Jamaica Rentals
From $585 per night (USD)VRBO
Wardsboro Family Home: 7 Mi to Mount Snow!
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 12
Whisk away on an all-season immersive getaway to this 5-bedroom, 2.5-bathroom vacation rental in Wardsboro. Perfect for ...
From $585 per night (USD)VRBO
From $149 per night (USD)Expedia
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Alpine Outlook Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $149 per night (USD)Expedia
From $1695 per night (USD)VRBO
1865 Vermont Farmhouse with Luxury Updates
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 13
Genuine 1865 Vermont VT Farmhouse with hand-hewn wood beams in rural setting. 3 floors and 3,000 sq ft. Totally update ...
From $1695 per night (USD)VRBO
From $584 per night (USD)VRBO
Bluebird - Large cottage for all season getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
House set in a natural setting < 5min min drive from Stratton parking. You will feel the true nature Vermont has to offe ...
From $584 per night (USD)VRBO
From $782 per night (USD)VRBO
Cool Runnings Cabin: Rustic + Spacious w. Fireplace + FirePit 12 min to Stratton
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
Experience Vermont's charm in every season @coolrunningscabin, only 12 minutes to Stratton! Explore summer hiking and fa ...
From $782 per night (USD)VRBO
From $541 per night (USD)Expedia
This house is a 2 bedroom(s), 1 bathrooms, located in Jamaica, VT.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-en ...
From $541 per night (USD)Expedia
From $346 per night (USD)VRBO
3 bed 2 bath 10 minutes to my snow 20 minutes to stratton
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Recently updated 3 bed 2 bathroom close to great skiing or just relaxing in the backyard or on the deck. Comfortable wid ...
From $346 per night (USD)VRBO
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*Ski Family Lodge* Renovated Kitchen & 4 bed
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Wake up in the morning and make coffee for the family in the newly renovated kitchen and drive just 10 minutes to Stratt ...
Click For PricingExpedia
From $481 per night (USD)VRBO
A Secluded Haven for Your Family Vacation!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Escape to Vermont's Hidden Gem: Drop Point Cabin in Jamaica Nestled in the picturesque town of Jamaica, Vermont, Drop P ...
From $481 per night (USD)VRBO
From $495 per night (USD)Expedia
Jamaica Vacation Home w\/ Deck: 8 Mi to Skiing!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The quintessential Vermont retreat awaits at this Jamaica vacation rental near ski resorts! This 4-bedroom, 3-bath home ...
From $495 per night (USD)Expedia
From $762 per night (USD)VRBO
Stratton + Mt. Snow family getaway with Hot Tub, Fire Pit, Game Room, and AC!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
*NEW Midea Air Conditioning window units in living room/basement for summer 2024!* Wel ...
From $762 per night (USD)VRBO
From $361 per night (USD)Expedia
Potter's Place | House in Jamaica with mountain views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Potter's Place Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $361 per night (USD)Expedia
From $1030 per night (USD)VRBO
Sweeping Views | Hot Tub | Two Living Areas | 5BR
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
This stunning 5-bedroom/3.5-bath home is located off the Stratton Mountain access road in Winhall, Vermont. It’s a short ...
From $1030 per night (USD)VRBO
From $886 per night (USD)Expedia
Plenty of Room For Everyone! - 5 Minutes to Stratton
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 17
Our large 4 bed, 4 bath home has everything you’re looking for in a VT vacation rental. Come home to hang out in the Hot ...
From $886 per night (USD)Expedia
From $512 per night (USD)VRBO
Summit View | Mtn\/ski-view townhouse with heated pool, wood stove, grill, W\/D
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summit View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $512 per night (USD)VRBO
From $597 per night (USD)VRBO
Newly renovated family friendly Chalet minutes to skiing!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Wanderlust. A unique Gambrel Style Chalet tucked away in the wooded neighborhood of Snow Mountain Farms. Enjo ...
From $597 per night (USD)VRBO
From $790 per night (USD)VRBO
Pet Friendly home with a barrel sauna
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Snowdrift- your next ultimate destination for a relaxing and fulfilling vacation experience! This beautiful a ...
From $790 per night (USD)VRBO
From $825 per night (USD)Expedia
MtSnow\/Stratton Chalet w\/Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Welcome to Our Vermont Retreat! Nestled in picturesque Vermont, our cozy cabin is your year-round getaway. Privately loc ...
From $825 per night (USD)Expedia
From $333 per night (USD)VRBO
Plush Vermont ski + summer chalet in serene Jamaica Vermont!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
When you stumble on Jamaica Vermont, during the crisp sun-filled summer swimming season, you'll find yourself promptly m ...
From $333 per night (USD)VRBO
From $570 per night (USD)Expedia
Stratton Mountain Escape w Hot Tub|Deck|Projector
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
4 different ski resorts to choose! Experience Vermont charm at my beautiful mountain home. Soaring ceilings and huge win ...
From $570 per night (USD)Expedia
From $904 per night (USD)VRBO
Cozy ski retreat 7 minutes from Stratton's Sunbowl!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Desired location for skiers (down hill mountain bikers, golfers and outdoor enthusiasts alike). Enjoy your stay with fam ...
From $904 per night (USD)VRBO
From $1808 per night (USD)VRBO
Updated Ski townhome with shuttle service to Stratton Mountain! 3BD\/3BA + loft
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated and spacious 3 Bedroom plus loft Piper Ridge Condo with Winter shuttle service to Stratton Mountai ...
From $1808 per night (USD)VRBO
From $720 per night (USD)VRBO
5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
Lovely private home with tons of natural light and plenty of space to spread out! With bedrooms and bathrooms but upstai ...
From $720 per night (USD)VRBO
From $1323 per night (USD)Expedia
Family Friendly Stratton Home for All Seasons, 7 min to ski mountain
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Come enjoy our year round mountain home! Upon entering, you will be greeted by a bright, open living concept with stunni ...
From $1323 per night (USD)Expedia
From $1973 per night (USD)VRBO
Paradise Vermont, Nature Chalet With Indoor Hot Tub\n
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from th ...
From $1973 per night (USD)VRBO
From $1161 per night (USD)VRBO
Stratton Mountain Home\n
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Sleeps 11, 4 bed, 3.5 bath. 11 min to Stratton, 15 to Bromley. Perfect for 2 families. Kick back and relax in this cal ...
From $1161 per night (USD)VRBO
From $498 per night (USD)VRBO
Near Magic Mtn & Stratton Mtn ski resorts, outdoor fun and great leaf peeping.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly Remodeled! The Snowflake Hideaway is a great house for all seasons. Located off Rt 30 in Southern Vermont, it is c ...
From $498 per night (USD)VRBO
From $1593 per night (USD)Expedia
Charming home with hot tub, game room, fireplace, & ski lodge parking
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 14
Ski You Later Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1593 per night (USD)Expedia
From $1057 per night (USD)VRBO
Amazing Family Luxury Home - Near Stratton Mountain - Seasonal Rental options!!!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
Wonderful Luxury Family Home in Vermont. Close to everything including Stratton Mountain. Private home with gourmet Eat ...
From $1057 per night (USD)VRBO
From $916 per night (USD)VRBO
STRATTON MOUNTAIN HOUSE , GOLF, SWIM, HIKE, DINING, SKI, SNOWBOARD & SHUTTLE.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Brand new four bedroom ski house. After a long day of skiing, boarding or hiking relax in our cozy home watching snow fa ...
From $916 per night (USD)VRBO
From $904 per night (USD)VRBO
5 miles to Stratton! Family-friendly with game room and deck!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy our centrally located 3 bedroom chalet, perfect for Vermont enthusiasts! We are nestled within the highly sought ...
From $904 per night (USD)VRBO
From $745 per night (USD)VRBO
Charming Stratton 4BR Chalet - a cozy ski retreat and family getaway!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ski the day and relax with the whole family at this peaceful Vermont retreat. Located 5 minutes from Stratton Mountain R ...
From $745 per night (USD)VRBO
From $632 per night (USD)VRBO
Cozy Country Chalet . Family friendly. Close to skiing, hiking, kayaking, golf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Great family fun awaits you at his owner-built, bright, contemporary country chalet, within minutes of four ski areas. ...
From $632 per night (USD)VRBO
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2-story mountain condo with fireplace, private deck, WFH setup, & jetted tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A Very Vermont Vacation Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
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From $191 per night (USD)VRBO
4BR Chalet Between Mt. Snow & Stratton, Sleeps 10, Fireplace, Clubhouse w\/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to The Last Run ... a warm, private, family-friendly ski chalet perfectly situated in the cozy Southern Vermont ...
From $191 per night (USD)VRBO
From $2617 per night (USD)Expedia
Shaw Chalet a private resort
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This very modern cozy house has spectacular views of six mountains. Located at the top of Stratton overlooks the valley ...
From $2617 per night (USD)Expedia
From $804 per night (USD)VRBO
Room for the whole family!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to The Bears Den, the perfect mountain retreat just 5 minutes away from Stratton mountain resort! With 4 bedroom ...
From $804 per night (USD)VRBO
From $427 per night (USD)VRBO
Modern and Cozy retreat minutes from Stratton mt.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our three bedroom chalet features SMART home technology {use Google tip control ligts,fan,music). House has an open con ...
From $427 per night (USD)VRBO
From $419 per night (USD)VRBO
This house is a 4 bedroom(s), 2 bathrooms, located in Windham, VT.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to The Knole House! A one-of-kind, cozy Vermont farmhouse central to several Vermont ski resorts and quaint, pic ...
From $419 per night (USD)VRBO
From $445 per night (USD)Expedia
3 minutes to Stratton. Cozy 1 bedroom\/ 1 bath apartment for 4. Private entrance
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Private entrance to apartment with parking in driveway directly next to apartment door. Cozy apartment has 1 bedroom wit ...
From $445 per night (USD)Expedia
From $537 per night (USD)VRBO
Secluded A-frame home near Mt. Snow and Stratton Ski with wood stove & streaming
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Enchanted Pine Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $537 per night (USD)VRBO
From $381 per night (USD)Expedia
Countryside, mountain-view house near eagle's nest with patios - dog-friendly
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Electric Mountain Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $381 per night (USD)Expedia
From $909 per night (USD)VRBO
Modern Cottage between Stratton and Mount Snow
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to this inviting, newly remodeled, charming chalet conveniently located between Mount Snow and Stratton. It offer ...
From $909 per night (USD)VRBO
From $370 per night (USD)Expedia
Cozy Home on 10 Acres: 'Yellowstone in Vermont'
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 6
Gather your friends and family for a true nature retreat at ‘Yellowstone in Vermont,’ a spacious 4-bedroom, 2-bath vacat ...
From $370 per night (USD)Expedia
From $658 per night (USD)VRBO
Wander In | Close to Mount Snow & Stratton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Discover the best of Southern Vermont from this newly built home completed in 2024. Nestled in a peaceful woode ...
From $658 per night (USD)VRBO
From $363 per night (USD)VRBO
Cozy Riverfront Home in beautiful Jamaica
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Surrounded by tall pines and mountains, with the tranquil sound of the West River outside, here you can escape into natu ...
From $363 per night (USD)VRBO
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Vermont Retreat: Enjoy Hot Tub, Fireplace, Game Room, & More Near Stratton
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Stratton Mountain Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
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From $860 per night (USD)Expedia
Cozy Retreat with Hot Tub Right Off the Master Bedroom!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this secluded mountain haven, nestled in the heart of Stratton Mountain, Vermont. This spacious home comfortab ...
From $860 per night (USD)Expedia
From $458 per night (USD)VRBO
Mountain View Home Minutes From Stratton
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Your home away from home in Winhall with Stratton Mountain Views . This charming house offers 4 bedrooms with a mix of 1 ...
From $458 per night (USD)VRBO
From $375 per night (USD)VRBO
Charming riverside cabin in Jamaica, VT with hot tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This charming cabin in Jamaica, VT is perfect for your getaway. With 4 bedrooms, it's ideal for families or a group of f ...
From $375 per night (USD)VRBO
From $630 per night (USD)VRBO
Spacious dog-friendly home, fireplace, firepit, sauna, jacuzzi, decks, wifi
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Secluded Mountain House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $630 per night (USD)VRBO
From $2212 per night (USD)VRBO
VT Family Oasis - 10 Mins to Stratton
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This 5-bedroom, 5 bath luxury home less than 5 miles from the base of Stratton Mtn. With it's expansive great room welco ...
From $2212 per night (USD)VRBO
From $545 per night (USD)VRBO
Secluded Mountain Retreat: Stunning Views, 7 mins to Stratton lift, Firepit
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Upgraded 5 bedrooms, 3.5 baths house on a premium lot. Majestic mountain views in the heart of ski country! Just 3.5 mil ...
From $545 per night (USD)VRBO
From $896 per night (USD)VRBO
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Located just minutes away from Sun Bowl and Stratton Base area don’t miss this opportunity to rent this newly updated si ...
From $896 per night (USD)VRBO
From $581 per night (USD)VRBO
Three Bears Log Cabin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY | Close to Ski Slopes | Community Indoor Pool (Open Year-Round) | Community Pickleball & Tennis Courts B ...
From $581 per night (USD)VRBO
From $980 per night (USD)Expedia
Townhouse w\/ hot tub, fireplace, pool, sauna, gym, tennis, shuttle, wifi, w\/d
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Piper Ridge B15 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $980 per night (USD)Expedia
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Spacious, updated 4-bedroom condo with shuttle to Stratton
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This spacious home is a great spot for a group looking to ski or explore the area. Compete with an updated kitchen and d ...
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From $644 per night (USD)Expedia
Cozy house w\/ mtn views, sauna, fire pit, BBQ, fireplace, w\/d, deck, wifi, EV
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Fawn Ledge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $644 per night (USD)Expedia
From $2890 per night (USD)VRBO
Vibes & Views In Stratton
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Indulge in breathtaking vistas of Stratton and Bromley Mountain from this expansive Adirondack-style residence. Designed ...
From $2890 per night (USD)VRBO
From $1300 per night (USD)Expedia
Charming 4-bedroom, 3 bath ski house 8 minutes from Stratton Mountain.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Your cozy getaway awaits in Stratton Mountain / Winhall at this fabulous house. With 4 bedrooms including a king, queen, ...
From $1300 per night (USD)Expedia
From $707 per night (USD)VRBO
Beautiful dog-friendly house w\/ fireplace, firepit, bbq, deck, patio, w\/d, wifi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Green Mountain Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $707 per night (USD)VRBO
From $674 per night (USD)Expedia
Beautiful house w\/ mountain views, hot tub, fireplace, air hockey, bbq, a\/c
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beauchamp Hill Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $674 per night (USD)Expedia