
Holiday rentals with outdoor seating in Cheshire County
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Cheshire County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Peaceful Mill with Waterfall - Top 1% Home
Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated remote workspace

Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Cozy and Romantic Granite Lake Cottage Getaway
Welcome to "Corgi Cottage" ~ your private peaceful getaway to pristine Granite Lake. Enjoy sunrise over the lake from the deck and sunset over the backyard barn. In between, spend the day on the lake in your private sandy cove with dock, fishing, hiking or relaxing. Three mile lake road for walking or biking. The area offers many hiking trails and Mt. Monadnock only 30 minutes away. Small convenience store offers basic amenities while Keene’s many shops and restaurants are only 15 minutes away.

Chalet Sonsie: A Sweetwater Stay
Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

Private Dublin apartment nestled in the woods
Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

Meadow View
Sunlit sanctuary in a 275-year-old farmhouse. Our 'in-law' suite is a cozy and full of art. Adjacent to Casalis State Forest, enjoy scenic trails for biking, hiking at all seasons. Trail starts from end of our property. Enjoy Peterborough's downtown (5min drive) with yoga studio, cute restaurants, bookstore, movie theater and neighborhood grocer. Meadow View offers a 750 sq ft private suite with a king-size bed, clawfoot bathtub, and a mini kitchen. Your comfort is our priority.

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.

Swiss Chalet Family Retreat!
Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.

1850 Waterfall Mill-Loft Style Chic
IMMACULATE COUNTRY HOME W/ FAST WiFi in fresh air New Hampshire. Snuggled in on a quiet street, yet steps away from DOWNTOWN, two "Mini Whole Food" markets! State-of-the-art gourmet kitchen fleshed out with organic spices, wares for entertaining, and other luxuries such as a rReverse Osmosis drinking faucet. Stunning sunlit water views and soothing water sounds! Beautiful antique furnishings and marble finishes add to the unique beauty of this New England home.

The Great Room in Historic Fitzwilliam
Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.
Popular amenities for Cheshire County outdoor seating rentals
Holiday House Rentals with Outdoor Seating

The Boat House on Granite Lake

Spacious Brattleboro home on river, walk to town

Hazelhurst Vacation House

The Brick House on Washington Street

Lovely Brick Schoolhouse

A Quaint Setting in the Center of Walpole Village

Newer Home on quiet 200 acre lake - sleeps 6

Governer's Brook Camp - 2 Bedroom
Apartment rentals with outdoor seating

Lovely light-filled 2 bedroom flat

Sunny Apartment with Goats

Dover by Downtown

On the Water at North Bridge Cove, Patio and Sauna

Schoolhouse No. 1

Private Apartment with a Mt. view

Privacy, View, Amenities, Gym, Garage included too

Apartment in Historic Home
Other holiday rentals with outdoor seating

Romantically Cheerful Country Cottage apt.

Willow Falls Home ~Hot tub & Waterfront

Charming Woodland Hideaway

Lakeside Retreat 4BR/2BA- 2hrs from Boston

Country Cottage

Sunnyside Farmhouse with lots of outdoor spaces

Owls Nest Treehouse

A Farmhouse Reimagined
Destinations to explore
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- Rentals with outdoor seating New Hampshire
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- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bear Brook State Park
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Snhu Arena
- Mount Sunapee Resort
- Southern Vermont Arts Center
- Smith College
- Mount Holyoke College
- Emerald Lake State Park
- Mount Monadnock
- Massachusetts Museum of Contemporary Art
- University of Massachusetts Amherst
- Look Memorial Park




