Vacation rentals with outdoor seating in Jamaica

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Jamaica

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Guest favourite

Tiny homes in Jamaica

4.88 out of 5 average rating, 345 reviews

Forest Cabin ~ 7min to Stratton, Cozy, Private

Authentic Vermont post and beam cabin is 3 miles from Stratton's Sun Bowl, a short 7 minute drive away. Swimming at the brook on the property. Dogs are welcome, $30 fee per dog. Sorry, no cats due to allergies. Vinyl record player & records, VHS & videos. Full kitchen. Satellite Internet/WiFi 20-100 mbps. The bathroom has a composting toilet - it is odorless and easy to use. Heat options: 2 gas wall furnaces, wood-stove & pellet stove. Front porch, picnic table, fire pit & propane BBQ grill.

Jun. 4 – 11

$154 CAD per night

Guest favourite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov. 5 – 12

$165 CAD per night

Guest favourite

Cabin in Jamaica

4.9 out of 5 average rating, 135 reviews

Jamaica Mod A Frame

Set above where the Wardsboro brook meets the West River in Jamaica, VT, our completely renovated A-frame blends the best of nature and modern living for a perfect getaway experience. Close to Stratton, Mt. Snow, Magic Mountain & Bromley as well as Ball Mountain Brook, Jamaica State Park, Hamilton and Pikes Falls. Put on some records and cozy up to the fire, listen to the river soaking in our wood burning hot tub or roast some marshmallows and check out the stars-this is the recharge you need.

Jul. 26 – Aug. 2

$470 CAD per night

Guest favourite

Home in Jamaica

5.0 out of 5 average rating, 101 reviews

Stratton Spa House with Man Cave

MANAGED BY A 5 STAR TEAM WITH MULTIPLE 5 STAR HOMES Perched on a babbling brook this 4700 square ft. contemporary has all your needs covered. Smart tech, 3 fireplaces, man cave, streaming entertainment, home theater, spa suite, hot tub, sauna, pool table, darts, poker room, dueling xbox room, giant master suite, big guest suite with wood burning stove, large dining table, fully equipped kitchen, Keurig, screened porch, 3 private acres, sun deck, bbq, 1/4m walk to water falls and swimming hole.

May 7 – 14

$649 CAD per night

Guest favourite

Cabin in Jamaica

4.99 out of 5 average rating, 187 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Sep. 12 – 19

$239 CAD per night

Guest favourite

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Sep. 20 – 27

$246 CAD per night

Guest favourite

Apartment in Jamaica

4.84 out of 5 average rating, 199 reviews

The Getaway

Nestled in the woods but yet only; 10 min. (5.3 mls) to Stratton Mtn, 11 min. (7.6 mls) to Bromely Mtn, 26 min. (18.2 mls) to Magic Mtn, 33 min. (19.2 mls) to Mount Snow, 50 min. (38.2 mls) to Okemo and 68 min. (51.2 mls) to Killington. Also only minutes away from Southern Vermont golf resorts, Appalachian, Long and West River Trails, beautiful ponds rivers and falls, state parks, Manchester outlet shopping and the Equinox, fine dining and the most brilliant foliage in New England.

Mar. 25 – Apr. 1

$215 CAD per night

Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Mar. 29 – Apr. 5

$231 CAD per night

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 495 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Sep. 20 – 27

$161 CAD per night

Guest favourite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

-The Ice Pond Camp, East Dover, VT. Small well equipped country cottage, surrounded by nature & quaint beauty. Enjoy the lovely Southern Vermont seasons as you relax, disconnect, recharge & spend your days living a slower pace - surrounded by authentic rural beauty. Close to Wilmington and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, green farms, brooks,ponds and lakes, walking trails & country roads.

Oct. 22 – 29

$190 CAD per night

Superhost

Cabin in Jamaica

4.88 out of 5 average rating, 264 reviews

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, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

Mar. 10 – 17

$865 CAD per night

Superhost

Home in Jamaica

4.84 out of 5 average rating, 232 reviews

Historic 1832 Parker House ~ Sleeps 10, Pool Table

Escape to a Serene Retreat in this Quintessential Vermont Farmhouse Nestled amidst the breathtaking landscapes of Southern Vermont, this charming 3,000-square-foot farmhouse offers a tranquil retreat for families and groups seeking a taste of Vermont's rustic charm. Just 10 miles from Stratton Ski Resort and within close proximity to Bromley and Magic Mountains, this idyllic property is the perfect base for exploring the region's vibrant winter sports scene.

Oct. 12 – 19

$311 CAD per night