
Pet-friendly vacation rentals in Jamaica
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Jamaica

Total vacation rentals
Explore 90 vacation rentals in Jamaica

Nightly prices starting at
Jamaica vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

Verified guest reviews
Over 8,110 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 of Jamaica vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Jamaica rentals

4.9 Average rating
Jamaica stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated pet-friendly home rentals in Jamaica
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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

Family Chalet Huge Yard Near Bike Hike Swim Golf!
Cozy chalet awaits your stay. This home sits on just under 4 acres. Sit back & enjoy the heated sunroom and stare out at the woods that surround you. You may be lucky enough to spot one of the moose or bear that visit the property. Kitchen remodeled 2023! Open floor plan w/wood burning fireplace. Main bedroom has new King Bed & twin bunks. Finished basement with new Queen size bed & twin bunk above. Kid friendly home! Mins to Stratton Mtn & Mt Snow for skiing & golf! Free Disc golf on property.

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.

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

Chic Cabin with Fireplace at Stratton Mountain
Originally built as a corn crib in the 1800s, this 2 bedroom, two bath cabin has been lovingly maintained and features many original details from wide pine floors to a brick fireplace. This beautiful post and beam cabin is nestled in the Green Mountains of Central Vermont with convenient access to some of the best skiing, hiking, & sightseeing: 10 min to Stratton Mountain and Bromley, 15 min to Manchester, 20 min to Magic Mountain, 30 min to Mount Snow, 40 min to Okemo, and 1 hour to Killington

The Woodland A-Frame
Welcome to The Woodland A-Frame! Built in 1965, our cozy cabin is located 20 mins from Stratton Mountain & Mt. Snow, and 30 mins from Bromley, & Magic Mountain! Vermont is a four-season state, allowing guests to enjoy the cabin anytime of year. Whether it's for fall foliage, winter activities, spring festivals, or a summer at the lake, we are happy to host you anytime during the year to experience your ideal Vermont getaway! Dogs welcome with a $100 pet fee per pet (two dog max). No cats

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.

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.

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, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Artists Chalet minutes from Stratton Ski Resort
One of a kind hand gem…built by the owner in the heart of the Green Mountains. House boasts spacious high ceilings, maple trim sourced from the property and custom windows that reflect the intention of the land. Pikes Falls is one mile down the road. Minutes to Stratton Mountain and Jamaica State Park. Mountain views from the deck! During the winter season, all wheel drive or 4WD is recommended. Pets are welcome on a case by case basis and may be subject to a Pet Fee

Cottage-Swim-View-Firepit-7min to Stratton-Dog OK
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.
Popular amenities for Jamaica pet-friendly home rentals
Pet-friendly house rentals

Clark Farm-2 Master-Suites, Great kitchen, views!

1863 Pierce House near Stratton ~ Sleeps 8

Pinecone Pond 30 min ski Mt Snow, 45 to Stratton

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

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

Wild Blossom Farmhouse - a lovely family getaway

Stylish Vermont Cabin | Views · Trails · Luxe

Private Hot Tub, 2 Min to Mt Snow, Cozy Fireplace!
Pet-friendly home rentals with a pool

The 1770 House

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

“Sugar Maple” Rustic 4x4 Cabin Getaway, Fireplace

Mt Snow Chalet: Peaceful Escape w/Hot Tub
Private, pet-friendly home rentals

The King's Cottage

Quaint stone house!

Private Cabin/PetsOK/AC/Minutes to Okemo/Fast Wifi

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal

Brook Haven Retreat - Minutes to Mt Snow&Stratton

10 min from Stratton! Log Cabin w/ Beautiful Views

Mountain side acres

Stratton Chalet | Barrel Sauna, Hot Tub & Views
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,271 | ﺩ.ﺇ 1,340 | ﺩ.ﺇ 929 | ﺩ.ﺇ 790 | ﺩ.ﺇ 797 | ﺩ.ﺇ 731 | ﺩ.ﺇ 848 | ﺩ.ﺇ 852 | ﺩ.ﺇ 826 | ﺩ.ﺇ 914 | ﺩ.ﺇ 845 | ﺩ.ﺇ 1,194 |
| 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 |
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- Chalet rentals Jamaica
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- Cabin rentals Jamaica
- House rentals Jamaica
- Family-friendly rentals Jamaica
- Rentals with a patio Jamaica
- Rentals with an EV charger Jamaica
- Rentals with pools Jamaica
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- Villa rentals Jamaica
- Rentals with a fire pit Jamaica
- Rentals with a sauna Jamaica
- Rentals with outdoor seating Jamaica
- Pet-friendly rentals Windham County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Dartmouth College
- Killington Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Montshire Museum of Science
- Mount Sunapee Resort
- Mount Monadnock
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Camp Plymouth State Park





