Vacation rentals with outdoor seating in Great Barrington

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Great Barrington

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

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Guest favorite

Home in Hudson

4.95 out of 5 average rating, 130 reviews

Hudson Retreat w/ Hot Tub, Fireplace + Fire Pit

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

Guest favorite

Rental unit in Copake Falls

4.92 out of 5 average rating, 299 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Superhost

Cottage in Hudson

4.8 out of 5 average rating, 102 reviews

Stylish Spa-Cottage Escape@Hudsons ClearCreekFarm

1 minute off Warren St - salt water pool and hot sauna respite! No expense spared reviving this Historic 18th century 80 acre estate - heated pool, cedar barrel sauna, heated bathroom floors, original wood finishes, french door patio under stain glass windows from NYC’s iconic Chelsea Hotel. You’ve found the perfect combination of transcendentalist oasis with modernity providing a most comfortable stay. Enjoy a dip, steam, rolling meadows, goat petting, cocktail by fire on your patio!

Guest favorite

Cottage in Ancram

4.99 out of 5 average rating, 173 reviews

Lake View & Pet Friendly Wood Burning Fireplace

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

Guest favorite

Home in Lake Katrine

4.95 out of 5 average rating, 109 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favorite

Home in Rhinebeck

4.93 out of 5 average rating, 205 reviews

3Br Creekside Cottage on 130 acre forest w/ trails

Creekside Cottage is an extraordinary private escape nestled against a winding creek running through the rocky gorge of an 130 acre magical historic farm. Explore miles of hiking trails through old forests, trout creeks, and a 90ft waterfall or simply relax by the fire pit while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplaces, great wifi and comfortable bedrooms with quiet workspaces- learn more on our site cascadafarm

Guest favorite

Camper/RV in Lee

5 out of 5 average rating, 131 reviews

"Glamping" getaway in the beautiful Berkshires

Nestled in the Berkshires with mountain views and incredible sunsets. Relax under the stars and sit around the campfire with your favorite people. Perfect for families, friends or couples. Minutes to Tanglewood! This is a beautiful spotless RV with two slides a private master bedroom and a 4 bed bunkhouse at the opposite end. Lovely dining area, living room, kitchen and full bathroom. On its own little gravel road. We have a fire pit with wood included along with delicious well water

Guest favorite

Camper/RV in Catskill

4.83 out of 5 average rating, 144 reviews

Camping in the Catskills

Come escape reality with a vacation in the beautiful Catskills. Enjoy your stay in a clean, comfortable camper. Hang out by the fire pit while dinner cooks on the BBQ grill. All cooking/dining ware included. Bring along your outdoor games! There is plenty of space for volleyball, corn hole, etc. Spend the day exploring the various hiking trails and swimming holes in the area. Located 7 minutes from the Village of Catskill, 20 minutes from Woodstock. Outdoor smoking OK. WiFi included.

Guest favorite

Home in Pittsfield

4.98 out of 5 average rating, 118 reviews

Hidden Oasis in the Mountains by Evergreen Home

Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial gardens & sip coffee as you watch the sunrise over the mountains from the screened-in porch. Unwind in the hot tub, relax on the stone patio by the fire pit, & dine on the deck. Just minutes from Lenox & Tanglewood, this attractive 5 BR home boasts a large, fully-outfitted kitchen, comfortable Tuft & Needle mattresses, & spacious living areas with stunning mountain views.

Guest favorite

Home in Freehold

4.95 out of 5 average rating, 155 reviews

Come and Stay at Our Catskill Hideaway

Follow us at catskill_hideaway Come and Stay at our Catskill Hideaway. We have some of the best places for skiing, snowmobiling, snow tubing, shopping, eating, swimming, hiking, mountain biking, and much more. Within only 30 minutes of this haven.5-Star Super Host for three years. This 900 sq. ft. home is very cozy, with three bedrooms and two bathrooms. This location is perfect when you need a break from the hustle & bustle of life. Relax & enjoy the beautiful Catskill mountains.

Superhost

Cabin in Ruby

4.9 out of 5 average rating, 105 reviews

Enchanting Upstate Cabin w Pool, Firepit

Welcome to our family-friendly haven in the heart of the beautiful Hudson Valley, just 10 minutes from Kingston, Saugerties, and Woodstock. Less than 2 hours from New York, our retreat offers an idyllic escape surrounded by enchanting forest views. Great for large groups, and year round stays with a heated pool and air conditioning in summer months. Just 40 mins away from skiing Hunter. Listing pics by @dirtandglass and @heypamcakes See more snapshots @theserenityhomes on IG.

Superhost

Treehouse in New Marlborough

4.91 out of 5 average rating, 122 reviews

Double 3 Bedroom Tree House in the Berkshires

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.