
Holiday rentals with outdoor seating in Jackson
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Top-rated rentals with outdoor seating in Jackson
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Vermont Dream Cabin~70 Acres w/Hot Tub & Fireplace
Log cabin w/ hot tub on 70 acres of Vermont forest with hiking/snowshoe trails, river & mountain stream. Cozy up with wine, games or book by the huge stone woodburning fireplace with fav music from the vintage Bose stereo, enjoy coffee & stargazing on the rocking porch while taking in the mountain views & wildlife or explore the forest & river trails. Enjoy making meals in the ample fully stocked kitchen, the outdoor grill & around the campfire. Crisp AC.*4x4/AWD a MUST for WINTER only BOOKINGS*

Guest House at Hummingbird Hill
Our small above-garage guesthouse on the New York-Vermont border is a retreat from busy life. The open floor plan, airy apartment has windows on all sides & overlooks woods & meadow. The guesthouse is ideal for those looking to get away from electronics and the internet (note: no Wifi), and hike and bike the area’s trails, and/or paddle the Battenkill River and area lakes. Or just sit on the deck with a book and cup of tea or glass of wine. Pets are welcome (we do charge a small fee for pets)!

The "Bird House" Cabin Retreat
Our Birdhouse Retreat is one of the most sought-after destinations for couples and individuals seeking to reconnect with nature. Nestled in the valley of the Taconic and Green Mountains just 30 minutes from Saratoga Springs, NY, boasting quiet solitude. It sleeps 1-3 people. 1000 acre wetland, easy access, unbelievable wildlife viewing. Fish, Ducks, Geese, Blue Heron, Otter, Bobcat, and beaver may be seen in this environment. Watch National Geographic's Building Wild Video: Float My Cabin!

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Out On a Limb • A Magical Treehouse Experience
Welcome to Out on a Limb, our magical treehouse nestled in the serene woods of upstate New York. This cozy, charming hideaway offers a peaceful & romantic escape, perfect for couples or solo travelers looking to connect with nature. Surrounded by towering trees, the treehouse provides a unique experience year round—from relaxing in the hot-tub on a snowy night, to stargazing by the campfire. The treehouse is always stocked with waffle mix & homemade frozen cookies. We can’t wait to host you!

The Farm Cottage- Quiet 1BR on Hobby Farm
Welcome to our peaceful 1-bedroom cottage on a small hobby farm, perfect for couples or solo travelers visiting the Bennington area. This cozy space is designed for rest and simplicity. Whether you're in town visiting family, exploring local trails, or just passing through for a few days, you’ll have a comfortable place to unwind and recharge. Thoughtful touches like fresh eggs from our chickens and homemade jams await you, while the cozy setup makes it easy to settle in and feel at home.

Apartment on the Battenkill 30 minutes to Saratoga
Enjoy the natural beauty of the Battenkill River in our private, charming, guest apartment located on the outskirts of Greenwich, New York just 20 miles from Saratoga Race Course and a lovely scenic drive to Lake George and Vermont. Our cozy space includes 1 private bedroom with a queen size bed (linens included), a couch that can sleep an additional 2, TV, dining space and a complete kitchen. Lounge on the spacious deck, fish, take a dip in the river and enjoy comfort of our cozy space!

A Bedroom in the woods with lovely views!
Picturesque location on farmland with views of the mountains. We are a micro farm. Wake up and watch the sunrise and go for a short hike on the property, and get to know the animals. We are located 35 minutes from Saratoga Springs and Lake George, NY and 45 minutes from Dorset and Manchester, VT. Hike the Adirondack or Green Mountains, paddle the streams or go to a nearby small city for a play, a festival, or a concert. There is a long list of things to do and see within an hour of us!

Schoolhouse Spa Retreat on a Vermont Farm
Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Cozy rustic cabin in the hamlet of Shushan. N.Y.
This cabin overlooks a nature preserve.lots of wildlife,with a peaceful and Serene atmosphere. animals are welcome. the battenkill river is closeby 30 min from Manchester v.t and Saratoga springs ny.cozy up to a fire with a good book,or head out for some designer shopping.hiking trails in Vermont and newyork and plenty of ski resorts ,and snowmobilng.within 30 min. we welcome all animals in the home. enjoy the quiet, and views of shushan NY.here..

LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Guest Cottage Battenkill BnB- A Peaceful Getaway
This newly renovated carriage house is nestled in the Battenkill River Valley alongside a picturesque spring fed Marsh . The post and beam structure is private and quiet as it is distanced from my family home . The kitchen is stocked with a bounty of delicious local and organic self serve breakfast choices plus a wide range of organic coffees and teas.Please feel free to let us know if you have any dietary restrictions.
Popular amenities for outdoor seating rentals in Jackson
House rentals with outdoor seating

High Oaks Lodge on Cossayuna Lake

Charming Vermont Schoolhouse

Cozy Modern Sugar House with spectacular views.

Quaint One-Story Vermont House with Mountain View

The Vermont Farmhouse|Hiking|Dog Trails|Village

The Gate House--Experience Vermont!

Vermont Mirror House

Quaint Williamstown Home 3 Bed
Apartment rentals with outdoor seating

Suite Sunset 311 Rice Lane Bennington VT

Cozy Riverside Apartment with Private Backyard

"The Parlors"

Shakespeare’s Folly Side Farm and AirBnB.

Charming Country Setting

Dog heavenly! Private, beautiful and relaxing.

Suite 23 - Spacious Sunny 2-BR with Mountain view

Cooper's Place
Apartment rentals with outdoor seating

Main St Escape | Explore Downtown Ludlow

Summer Dream! The Handle Lodge at Snowtree Condos

Heart of Saratoga: Track, SPAC & Broadway

Okemo Clock Tower Base Ski-in/Ski-out Condo

Great Amenities-Season Condo gym-sport center-pool

Great 2 bedroom condo at Stratton Mountain

Cozy Mt Snow Ski In / Out

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Providence Holiday rentals
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- June Farms
- Thacher State Park
- Killington Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Rensselaer Polytechnic Institute
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Adirondack Extreme Adventure Course
- MVP Arena
- New York State Museum
- National Museum of Racing and Hall of Fame





