
Holiday houses in Jamaica
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Top-rated holiday rentals in Jamaica
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1850's VT Farmhouse on the River
Step Back in Time at this 1850s Farmhouse with a Private Riverfront Backyard Nestled amidst the breathtaking landscapes of Southern Vermont, this lovingly restored 1850s farmhouse offers a unique blend of rustic charm and modern conveniences. With its original wide pine floors, plaster walls, slate roof, and classical lines, this property embodies the essence of Vermont's architectural heritage. Just 10 mi from Stratton, experience the tranquility of Jamaica State Park and the West River Falls.

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

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.

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.

Rustic Cabin in foothills of Green Mountains
Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

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.

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

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.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

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! Pets welcome with a $100 pet fee.
Popular amenities for Jamaica holiday rentals
Other great holiday rentals in Jamaica

Charming Vermont Schoolhouse

2-Bedroom Home, 7 Minutes From Stratton Mountain

Scandinavian Serenity Close to Okemo

Mountain View Glamping Cabin

Stratton Ski Haus~7min, Sauna, HotTub, BootWarmers

Designer Chalet w/ Mountain Views close to it all

The Overlook VT by Stratton Mountain : New Listing

Vermont Mirror House
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $499 AUD | $543 AUD | $449 AUD | $333 AUD | $342 AUD | $326 AUD | $351 AUD | $342 AUD | $342 AUD | $388 AUD | $412 AUD | $519 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.
Do chalet rentals in Jamaica have a bbq area?
Absolutely! We offer over 10 chalet rentals with a bbq area in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Do chalet rentals in Jamaica have wifi?
Absolutely! We offer over 10 chalet rentals with wifi 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.
Do chalet rentals in Jamaica have air conditioning?
Absolutely! We offer over 10 chalet rentals with air conditioning in Jamaica. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Jamaica?
Jamaica has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Jamaica?
Experience the best of Jamaica with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 $30 AUD per night before taxes and fees

Verified guest reviews
Over 12,580 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
190 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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- Rentals with a fire pit Jamaica
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- The Shattuck Golf Club
- Dorset Field Club
- Whaleback Mountain
- Pineridge Cross Country Ski Area
- Northern Cross Vineyard




