Windsor Area Rentals
From $377 per night (USD)VRBO
Log cabin near Okemo \/ Ludlow on 25 acres borders state forest w\/trails nearby
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful hilltop cabin on 25 private acres bordering the William's River State Forest. Relax at this private retreat o ...
From $377 per night (USD)VRBO
From $804 per night (USD)VRBO
\"Whispering Pines\" Ski House in the heart of the Green Mountains
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Fantastic 5BR ski house located in private neighborhood in prime location in the heart of the Green Mountains. Enjoy tru ...
From $804 per night (USD)VRBO
From $556 per night (USD)VRBO
Amherst Lake Views - Minutes To Okemo And Killington - 5 Bedrooms
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Relax and enjoy stunning views of beautiful Amherst Lake and surrounding mountains from the house and deck. Located just ...
From $556 per night (USD)VRBO
From $357 per night (USD)VRBO
Beautiful Mountain Getaway for Skiing
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Mountain getaway with beautiful views , minutes from Okemo & Killington . Private home at Hawk Resort 8 mi to Okemo and ...
From $357 per night (USD)VRBO
From $266 per night (USD)VRBO
Charming Historic Home in Vermont
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunshine, flowers, Farmers' Markets, hikes and starry nights are here. Scents fill the air and the birds are calling. S ...
From $266 per night (USD)VRBO
From $853 per night (USD)Expedia
Resort on a Farm
- Bedrooms:
- 4
- Bathrooms:
- 0
- Sleeps:
- 0
Gorgeous estate on a 23 acre farm with resort amenities available for monthly occupancy. Located just a few minutes from ...
From $853 per night (USD)Expedia
From $233 per night (USD)VRBO
Okemo Base Slopeside Ski-in\/ Ski-Out Condo - FULL WINTER SEASON Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Available for Full Winter Season Rental only 12/1/24 - 04/15/25. Please message host for winter season so property can ...
From $233 per night (USD)VRBO
From $1632 per night (USD)VRBO
Gorgeous Slopeside - Winterplace\/Okemo Vail Resorts - Holiday weeks available!
- 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 $1632 per night (USD)VRBO
From $545 per night (USD)VRBO
Kettle Brook 2 BR & 2 BA ski in\/out condo on Okemo Mountain
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Last minute listing: Friday 1/26 is available but cannot be booked via vrbo so send a message if interested in staying F ...
From $545 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $508 per night (USD)VRBO
Long Range Mountain Views in West Windsor
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to Thistle Hill, a beautiful private property on 17 acres. Home is located 12 miles from Woodstock in the heart ...
From $508 per night (USD)VRBO
From $1131 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 $1131 per night (USD)VRBO
From $766 per night (USD)VRBO
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 $766 per night (USD)VRBO
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 $919 per night (USD)VRBO
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 $919 per night (USD)VRBO
From $614 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 $614 per night (USD)VRBO
From $1057 per night (USD)VRBO
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 $1057 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 $309 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 $309 per night (USD)VRBO
From $616 per night (USD)VRBO
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)VRBO
From $600 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 $600 per night (USD)VRBO
From $329 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 $329 per night (USD)Expedia
From $1581 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 $1581 per night (USD)VRBO
Click For PricingExpedia
Luxury Alpine Retreat: A Premier Lodge Experience Near Dartmouth & Woodstock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the epitome of luxury and adventure at our exclusive summer and ski lodge, nestled within a serene landscape th ...
Click For PricingExpedia
From $587 per night (USD)VRBO
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 $587 per night (USD)VRBO
From $168 per night (USD)Expedia
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)Expedia
From $437 per night (USD)VRBO
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 $437 per night (USD)VRBO
From $519 per night (USD)Expedia
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 $519 per night (USD)Expedia
From $224 per night (USD)VRBO
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 $224 per night (USD)VRBO
From $224 per night (USD)Expedia
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 $224 per night (USD)Expedia
From $224 per night (USD)VRBO
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 $224 per night (USD)VRBO
From $224 per night (USD)Expedia
Deluxe one bedroom suite located on 2nd floor with outdoor heated pool 21921
- 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 $224 per night (USD)Expedia
From $627 per night (USD)VRBO
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 $627 per night (USD)VRBO
From $242 per night (USD)Expedia
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 $242 per night (USD)Expedia
From $213 per night (USD)VRBO
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 $213 per night (USD)VRBO
From $328 per night (USD)Expedia
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 $328 per night (USD)Expedia
From $443 per night (USD)VRBO
Modern Home Close to Okemo w\/Private Hot Tub, Pool Table, and Free WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 2
The Foxhole Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $443 per night (USD)VRBO
From $589 per night (USD)Expedia
Ski Mountain View Estate
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We are new on VRBO If you would like to see reviews to help with decision making you can check out us out on other short ...
From $589 per night (USD)Expedia
From $148 per night (USD)VRBO
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 $148 per night (USD)VRBO
From $793 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 $793 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 $884 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 $884 per night (USD)Expedia
From $636 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 $636 per night (USD)VRBO
From $565 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 $565 per night (USD)Expedia
From $128 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 $128 per night (USD)VRBO
From $847 per night (USD)VRBO
On Silver Lake & Close to Ski Areas with Sauna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Perched on the edge of pristine Silver Lake, my country home sits on a large rolling lot overlooking the lake enjoyed by ...
From $847 per night (USD)VRBO
From $866 per night (USD)VRBO
Modern & Updated Winterplace 3Br- Sleeps 12 by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
New protocols include the following: This beautiful mountainside, located a short walk from the top of the A+B Base Qu ...
From $866 per night (USD)VRBO
From $591 per night (USD)Expedia
2Br Solitude -Ski-in, Ski-out Access to Promenade Trail by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
During check-in, we may ask for a valid credit card for incidentals or room charges. Please let us know in advance if th ...
From $591 per night (USD)Expedia
From $571 per night (USD)VRBO
1Br Ski-in, Ski-out With King Bed- Okemo Mtn Lodge by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
During check-in, we may ask for a valid credit card for incidentals or room charges. Please let us know in advance if th ...
From $571 per night (USD)VRBO
From $562 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 $562 per night (USD)Expedia
Click For PricingVRBO
Spacious Winterplace 2 Br Condo- Okemo by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 depend ...
Click For PricingVRBO
From $348 per night (USD)Expedia
1Br Ski-in, Ski-Out at Okemo Mountain Lodge by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
During check-in, we may ask for a valid credit card for incidentals or room charges. Please let us know in advance if th ...
From $348 per night (USD)Expedia
From $220 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 $220 per night (USD)VRBO
From $448 per night (USD)Expedia
Mountain Lodge at Okemo-1Br Fireplace & Updated Kitchen by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
During check-in, we may ask for a valid credit card for incidentals or room charges. Please let us know in advance if th ...
From $448 per night (USD)Expedia
From $508 per night (USD)VRBO
Mountain Lodge at Okemo-1Br Newly Renovated by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
During check-in, we may ask for a valid credit card for incidentals or room charges. Please let us know in advance if th ...
From $508 per night (USD)VRBO
From $567 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 $567 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)VRBO
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)VRBO
From $595 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 $595 per night (USD)VRBO
From $1476 per night (USD)VRBO
Cozy ski in\/ski out condo in Okemo’s Trailside Village
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Christmas and New Years in Vermont! Stay at this cozy and rustic condo on Okemo Mountain! Come enjoy this newly renova ...
From $1476 per night (USD)VRBO
From $496 per night (USD)VRBO
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 $496 per night (USD)VRBO
From $417 per night (USD)Expedia
Huge Home with Private Pond - Ideal Remote Getaway for Family, Friends & More
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
HUGE 4 BD 3.5 BA HOME FOR LONG TERM STAYS & FAMILY GATHERINGS. 2 TV ROOMS, WORKING FIREPLACES, WIFI, INCREDIBLE VIEWS, S ...
From $417 per night (USD)Expedia
From $717 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 $717 per night (USD)VRBO
From $721 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 $721 per night (USD)Expedia
From $514 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 $514 per night (USD)VRBO
From $392 per night (USD)VRBO
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 $392 per night (USD)VRBO
From $343 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 $343 per night (USD)VRBO
From $358 per night (USD)VRBO
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 $358 per night (USD)VRBO
From $711 per night (USD)VRBO
Pet Friendly Timber Frame Home in a True Vermont Setting with New Hot Tub, Deck
- 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 $711 per night (USD)VRBO
From $1253 per night (USD)Expedia
Luxe Plymouth Chalet w\/ Indoor Pool & 3 Decks!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 8
Discover one of Vermont's hidden gems when you book this Plymouth vacation rental, known as the 'Mountain Casa'. Featuri ...
From $1253 per night (USD)Expedia
From $1616 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 $1616 per night (USD)VRBO
Click For PricingExpedia
Ski In\/Ski Out 2BR + Loft Winterplace Condo
- 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 ...
Click For PricingExpedia
From $226 per night (USD)VRBO
Log cabin located in a quiet hollow in central VT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our cabin has a good sized covered porch to enjoy the outdoors yet be protected from the weather. It also has a great op ...
From $226 per night (USD)VRBO
From $420 per night (USD)Expedia
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)Expedia
From $989 per night (USD)VRBO
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 $989 per night (USD)VRBO
From $704 per night (USD)Expedia
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 $704 per night (USD)Expedia
From $606 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 $606 per night (USD)VRBO
From $420 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 $420 per night (USD)VRBO
From $618 per night (USD)VRBO
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 $618 per night (USD)VRBO
From $1922 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 $1922 per night (USD)VRBO
From $626 per night (USD)VRBO
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 $626 per night (USD)VRBO
From $579 per night (USD)VRBO
Post and Beam-Great for a Golf Get-A-Way for multiple families\/couples
- 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 $579 per night (USD)VRBO
From $1258 per night (USD)VRBO
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 $1258 per night (USD)VRBO
From $1543 per night (USD)Expedia
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 $1543 per night (USD)Expedia
From $369 per night (USD)VRBO
\"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 $369 per night (USD)VRBO
From $532 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 $532 per night (USD)VRBO
From $399 per night (USD)VRBO
Ski In\/Out Studio at Okemo on Sachem Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Studio on the Sachem Trail at Okemo Mountain. This two-family home has a studio on the first floor. There will be anothe ...
From $399 per night (USD)VRBO
From $574 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 $574 per night (USD)VRBO
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Spacious home with WiFi, Private Pool, & Hot Tub - Near Slopes & Lake
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Ludlow Landing Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
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From $532 per night (USD)Expedia
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 $532 per night (USD)Expedia
From $424 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 $424 per night (USD)VRBO
From $2113 per night (USD)VRBO
🌺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 $2113 per night (USD)VRBO
From $3134 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 $3134 per night (USD)VRBO
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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 ...
Click For PricingExpedia
From $594 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 $594 per night (USD)VRBO
From $435 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 $435 per night (USD)Expedia
From $447 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 $447 per night (USD)VRBO
From $384 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 $384 per night (USD)Expedia
From $337 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 $337 per night (USD)VRBO
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Newly Renovated Cottage with hot tub, fire place, and 5min to Killington 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 ...
Click For PricingExpedia