Jamaica Rentals
From $408 per night (USD)VRBO
Near Magic Mtn &Stratton Mtn ski resorts, outdoor is fun and great leaf peeping.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly Remodeled! The Snowflake Hideaway is a great house for all seasons. Located off Rt 30 in Southern Vermont, it is c ...
From $408 per night (USD)VRBO
From $1020 per night (USD)Expedia
Charming home with hot tub, game room, fireplace, & ski lodge parking
- Bedrooms:
- 7
- 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 $1020 per night (USD)Expedia
From $1122 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 $1122 per night (USD)VRBO
From $652 per night (USD)VRBO
Charming Stratton 4BR Chalet - a cozy ski retreat and family getaway!
- Bedrooms:
- 2
- 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 $652 per night (USD)VRBO
From $622 per night (USD)VRBO
Family Friendly Cozy Country Chalet -- 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 $622 per night (USD)VRBO
From $2233 per night (USD)Expedia
Luxury Mountain Chalet, Hot Tub, Fire Pit & Panoramic Stratton Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to Shaw Chalet, a modern mountain retreat with breathtaking views of eight surrounding peaks and the Stratton Va ...
From $2233 per night (USD)Expedia
From $774 per night (USD)VRBO
Room for the whole family!
- Bedrooms:
- 3
- 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 $774 per night (USD)VRBO
From $433 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 $433 per night (USD)VRBO
From $508 per night (USD)VRBO
Knole House: a true Vermont farmhouse escape
- 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 $508 per night (USD)VRBO
From $458 per night (USD)VRBO
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 $458 per night (USD)VRBO
From $511 per night (USD)VRBO
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 $511 per night (USD)VRBO
From $870 per night (USD)Expedia
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 $870 per night (USD)Expedia
From $551 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 $551 per night (USD)VRBO
From $335 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 $335 per night (USD)VRBO
From $449 per night (USD)VRBO
Cozy Retreat with Hot Tub Right Off the Master Bedroom!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to this secluded mountain haven, nestled in the heart of Stratton Mountain, Vermont. This spacious home comfortab ...
From $449 per night (USD)VRBO
From $548 per night (USD)Expedia
Chalet 7 minutes to Ski Stratton, Woodstove, Starry Skies, FirePit, View, DogsOK
- 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 $548 per night (USD)Expedia
From $442 per night (USD)VRBO
Cabin 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,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 $442 per night (USD)VRBO
From $520 per night (USD)Expedia
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,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 $520 per night (USD)Expedia
From $386 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 $386 per night (USD)VRBO
From $1011 per night (USD)Expedia
Spacious dog-friendly home, fireplace, firepit, sauna, jet tub, decks, wifi
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Secluded Mountain House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $1011 per night (USD)Expedia
From $2105 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 $2105 per night (USD)VRBO
From $713 per night (USD)Expedia
Secluded Mountain Retreat: Gorgeous Views, Five Mins to Stratton, Sauna, Firepit
- Bedrooms:
- 3
- 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 $713 per night (USD)Expedia
From $699 per night (USD)VRBO
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge
- Bedrooms:
- 3
- 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 $699 per night (USD)VRBO
From $724 per night (USD)Expedia
Townhouse w/hot tub, fireplace, shuttle, wifi, w/d, community sports club
- 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 $724 per night (USD)Expedia
From $409 per night (USD)VRBO
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 $409 per night (USD)VRBO
From $2906 per night (USD)Expedia
Vibes & Views In Stratton
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Indulge in breathtaking vistas of Stratton and Bromley Mountain from this expansive Adirondack-style residence. Designed ...
From $2906 per night (USD)Expedia
From $695 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 $695 per night (USD)VRBO
From $841 per night (USD)Expedia
Red Hemlock Retreat | Hot Tub & Close To Mountains
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: Escape to Vermont in this spacious retreat, perfect for families or groups! Just 15 minutes to Mount Snow and 2 ...
From $841 per night (USD)Expedia
From $574 per night (USD)VRBO
Rustic cabin in serene location with fireplace and pool access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Clark's Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $574 per night (USD)VRBO
From $327 per night (USD)Expedia
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy, rustic Log cabin sits on 1 acre in the Snow Mountain community. Located 10 minutes from Mt. Snow (7 miles) 2 ...
From $327 per night (USD)Expedia
From $1601 per night (USD)VRBO
Secluded Luxury Lodge | Minutes to Stratton
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
STUNNING PANORAMIC MOUNTAIN VIEWS FROM EVERY ROOM Escape to nature at Whispering Pines Lodge, a private luxury retreat ...
From $1601 per night (USD)VRBO
From $539 per night (USD)Expedia
Mountain Haven for Families | Deck | Shuttle | Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Escape the everyday at this mountain retreat with stunning views and a private deck - Spacious townhome with 3 bedroom ...
From $539 per night (USD)Expedia
From $1348 per night (USD)VRBO
New 6-BR Luxury Home 6 Min from Stratton w/hot tub
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Summary: Escape to this newly built 6-BR home, located on the Stratton Mountain access road, just 6 minutes from the lif ...
From $1348 per night (USD)VRBO
From $1069 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 $1069 per night (USD)VRBO
From $367 per night (USD)VRBO
Charming gingerbread A-frame situated on 3 acres, woodstove, A/C, deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Koliba Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $367 per night (USD)VRBO
From $584 per night (USD)Expedia
The Great Escape!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in the forest just 7 minutes to Mt Snow and 15 minutes to Stratton, this charming cabin seamlessly blends comfor ...
From $584 per night (USD)Expedia
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Greek Revival Ski/Farmhouse, Saltwater Hot Tub, 10 minutes to Stratton Mountain.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Nestled in Jamaica, this lovely 1830 farmhouse is a haven for guests seeking a soothing retreat. Take a hike out the fro ...
Click For PricingVRBO
From $767 per night (USD)VRBO
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Secluded Natural Surroundings | Sun-Soaked Living Space Enjoy all-season adventures just beyond your doorstep at this ...
From $767 per night (USD)VRBO
From $460 per night (USD)VRBO
Cabin 7 min to Ski Stratton, Wood-Fired Sauna, Brook View, Woodstove, Dogs 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 $460 per night (USD)VRBO
From $1736 per night (USD)VRBO
Stratton Vermont Ski House with Stunning Views of Bromley Mountain
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Rainbow's End, our home away in the Green Mountains of Vermont. Our home is in the town of Bondville, just 10 ...
From $1736 per night (USD)VRBO
From $836 per night (USD)VRBO
Updated Mountain Chalet with shuttle to Stratton
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This spacious home, situated on a beautiful pond, is a great spot for a family looking to ski or explore the area year-r ...
From $836 per night (USD)VRBO
From $605 per night (USD)Expedia
Cozy house w/ clubhouse heated pool, fireplace, balcony, jacuzzi, w/d, wifi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
The Last Run Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $605 per night (USD)Expedia
From $249 per night (USD)VRBO
Dog friendly, near Stratton, Magic & Bromley
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Just miles from Stratton, Bromley, and Magic Mountains. Close to Lowell Lake and Jamaica Falls for hiking and water spo ...
From $249 per night (USD)VRBO
From $234 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 $234 per night (USD)VRBO
From $1510 per night (USD)VRBO
Delightful updated farmhouse with original features, patio, and & W/D
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
Sweet Berry Farm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $1510 per night (USD)VRBO
From $464 per night (USD)Expedia
The Deerwood Tiny Home | Mtn Views w/ Fireplace!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Enjoy the sounds of nature when you stay in this unique tiny home in Londonderry, Vermont. Perfectly located in ...
From $464 per night (USD)Expedia
From $684 per night (USD)VRBO
Lucky Log Cabin- Hottub fireplace 12min to Mt Snow
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Escape to the tranquility of Vermont in this cozy, lucky mountain log cabin tucked away on a quiet, wooded hillside. Des ...
From $684 per night (USD)VRBO
From $1040 per night (USD)Expedia
4-bedroom Lake Front House in Quntisential Private Vermont Setting
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Experience Vermont at its finest with this exceptional lakefront property, offering direct backyard access to a pristine ...
From $1040 per night (USD)Expedia
From $741 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 $741 per night (USD)VRBO
From $522 per night (USD)Expedia
Peaceful mountain home near skiing, hiking, mtn biking & more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Frozen Jamaica Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $522 per night (USD)Expedia
From $280 per night (USD)VRBO
Charming Riverfront Vermont Farmhouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming old Vermont farmhouse on 1.4 acres next to a beautiful brook and historic stone bridge. Swim on our property, o ...
From $280 per night (USD)VRBO
From $1245 per night (USD)Expedia
Stratton; 4 min! Shuttle, King Beds, Hot Tub, 2 FP
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
With soaring cathedral ceilings, abundant natural light, a hot tub with views for days and multiple living spaces to spr ...
From $1245 per night (USD)Expedia
From $526 per night (USD)VRBO
New! 7 min to Stratton access road, HotTub, Sauna EV
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to a private 4-bedroom retreat just 7 min from Stratton Mountain access road. After adventure, unwind in the 6-pe ...
From $526 per night (USD)VRBO
From $441 per night (USD)Expedia
Superb 3-bedroom house on the river - Fall for the Leaves, Stay for the Slopes!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to our Vermont retreat, lovingly built from the ground up by my husband for our family to relax, recharge, and c ...
From $441 per night (USD)Expedia
From $640 per night (USD)VRBO
Designer 4-bedroom house in charming Stratton home sleeps 12.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Discover this 4-bedroom gem in Stratton. This amazing house features 3 king beds, 1 bunk bed, and 3 bathrooms with a jet ...
From $640 per night (USD)VRBO