Windsor Area Rentals
From $165 per night (USD)VRBO
Ski-in/out mountainside condo w/ mountain views, private deck, fireplace, w/d
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Okemo Mountain Lodge A208 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $165 per night (USD)VRBO
From $226 per night (USD)VRBO
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Scenic Views | Year-Round Activities | Near Outdoor Recreation Step into the rustic charm of Chester at this 3-bedroom, ...
From $226 per night (USD)VRBO
From $708 per night (USD)VRBO
Cozy log cabin & loft, close to recreation, dog-friendly, bbq, balcony, a/c, w/d
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Cabin & Loft Fort Defiance Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $708 per night (USD)VRBO
From $2288 per night (USD)Expedia
Casita Alta: Main House & Pool House w/ Pool Use
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Casita Alta – A Luxury Vacation Rental in Woodstock, Vermont The Ultimate Private Retreat with Heated Pool & Breathtaki ...
From $2288 per night (USD)Expedia
From $908 per night (USD)VRBO
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
To the people who have seen it, Light Hill is considered one of the most beautiful properties in the Barnard area. With ...
From $908 per night (USD)VRBO
From $327 per night (USD)VRBO
Charming Cabin on Lake Amherst - Private Dock, Fireplace, Firepit, Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Renovated, rustic, pet-friendly cabin perched above Lake Amherst with dock and lake access. 10 minutes to Okemo's Jackso ...
From $327 per night (USD)VRBO
From $400 per night (USD)VRBO
Convenient village condo w/ mountain views, close to Okemo, partial a/c, w/d
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
North Country 6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $400 per night (USD)VRBO
From $430 per night (USD)Expedia
Cozy 4 BR home with hot tub in Weston near 4 ski areas & many hiking trails!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to picturesque Weston, home of the famous Vermont Country Store, and the perfect retreat for nature lovers and ad ...
From $430 per night (USD)Expedia
From $360 per night (USD)VRBO
RoundTop Chalet- Hot Tub, Grill, Hiking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this luxurious 3-bedroom, 2-bathroom chalet in Plymouth, Vermont, located on a former ski mountain. With stunn ...
From $360 per night (USD)VRBO
From $462 per night (USD)VRBO
Modern cabin oasis close to Stratton, Okemo, Bromley and Magic
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in the heart of Southern Vermont, this cozy, modern chalet offers the perfect winter getaway. The house is nea ...
From $462 per night (USD)VRBO
From $633 per night (USD)VRBO
Spacious 6-bedroom house with AC, WiFi in charming Springfield
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Vermont is waiting for you at this 6-bedroom gorgeous antique house with all modern amenities and yesteryear charm. With ...
From $633 per night (USD)VRBO
From $1722 per night (USD)Expedia
The All Seasons - Enclosed Heated Pool, Hot Tub, Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Take it easy at this unique and tranquil getaway with year-round pool, outdoor hot tub, and close proximity to area attr ...
From $1722 per night (USD)Expedia
From $934 per night (USD)VRBO
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Bear Foot Lodge – Spacious Vermont Mountain Chalet Near Killington Resort and Riverside Farm Discover the perfect Vermo ...
From $934 per night (USD)VRBO
From $320 per night (USD)VRBO
Romantic Retreat secluded in Vermont with WiFi and AC included
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Romantic Retreat in Vermont – Secluded Cabin with Private Deck & Scenic Views Escape to this beautifully furnished, priv ...
From $320 per night (USD)VRBO
From $392 per night (USD)VRBO
Highland Golf, Walk to Club - Lakeland Village 2D
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to the serene beauty of Quechee, Vermont, with this spacious 3-bedroom, 2-bath retreat featuring a stunn ...
From $392 per night (USD)VRBO
From $594 per night (USD)Expedia
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Unwind at this Hartford home with tall windows highlighting breathtaking mountain views. It's the perfect tranquil spot ...
From $594 per night (USD)Expedia
From $326 per night (USD)VRBO
Cozy condo w/ balcony, river view, electric woodstove, w/d, wifi, kitchen, a/c
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Mill Run 3C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $326 per night (USD)VRBO
From $1270 per night (USD)Expedia
Ski-In/Out to S6, Sauna & Hot Tub - Little House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Experience true ski-in/ski-out luxury at the very top of Saskadena Six in Woodstock, VT, where a stunning, ligh ...
From $1270 per night (USD)Expedia
From $351 per night (USD)VRBO
Charming 2-Bedroom Ski-In/Ski-Out at Jackson Gore
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy year-round access to Okemo Mountain from this thoughtfully appointed 2-bedroom unit nestled in Jackson Go ...
From $351 per night (USD)VRBO
From $542 per night (USD)Expedia
Walk to S6! Pool Table/Fireplace - Saskadena Lodge
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Enjoy ultimate Vermont living in this beautifully renovated family home, just steps from ski slopes and featuri ...
From $542 per night (USD)Expedia
From $343 per night (USD)VRBO
Terrific 3-bedroom cottage with AC in charming Cavendish
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Cavendish at this pleasant cottage. With 3 cozy bedrooms including 2 full beds and 1 queen bed, guests can rel ...
From $343 per night (USD)VRBO
From $263 per night (USD)Expedia
Walk-to-village end-unit condo, mountain views, large deck, woodstove, bbq, a/c
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Quechee Hollow 1F Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $263 per night (USD)Expedia
From $343 per night (USD)VRBO
Fabulous 2-bedroom house with WiFi in charming Andover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a peaceful stay at this lovely 2-bedroom house in Andover. The bedrooms feature 2 king beds, perfect for a comfort ...
From $343 per night (USD)VRBO
From $549 per night (USD)Expedia
Family-friendly log cabin with Fireplace & Mountain Views near 4 Ski Resorts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Make Highland View Lodge in Weston your family or group's home for the winter season. This spacious 4-bedroom, 3-bathroo ...
From $549 per night (USD)Expedia
From $470 per night (USD)VRBO
Charming 4-Bedroom Mountain Escape–1 Minute drive to Slopes & Walk to Main St
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your perfect Ludlow getaway! Our spacious, well-appointed 4-bedroom, 2-bath ski retreat is just 1 minute from ...
From $470 per night (USD)VRBO
From $703 per night (USD)Expedia
Luxury Snow Village Ski-In/Out, Golf & Club Access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Experience timeless Vermont elegance at Snow Village 9A—an expansive, modern mountain retreat designed for year ...
From $703 per night (USD)Expedia
From $550 per night (USD)VRBO
2BR Winterplace Ski Condo w/ Fireplace + Hot Tubs
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Enjoy mountain fun with the family at this 2BR Winterplace condo at Okemo. A short walk puts you on the slopes ...
From $550 per night (USD)VRBO
From $1305 per night (USD)Expedia
Secluded 5-BR Estate 10-Min to Okemo
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Experience a truly private escape at this elegant 5-bedroom, 4-bathroom residence, gracefully set on 13.8 acres ...
From $1305 per night (USD)Expedia
From $283 per night (USD)VRBO
Ski in/ski out condo w/ pond & mtn views, fireplace, tennis courts & w/d
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Kettle Brook A6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $283 per night (USD)VRBO
From $428 per night (USD)VRBO
Spacious 4-Bedroom in Quechee VT
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy all the beauty Vermont has to offer and more in this air-conditioned 4-bedroom, 4-bath townhouse in Quechee. Walk ...
From $428 per night (USD)VRBO
From $576 per night (USD)VRBO
The Woodstead in Quechee- New Listing to VRBO!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
NEW LISTING! Very spacious, 3,000 sq. ft home with 3 floors of living, surrounded by 6+ acres of woodland and big sky vi ...
From $576 per night (USD)VRBO
From $458 per night (USD)VRBO
8 Mi to Okemo Mountain Resort: Mtn-View Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Pets Welcome w/ Fee | Pond On-Site | 2-Level Deck Escape to the Green Mountains and stay at this spacious 4-bedroom, 3- ...
From $458 per night (USD)VRBO
From $462 per night (USD)VRBO
Four bedroom retreat in Vermont's Golden Triangle
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
In the heart of the Green Mountains, our newly renovated four-bedroom home blends rustic charm with modern luxury. Set o ...
From $462 per night (USD)VRBO
From $529 per night (USD)Expedia
One of a Kind Farmhouse with Incredible Okemo & Sunset Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this authentic unique vintage farmhouse set on a hill amongst open fields that oozes charm! It's the perfect ...
From $529 per night (USD)Expedia
From $351 per night (USD)VRBO
Spacious 5-bedroom cabin in charming Chester
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Relax with the whole family at this perfect all season VT retreat. Nestled into a hill, surrounded by scenic views. Cent ...
From $351 per night (USD)VRBO
From $534 per night (USD)Expedia
Acres & Views! Firepit, BBQ - Bayley Way Getaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: The ultimate privacy & tranquility at Bayley Way Getaway, tucked away on nearly 4 acres just a mile from Queche ...
From $534 per night (USD)Expedia
From $1026 per night (USD)VRBO
Premier Woodstock Village Riverfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to one of Woodstock's most iconic houses — Where history, elegance, and nature meet. Step into a piece of cinem ...
From $1026 per night (USD)VRBO
From $384 per night (USD)Expedia
Fairway Village condo on golf course w/ private patio, fireplace & amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fairway Village 7A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $384 per night (USD)Expedia
From $473 per night (USD)VRBO
Cabin on the hill Ascutney Vt - 4 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Nestled in the serene woods of Brownsville Vermont, this charming cabin offers a perfect retreat from everyday life. The ...
From $473 per night (USD)VRBO
From $860 per night (USD)Expedia
Slopeside Solitude | Ski-In/Out & Cozy Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Ski-in/ski-out 3BR, 2.5BA condo in Solitude at Okemo with a wood-burning fireplace, mountain-view balcony, and ...
From $860 per night (USD)Expedia
Click For PricingVRBO
Cozy Mountain-Style Condo Near the Slopes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Experience mountain comfort at this newly renovated condo near Okemo! Sleeps 7 across a king suite, queen room, ...
Click For PricingVRBO
From $773 per night (USD)Expedia
Three Decks Hot Tub Fire Table - DeckHouse Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience unforgettable Vermont getaways at Deckhouse Retreat, where panoramic views, expansive decks, and ups ...
From $773 per night (USD)Expedia
From $624 per night (USD)VRBO
Lakeview Lodge • Hot Tub • Sleeps 16+ • Okemo
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
☆☆ HIGHLIGHTS ☆☆ ✹ Primary bedroom w/ King Sized bed + Full Ensuite bathroom ✹ Four additional bedrooms offer a total of ...
From $624 per night (USD)VRBO
From $622 per night (USD)Expedia
Lake Rescue • Hot Tub • Dock • Mins to Okemo Ski
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
☆☆ HIGHLIGHTS ☆☆ ✹ Primary bedroom w/ queen bed overlooking lake + Twin and trundle ✹ 2 Additional bedrooms with double ...
From $622 per night (USD)Expedia
From $595 per night (USD)VRBO
Private house & cottage, pond, mountain view, balcony, outdoor dining, fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Auger Hole Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $595 per night (USD)VRBO
From $436 per night (USD)Expedia
Walk to Trails & Village +Pets - Highland Cabin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to Highland Cabin, a sunlit Woodstock retreat—just steps from scenic trails & the vibrant village. Start ...
From $436 per night (USD)Expedia
From $521 per night (USD)VRBO
Quiet country home w/ large deck & fireplace, near Okemo Mtn & town
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
North Hill Cross Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $521 per night (USD)VRBO
From $360 per night (USD)Expedia
Historic Vermont farmhouse in 100+ acres, balcony, sunroom, office, window a/c
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Kingdom Valley Farmhouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $360 per night (USD)Expedia
From $424 per night (USD)VRBO
Quaint Quechee Lakes Condo - walk to Lake Pinneo & the Clubhouse!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the heart of Vermont in this recently renovated 3-bedroom, 2- bathroom condo. Featuring a modern kitchen, cozy ...
From $424 per night (USD)VRBO
From $274 per night (USD)Expedia
MUST-SEE VERMONT MAGICAL FALL FOLIAGE SEASON BOOK NOW
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Your peaceful retreat in Springfield with 3 cozy bedrooms awaits. This superb house features 2 queen beds and 1 full bed ...
From $274 per night (USD)Expedia
From $1261 per night (USD)VRBO
Direct Ski Access from J Building Okemo Winterplace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 Bedroom/2 Bath Winterplace condominium couldn`t be more convenient. The mid-mountain location boasts easy access ...
From $1261 per night (USD)VRBO
From $363 per night (USD)Expedia
Beautiful house w/ mountain view, balcony, grill, central a/c, close to skiing
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Green Mountain Zen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $363 per night (USD)Expedia
From $472 per night (USD)VRBO
Serene 4-BR Retreat 10 Mins to Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Discover your ideal Vermont escape at this charming 4-bedroom, 3-bathroom home in Andover. Nestled amidst tranq ...
From $472 per night (USD)VRBO
From $241 per night (USD)Expedia
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your cozy luxury escape in the heart of Vermont. This thoughtfully designed tiny home is nestled in a quiet a ...
From $241 per night (USD)Expedia
From $326 per night (USD)VRBO
Live the Vermont Life in 1840 Classic Renovated Cape
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Classic 1840 farmhouse that has called home for over 40 years. We are offering a nice 2 BR- 2 bath unit on 2 floors much ...
From $326 per night (USD)VRBO
From $756 per night (USD)Expedia
Ski-in/Out Okemo Mountain Resort Condo w/ Balcony
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
SouthFace Village Community | 8 Mi to Camp Plymouth State Park Epic slopes, scenic views, and a luxury basecamp — it’s ...
From $756 per night (USD)Expedia
From $290 per night (USD)VRBO
Connecting condos w/ electric fireplace, near Okemo mountain, wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Cozy Ludlow Escape & Teddy's Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $290 per night (USD)VRBO
From $295 per night (USD)Expedia
Cozy studios in Ludlow, kitchenette, TV, wifi, close to Okemo Resort
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Sweet Retreat & Dream Weaver Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $295 per night (USD)Expedia
From $928 per night (USD)VRBO
6 Cozy Condos in the heart of Ludlow, fireplace, kitchenettes, shuttle nearby
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 24
Ludlow A Go Go Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $928 per night (USD)VRBO
From $484 per night (USD)Expedia
Cozy log cabin w/ wood-burning fireplace, balcony, close to recreation, pond
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Parker Lane Cabin Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $484 per night (USD)Expedia
From $370 per night (USD)VRBO
Comfortable condo w/ two fireplaces, balcony, pool, tennis, close to recreation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newton Village 1A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $370 per night (USD)VRBO
From $133 per night (USD)Expedia
Quaint Queen room at the Chester Inn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a private room & bathroom with tub in the historic Chester Inn, circa 1780. This charming property is conveniently ...
From $133 per night (USD)Expedia
From $231 per night (USD)VRBO
Spacious 4-bedroom house in charming Springfield with AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Vermont Ski and Stay. Get ready to relax in this 4-bedroom house in Springfield. The bedrooms feature 1 king bed, 2 quee ...
From $231 per night (USD)VRBO
From $994 per night (USD)VRBO
Three Bedroom Country home with private hot tub and 5 min drive to Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to this quintessential Vermont farmhouse, where rustic character meets modern comfort. Just five minutes from Oke ...
From $994 per night (USD)VRBO
From $1022 per night (USD)VRBO
Luxurious, modern 6BR home on 436 acres, stunning views, hiking, near skiing
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Come enjoy the unique experience offered at Wild Trails Farm. “A perfect little piece of paradise.” “Spent ou ...
From $1022 per night (USD)VRBO
From $1525 per night (USD)VRBO
New construction: 4-bed, 4-bath house at Okemo Ski Mountain in Ludlow, VT
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Your Vermont getaway awaits at this 4-bedroom house. With 1 king bed, 3 queen beds, and 1 full bed, this peaceful retrea ...
From $1525 per night (USD)VRBO
From $1027 per night (USD)VRBO
Walk to Trail and Amenities at this Solitude Village Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This ski home is convenient and comfortable. Get cozy by the woodburning fireplace after a long day on the slopes. Unwi ...
From $1027 per night (USD)VRBO
From $659 per night (USD)VRBO
3-Bedroom Townhome Overlooking 12th Hole in Quechee, VT Recently Renovated!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stay comfortably in Quechee at this 3-bedroom townhome. Each bedroom features a king bed, ensuring a good night's sleep ...
From $659 per night (USD)VRBO
From $518 per night (USD)VRBO
Okemo Mountain Lodge unit with Direct Access to Clocktower Base Area at Okemo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on mountain at the Okemo Mountain Lodge at the Clocktower Base Area, this unit is near all the action. Assigned ...
From $518 per night (USD)VRBO
From $298 per night (USD)VRBO
Hawks Mountain Village Retreat - 10 min. to Okemo!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Hawks Mountain Village Retreat! A charming, historic home with modern conveniences minutes from Okemo, Ludlow ...
From $298 per night (USD)VRBO
From $621 per night (USD)VRBO
Cozy Modern Cabin w/ Hot Tub & Beautiful View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Plan a relaxing escape to this cozy & contemporary-outfitted cabin w/ an unparalleled mountain view! Just an eight-minu ...
From $621 per night (USD)VRBO
From $177 per night (USD)VRBO
Charming rural 2-bedroom cottage with amazing view in Hartland, Vermont
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This cozy cottage sits on a well-maintained dirt road overlooking fields, woods, and the NH mountains, As you walk ...
From $177 per night (USD)VRBO
From $601 per night (USD)VRBO
Four Season Escape | Near Lakes,Trails,Killington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Take some TymeOff and have the time of your life at our cozy all-season cabin in the heart of Vermont. Settle in, breath ...
From $601 per night (USD)VRBO
From $347 per night (USD)VRBO
Bright and spacious 3 Bed/3 Bath in Chester, VT
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This bright and spacious 3 bed/3 bath home is within walking distance of shops, restaurants, a local pub, and small groc ...
From $347 per night (USD)VRBO
From $1014 per night (USD)VRBO
8 Bedroom Roadhouse btw. Killington & Okemo
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 16
“Coolidge Roadhouse” (Coolidge Retreats) 9 bedroom w/ Hot tub. Inquire if you are more than 16 ppl as the house can fit ...
From $1014 per night (USD)VRBO
From $367 per night (USD)VRBO
Soothing family-friendly townhome in Quechee Lakes
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this lovely townhome in Quechee. This adorable property boasts 4 bedrooms, including a king bed, 2 queen beds ...
From $367 per night (USD)VRBO
From $357 per night (USD)VRBO
Walk to Club, Golf Course! - Lakeland Village 4C*
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Lakeland Village Privately Situated Updated Condo with Lake Views. Please SEE: Other Things to Note For Area D ...
From $357 per night (USD)VRBO
From $362 per night (USD)VRBO
End Unit, Golf Views, Club | Lakeland Village 2A*
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Private Back Deck Offers Views of Golf Course and Cross Country Ski Trails. Please SEE: Other Things to Note F ...
From $362 per night (USD)VRBO
From $566 per night (USD)VRBO
Kettlebrook Two Bedroom Great Spot for a Skiing Family or Couples
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located near the Kettlebrook and Bull Run ski trails, this location offers ease and convenience. Gather around the wood ...
From $566 per night (USD)VRBO
From $1532 per night (USD)VRBO
Three Bedroom House Sized Condo with Private Hot Tub Walk to Trail
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Snowtrak, a premier community nestled on Okemo Mountain! Walk to the nearby ski access through the Kettlebroo ...
From $1532 per night (USD)VRBO
From $603 per night (USD)VRBO
Ludlow Village Home -- Okemo Shuttle -- Walk to Town -- Hot Tub -- Roomy Space!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Excited to be back on VRBO after a long hiatus! Great home that is close to town, on the Okemo Shuttle route with plenty ...
From $603 per night (USD)VRBO
From $603 per night (USD)VRBO
Charming 3-bedroom house in Ludlow beside the Blue Lot at Okemo, close to town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Your Ludlow adventure begins at this 3-bedroom house. With 2 king beds, 1 queen bed, and 1 twin bed, this charming prope ...
From $603 per night (USD)VRBO
From $541 per night (USD)VRBO
Norwich Cottage 3BD/2BA - 1mi to Dartmouth
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome professionals, families and outdoor enthusiasts! This cozy, charming fully remodeled 3-bed, 2-bath cottage is n ...
From $541 per night (USD)VRBO
From $859 per night (USD)VRBO
Beautiful Hawk Mountain home with Mountain Views, Hot Tub and Sauna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This 4 bedroom, 3.5 bath multi-level single family home is built into a wooded hillside and offers beautiful mountain vi ...
From $859 per night (USD)VRBO
From $381 per night (USD)VRBO
THE OTTO: A Warm + Cozy Ski In Ski Out Lodge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
THE OTTO, eponymously named, inspired, and much like the marvelous man himself, is a lovely and uniquely mysterious ski ...
From $381 per night (USD)VRBO
From $239 per night (USD)VRBO
Custom built 2-bedroom cabin on 3 acres, Two miles to Ludlow town center.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Built in 2023, this custom built home is the ideal, private getaway to enjoy Okemo Mountain and charming Ludlow, Vt. The ...
From $239 per night (USD)VRBO
From $2013 per night (USD)VRBO
Spacious and Close to Ski Lifts Family Friendly Condo at Solitude on Okemo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a spacious two story floor-plan with 3.5 baths and cathedral ceilings. Sip a glass of wine by the wood-burning fir ...
From $2013 per night (USD)VRBO
From $1616 per night (USD)VRBO
Convenient Whispering Pines Estate Panoramic Views\n\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Hailed as, “The most magnificent views of the Upper Valley and Dartmouth,” the panoramic views can be seen from the spac ...
From $1616 per night (USD)VRBO
From $220 per night (USD)VRBO
NEW LISTING Winter Seasonal 2025-2026 - On Lake Rescue & 9 min to Okemo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Available for WINTER SEASONAL 2025-2026 Enjoy a picturesque Vermont getaway at The Snuggery, a meticulously maintained ...
From $220 per night (USD)VRBO
From $683 per night (USD)Expedia
Okemo Ski Condo: 3BR +Loft Sleeps 10 w/ Fireplace
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Discover ski-in/ski-out bliss at our top-floor condo on Okemo Mountain. Nestled in the Winterplace community at ...
From $683 per night (USD)Expedia
From $602 per night (USD)VRBO
All-seasons fun in Ludlow, Vermont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy 4 seasons of outdoor, whole-family fun in this modern, brand-new build that features unparalleled privacy. Nestle ...
From $602 per night (USD)VRBO
From $268 per night (USD)Expedia
Cozy Cabin near Okemo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Cozy private cabin located just 10 minutes from Okemo! This cabin features a mud room to store all your ski gear. One be ...
From $268 per night (USD)Expedia
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Less than 5 mi. to Killington Skyeship Gondola
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Private, soundproofed, high-tech security, hard-wired fire/heat/smoke/carbon monoxide, fire doors, keyless entry, FOB se ...
Click For PricingVRBO
From $434 per night (USD)Expedia
Pet-Friendly Near Simon Pierce | The House on Main
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Summary: Welcome to this stunning newly restored, dog friendly, home located in the heart of Quechee Village! Don't miss ...
From $434 per night (USD)Expedia
From $725 per night (USD)VRBO
Birch Lodge - mountain views, hottub, minutes to Okemo!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Located in a private development, this home sits surrounded by the lush forest with a clearing exposing the face of Okem ...
From $725 per night (USD)VRBO
From $564 per night (USD)Expedia
Condo on Quechee Golf Course 3bd/2bt Private Feel
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<p>Located next to a golf course, this 3-bedroom, 2-bathroom condo brings all of Quechee within your reach. Fans of natu ...
From $564 per night (USD)Expedia
From $462 per night (USD)VRBO
New! Steps from Ski Hill 4BR/3.5Ba - Kingswood 10A
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to the perfect mountain retreat! This stunningly renovated end-unit condo is located just steps away fr ...
From $462 per night (USD)VRBO
From $611 per night (USD)Expedia
Luxe Log Cabin, Summer Comfort - Cabin Fever
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to your Vermont getaway! Picture yourself in this exquisite four bedroom, three full and two-half bath ...
From $611 per night (USD)Expedia
From $214 per night (USD)VRBO
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Looking for an affordable getaway near the scenic mountains of VT? Look no further! Our cozy one-bedroom apartment is ju ...
From $214 per night (USD)VRBO
From $491 per night (USD)Expedia
Sauna, Hot Tub, Game Room - The Gathering Place
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience the all-new Gathering Place, freshly renovated with a gourmet kitchen, luxurious primary suite, and ...
From $491 per night (USD)Expedia