
Vacation rentals with outdoor seating in Chesterfield
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Chesterfield
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

Modern Spacious Home with Mountain Views
Modern Home in Brattleboro with mountain view & many extras: Italian-Marble master-suite, Jacuzzi/Shower for 2, walk-in closet, king bed, grill, heated garage, cable, WiFi. Open-concept living room w/ cathedral ceiling, office, & movie screen. Large open kitchen w/ wine fridge. Second bedroom w/ loft. Explore hiking trails from backyard. Pets ok! 3 mins from Vermont Country Deli & I91 Exit 2. Walking distance to dog park, swimming holes. Downtown: 4 mins Mount Snow: 40 mins Stratton: 54 mins

Governer's Brook Camp - 2 Bedroom
Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Monadnock Sunrise Forest Hideaway
Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

In town, newly renovated studio with private deck
Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Mahalo Temple Retreat
Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

River View apartment
Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Bright and Modern Chestnut Street Apartment
Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful decor, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.

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.

Minimal organic hideaway inspired by nature
Akasha, the first floor of this historic 1800’s carriage house in the center of Putney Village, was gutted and meticulously renovated by the hosts into a unique wellness apothecary and cafe and now serene and beautifully conceptualized open concept studio apartment. Aged wood tones, textured plaster walls, poured concrete counter tops and elegant dining bar imbue an old world tea house aesthetic with modern sensibilities. A unique space for quiet contemplation and relaxation.

Charming studio in renovated 19th century church.
This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

Contemporary forest eco-retreat, mountain views
This is an open, light-filled one-Bdm apartment on the lower level of our hillside home, surrounded by forests, with stunning views. Your space is 719 sf + access to laundry. We are fully vaccinated, and ask the same of guests. If you think you may have Covid please tell us. We welcome all kinds of people, regardless of race, ethnicity, gender, etc. We may ask questions before accepting people who don’t have many prior reviews. We don't take pets, sorry.

Vermont Retreat Cabin, Romantic, Nature Immersion
A romantic and private getaway on a peaceful six-acre farm with views of fields and forest. ☽ Featured in STAY; Gorgeous Cabins of the East Coast ☽ Elevated design; thoughtful lighting; deeply romantic ☽ Quiet & private; star-studded skies ☽ Woodstove, deck, reading nook, firepit ☽ Local's Area Guide with our favorite spots ☽ Strong wifi, no TV ☽ Scrupulously clean using unscented products
Popular amenities for Chesterfield outdoor seating rentals
House rentals with outdoor seating

Green River Cottage-A Peaceful Country Retreat

Frosted Willows

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

The Brick House on Washington Street

Modern Downtown 12ppl Hot Tub Fire Pit Games

Vermont Winter Escape

Cozy Home for 2-5 People in Vermont

Charming House on 7 Acres in Rural New Hampshire
Apartment rentals with outdoor seating

Sunny, light filled loft in 1873 Colonial

"Up Top” at Ro & Oak House

Globetrotter Retreat too - Minutes to the Mountain

Private Dublin apartment nestled in the woods

Vermont Getaway Apartment

Mohawk Trail View/ private apt. no cleaning Fee

Quiet country apartment in farmland setting.

Cozy Stay in South Deerfield
Condo rentals with outdoor seating

Main St Escape | Explore Downtown Ludlow

Mount Snow Ski Chalet

Winter Dream! The Handle Lodge at Snowtree Condos

Seasons Condo on mtn-sports center-pool-Ski in-out

Great 2 bedroom condo at Stratton Mountain

Okemo Ski-in/Ski-out, Steps to lift Condo

3 Story Condo - 5 Minutes to Mount Snow!

Historic house in 4 Corners area
Quick stats about vacation rentals with outdoor seating in Chesterfield

Total vacation rentals
Explore 20 vacation rentals in Chesterfield

Nightly prices starting at
Chesterfield vacation rentals start at $112 CAD per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wifi availability
20 of Chesterfield vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesterfield rentals

4.9 Average rating
Chesterfield stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with outdoor seating Cheshire County
- Rentals with outdoor seating New Hampshire
- Rentals with outdoor seating United States
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Manchester Country Club - NH
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Mount Tom State Reservation
- Crotched Mountain Ski and Ride
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Dorset Field Club
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Fox Run Golf Club
- Clarksburg State Park
- Brattleboro Ski Hill
- Ekwanok Country Club




