
Holiday rentals with outdoor seating near Stratton Mountain Resort
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Top-rated rentals with outdoor seating near Stratton Mountain Resort
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Mountain side acres
10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit
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.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

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.

Yellow Sweetie at the Base of Stratton
Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

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.

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

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. I am as close or as far away as you would like me to be with my house right next door.

Cottage-7 min to Ski Stratton-Woodstove-View-DogOK
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.

Stunning mid-century house on 2.5 private acres
Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.

Vermont Farm Schoolhouse w/ Hot Tub, Sauna & Views
Escape to our historic schoolhouse on a 250-acre 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.

Modern Cabin ~ 3min to Stratton Resort
Enjoy your stay in this secluded mountain cabin a 3 minute drive to Stratton resort. The cabin offers a lovely space to unwind and relax after a day on the slopes. Hosts are happy to provide local guidance for skiing, shopping, and food. Situated amongst 45 private acres.
Popular amenities for rentals with outdoor seating near Stratton Mountain Resort
House rentals with outdoor seating

Clean, Captivating VT Farmhouse near Stratton!

Cozy Modern Sugar House with spectacular views.

The Vermont Farmhouse: Picturescue Country Escape

1850 Marble Path House

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Vermont Mirror House

Cozy Train Depot in Putney Vermont

Cheerful 1 bedroom cottage
Apartment rentals with outdoor seating

Comfort & Style for Winter and Spring Vacations

Private Apt. on Farm, Hot Tub with views!

Shakespeare’s Folly Side Farm and AirBnB.

HeART Barn Retreat

Globetrotter Retreat too - Minutes to the Mountain

Minimal organic hideaway inspired by nature

Cooper's Place

Yellow Door Inn
Apartment rentals with outdoor seating

Main St Escape | Explore Downtown Ludlow

Mount Snow Ski Chalet

Winter Dream! The Handle Lodge at Snowtree Condos

Ski In/Out, Cozy 3Bed condo steps to Village

Your Vermondo awaits: Steps to Lifts & Village.

Mtn. view, easy access to village

3 Story Condo - 5 Minutes to Mount Snow!

Okemo Ski-in/Ski-out, Steps to lift Condo
Other holiday rentals with outdoor seating

7 Min Stratton Mtn/15 Min Mt Snow /Wood Fireplace!

Log Cabin: Amazing Views, River Frontage, Hot Tub

Architectural GuestSuite

Beautiful Timber Frame Retreat

LUXE Forest Retreat

Charming studio in renovated 19th century church.

Barrel Sauna + Hot Tub & Mtn Views

Modern Cabin with Outdoor Spa on Vermont Farm
Destinations to explore
- Apartment rentals Stratton Mountain Resort
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- Rentals with a hot tub Stratton Mountain Resort
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- Pet-friendly rentals Stratton Mountain Resort
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- Family-friendly rentals Stratton Mountain Resort
- Rentals with a fireplace Stratton Mountain Resort
- Rentals with outdoor seating Stratton
- Rentals with outdoor seating Windham County
- Rentals with outdoor seating Vermont
- Rentals with outdoor seating United States
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Saratoga Spa State Park
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Lake George Expedition Park
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Peebles Island State Park
- Hooper Golf Course
- Dorset Field Club
- Fox Run Golf Club
- National Museum of Racing and Hall of Fame
- Pineridge Cross Country Ski Area




