
Holiday houses in Jamaica
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Top-rated holiday rentals in Jamaica
Guests agree: these stays are highly rated for location, cleanliness and more.

Stone Fence Cabin
Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

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.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Log Cabin, King Beds & 7 Min from Stratton Mtn
Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!

Green Mountain Modern House: iconic modern getaway
Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

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

New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

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!

West Wing at Mantana Meadows on the West River
Welcome to Mantana Meadows! This 1970's contemporary is able to allow large families and friends a great space to enjoy VT. We are centrally located in Vermont within a half hour of five great ski resorts and all of the shopping Manchester has to offer. The grounds are scenic and peaceful, and the back of the house is 25' away from the West River. Great for Spring, Summer, Fall and Winter recreation and relaxation. We've also got a high speed 50 amp 240 Volt outlet for EV charging!

The Rafters Lodge
A unique VT experience! This 1860s barn was converted into a Girl Scout camp in the 1950s and served many years training leaders and scouts. Today, the Rafters continues to be a special part of many families lives, who come to enjoy the rustic camping experience and beautiful ninety acre farm. The lodge has accommodated large youth groups, families and even the occasional wedding party. With the close proximity to Stratton and Bromley, visitors enjoy countless recreational opportunities.

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK
Authentic post & beam cottage surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Nearby swimming hole at brook on property. Fire pit, propane BBQ, picnic table, spectacular Stratton Mountain view. Front porch & back porch with hammock, table & chairs. VCR/DVD & videos, boardgames & puzzles, kids toys, turntable & records, Satellite Internet & WiFi 20-100 mbps, TV & Roku. Gas heat, wood stove. Dog friendly.

Romantic Wooded Vermont Cabin
Enjoy this private getaway for two in our charming and rustic home nestled on a peaceful, wooded lot at the edge of a national forest. First floor only, open floor plan and it's all yours! Conveniently located 2 miles from Jamaica Village, 10 miles from Stratton Mountain, 16 miles from Manchester and 30 miles north of Brattleboro.
Popular amenities for Jamaica holiday rentals
Other great holiday rentals in Jamaica

Charming Vermont Schoolhouse

Log Cabin Near Stratton/Mt Snow

Goldfinch Cottage: Timber Frame on 5 Private Acres

2-Bedroom Home, 7 Minutes From Stratton Mountain

Kloki - River Lovers Treehouse - sauna & hot tub!

Stratton Mountain Escape w Hot Tub|Deck|Projector

Pristine Magical Retreat Cottage 15 min to Mt Snow

Rustic Cabin in between MountSnow & Stratton
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $471 AUD | $512 AUD | $423 AUD | $314 AUD | $323 AUD | $307 AUD | $331 AUD | $323 AUD | $323 AUD | $359 AUD | $353 AUD | $524 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 |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Jamaica?
Four-legged friends are welcome in Jamaica. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Jamaica?
Yes! Work meets play with ease at over 100 vacation rentals in Jamaica featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly house rentals in Jamaica?
Jamaica has more than 110 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cabin rentals in Jamaica?
Experience the best of Jamaica with our cabin rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Jamaica have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Jamaica have wifi?
Absolutely! We offer over 20 cabin rentals with wifi in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Jamaica have a bbq area?
Absolutely! We offer over 80 house rentals with a bbq area in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Jamaica have a gym?
Absolutely! We offer over 10 house rentals with a gym in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Jamaica

Total holiday rentals
Explore 200 holiday rentals in Jamaica

Nightly prices starting at
Jamaica holiday rentals start at $29 AUD per night before taxes and fees

Verified guest reviews
Over 13,250 verified reviews to help you choose

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

Pet-friendly accommodation
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
200 of Jamaica holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Jamaica rentals

4.9 Average rating
Jamaica stays are highly rated by guests—averaging 4.9 out of 5!
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- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Pats Peak Ski Area
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Dartmouth College
- Mount Sunapee Resort
- Mount Greylock
- Emerald Lake State Park
- Southern Vermont Arts Center
- Massachusetts Museum of Contemporary Art
- Mount Monadnock




