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

Total holiday rentals
Explore 100 holiday rentals in Jamaica

Nightly prices starting at
Jamaica holiday rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 9,020 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 of Jamaica holiday rentals include wifi 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

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!

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

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!

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.

Log Cabin Near Stratton/Mt Snow
Rustic log cabin for those looking for a getaway and a real Vermont experience. Pets allowed with *PET FEE* - add to your reservation There is Wifi &cell service (AT&T, Verizon). Please be aware this is not a luxury cabin, it is an authentic log cabin that we enjoy as a family during all seasons. No cable television - there is a TV with a Chromecast that you can use to stream from your phone over wifi. Firewood not provided 20 minutes to Stratton and 15 minutes to Mt. Snow

Brook Haven Retreat - Minutes to Mt Snow&Stratton
Welcome to Brook Haven Retreat! We are situated directly on Wardsboro Brook, just minutes away from the best skiing and riding, hiking, biking, fishing and relaxation in Southern Vermont.The property features a private fenced yard and deck to take in all the beauty alongside the brook. The home is fully updated with modern conveniences including three sleeping areas, living room, and a fully stocked kitchen. We love and allow well-behaved furry friends in our home!

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.

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.
Popular amenities for Jamaica pet-friendly home rentals
Pet-friendly house rentals

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

2-Bedroom Home, 7 Minutes From Stratton Mountain

Shred Shack: A/C | Hot Tub | Sauna | EV charger

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Cozy private cabin near Okemo! Large Hot tub!

MOUNTAIN NEST, views, Manchester, hot tub,

The Grafton Chateau

Sawmill Road - between Stratton and Mount Snow
Pet-friendly home rentals with a pool

“Elm” Cozy Pond-side Cabin w/wood stove

The 1770 House

Moon Valley Country Retreat no clean fee pets yes

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

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

Rustic Cabin in foothills of Green Mountains

Classic A-Frame in Jamaica

Artists Chalet minutes from Stratton Ski Resort

The Rafters Lodge

Mountain side acres

Mod Cabin in woods Hot Tub near Stratton & MtSnow

Stratton Chalet | Barrel Sauna, Hot Tub & Views

The Mountain A-Frame at Mount Snow
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €300 | €317 | €220 | €187 | €188 | €173 | €200 | €201 | €195 | €216 | €200 | €282 |
| 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 |
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- Chalet rentals Jamaica
- Rentals with outdoor seating Jamaica
- Rentals with a hot tub Jamaica
- Waterfront rentals Jamaica
- Fitness-friendly rentals Jamaica
- Rentals with a fireplace Jamaica
- 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
- Rentals with a washing machine and dryer Jamaica
- Villa rentals Jamaica
- Rentals with a firepit Jamaica
- Rentals with a sauna Jamaica
- Pet-friendly rentals Windham County
- Pet-friendly rentals Vermont
- Pet-friendly rentals United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- West Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Killington Resort
- Bromley Mountain Ski Resort
- Mount Monadnock
- Montshire Museum of Science
- Mount Sunapee Resort
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Camp Plymouth State Park
- Quechee Gorge
- Jamaica State Park





