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.

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Guest favourite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 243 reviews

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

Top Guest favourite
The log cabin is illuminated against the night sky, showcasing its rustic charm. Snow accumulates around the entrance and pathway, while warm light spills from the windows, creating a cozy atmosphere. The sloped roof features wooden beams, enhancing the cabin's unique design.
Cabin in Stratton
5 out of 5 average rating, 188 reviews

Log Cabin King Beds AC Near Hike Bike Swim Golf!

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!

Guest favourite
A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.
Home in Winhall
4.95 out of 5 average rating, 330 reviews

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

Top Guest favourite
A cozy log cabin is nestled among tall trees, with sunlight filtering through the leaves. The surrounding ground is covered in vibrant autumn leaves, and a winding path leads to the front entrance of the home, offering a serene and inviting atmosphere.
Chalet in Londonderry
4.95 out of 5 average rating, 128 reviews

10 min from Stratton! Log Cabin w/ Beautiful Views

Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!

Top Guest favourite
The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.
Cabin in Jamaica
4.99 out of 5 average rating, 299 reviews

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.

Top Guest favourite
A spacious bedroom features a king-sized bed adorned with colorful pillows, framed by large windows that offer views of the surrounding greenery. A decorative bench at the foot of the bed displays neatly arranged towels, complemented by bedside lamps on either side.
Guesthouse in Jamaica
4.96 out of 5 average rating, 182 reviews

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

Top Guest favourite
The chalet is set against a backdrop of trees, showcasing a combination of natural stone and wood siding. Multiple outdoor seating areas are visible, featuring colorful chairs with a fire pit nearby. Dim evening light gently illuminates the home, highlighting the windows and inviting ambiance.
Chalet in Jamaica
4.99 out of 5 average rating, 100 reviews

Designer Chalet w/ Mountain Views close to it all

A perfect little getaway. This stylish 3 bedroom/2 bath chalet is surrounded by endless outdoor activities. Swimming, hiking, biking, visiting the local waterfalls, golf courses, or rent an ATV from local outfit. This beautiful home is perfect for 6-8 people. Situated on 2.5 acres, this private setting with mountain views, has everything you need to feel at home. Multiple restaurants, cafes, markets for food, beer & wine less than a 5 min drive as well to sporting stores for supplies.

Guest favourite
The tiny house exterior features a charming porch with colorful railings and vibrant green doors. Tall trees surround the cottage, and a light dusting of snow covers the ground, adding to the serene atmosphere of the setting.
Tiny home in Jamaica
4.94 out of 5 average rating, 1,339 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Guest favourite
A cozy cabin is nestled in a snow-covered landscape, featuring a blue hammock hanging from the porch. Snowflakes gently fall around a dog wearing a blue coat, playing in the deep snow in front of the entrance. Wooden stools are positioned near the entrance.
Cottage in Jamaica
4.85 out of 5 average rating, 607 reviews

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.

Guest favourite
Chalet in Jamaica
4.98 out of 5 average rating, 283 reviews

Classic Vermont A-Frame | Fire Pit | Near Stratton

Escape to a classic Vermont A-Frame in Jamaica, Vermont on a private wooded 3-acre property along scenic Route 100. Near Stratton Mountain, Mount Snow, Jamaica State Park, and Pike Falls, this peaceful mountain retreat is perfect for hiking, swimming holes, fall foliage, scenic drives, and outdoor adventures. Enjoy mornings on the screened porch and evenings around the fire pit listening to the river across the street under the Vermont stars.

Top Guest favourite
The bedroom is designed with a spacious bed adorned with crisp white linens. A large triangular window provides a serene view of lush greenery outside, allowing natural light to fill the room.
Cabin in Townshend
4.96 out of 5 average rating, 191 reviews

Modern Cabin with Outdoor Spa on Vermont Farm

Romantic modern cabin with private hot tub on a 100-acre Vermont farm. This Scandinavian-style retreat features soaring windows, a king bed with luxury linens, a cozy fireplace, and a sleek kitchen. Perfect for couples seeking a peaceful getaway, farm stay, or eco-friendly escape. Soak under the stars, meet our friendly goats, and enjoy the beauty of southern Vermont from your light-filled solar-powered cabin.

Top Guest favourite
A spacious living area features large floor-to-ceiling windows offering a view of the green outdoor space. A plush sofa, accented with colorful cushions, sits in front of a wooden coffee table. A modern dining area is visible in the background, illuminated by soft lighting.
Home in Winhall
4.98 out of 5 average rating, 419 reviews

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 Jamaica holiday rentals

When is the best time to visit Jamaica?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$565 NZD$615 NZD$508 NZD$377 NZD$388 NZD$369 NZD$398 NZD$388 NZD$388 NZD$431 NZD$424 NZD$629 NZD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°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 cabin rentals in Jamaica?

    Jamaica has more than 10 family-friendly cabin 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 cabin rentals in Jamaica have air conditioning?

    Absolutely! We offer over 10 cabin 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 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 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 220 holiday rentals in Jamaica

  • Nightly prices starting at

    Jamaica holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 13,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    170 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

    210 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!

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Jamaica