
House vacation rentals in Jamaica
Find and book unique houses on Airbnb
Quick stats about house rentals in Jamaica

Total vacation rentals
Explore 120 vacation rentals in Jamaica

Nightly prices starting at
Jamaica vacation rentals start at G$18,822 GYD per night before taxes and fees

Verified guest reviews
Over 4,270 verified reviews to help you choose

Family-friendly vacation rentals
110 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Jamaica vacation 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!
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!

Hot Tub & Game Room - Ski Mt. Snow/Stratton
Nestled in the heart of Southern Vermont, our cozy and inviting home sits 10 min from Mt Snow and 15 min from Stratton, making it the ideal base for your adventure. Whether you're hitting the slopes, exploring hiking trails, or simply unwinding, you'll find everything you need for a memorable stay. Soak under the stars in our 7-person hot tub or cozy up inside for a night of relaxation. Discover the charm of Vermont and visit local breweries, farm-to-table restaurants, farms, and quaint towns.

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

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.

Shred Shack: A/C | Hot Tub | Sauna | EV charger
Escape to the Shred Shack by 42 North LP, your ultimate mountain escape in Vermont! The Shred Shack offers stunning mountain & valley views from its expansive great room. Relax & recharge by the grand fireplace, in the private indoor sauna, or the mountain-view hot tub. Entertain effortlessly in the open-concept kitchen, dining, and living area – perfect for memorable meals & gatherings. Kids will love the unique indoor swing! Your perfect blend of adventure and comfort awaits!

Charming Vermont Schoolhouse
Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Modern 3-bedroom A-frame in Londonderry w/ Pond
This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

The Architect's Cabin, on 10 Secluded Acres
Nestled on a rise in a woodland clearing is this intriguing cubist design reminiscent of Post and Beam ambiance. Stone and wood materials from the property have been assimilated into intriguing modern design features throughout. Walls of windows share the tranquil and private outdoor setting with the indoor livings areas. We require all guests have a verified account and positive host reviews. There is no Air Conditioning.

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.

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER
This beautiful circa 1850 farmhouse sits between two rivers in the heart of Grafton Village. While the setting feels peaceful and secluded, you are only a two-minute walk from the historic Grafton Inn and the village center. Guests are also welcome to use our collection of bikes, tubes, and snowshoes stored in the garage for adventures around the village and nearby trails.
Popular amenities for Jamaica house rentals
House rentals with a pool

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

Magical Farm Getaway - a must visit!

The 1770 House

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Idyllic Dorset Home: Serene Escape w/amazing views

Stratton ski/walk on/off, King beds, FP, Hot tub

Hollywood Bungalow in the Berkshires #C0191633410
Weekly house rentals

Stratton Summer House | Trails + Swim Holes + AC

Luxury VT Retreat. Breathtaking Views & Sunsets

2-Bedroom Home, 7 Minutes From Stratton Mountain

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

The MountainTop | Stratton & Mt Snow | Fire Pit

Bear Den: Hot Tub + Secluded | Sleeps 8 | Modern

Pettengill Schoolhaus scenic 2 min to main village

Mountain Retreat | Hot Tub | 9 Acres | Views
Private house rentals

Brewster's Hollow

Magical Retreat Cottage -Vermont holiday paradise

Modern Chalet: Magic Mountain

Cozy A-Frame with Hot Tub | 10 Min to Stratton!

The Cabin on Main - Manchester, Vermont

5BR near Stratton- Hot tub, sauna, fire pit, views

A-Frame | Hot Tub| Dog Friendly | Near Mt. Snow

Artist Forest Retreat
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$113,350 GYD | G$125,061 GYD | G$88,254 GYD | G$67,341 GYD | G$68,386 GYD | G$65,667 GYD | G$58,975 GYD | G$61,485 GYD | G$60,648 GYD | G$65,249 GYD | G$70,896 GYD | G$98,919 GYD |
| 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 |
Destinations to explore
- New York Vacation rentals
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- Chalet rentals Jamaica
- Rentals with a hot tub Jamaica
- Pet-friendly rentals Jamaica
- Waterfront rentals Jamaica
- Fitness-friendly rentals Jamaica
- Rentals with a fireplace Jamaica
- Cabin rentals Jamaica
- Family-friendly rentals Jamaica
- Rentals with a patio Jamaica
- Rentals with an EV charger Jamaica
- Rentals with pools Jamaica
- Rentals with a washer and dryer Jamaica
- Rentals with a fire pit Jamaica
- Rentals with a sauna Jamaica
- Rentals with outdoor seating Jamaica
- House rentals Windham County
- House rentals Vermont
- House rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Dartmouth College
- West Mountain Ski Resort
- Killington Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Mount Monadnock
- Mount Sunapee Resort
- Montshire Museum of Science
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Camp Plymouth State Park





