
Pet-friendly holiday rentals in Jamaica
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Top-rated pet-friendly home rentals in Jamaica
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike
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!

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

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.

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

Luxury “Tiny” House With Sauna (Timbery)
The Timbery: This is a new, fully handmade, timber frame "tiny" house featuring a custom Norwegian Sauna. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down in a tent on the forest floor, except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen, sauna and 71in soaking tub.

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.

Stunning Studio in historic Downtown Bellows Falls
Beautifully curated and spacious studio located in historic downtown Bellows Falls, VT. Come to escape the hustle and bustle of a big city without giving up metropolitan amenities. With a great location, you can walk to the train station, local bars and restaurants, shops, movie theater, etc. From the studio, you are a short distance drive to many outdoor activities that Vermont has to offer such as hiking, kayaking, mountain biking, etc.

Cozy Cabin in Southern VT
Take it easy at this tranquil getaway. Fall asleep to chirping bugs and wake up to birdcalls. This is a quiet, lovely cabin in Newfane VT. Read a book, walk the meditation circle, swing in the hammock, and explore all that Southern VT has to offer. Close to swimming holes, hikes, country stores, flea and farmers' markets, and ski mountains (Mt Snow and Stratton) Pets and children are welcome, but there is only one queen bed.

Classic A-Frame in Jamaica
This classic A-Frame chalet awaits you and your friends and family, whether you enjoy skiing/snowboarding, hiking, kayaking or just reading in front of a fire. With 2 bedrooms and a loft, galley kitchen and open living area, you can relax and enjoy all that Southern Vermont has to offer. Centrally located to Stratton, Mount Snow, Magic and Bromley ski resorts.

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 pet-friendly home rentals
Pet-friendly house rentals

Pinecone Pond

Modern 3-bedroom A-frame in Londonderry w/ Pond

Cozy Home in Village of Grafton

Comfortable farmhouse with stunning views

Wild Blossom Farmhouse - a lovely family getaway

The Grafton Chateau

Stylish Ascutney Cabin with Mountain Views

Modern Spacious Home with Mountain Views
Pet-friendly home rentals with a pool

Rustic Sunny Vermont Home near Mount Snow

Moon Valley Country Retreat no clean fee pets yes

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

The Brick House on Washington Street

Beautiful rustic woods and fields retreat.

Cozy Vermont Antique Sugar House with Fireplace

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Hollywood Bungalow in the Berkshires #C0191633410
Private, pet-friendly home rentals

2-Bedroom Home, 7 Minutes From Stratton Mountain

The Owl’s Nest in Landgrove

Quaint stone house!

Designer Chalet w/ Mountain Views close to it all

Cozy summer cottage in the woods of S. Vermont

Mountain Chalet mins from Mt Snow Skiing/hiking

The Woodland A-Frame

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $578 NZD | $622 NZD | $493 NZD | $381 NZD | $385 NZD | $353 NZD | $409 NZD | $411 NZD | $399 NZD | $452 NZD | $487 NZD | $651 NZD |
| 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 holiday rentals that are pet-friendly in Jamaica

Total holiday rentals
Explore 90 holiday rentals in Jamaica

Nightly prices starting at
Jamaica holiday rentals start at $53 NZD per night before taxes and fees

Verified guest reviews
Over 7,910 verified reviews to help you choose

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

Rentals with dedicated workspaces
50 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Jamaica rentals

4.9 Average rating
Jamaica stays are highly rated by guests—averaging 4.9 out of 5!
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- Pet-friendly rentals Windham County
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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
- Six Flags Great Escape Lodge & Indoor Water park
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Pico Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Dorset Field Club
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Hooper Golf Course
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Northern Cross Vineyard
- Whaleback Mountain