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

HeART Barn Retreat
Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

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.

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!

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

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.

Dog Friendly A-Frame Retreat near Hiking, Skiing
The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

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.

Vermont Retreat Cabin, Romantic, Nature Immersion
A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Gorgeous Cabins of the East Coast ☽ Elevated design; thoughtful lighting; deeply romantic ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products

Private Hilltop farm apartment
Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

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.

Serene Bus Getaway Among Rolling Farm Land
Tucked off a quiet dirt road, this stationary bus promises to provide you and yours an unforgettable accommodation for your next Upstate NY retreat. Come stay in the Sleepy Tire, and wake up to beautiful views of Vermont’s Green Mountains, an indoor bathroom with flushing toilet and hot shower, and WiFi so you can stay connected to those that matter.
Popular amenities for Jamaica pet-friendly home rentals
Pet-friendly house rentals

Frosted Willows

Winter Fun Enjoy Southern Vt

Vermont Winter Escape

Fresh Snow- Luxury Cabin near Ski Areas

Private & Cozy Farmhouse in New Hampshire

Modern Spacious Home with Mountain Views

Meadow View. 35 acres outside your door!

Comfy and Cozy House on 67 acres
Pet-friendly home rentals with a pool

Rustic Sunny Vermont Home near Mount Snow

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

Moon Valley Country Retreat no clean fee pets yes

Cozy Vermont Antique Sugar House with Fireplace

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Hollywood Bungalow in the Berkshires #C0191633410

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Private, pet-friendly home rentals

7 Min Stratton Mtn/15 Min Mt Snow /Wood Fireplace!

The Birchwood Cabin - Stunning Mountain Views

Quaint stone house!

Chalet Sonsie: A Sweetwater Stay

Romantic Barn Guesthouse in Village Center

Serene & Stylet Chalet•HOT TUB•Skiing•Manchester

Private Cabin/PetsOK/Minutes to Okemo/Fast Wifi

Artists Chalet minutes from Stratton Ski Resort
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $486 AUD | $524 AUD | $415 AUD | $321 AUD | $324 AUD | $297 AUD | $345 AUD | $346 AUD | $336 AUD | $380 AUD | $410 AUD | $548 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 |
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 $45 AUD 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!
Destinations to explore
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- Pet-friendly rentals Windham County
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- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Fox Run Golf Club
- Dorset Field Club
- Northern Cross Vineyard
- Willard Mountain




