Vacation rentals with outdoor seating in Pittsfield

Find and book unique outdoor seating rentals on Airbnb

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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Guest favorite

A living area is visible, featuring a sleek gray couch and a modern chair positioned near a stylish fireplace. Artwork is displayed on the wall, and natural light illuminates the space. A neutral rug adds texture to the polished floor, with a bedroom area partially seen in the background.

Apartment in Copake Falls

4.91 out of 5 average rating, 323 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!

Top guest favorite

Home in Ancram

4.99 out of 5 average rating, 178 reviews

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

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

Top guest favorite

A spacious deck area features a propane fire pit surrounded by Adirondack chairs. The view overlooks the serene lake, framed by trees. The scene captures natural light and greenery, creating a peaceful outdoor setting for relaxation.

Cottage in Southwick

4.98 out of 5 average rating, 104 reviews

4 Kayaks Fire Pit & Lake Views from Hot Tub

Congamond House is the perfect lake home getaway. Kayak the calm North Pond. Get your breathtaking pics of the surrounding wildlife. Cuddle up on the deck and enjoy the stars or relax in the hot tub under the deck while gazing upon the lake. This 1500 sq ft cottage is the perfect size for 2 families. (4 adults w/4 kids or 6 adults) Minutes from Six Flags Amusement Park, the Big E and the Basketball Hall of Fame 4 Kayaks that seat 6. Paddles and life vests provided 20 min. from Bradley Airport

Superhost

A spacious Bell tent is positioned on a custom-built platform in a tranquil setting. Solar-powered string lights illuminate the tent, while Adirondack chairs and a campfire ring are arranged nearby, providing a cozy outdoor gathering space.

Campsite in Hillsdale

5 out of 5 average rating, 5 reviews

Cute Bell Tent at Upper Shire in Hudson Valley, NY

A 13-ft diameter White Duck Bell Tent on a custom-built tent platform in a Pine Grove next to a shady pond. We've included a campfire ring with a grill, solar-powered string lights, Adirondack chairs, and campfire blankets. Our Bell tent is outfitted with a small Jackery power station, one queen-sized air mattress, and a sleeping cot with a Japanese futon. Hillsdale, NY has a brewery, cidery, the longest Zipline in North America and so much great hiking nearby. Hudson is 22 minutes away.

Guest favorite

A camper is positioned on a grassy area surrounded by trees. A fire pit is visible with several chairs arranged nearby. An outdoor table is shaded by an umbrella, and a BBQ grill stands beside it. A patterned mat lies on the ground.

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.

Top guest favorite

The outdoor space features a gravel area adorned with a decorative rug. A picnic table is positioned under a well-lit awning, and a small outdoor kitchen area is visible. Surrounding greenery provides a natural ambiance, while a potted plant adds a touch of color.

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 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

A cozy living area is featured with a dark sofa adorned with various decorative cushions. Two colorful art pieces hang on the light gray walls, complementing the modern wood flooring. A round coffee table is positioned at the center, and a small side table holds a decorative vase with flowers.

Apartment in Waterford

4.91 out of 5 average rating, 282 reviews

HOT TUB & New Stylish Saratoga County Efficiency

About the space Brand New Everything. This newly created space offers city style interior decor with outside space to enjoy. This includes the New Trex deck with HOT TUB and outdoor relaxation. Situated on large lot- this space offers convenient access to local highways (5 min from I-87, 10 min from 787). Off street parking for 2 vehicles. RV, boat, trailer space available on site. Within 2 min -be at convenience store, pizza shop, ice cream, mini golf, town park and more..

Guest favorite

The kitchen area features a light countertop with modern cabinetry and a stylish backsplash. A coffee maker, dish drying rack, and sink are visible. Organized jars hold various kitchen supplies, creating a functional and tidy space for meal preparation.

Camper/RV in Westhampton

4.89 out of 5 average rating, 157 reviews

AirbytheStream waterfront, private, clean and cozy

Beautiful private camper with outdoor deck on the water. All the creature comforts but half the price. Very private yet 15 minutes to Northampton or Easthampton. Kitchen sink, 2 burner stove, refrigerator, toilet and shower, one queen bed and twin bunk beds, dinette can also turn into a bed. Pots and pans, silverware and cooking utensils are provided. Camper has power and water as well as heat and air conditioning. There is a Blackstone griddle for outdoor cooking.

Guest favorite

A rustic treehouse is nestled among verdant trees, showcasing a mix of reclaimed materials. Steps lead to a welcoming entrance, with soft lighting illuminating the exterior. A gravel area is visible in the foreground, with outdoor seating options set up nearby.

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.

Guest favorite

The exterior of a charming yellow cottage is visible, featuring dark green shutters and a welcoming porch with decorative elements. A well-kept garden with colorful flowers and greenery surrounds the cottage, while a gravel pathway leads to the entrance under a partly cloudy blue sky.

Cottage in Monroe

4.9 out of 5 average rating, 126 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Top guest favorite

A spacious canvas tent is shown, featuring a queen-sized mattress with natural linens. Two rustic wooden chairs are positioned outside on the wooden deck, with a small table nearby. Natural light enters through the tent's entrance, illuminating the cozy interior.

Farm stay in Johnsonville

4.98 out of 5 average rating, 317 reviews

Overlook at Graceful Acres Farmstay

Enjoy the grace of a historic family farm in the heart of eastern NY. Let the cool, fresh air and sounds of the outdoors start your day. Fill your time with a hike across our 440 acre farm then spend time with the animals and learn more about regenerative farming during a scheduled farm tour. Graceful Acres Farmstay is situated an hour south of the Adirondack State Park and within 35 minutes of Saratoga Springs, Albany, Troy, NY and Bennington, VT.

Guest favorite

A tranquil deck area features a dark wicker table with a glass top, surrounded by wooden flooring. A small potted plant adds greenery to the space, while the view showcases a calm lake framed by trees, creating a serene atmosphere.

Home in Copake

4.96 out of 5 average rating, 192 reviews

Lakefront +pets +skiing +bbq +firepit +games

With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everything or nothing. This is the best location on Robinson Pond with beautiful views and access to the private beach and deepest part of the lake. Clear your headspace and enjoy this year-round escape with four seasons of activities and a cozy home to remind you of the greater things in life.

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What guests are saying

Glamping Tent with Heater & Amazing Views

5 out of 5 average rating, 10 reviews5 months ago

Brian’s place is awesome, really neat space. The view is gorgeous, Brian provides everything you could need for a night or more of camping. The bed was soft & toasty. Plenty of light inside, great options to cook on/utensils etc. Mr Heater was nice and toasty! Space is big and plentiful, doesn’t feel cramped. Outdoor fireplace and bonfire are cool. Outhouse was VERY clean. Highly recommend & would (probably will) stay again. Very peaceful and private. Thank you!

Yurt in Cambridge

What guests are saying

Lake house retreat Granby CT

5 out of 5 average rating, 7 reviews1 week ago

We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!

Home in Granby

What guests are saying

Charming House by Saratoga Lake - Prime Location

4.88 out of 5 average rating, 16 reviews2 months ago

Rebecca's bungalow was a great place for our family, including our dog to stay. It's rare to find such a welcoming space for pets. Ample blankets and pillows were greatly appreciated as many hosts don't include these items. The space was larger than anticipated which was also a nice bonus. If you're looking for hospitality and location at an affordable price, definitely consider this as your next option if you're headed to Saratoga Lake.

Home in Saratoga Springs

What guests are saying

Summit Lake Yacht Club | Starboard

5 out of 5 average rating, 23 reviews3 months ago

This place was amazing, exactly like the photos. Whatever cleaning service they use is pristine, it felt like everything was brand new out of the box, not even a fuzz or spec in the bathroom or kitchen. I really appreciated that. The backyard is huge, and a nice unexpected surprise. It’s extremely private and dark at night so recommend getting there during daylight. Hudson is less than 20 mins away and there are great little spots like local 111 in the neighborhood. Had a lot of cooking dishware, also very appreciated. Over all absolutely loved my stay and will absolutely be booking again!

Apartment in Hudson

What guests are saying

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

5 out of 5 average rating, 13 reviews1 month ago

We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!

Home in Great Barrington

What guests are saying

Waterfront, Dock, Sunsets and Kayaks!

5 out of 5 average rating, 20 reviews9 months ago

We loved our time here. The house was perfect—clean, well appointed, new appliances. We cooked and grilled often. Being right on Lake Buel made for pristine, beautiful mornings and evenings, meals at sunset, long leisurely talks at the lake, it was truly a wonderful time away. The more athletic among us swam and kayaked. The rest of us loved just sitting, reading and talking at the dock. The house is an easy drive to all the Berkshire sites. My only caution is parking. I wouldn’t bring more than two cars preferably sedans or small SUV’s—nothing bigger. Parking is plentiful for that, but no more. The owners were so very responsive, kind, and really helpful. They wanted to make sure we had all we needed. We had some questions at the beginning, and they were easy to reach and solved our problems. Highly, highly recommend this beautiful home.

Home in Great Barrington

What guests are saying

Lakefront cottage on burden lake in Averill park

4.89 out of 5 average rating, 9 reviews5 months ago

Very peaceful! Space was comfortable and it was nice to have a relaxing getaway and take a step back from work. Can’t wait to book again in the summer and take full advantage of what the lake has to offer! Lauren was an excellent host and very communicative.

Home in Averill Park

What guests are saying

WATERFRONT on the Hudson oasis🎒🛶🎣🔥Bring your boat!

4.89 out of 5 average rating, 56 reviews6 months ago

So, this space is an RV. I had never stayed in an RV, so there were a few things that I had to get used to. Firstly, the space is bigger than I had expected, which was a nice surprise. That said, the shower is incredibly tiny. Barely room to turn around, so be ready for that. The big difference is that this home is designed to be moved, so anything that can open and close has a very strong and sometimes complex locking system. Took a while to figure out how to open the fridge and the front door. Latches and doubly secure I assume so that nothing will open up while the home is in motion. The light switches are in odd places, the temperature control is a bit complex. Be sure to get clear instructions on using them. The RV has its own yard that is extremely well equipped. It's on a lovely creek. There's a gazebo and a fire pit and a swing, which are all nice additions for your stay.

Camper/RV in Saugerties

What guests are saying

Sunset Bungalow on the lake.

4.96 out of 5 average rating, 27 reviews7 months ago

Our stay was fantastic. Great location being right on the lake and waking up to that view every morning. Short drive to the main town. Close to restaurants, activities and gas stations. So many thoughtful touches put into the home that made it feel like home. Host provided many amenities (kayaks, paddleboat/board, fire pit, outside lounges, food goodies, coffee, toothbrush, games etc.) Host was very responsive and flexible. For a pet friendly location it was very clean. We are so grateful we got to bring our boy and share this amazing trip with him. He loved the dock. Would love to stay here again and would suggest this location to anyone wishing to visit Saratoga!

Bungalow in Saratoga Springs