Vacation rentals with outdoor seating in Pittsfield

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Top-rated outdoor seating rentals in Pittsfield

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious tent is set on a grassy area, flanked by trees. A vehicle is parked nearby, offering convenient access. The entrance of the tent is framed by potted flowers, enhancing the natural surroundings.

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.

Guest favorite

Hut in Ripton

4.92 out of 5 average rating, 169 reviews

Skylight Hut. Glamping, hiking, biking, foliage

Hiker, gravel/mountain biker's paradise! Our quiet glamping retreat provides easy access to miles of wilderness. The hut has a cozy bed, kitchenette, and camping basics making for an easy and cozy getaway. Follow a trail to the Catamount Trail or drive a few minutes to the Long Trail. Enjoy miles of gravel biking from the door or go to Moosalamoo or Rochester for prime mountain biking trails. In the evening, sit on the deck under a blanket of stars and warm your toes by the fire. Paradise!

Top guest favorite

A serene outdoor area is visible, featuring a gravel patio with a dining table surrounded by chairs. Vibrant purple flowers frame the scene, while a tranquil pond and greenery provide a backdrop. The space is illuminated by bright sunlight, creating a relaxed atmosphere.

Home in Sharon

4.99 out of 5 average rating, 102 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).

Top guest favorite

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 favorite

A yurt with a beige and red exterior is surrounded by lush greenery. A wooden deck leads to the entrance, with comfortable seating visible. The backdrop features trees and an open view of the hillside, illuminated by natural light under a clear blue sky.

Yurt in Randolph

5 out of 5 average rating, 129 reviews

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Top guest favorite

A private patio set is displayed under a large red umbrella, featuring a glass-topped table surrounded by four chairs. A patterned rug covers the ground, with lush greenery and a hammock visible in the background.

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 favorite

The exterior of the cabin is presented with a spacious deck featuring seating and a dining area. Two claw foot bathtubs sit on the side, surrounded by a landscaped area with small plants. The cabin is framed by apple trees under a clear sky.

Cabin in Plainfield

4.96 out of 5 average rating, 149 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 favorite

A spacious living area features large windows framing mountain views and a cozy fireplace. Natural wood accents complement the soft furnishings, including a circular glass coffee table atop a patterned area rug. A dining table for two is positioned near the sliding doors leading to the outdoor deck.

Home in Moretown

4.99 out of 5 average rating, 271 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 favorite

A wooden dock extends over calm waters, reflecting a clear blue sky dotted with fluffy white clouds. The distant mountains along the shoreline provide a picturesque backdrop, enhancing the serene lakeside environment.

Home in Addison

4.96 out of 5 average rating, 225 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 favorite

A charming wooden cabin is situated among lush greenery, featuring a covered porch with Adirondack chairs. A stone table with granite top stands nearby, crafted from layered stones, creating a natural outdoor dining area. Vibrant flowers adorn the entrance, adding a touch of color.

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 favorite

Aerial view of a large purple house set against a backdrop of rolling hills and trees. The expansive lawn surrounds the property, showcasing natural greenery and a gravel driveway with parked vehicles. The scene is illuminated by bright daylight, highlighting the serene rural atmosphere.

Home in Fairlee

4.95 out of 5 average rating, 238 reviews

The Upper Valley Retreat

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