Jamaica Rentals
From $351 per night (USD)VRBO
Two Bedroom Chalet, Charming, Quiet, River Front
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom Chalet, in a secluded area very romantic, facing a river, on the back road to Stratton Mountain.Only six mil ...
From $351 per night (USD)VRBO
From $710 per night (USD)VRBO
Beautiful Lakefront Home is located in Woods on Cole Pond. Near Stratton
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Unique newly renovated lake front home built around antique log cabin. Spectacular views of picturesque Cole Pond and ev ...
From $710 per night (USD)VRBO
From $599 per night (USD)VRBO
Newly Designed Chalet w/Views, Minutes to Stratton
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A perfect little getaway. This 3 bedroom, 2 bath chalet is less than 10 minutes from Stratton, and just a little further ...
From $599 per night (USD)VRBO
From $336 per night (USD)VRBO
Minutes from Stratton Mountain for Less Money
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This quiet and private chalet in the heart of the southern Vermont Green Mountains is just 3 miles from the Stratton Mou ...
From $336 per night (USD)VRBO
From $419 per night (USD)VRBO
Wishing Well Cabin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Great family space with open areas, 2 bathrooms and 3 bedrooms. Sleeps 8 plus a pull out couch for flexibility. Large b ...
From $419 per night (USD)VRBO
From $1187 per night (USD)VRBO
Western Mountain Lodge on River and Close to Stratton
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
All season mountain lodge with spectacular river views and close to Stratton. The house has five master suites all with ...
From $1187 per night (USD)VRBO
From $486 per night (USD)VRBO
Beautifully Maintained Custom Built Home on 7 acres - 3 mi from Stratton Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful custom built 3 Bedroom home with 2 full bathrooms, and a 2 car garage sits on 7 acres of very private lan ...
From $486 per night (USD)VRBO
From $557 per night (USD)VRBO
Enjoy Privacy and Beautiful views of Southern VT
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This 3200 sq.ft. custom home is surrounded by breathtaking views of Vermont & New Hampshire. The open layout and southea ...
From $557 per night (USD)VRBO
From $190 per night (USD)VRBO
Stratton Mountain On A Budget
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Perfect for a small family on a budget. Clean, updated and well furnished 2 bedroom apartment. Nice quiet area with ni ...
From $190 per night (USD)VRBO
From $610 per night (USD)Expedia
Cozy Vermont A-frame on a quiet private road, minutes from Stratton. Enjoy year-round adventure, then unwind in the hot tub under the stars. Spacious, stylish, and perfect for groups seeking both relaxation and outdoor fun.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this charming Vermont A-frame on a peaceful private road, just minutes from Stratton. In winter, hit the slope ...
From $610 per night (USD)Expedia
From $1493 per night (USD)VRBO
Forest Lodge - Near 6 Ski Resorts
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
This 4,300 sq ft retreat is nestled in the beautiful Green Mountains on 11 private forested acres, near 6 ski resorts. T ...
From $1493 per night (USD)VRBO
From $548 per night (USD)Expedia
Spacious Riverfront Home 7 Minutes to Stratton!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Operated as a bed and breakfast for years, this newly updated Farmhouse is spacious enough for multiple families to comf ...
From $548 per night (USD)Expedia
From $1247 per night (USD)VRBO
Renovated 5BR ski house minutes from Stratton, Bromley, Mt. Snow & Magic Mtn!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Floor to ceiling windows and an open floor plan in this newly renovated quintessential A-frame house located in a beauti ...
From $1247 per night (USD)VRBO
From $387 per night (USD)VRBO
Ski condo a mile from Stratton Mtn, shuttle bus and wood included. No Pets.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The master bedroom has a king bed, one bedroom has two twin bed and the third bedroom has a bunk bed. Linen and a fully ...
From $387 per night (USD)VRBO
From $2181 per night (USD)VRBO
Stratton Spectacular - March Ski Dates Available !
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 16
Spectacular Timberframe Home very near Stratton Mountain, Vermont. Extraordinary soaring ceilings with fieldstone firep ...
From $2181 per night (USD)VRBO
From $398 per night (USD)VRBO
All Season Paradise. Swim, Hike, Ski and More!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our Jamaica farmhouse, a place with space to live and breathe the beauty that Vermont has to offer. Simple, a ...
From $398 per night (USD)VRBO
From $325 per night (USD)VRBO
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Situated on 13 acres of forest with stunning views from indoors/out and flooded with light from the southern exposure. F ...
From $325 per night (USD)VRBO
From $968 per night (USD)VRBO
Farmhouse; <2 Miles to Stratton Mtn.; 4 bedrooms, 3 bathrooms; Winter Season opt
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
*Full Winter Season lease available at $32,000 + utilities Summers are also amazing here! Spacious Farmhouse, 8 minut ...
From $968 per night (USD)VRBO
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New Beautiful Modern Home - Weekly or Monthly - Isolated but Centrally Located
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Ten year old custom built modern home with the finest material. Set on 20 acres on the end of a long private road. Bu ...
Click For PricingVRBO
From $352 per night (USD)VRBO
Privacy in the Green Mountains! Hike, bike, swim and enjoy VT all summer.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Peaceful and private retreat! Wind up a long driveway to our home, located 2 miles to the Stratton access Road, 20 minut ...
From $352 per night (USD)VRBO
From $310 per night (USD)VRBO
Secluded, cozy and affordable! Beautiful setting in the woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This contemporary design, cozy cabin sits high up in the woods on 10 acres of Pikes Falls Road between Stratton and Jama ...
From $310 per night (USD)VRBO
From $719 per night (USD)VRBO
Perfect Family Retreat! Minutes From Stratton Mtn. Close To Mt. Snow & Bromley
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a Log Cabin that's anything but Rustic! Sleeps 10, 4 Bedrooms. King master suite, 2 Queen bedrooms and 2 sets of ...
From $719 per night (USD)VRBO
From $753 per night (USD)VRBO
One of a Kind Post and Beam Home on Private 100 acre Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This home is very unique and special to me. I am a builder from Martha's Vineyard and put my heart, soul and experience ...
From $753 per night (USD)VRBO
From $1878 per night (USD)VRBO
1865 Vermont Farmhouse with Luxury Updates
- Bedrooms:
- 4
- 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 $1878 per night (USD)VRBO
From $293 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 $293 per night (USD)VRBO
From $730 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 $730 per night (USD)VRBO
From $519 per night (USD)VRBO
Stratton; 6 min. King beds. Pool Table. Wood Stove. Dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 14
A FEW HIGHLIGHTS: •6 min drive to Stratton!! •3 min walk to Pikes Falls •27 min to Manchester Center •5 bedrooms •2 bath ...
From $519 per night (USD)VRBO
From $1393 per night (USD)VRBO
Amazing Family Luxury Home - Near Stratton Mountain - Seasonal Rental options!!!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Wonderful Luxury Family Home in Vermont. Close to everything including Stratton Mountain. Private home with gourmet Eat ...
From $1393 per night (USD)VRBO
From $901 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 $901 per night (USD)VRBO
From $450 per night (USD)VRBO
Cozy Riverfront Home in beautiful Jamaica
- Bedrooms:
- 1
- 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 $450 per night (USD)VRBO
From $204 per night (USD)VRBO
Chalet-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Authentic mountain chalet surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-min ...
From $204 per night (USD)VRBO
From $145 per night (USD)Expedia
Cabin-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-m ...
From $145 per night (USD)Expedia
From $206 per night (USD)VRBO
Cottage-Swim-Brook on Property-Views-Firepit-Woodstove-7 min to Stratton-Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7 ...
From $206 per night (USD)VRBO
From $581 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 $581 per night (USD)VRBO
From $2678 per night (USD)VRBO
VT Family Oasis - 10 Mins to Stratton
- Bedrooms:
- 5
- 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 $2678 per night (USD)VRBO
From $1342 per night (USD)Expedia
Secluded Luxury Stratton Lodge | Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The space KEY FEATURES: ☀️ Panoramic mountain views from every room ☀️ Resort-style backyard: Seasonally heated pool, h ...
From $1342 per night (USD)Expedia
From $1093 per night (USD)VRBO
Stratton MTN Retreat~4BR/10Bed Ski House w/2 MSTRS-Jacuzzi-Game RM-3mins to MTN!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Great Escape - Spacious Ski House at Stratton Mountain! Come make memories in our warm and inviting 4-bedroom (2 Master ...
From $1093 per night (USD)VRBO
From $130 per night (USD)Expedia
Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unique glamping cabin across from babbling brook. Non-piped water system includes foot pumps for faucets, hand pump for ...
From $130 per night (USD)Expedia
From $287 per night (USD)VRBO
Cozy Cottage at Cold Moon Farm!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Just minutes to Stratton Mountain, and within 30 minutes of four other mountains, this cozy cottage on Cold Moon Farm wi ...
From $287 per night (USD)VRBO
From $591 per night (USD)Expedia
1830 Greek Revival Farmhouse + saltwater hot tub near Stratton Mountain
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Escape the crowds and relax in the solitude of the Green Mountains of Vermont. Being right next to Stratton and close to ...
From $591 per night (USD)Expedia
From $868 per night (USD)VRBO
Cold Moon Farm!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Just minutes to Stratton Mountain, and within 30 minutes of four other mountains, this huge house on Cold Moon Farm will ...
From $868 per night (USD)VRBO
From $606 per night (USD)Expedia
Vermont A-Frame | Sleeps10, Hot Tub, Sauna, EV, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Your mountain summer escape. Nordic A-frame in the forests of Jamaica, Vermont. Sleeps 10 across four bedrooms, with flo ...
From $606 per night (USD)Expedia
From $968 per night (USD)VRBO
Beaver Pond Compound- 3 Homes On 1 Property! Ski, Golf, Hike-10 mins to Stratton
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Beaver Pond Compound-Southern upscale one-of-a-kind VT retreat! THREE HOMES • ONE UNFORGETTABLE STAY The p ...
From $968 per night (USD)VRBO
From $520 per night (USD)Expedia
15 minutes to Stratton
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the picturesque town of Jamaica, Vermont, Drop Point Cabin offers a serene retreat from the chaos of urban li ...
From $520 per night (USD)Expedia
From $450 per night (USD)VRBO
Jamaica Modern Aframe
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Stay comfortably in Jamaica at this 2-bedroom mod A Frame house. The space has been thoughtfully designed with mid centu ...
From $450 per night (USD)VRBO
From $957 per night (USD)Expedia
Stratton; 4 min. Renovated, games, fireplace!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The perfect place to unwind for the week/weekend! With a covered carpark, a kitchen to die for, games for days and an am ...
From $957 per night (USD)Expedia
From $456 per night (USD)VRBO
Historic Ski House, Walk to Town, Short Drive to Slopes
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
- Vermont Farm House with two comfortable, cozy, living rooms - 4 Bedrooms (all with Queen beds with fresh linens) + Q ...
From $456 per night (USD)VRBO
From $810 per night (USD)Expedia
Luxe 5,000 Sq Ft Retreat: 5 Mi to Stratton Resort
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
All-Ages Entertainment + Gaming Lounge | Dedicated Workspace | Sauna Craving adventure, indulgent comforts, and space t ...
From $810 per night (USD)Expedia
From $792 per night (USD)VRBO
4 Mi to Stratton Mountain Resort! Cabin w/ Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
7 Mi to Jamaica State Park | Bring Your Pup | Wildlife Viewing On-Site | All-Season Escape Find your rhythm in the Gree ...
From $792 per night (USD)VRBO
From $281 per night (USD)Expedia
2-story mountain condo w/ private deck, close to resort, jetted tub, w/d, wifi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your perfect getaway in Jamaica, Vermont! This charming dog-friendly condo offers a cozy retreat for families ...
From $281 per night (USD)Expedia
From $252 per night (USD)VRBO
Potter's Place | House in Jamaica with mountain views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bordered by Jamaica State Park, Potter's Place offers a charming and private retreat for outdoor lovers and adventure en ...
From $252 per night (USD)VRBO
From $391 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
Perched in the picturesque town of Jamaica, VT, this stunning 3-bedroom, 3-bathroom private house offers breathtaking vi ...
From $391 per night (USD)Expedia
From $558 per night (USD)VRBO
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Escape to this spacious and expansive five-bedroom house nestled in a serene wooded setting in Jamaica, VT and just 15-m ...
From $558 per night (USD)VRBO
From $459 per night (USD)Expedia
Peaceful mountain home near skiing, hiking, mtn biking & more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape to the serene beauty of Jamaica, Vermont, where adventure and relaxation await in this charming house. Perfectly ...
From $459 per night (USD)Expedia
From $1894 per night (USD)VRBO
Delightful updated farmhouse with original features, patio, and & W/D
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
Ready to spend your winter in a historic home near the the Stratton Mountain ski area? An enchanting stay awaits at this ...
From $1894 per night (USD)VRBO
From $633 per night (USD)Expedia
Cozy A-Frame Cabin with Hot Tub & Sauna near Stratton Mountain, Vermont
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
A-Frame | Hot Tub Sauna EV | Stratton 🌲 13 min to Stratton 🎿 <30 min to Magic, Bromley, Okemo & Mt Snow | ~1 hr ...
From $633 per night (USD)Expedia
From $611 per night (USD)VRBO
The Post Haus: one-of-a-kind modern VT experience
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. Th ...
From $611 per night (USD)VRBO
From $1208 per night (USD)Expedia
West Hill Lodge | 6-BR Estate Near Stratton
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Set on 27 private acres in Jamaica, Vermont, West Hill Lodge is a secluded mountain retreat just 8 minutes fro ...
From $1208 per night (USD)Expedia
From $438 per night (USD)VRBO
Jamaica Chalet: 3 Kings + Arcade | Starlink
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this modern chalet in Jamaica! This home is designed for comfort. It is rare to find a rental with THREE King ...
From $438 per night (USD)VRBO
From $557 per night (USD)Expedia
Stratton Log Lodge: Hot Tub + Privacy | Sleeps 13
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Welcome to the Stratton Log Lodge! This place is special. it’s a true log cabin perched at the top of a hill with a `Gra ...
From $557 per night (USD)Expedia
From $481 per night (USD)VRBO
Peaceful 3-bedroom+loft house perfect for relaxing stays close to Stratton
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Stratton Mountain Gem — Summer Weekly Rental 3 Bedrooms + Loft • 2 Bathrooms • Sleeps 10 • Private, Sprawli ...
From $481 per night (USD)VRBO