
House holiday rentals in Jamaica
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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!

Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Private Riverfront Getaway with Mountain Views
Be close to everything Manchester has to offer while enjoying gorgeous views and total privacy in a comfortable home you will have all to yourself! The perfect getaway any time of year. Feels like you are away from it all, but just minutes from amazing hiking, skiing, shopping, dining, and entertainment! 5 minutes to town and Bromley is less than 10 min away. Stratton and Magic Mt are both less than 25 min drives. Hiking trails, kayaking, fly fishing, and more are all right in your backyard.

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 .

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

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!

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.

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.

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.

The Post Haus: one-of-a-kind modern VT experience
Welcome to The Post Haus! A one-of-a kind, modern Vermont mini cabin in the Green Mountain National Forest. This high-end, mid-century mod getaway offers an indoor wood-burning fireplace, sauna, high-end kitchen, and two acres alongside the beautiful Ball Mountain Brook. Come enjoy our truly special piece of Vermont!
Popular amenities for Jamaica house rentals
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

Charming Vermont Retreat

Charming Vermont Schoolhouse

Cornish-Windsor Bridge Retreat with Amazing Views

Ski & Play in Style-Luxury Mt. Snow Getaway-HotTub

Scandinavian Serenity Close to Okemo

Vermont Historic Farmhouse Ski/Hike/River

Cedar Hill Lodge | 10 Min to Mt Snow w/Hot Tub

Minutes from Stratton Mountain
Private house rentals

Mountain Log Cabin near Stratton

Secluded Getaway, VT - 15 min from Woodstock

Pristine Magical Retreat Cottage 15 min to Mt Snow

Family, Friends, and Fun! Relax on 4 Private Acres

Hilltop Hideaway: Stratton Views | Hot Tub | A/C

Ludlow Retreat-Hot Tub, Sauna & Game Room

Riverside cabin

Perfect Mountain Getaway
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $729 AUD | $710 AUD | $588 AUD | $457 AUD | $465 AUD | $446 AUD | $401 AUD | $418 AUD | $412 AUD | $443 AUD | $482 AUD | $672 AUD |
| 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 $128 AUD per night before taxes and fees

Verified guest reviews
Over 4,540 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Jamaica holiday rentals include Wi-Fi 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
- Rentals with a fire pit Jamaica
- Cabin rentals Jamaica
- Rentals with a washing machine and dryer Jamaica
- Rentals with a hot tub Jamaica
- Rentals with a patio Jamaica
- Waterfront rentals Jamaica
- Rentals with an EV charger Jamaica
- Family-friendly rentals Jamaica
- Rentals with a fireplace Jamaica
- Pet-friendly rentals Jamaica
- Chalet rentals Jamaica
- Fitness-friendly rentals Jamaica
- Rentals with a sauna Jamaica
- Rentals with outdoor seating Jamaica
- Villa rentals Jamaica
- House rentals Windham County
- House rentals Vermont
- House rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Pats Peak Ski Area
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Emerald Lake State Park
- Mount Sunapee Resort
- Mount Greylock
- Southern Vermont Arts Center




