Holiday rentals with outdoor seating in Stockbridge

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Stockbridge

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

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Top Guest favourite

Tent in Middletown Springs

5 out of 5 average rating, 43 reviews

Green Mountain Nugget Private tent site for two!

Closed Sept 15-July 1. New 9-18 holes DiscGolf onsite! Enjoy a get-a-way for two in a private, spacious tent, listen to the river as you relax out of doors on a queen size bed. Set in our meadow between a pond and river and engage with nature. Spend the evening under the stars and around the campfire (wood included), relax at the private beach, or visit the nearby lakes, state parks, stores, restaurants or Slate Valley Trails. Convenient drive to the tent. Bring towels, water shoes, & charcoal.

Top Guest favourite

Home in Sharon

4.99 out of 5 average rating, 101 reviews

The Willow House: a Modern Vermont Retreat

Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

Guest favourite

Home in West Windsor

4.93 out of 5 average rating, 43 reviews

Chuck's Place

Chuck's is a neat and tidy stand alone home dedicated to vacation rentals. Fully stocked! Private and convenient on 7 sunny acres overlooking Mt Ascutney. Plenty to do out your door- hiking, snow-shoeing, skating, sledding, skinning and family-friendly skiing over at Ascutney. Brownville Butcher and Pantry is an active gathering place in the village. The best meats and fish anywhere! More downhill and cross-country/skate skiing, restaurants, pubs, and breweries all within 25 minute drive.

Guest favourite

Home in Fairlee

4.95 out of 5 average rating, 238 reviews

The Upper Valley Retreat

This Top Rated Property was asked to be on The Emmy Award Winning Show “Staycation” and Guests always say “Pictures Don’t Do It Justice!” A Massive 20 Acre Estate & Apple Orchard that sleeps 36+! Only 25min from Dartmouth! Majestic rolling lawns nestled along Brushwood Forest. Private outdoor space that will allow you to enjoy breathtaking sunsets or latenight stargazing. Everything you will need for an unforgettable retreat provided, including a pooltable, pingpong table, grill and fire-put

Top Guest favourite

Home in Bridgewater

4.96 out of 5 average rating, 45 reviews

Killington Ski House Close to Skyeship, Woodstock

Escape to Vermont with central access to the mountain, dining, breweries, shopping, and more! The iconic Gondola House is a 3-level home comfortably sleeping up to 10 people with 5.5 bedrooms and 2 bathrooms. 10 min to Skyeship Lodge. 5 min to Long Trail Brewery. 15 min to Woodstock. 16 min to Bear Mountain lodge. The space includes a large open living, dining and stocked kitchen with dishwasher. Mud room with laundry. Gorgeous outdoor hot tub, covered porch with grill and plenty of seating.

Top Guest favourite

Place to stay in Corinth

5 out of 5 average rating, 17 reviews

Dante’s Inferno Luxury queen bed + many extras

Gorgeous canvas bell tent in secluded setting, outfitted with luxuriously dressed queen memory foam bed, pillows, table, lighting, chairs, outdoor patio set + hammocks. Coffee and tea with cream & sugar avail all day. We provide drinking water, a cooler to use, everything but your clothes and meals (except breakfast, we have that covered!) *Solo Stove for a private Glampsite fire available to rent for $50/night, all wood provided. Limited inventory, must reserve, first come first served

Guest favourite

Cabin in Plainfield

4.96 out of 5 average rating, 148 reviews

Magical cabin with amazing views

100 year old , freshly renovated cabin that is in the middle of five 100 year old apple trees with incredible Mountain View’s. The cabin sits 100ft uphill from my 1842 brick farmhouse and is surrounded by apples trees, an ancient elm tree, fields and my berry patches. The huge deck has a dining table, lots of seating and and outdoor shower. Off the side of the deck are two claw foot bathtubs with hot and cold water for you to soak in. Note, tubs aren’t usable during the freezing months.

Superhost

Cabin in Bridgewater

4.91 out of 5 average rating, 100 reviews

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Top Guest favourite

Home in Moretown

4.99 out of 5 average rating, 270 reviews

Dramatic Views at the Above the Clouds Guesthouse

As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike! COMPLETE COVID-19 CLEANING

Top Guest favourite

Home in Addison

4.96 out of 5 average rating, 221 reviews

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

Guest favourite

Campsite in Vershire

4.88 out of 5 average rating, 172 reviews

Camping on a Private Pond

Picturesque setting on a small pond and a brook for fishing. A bit off the beaten path, yet three miles to the closest store. (There is NO wi-fi or cell service on the pond but you may come up to the house if necessary). We have local hiking and two large lakes close by. Farmer's markets and acclaimed theatre are available throughout the Fall along with local beer-fests. Most of all, we have one of the most stunning foliage seasons in the country!

Guest favourite

Home in Bradford

4.89 out of 5 average rating, 70 reviews

Town Country Home

Relax with the whole family at this peaceful place to stay. Enjoy large outdoor lawn and gardens, spacious deck with mountain views. Prime location at end of country road, yet close to town for shopping and restaurants. A getaway location that allows you both indoor and outdoor spaces to relax, unwind from the hustle and bustle of daily life. Great walking area on wooded trails or through 70+ acres of fields.