
House holiday rentals in Jamaica
Find and book unique houses on Airbnb
Top-rated house rentals in Jamaica
Guests agree: these houses are highly rated for location, cleanliness and more.

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 🐣

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Summit View Ski and Golf Retreat w/hot tub & Sauna
Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Clark Farm-2 Master-Suites, Great kitchen, views!
The historic Clark Farm boasts beautiful mountain views as well as of our apple orchard and early 19th Century barn. The farmhouse sleeps 8 comfortably with 2 king-size master suites that are tucked away each on their own floor. The queen room and the kids room (twins) share 1.5 baths in the "new" side of the house. The spacious light-filled farmhouse has an open floor plan with a gas fireplace in both the living room and tv/game room. Outdoors enjoy the 8 adirondack chairs and a fire pit .

Country Colonial Home with rolling fields & stream
This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

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

The Vermont Farmhouse|Hiking|Dog Trails|Village
Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

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.

Stunning mid-century house on 2.5 private acres
Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.
Popular amenities for house rentals in Jamaica
House rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

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

Idyllic Dorset Home: Serene Escape w/amazing views

Wander In | Close to Mount Snow & Stratton
Weekly house rentals

Charming Vermont Schoolhouse

Stratton Ski House

2-Bedroom Home, 7 Minutes From Stratton Mountain

Minutes from Stratton Mountain

Stratton; 4 min. Renovated, games, fireplace!

Midcentury Hillside Retreat - Summer Paradise

Barnside Cottage at Fruition Farm

Cozy 3BR Vermont Artistic Retreat w/ Trails
Private house rentals

Modern cabin close to all mountains

Scandinavian Serenity Close to Okemo

Magical Retreat Cottage 25% off, now to June 17

Relaxing Mountain Retreat with a View

Historic Riverfront 3BR Farmhouse, Pet-Friendly

A-Frame w/ Hot Tub | Ski & Board Stratton 10min

Pettengill Schoolhaus scenic 2 min to main village

Raven Wood Cottage
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £398 | £439 | £310 | £236 | £240 | £230 | £207 | £216 | £213 | £229 | £249 | £347 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about house rentals in Jamaica

Total holiday rentals
Explore 120 holiday rentals in Jamaica

Nightly prices starting at
Jamaica holiday rentals start at £66 per night before taxes and fees

Verified guest reviews
Over 4,400 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
120 of Jamaica holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Jamaica rentals

4.9 Average rating
Jamaica stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Rentals with pools Jamaica
- Pet-friendly rentals Jamaica
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- Rentals with a hot tub Jamaica
- Rentals with a fireplace Jamaica
- Rentals with a firepit Jamaica
- Rentals with a sauna Jamaica
- Rentals with a patio Jamaica
- Rentals with outdoor seating Jamaica
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- Rentals with an EV charger Jamaica
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- Family-friendly rentals Jamaica
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- Waterfront rentals Jamaica
- Fitness-friendly rentals Jamaica
- House rentals Windham County
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- House rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Killington Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Dartmouth College
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Southern Vermont Arts Center
- Mount Monadnock
- Mount Greylock





