
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

7min-Stratton Dogs OK Fire Pit EV Charger Arboreal
7min drive to pickleball, tennis, pool, golf, mountain biking and skiing @Stratton Resort. Soak up 13 acres of arboreal views from your private chalet. Light-filled w/ southern exposure. Deck and fire pit for stargazing, mid-century modern furnishings, new appliances, and 300Mbps Wi-Fi and a Mini Split AC/Heat. Convenient to ski areas, restaurants, shops, and swimming holes, yet secluded and quiet. Walk to Pikes Falls 29min to Bromley and Mt Snow AWD required for spring/winter. Pet fee $187.

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!

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

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.

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.

Cabin w/Hot tub, Sauna near Mt.Snow & Stratton.
Rustic cabin situated on a quiet cul-de-sac between Mt. Snow & Stratton Mtns. Features 2 beautiful wood burning fireplaces, sauna, outdoor hot tub & fire pit and Generac stand by generator. Modern kitchen on main floor w/4 bedrooms and 2 full bathrooms . Huge open concept layout perfect for entertaining. Natural light beams in onto the loft and master bedroom just upstairs from the main floor. Basement offers a pull out couch w/ easy access from driveway. Coffee /Firewood included.

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

50 Acres · Fall Foliage · West River Valley Views
Walk out the door onto 50 private acres of Vermont farmland, with a half-mile of West River rolling right through your backyard. In fall, the valley views from every window become something else entirely. Stratton Mountain is near by, just 10 minutes away and your furry friend will love the toasty warm wood stove. A private oasis escape. Prindle Cottage is a 1,400sqft rustic countryside cottage offering captivating views that will impress first-time visitors.

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.

Designer Chalet w/ Mountain Views close to it all
Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.
Popular amenities for Jamaica pet-friendly home rentals
Pet-friendly house rentals

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

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

The Grafton Chateau

Wild Blossom Farmhouse - a lovely family getaway

Charming Chester Farmhouse Near VT Slopes

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

Ski and Play in Manchester Center!

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

Heated Pool, EV Charging, Hot Tub & Barrel Sauna

Cozy Vermont Antique Sugar House with Fireplace

Log Cabin Near Stratton/Mt Snow

Beautiful rustic woods and fields retreat.

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

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Moon Valley Country Retreat no clean fee pets yes
Private, pet-friendly home rentals

Brook Haven Retreat - Minutes to Mt Snow&Stratton

Mountain side acres

Stunning Rustic Apple Barn - hot tub & sauna

Bread and Butter Apartment

Classic A-Frame in Jamaica

Little Red House Vermont

Rustic Cabin in foothills of Green Mountains

Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
When is the best time to visit Jamaica?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €297 | €313 | €217 | €202 | €184 | €190 | €198 | €199 | €193 | €214 | €197 | €279 |
| 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 Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Jersey City Holiday rentals
- Portland Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Chalet rentals Jamaica
- Rentals with a hot tub Jamaica
- Waterfront rentals Jamaica
- Cabin rentals Jamaica
- House rentals Jamaica
- Family-friendly rentals Jamaica
- Rentals with pools 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
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Jiminy Peak Mountain Resort
- Monadnock State Park
- 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
- Emerald Lake State Park
- Massachusetts Museum of Contemporary Art
- Montshire Museum of Science
- Mount Sunapee Resort
- Mount Greylock
- Camp Plymouth State Park
- The Montague Bookmill
- Quechee Gorge





