Windsor Area Rentals
From $1000 per night (USD)VRBO
Gorgeous Slopeside Winterplace\/Okemo Vail Resorts Available Feb holiday\/March!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Renovated, Winterplace at Okemo Vail Resorts Slope Side: This Top Floor, End Unit, Front Line Winterplace condo fe ...
From $1000 per night (USD)VRBO
From $532 per night (USD)Expedia
Kettle Brook 2 BR & 2 BA ski in\/out condo on Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Kettle Brook is scenic ski in/out complex between the Bull Run and Kettle Brook trails on Okemo Mountain. Direct ski a ...
From $532 per night (USD)Expedia
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Amazing family friendly 3+ Bedroom, 3 Full Bath in Quechee
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
If you are looking for a spacious stand-alone home with a wrap-around porch set in a picturesque VT setting, this is it! ...
Click For PricingVRBO
From $461 per night (USD)Expedia
Long Range Mountain Views in West Windsor
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Thistle Hill, a beautiful private property on 17 acres. Home is located 12 miles from Woodstock in the heart ...
From $461 per night (USD)Expedia
From $1112 per night (USD)VRBO
Ski house. Okemo Ludlow Vermont
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Large timber frame family style ski home with a spectacular veiw of the mountain Professional kitchen,Games, Hot Tub, s ...
From $1112 per night (USD)VRBO
From $445 per night (USD)Expedia
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This cozy ski Chalet home sleeps up to 12 people- an unbeatable choice for a ski trip with friends or family for a memor ...
From $445 per night (USD)Expedia
From $3164 per night (USD)VRBO
Havenwood, a beautiful private, gated estate in Woodstock, Vermont
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
This secluded 125 acre estate is aptly named. A few nights at Havenwood will leave one feeling both relaxed and energiz ...
From $3164 per night (USD)VRBO
From $949 per night (USD)Expedia
The Cottage on private gated 400 acre Reading Farms Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This home is one of 3 on a 400 gated acre estate . It has a kitchen, 3 bedroom, 1.5 bathrooms. Main floor bedroom has a ...
From $949 per night (USD)Expedia
From $573 per night (USD)VRBO
Log Cabin Retreat on 40 Acres
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This New England log home, located in the foothills of the Green Mountains, overlooks 40+ acres of forest and a year-rou ...
From $573 per night (USD)VRBO
From $811 per night (USD)Expedia
Bear-Foot Lodge Killington, Private! Sauna\/Gameroom. Perfect for Large Groups!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Come enjoy the stunning scenery of Vermont's countryside while you relax in this gorgeous 5,000 sq ft. lodge. This year- ...
From $811 per night (USD)Expedia
From $328 per night (USD)VRBO
Beautiful and Brand New Ski House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Brand new and beautiful house within walking distance of the village's many restaurants, shops and galleries. This 2 be ...
From $328 per night (USD)VRBO
From $1440 per night (USD)Expedia
Luxury 100 acre 3 building Compound
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
100 acre farm located equidistant ( 15 mins) between Stratton and Okemo. Hiking, tennis, apple picking(on premises), pin ...
From $1440 per night (USD)Expedia
From $288 per night (USD)VRBO
Circa 1868 Chester Home-Less than 20 MIN TO OKEMO
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
OVERVIEW Our historic 1868 'Elm House' is located in the picturesque town of Chester, nestled in the heart of Chester De ...
From $288 per night (USD)VRBO
From $616 per night (USD)Expedia
Luxurious Mountain Cabin near Okemo with High-End Modern Amenities for up to 12
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Located in Ludlow, this professionally decorated home, with over 3000 Sq ft of living space, includes 4 bedrooms and 4 b ...
From $616 per night (USD)Expedia
From $481 per night (USD)VRBO
Castle Hill Resort Condo (with on-site Aveda Spa)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome home! This charming 1500 square foot 3 bedroom condo at the historical Castle Hill Resort and Spa, has everythin ...
From $481 per night (USD)VRBO
From $171 per night (USD)Expedia
Romantic Riverside Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Romantic Riverside Getaway. Located in the heart of Ludlow, this 1 Bedroom 1 Bath with sofa bed condo sleeps 4. Have cof ...
From $171 per night (USD)Expedia
From $616 per night (USD)VRBO
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful new mountain home steps to Okemo Clock Tower and The Loft Tavern. This newly renovated mountain home has ever ...
From $616 per night (USD)VRBO
From $215 per night (USD)Expedia
Pamper Yourself at Jackson Gore
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This plush two room suite is steps from skiing, riding, snow-tubing, skating and more. Pull your car into our under cove ...
From $215 per night (USD)Expedia
From $168 per night (USD)VRBO
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a secluded mountainside retreat. Perfect for a getaway for two and room enough for 4 it is located on eleven pri ...
From $168 per night (USD)VRBO
From $264 per night (USD)Expedia
Beautiful Ludlow Mill Condo W\/ Free Shuttle To Okemo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Come and experience our piece (peace!) of heaven near Okemo Mountain in a Mill condo right in the heart of Ludlow Villag ...
From $264 per night (USD)Expedia
From $395 per night (USD)VRBO
Beautiful home offering privacy on 7 acres with private pond
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Peaceful home in Vermont’s Upper Valley. This is a beautiful three BR, two BA home offering privacy and relaxation on 7 ...
From $395 per night (USD)VRBO
From $177 per night (USD)Expedia
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21517
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $177 per night (USD)Expedia
From $213 per night (USD)VRBO
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21820
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $213 per night (USD)VRBO
From $214 per night (USD)Expedia
Deluxe one bedroom suite located on first floor with outdoor heated pool 11517
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in central Vermont's Green Mountains, Cedarbrook is perfectly located for skiing in all the local mountains. One ...
From $214 per night (USD)Expedia
From $213 per night (USD)VRBO
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21921
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of Vermont's Green Mountains, Cedarbrook offers the ideal year-round retreat for guests looking to ...
From $213 per night (USD)VRBO
From $258 per night (USD)Expedia
Updated Village Victorian on Ski Shuttle, walk to all amenties in town!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
New to market, freshly renovated Ski Village Victorian with 4 bedrooms directly on Okemo shuttle route. Enjoy the old ...
From $258 per night (USD)Expedia
From $193 per night (USD)VRBO
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Renovated one bedroom guest cottage in Ludlow, Vermont. Prime ski location, 12 houses down from the Mountain Road entr ...
From $193 per night (USD)VRBO
From $202 per night (USD)Expedia
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and taverns, antique shops, ...
From $202 per night (USD)Expedia
From $282 per night (USD)VRBO
Cottage in Barnard
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Charming Vermont cottage, just up the road from Silver Lake and the Barnard General Store. Bright, warm, and welcoming, ...
From $282 per night (USD)VRBO
From $260 per night (USD)Expedia
Enjoy snowball fights or romantic nights in a 1BD vacation apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make some memories at this unique and family-friendly pA Beautiful Mountainside Escape Vacationing in Vermont brings a ...
From $260 per night (USD)Expedia
From $504 per night (USD)VRBO
Condo with a shared seasonal pool & tennis courts - walk to ski trails!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Quaint 1bedroom,1 bath short walk to the Okemo Sachem trail, convenient private parking right outside of front entranc ...
From $504 per night (USD)VRBO
From $774 per night (USD)VRBO
Gorgeous Log Home With Mountain Views with Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Please note: The Sauna is currently out of order and being repaired ASAP. New hot tub installed as of 11/23. Hill top h ...
From $774 per night (USD)VRBO
From $260 per night (USD)VRBO
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Sportsman themed, real log cabin that has comfortable wood stove & hearth, plus backup regular heat. Bathroom with show ...
From $260 per night (USD)VRBO
From $914 per night (USD)Expedia
Remodeled home with three separate condos - steps from ski lift bus pickup
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 13
Pleasant Street Apartments Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $914 per night (USD)Expedia
From $399 per night (USD)VRBO
Remodeled condo with shared washer\/dryer - walk to dining & ski lift bus pickup
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Seatoller Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $399 per night (USD)VRBO
From $340 per night (USD)Expedia
First-floor condo with shared laundry - steps to ski bus pickup, walk to dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Aspatria Unit A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $340 per night (USD)Expedia
From $133 per night (USD)VRBO
Hawks Mountain Farm, full apartment on a working farm.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Hello and welcome to Hawks Mountain Farm, a working farm with gardens, chickens, two yaks, four donkeys and an 1820 farm ...
From $133 per night (USD)VRBO
From $857 per night (USD)Expedia
On Silver Lake & Close To Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perched on the edge of pristine Silver Lake, my country home sits on a large rolling lot overlooking the lake enjoyed by ...
From $857 per night (USD)Expedia
From $293 per night (USD)VRBO
Modern & Updated Winterplace 3Br- Sleeps 12 by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
**** New protocols include the following: This beautiful mountainside, located a short walk from the t ...
From $293 per night (USD)VRBO
From $283 per night (USD)Expedia
2Br Solitude -Ski-in, Ski-out Access to Promenade Trail by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This 2BR, 2BA unit sleeps 7, with a queen bed in master bedroom, a twin over double bunk bed in guest bedroom, plus a q ...
From $283 per night (USD)Expedia
From $192 per night (USD)VRBO
1Br Ski-in, Ski-out With King Bed- Okemo Mtn Lodge by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
B303 is a non air-conditioned 1 bedroom/1 bath unit on the third floor of building B in the Mountain Lodge. This unit s ...
From $192 per night (USD)VRBO
From $504 per night (USD)Expedia
Okemo LARGE home SKI DATES still available NEW Hot tub. pool table 3 full baths
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Welcome to a relaxing vacation, right in the heart of the OKEMO Valley with convenient access to major routes and only 3 ...
From $504 per night (USD)Expedia
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Spacious Winterplace 2 Br Condo- Okemo by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bedding is a Queen in the master bedroom, and 2 twins in the 2nd bedroom, and a queen sleeper sofa. Units sleep 6 depen ...
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From $189 per night (USD)Expedia
1Br Ski-in, Ski-Out at Okemo Mountain Lodge by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/ 1 bath non air-conditioned unit is located on the 1st floor of C building in the Mountain Lodge at Okem ...
From $189 per night (USD)Expedia
From $232 per night (USD)VRBO
Cozy private country setting - 15 miles from Woodstock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy home located in the rolling hills of scenic North Road Bethel, Vermont. Our house located on our 70-acre tree far ...
From $232 per night (USD)VRBO
From $192 per night (USD)Expedia
Mountain Lodge at Okemo-1Br Fireplace & Updated Kitchen by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
C305 is a non air-conditioned 1 bedroom/1 bath unit on the third floor of building C in the Mountain Lodge. This unit s ...
From $192 per night (USD)Expedia
From $190 per night (USD)VRBO
Mountain Lodge at Okemo-1Br Newly Renovated by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/ 1 bath non air-conditioned unit is located on the 1st floor of A building in the Mountain Lodge at Okem ...
From $190 per night (USD)VRBO
From $343 per night (USD)Expedia
Chester Home w\/ Views ~ 10 Mi to Okemo Mtn Resort!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunn ...
From $343 per night (USD)Expedia
From $250 per night (USD)VRBO
Historic Ski Lodge on 112-Acre Vineyard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**10% discount on 7 nights or more; 25% discount on 28 nights or more. Rental Amenities: Over 900 square feet of liv ...
From $250 per night (USD)VRBO
From $1026 per night (USD)Expedia
Luxury, private, peaceful home with Instagram worthy amenities!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
Leading Fields is situated on a dead end road on over 180 acres of private hilly land with trails for hiking, a meditati ...
From $1026 per night (USD)Expedia
From $562 per night (USD)VRBO
The Full Vermont Experience, minutes from Okemo: Transcend to the VT Life
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Ski Okemo? Check Sledding in the back yard? Check Ice Skating on your own pond? Check Snowshoeing in your own trails? Ch ...
From $562 per night (USD)VRBO
From $368 per night (USD)Expedia
Killington ski house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Recently remodeled and tastefully decorated lower level duplex located a short distance from Killington ski area (a twel ...
From $368 per night (USD)Expedia
From $471 per night (USD)VRBO
Sweet chalet with private hot tub, firepit, game room & minibar
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Sunny Mountainside Chalet Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $471 per night (USD)VRBO
From $656 per night (USD)Expedia
4bdrm Cottage central to year round fun w\/fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Adventure awaits at this peaceful centrally located 4 bedroom cottage. So whatever adventure you're looking for you will ...
From $656 per night (USD)Expedia
From $327 per night (USD)VRBO
Mountainside Luxury 2-Level Condo at Okemo. Ski-In\/Out.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The newest Okemo luxury mountainside ski-in, ski-out condo home with private ski locker and covered garage located in th ...
From $327 per night (USD)VRBO
From $335 per night (USD)Expedia
Oma Kieferts Kottage
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 8
Upon arrival at our charming home you will not need to drive again. The Kottage is located conveniently in the Village o ...
From $335 per night (USD)Expedia
From $334 per night (USD)VRBO
Beautiful craftsman-built home with natural wood and large windows in every room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located on a quiet road approximately one mile from the center of Brownsville, the property is a short drive from Woodst ...
From $334 per night (USD)VRBO
From $330 per night (USD)Expedia
Ski-in\/ski-out with the views! Solitude Village O 203
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Located at the top of Okemo Mountain in Solitude Village this condo has all the views! This true ski-in/ski-out 2 bedroo ...
From $330 per night (USD)Expedia
From $525 per night (USD)VRBO
Pet Friendly Timber Frame Home in a True Vermont Setting, Deck with New Hot Tub,
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
“Tuckered Out” 2,950 sq ft | Quiet Location | Spacious Yard | 5 Miles to Okemo This unique and modern timber frame hom ...
From $525 per night (USD)VRBO
From $1559 per night (USD)Expedia
Luxe Plymouth Chalet w\/ Indoor Pool & 3 Decks!
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 8
Discover one of Vermont's hidden gems when you book this Plymouth vacation rental, known as the 'Mountain Casa'. Featuri ...
From $1559 per night (USD)Expedia
From $1736 per night (USD)VRBO
Ski On\/Off ~ Beautiful Corner Unit ~ Well-Equipped And Perfect For Families!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
4 bedrooms, 3 and 1/2 baths. Beautifully decorated and furnished. Ski on/off townhouse located directly on the trail, ...
From $1736 per night (USD)VRBO
From $1480 per night (USD)Expedia
Ski In\/Ski Out Winterplace Condo Hot Tub and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Enjoy Okemo in luxury! This top floor loft space sits in the Okemo Winterplace complex in Building C with quick access t ...
From $1480 per night (USD)Expedia
From $420 per night (USD)VRBO
Country-style 3 bedroom, 2.5 bath condo in Quechee, Vermont
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated 3 bedroom 2 1/2 bath condo is located in the lovely village of Quechee, Vermont, located just a few ...
From $420 per night (USD)VRBO
From $396 per night (USD)Expedia
Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
A @Vermont_Escapes property - Escape to Vermont with us! Looking for the perfect blend of rustic charm and modern amen ...
From $396 per night (USD)Expedia
From $478 per night (USD)VRBO
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Lake Rescue Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $478 per night (USD)VRBO
From $612 per night (USD)VRBO
WINTER RENTAL - The Fairway House - Bright 3 Master BR
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
REACH OUT DIRECTLY FOR WINTER RENTAL. This property is located on the 13th fairway of the Quechee Club's Highland Golf C ...
From $612 per night (USD)VRBO
From $557 per night (USD)VRBO
The Okemo Love Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Inspiring playful creativity, heartfelt joy and long warm cuddles, The Okemo Love Lounge is a luxuriously curated, roma ...
From $557 per night (USD)VRBO
From $625 per night (USD)Expedia
Spacious 4 Bedroom\/3 Full Bathroom Family Friendly Townhouse in Quechee Lakes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Recently updated, Ideal, Air Conditioned family vacation Deere Run 2700 sq ft Townhouse in Quechee. 4 bedrooms (sleeps M ...
From $625 per night (USD)Expedia
From $1594 per night (USD)VRBO
Guest wing on a 400 private acre estate. Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Come and enjoy a stay in beautiful Vermont! The 30,000 square foot estate is now available for smaller groups. Enjoy al ...
From $1594 per night (USD)VRBO
From $313 per night (USD)Expedia
Ludlow Village Home with Pool Table - Walk to Restaurants
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The "Bear's Den" is conveniently located in Ludlow, VT across main street from Okemo Mountain School and Sports Odyssey ...
From $313 per night (USD)Expedia
From $544 per night (USD)VRBO
Post and Beam-Great for a Golf, Hiking Get-A-Way for multiple families
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 12
Beautiful Post and Beam architecture built in 2001, for families to make memories and enjoy beautiful Vermont in both su ...
From $544 per night (USD)VRBO
From $1616 per night (USD)Expedia
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 13
Skiing Theatre Food Beer Farm-Cheese Music and a Monastery! This is The Apple Knoll Inn at Weston, a Gertrude Rentals pr ...
From $1616 per night (USD)Expedia
From $1895 per night (USD)VRBO
Fireplace, Ski-Okemo, Apple Trees, Piano, Amazing Views, Firepit, Priory, Pool, Fields, Theatre!
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 17
Skiing Theatre Food Beer Farm-Cheese Music and a Monastery! This is The Apple Knoll Inn at Weston, a Gertrude Rentals pr ...
From $1895 per night (USD)VRBO
From $406 per night (USD)Expedia
\"Everything VT\" Getaway Centrally Located: Ski, Shop, Golf, Hike, Relax
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Cozy cape is centrally located near OKEMO, STRATTON, MAGIC, BROMLEY and KILLINGTON (Ludlow, Chester, and Weston, VT ...
From $406 per night (USD)Expedia
From $544 per night (USD)VRBO
Cozy Mountain View Chalet Near Okemo
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Our chalet architecture is perfect for appreciating all the natural beauty that the four seasons have to offer. Relax on ...
From $544 per night (USD)VRBO
From $362 per night (USD)Expedia
Ski In\/Out Studio at Okemo on Sachem Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Studio on the Sachem Trail at Okemo Mountain. This is a perfect location right on the Sachem Trail. The studio has a ful ...
From $362 per night (USD)Expedia
From $434 per night (USD)VRBO
MapleDreams - Cozy Ski Chalet w\/Hot Tub on Wooded Lot
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Escape the hustle and bustle of city living to the beautiful mountains of Vermont. Our home is nestled in a private wood ...
From $434 per night (USD)VRBO
From $351 per night (USD)Expedia
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gather with family and friends at our spacious home nestled in the Vermont woods. The Blue Moon Bungalow is your home a ...
From $351 per night (USD)Expedia
From $225 per night (USD)VRBO
Perfect Home Away near Town & Skiing w\/ Private Gas Grill, Large Deck
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Ludlow Hideout Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $225 per night (USD)VRBO
From $1251 per night (USD)Expedia
🌺Luxury Estate🌳 25 Gorgeous Acres of Privacy 🌳Family Getaway🌳Swimming Pond🌺
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
🌳 Gorgeous family home on a 25-acre estate in a picturesque natural setting. Escape the bustle of city life. 👨👩👦 ...
From $1251 per night (USD)Expedia
From $3048 per night (USD)VRBO
Ski in Ski out! top of the A quad chairlift
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
2 Bed 2 Bath. Pull out sleep sofa. Sleeps 4 Adults and 4 children. Located at the top of the chairlift with a balcon ...
From $3048 per night (USD)VRBO
From $100 per night (USD)Expedia
2 Room Studio 10 minutes from Killington
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cedarbrook is 6 miles to your favorite winter activities and Killington/Pico Mountains on the Killington access road. Fo ...
From $100 per night (USD)Expedia
From $555 per night (USD)VRBO
Renovated Farmhouse < 1 Mile to Okemo Mountain!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
Experience the beauty of Vermont from this chic and charming farmhouse with 4 bedrooms and 2 bathrooms. The vacation ren ...
From $555 per night (USD)VRBO
From $337 per night (USD)Expedia
Beautifully Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $337 per night (USD)Expedia
From $342 per night (USD)VRBO
Mountain Bliss: Hot Tub, Shuttle to Okemo, Quiet Ludlow Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
MRT-11088876 Enjoy a dreamy Vermont getaway in this updated 3-bedroom condo, just 2 minutes from the Clock Tower Base at ...
From $342 per night (USD)VRBO
From $302 per night (USD)Expedia
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Our year round cottage is located on Lake Pauline in Ludlow Vermont, with 900 ft of lake frontage! Just 1.5 miles from O ...
From $302 per night (USD)Expedia
From $263 per night (USD)VRBO
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Hi, we are using Homeaway/VRBO for renters who love the slopes, the outdoors and places like Okemo. We are always open ...
From $263 per night (USD)VRBO
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Newly Renovated Cottage, Hot Tub, Fire place, 5min to Killington Ski Gondola
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stone’s Throw Vermont is a charming 3bed 1.5 bath cottage with hot tub, fireplace, outdoor covered dinning space, and mo ...
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From $597 per night (USD)VRBO
Ski-in Ski-Out Okemo Oasis w\/ Deck + Mtn View!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Boasting easy access to the slopes and local hiking trails, this 3-bedroom, 2-bathroom vacation rental is great for fami ...
From $597 per night (USD)VRBO
From $410 per night (USD)Expedia
Ski Chalet with Hot Tub on Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Newly renovated in fall 2023, this 3-level, 1700+ sq. ft. ski chalet is just a 4 min drive to Okemo Mountain Resort and ...
From $410 per night (USD)Expedia
From $1162 per night (USD)VRBO
5 bedroom, 4 bath OKEMO Ski and LAKE Home with A\/C
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
A wonderful SKI and LAKE home with sandy bottom lake access and dock on LAKE RESCUE is the perfect place to call home du ...
From $1162 per night (USD)VRBO
From $570 per night (USD)Expedia
All Season, Open Plan Contemporary With Stunning Views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 6
This contemporary 4 bedroom house is situated on 80 rolling acres of woods and fields only 2 1/2 miles from Woodstock vi ...
From $570 per night (USD)Expedia
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Your Vermont Vacation Awaits!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Mountain View Retreat is truly your home away from home for "Your Vermont Vacation". This bright, airy and comfortable f ...
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From $366 per night (USD)Expedia
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the best of Ludlow when you stay in our fabulously decorated updated historic home built in 1835, located in th ...
From $366 per night (USD)Expedia
From $1391 per night (USD)VRBO
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 15
This property doubles as the award winning Woodbridge Inn. This listing is for a full home rental. There are 6 bedrooms, ...
From $1391 per night (USD)VRBO
From $525 per night (USD)Expedia
Amazing Custom Home on 40+ Acres
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Beautiful views and lots of privacy but still only 2 miles from town. 5 bedrooms and 6 bathrooms with exercise room, gam ...
From $525 per night (USD)Expedia
From $553 per night (USD)VRBO
Ski House with Lake Living - Little Chief's Retreat
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Our warm & spacious SKI and LAKE house has 5 bedrooms & 3 full baths and is only 3.5 miles from the base of Okemo Ski Re ...
From $553 per night (USD)VRBO
From $174 per night (USD)Expedia
Evergreen is a family friendly retreat located in Weston Vt.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This two family,fully furnished dwelling is comfortable,affordable and clean. The 2 BR upstairs[sleeps 4] rents in the w ...
From $174 per night (USD)Expedia
From $527 per night (USD)VRBO
Colonial-style solid-timber home in a quiet setting
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
'Sanctuary' describes this green-built, two-story solid-timber home perfectly. Peaceful, quiet, nestled on a wooded moun ...
From $527 per night (USD)VRBO
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Your Beautiful Victorian Getaway
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful New England Victorian, built in the 1890's, has 5 bedrooms and sits back on two private acres, situated j ...
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