all. ...

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  • Bide-a-Wee- Hike the Trails! Close to the slopes!
    From $435 per night (USD)

    VRBO

    Bide-a-Wee- Hike the Trails! Close to the slopes!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Bide-a-Wee! This cozy mid-century modern mountain home has 3 bedrooms and 2 baths within a 10-minutes walking ...

    From $435 per night (USD)

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  • Golf Front Home
    From $302 per night (USD)

    VRBO

    Golf Front Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    3 Bedroom + Loft and Basement, 2 Bath on Devil's Knob #5 Beautiful, custom built and spacious three bedroom home locate ...

    From $302 per night (USD)

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  • Updated spacious home with top of the mountain view!
    From $724 per night (USD)

    VRBO

    Updated spacious home with top of the mountain view!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    13

    Experience “top of the mountain” living and enjoy the spectacular views in this spacious and updated 5 bedroom, 4.5 bath ...

    From $724 per night (USD)

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    Details
  • The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
    From $145 per night (USD)

    Expedia

    The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This beautifully restored home is located in the City of Waynesboro just a short drive from the Blue Ridge Parkway. Mode ...

    From $145 per night (USD)

    Expedia

    Details