
House holiday rentals in Jamaica
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Top-rated house rentals in Jamaica
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Lovers Honey Pond Treehouse with hot tub & sauna
Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Vermont Botanical Studio Apartment
This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Cozy Riverfront Home in beautiful Jamaica
. Surrounded by tall pines and mountains, with the tranquil sound of the West River outside, here you can escape into nature while still enjoying all the cozy comforts of home. Our newly renovated home has been transformed into a getaway spot for romance, friends or family. The deck, set on the waterfront, is a beautiful, serene space to dine or take a soak in our wood burning hot tub. Put on some records, make a meal and cuddle up in front of the fire after a long day of playing outdoors.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Stunning Okemo Views - 3BD 3BA on 10 Private Acres
Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

Clean, Captivating VT Farmhouse near Stratton!
Let us welcome you to our beautifully appointed, circa 1901 Vermont farmhouse resting on four acres of lush, rolling pastures--the quintessential Vermont experience! The house exudes warmth, coziness and tranquility with no detail left untouched. 4 BR 2 bath with huge family room. Minutes to 3 of the best ski-mountains on the east coast - Stratton, Bromley, Magic Mtn and close to Manchester shopping. A few miles from renowned Solo Farm & Table, HoneyPie and West River Farmer's market.

Yellow Sweetie at the Base of Stratton
Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Magic Creek
Come enjoy our brand new hot tub! Magic Creek is quintessential Vermont- an antique made modern. The cozy living room with fireplace is an ideal spot to gather at the end of your day. The house has 3 bedrooms and a play room that doubles as a guest room. The house is bordered by a creek with peaceful water falls. Centrally located in the heart of ski country, minutes to Magic Mountain, 20 minutes to Bromley, and 30 to Stratton or Mt Snow, and 40 minutes to Okemo. Come and enjoy it all.

Stay mins from Mt. Snow & Stratton w/ EV charger
Enjoy the ultimate ski getaway in this private home that sits on 1 acre of beautiful wooded land. Park your car in the detached garage (w/Tesla charger). The spacious house comfortably sleeps 8 guests and sits between Stratton Mountain and Mount Snow with hiking trails and lakes just minutes away. Sit outside on the deck to enjoy serene views, warm sunshine and sounds of nature. Leave your worries and just relax, BBQ and enjoy the fire pit for cozy evenings with friends & family.

3BR 2BA Stratton Condo w/ Fireplace & Forest Views
Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

Cozy Modern Sugar House with spectacular views.
This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.
Popular amenities for house rentals in Jamaica
House rentals with a pool

Magical Farm Getaway - a must visit!

The 1770 House

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Historic Home on 17 acres of land. Go escape!

Historic 1850’s Renovated Farmhouse w/ Pool!

Hollywood Bungalow in the Berkshires #C0191633410
Weekly house rentals

Stratton; 6 min. King beds. Game rm. Dog friendly

Charming Vermont Schoolhouse

Magic Cottage in Jamaica Vermont

The Vermont Farmhouse+Charming Countryside Views

Magical Retreat Cottage Autumn Colors & Waterfalls

Cozy Cottage at Cold Moon Farm!

Historic Riverfront 3BR Farmhouse, Pet-Friendly

Vermont Mirror House
Private house rentals

Luxury VT Retreat. Breathtaking Views & Sunsets

Highland Haus: stunning ski getaway with hot tub

Mountain Log Cabin near Stratton

4 Bedroom on 90 Acres in the mountains of Vermont!

Stratton Ski/Yoga retreat

Modern Chalet: Magic Mountain

Black Star Barn, Mountain Retreat w/ Hot Tub

Secluded Mountain Retreat:Fall Views Firepit Sauna
Quick stats about house rentals in Jamaica
Total rentals
110 properties
Nightly prices starting at
$117 SGD before taxes and fees
Total number of reviews
4K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
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- Pet-friendly rentals Jamaica
- Rentals with a hot tub Jamaica
- Rentals with a firepit Jamaica
- Fitness-friendly rentals Jamaica
- Waterfront rentals Jamaica
- Rentals with an EV charger Jamaica
- Rentals with pools Jamaica
- Rentals with outdoor seating Jamaica
- Rentals with a patio Jamaica
- Family-friendly rentals Jamaica
- Cabin rentals Jamaica
- Rentals with a fireplace Jamaica
- Rentals with a washing machine and dryer Jamaica
- Villa rentals Jamaica
- Chalet rentals Jamaica
- House rentals Windham County
- House rentals Vermont
- House rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- The Shattuck Golf Club
- Hooper Golf Course
- Crotched Mountain Ski and Ride
- Northern Cross Vineyard
- Autumn Mountain Winery
- Brattleboro Ski Hill
- Fox Run Golf Club