
Holiday rentals with outdoor seating in Hampshire County
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Top-rated rentals with outdoor seating in Hampshire County
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Popular amenities for outdoor seating rentals in Hampshire County
House rentals with outdoor seating

Beautiful, quiet and cozy home in Becket!
My wife and I stayed here 2 night with our dog and had a great time. The cabin was super cozy and had everything we needed during our stay. Special shoutout to the couch, which was extremely comfortable for late night movie watching! If you are looking for a quiet weekend away to do some hiking, I would certainly recommend staying here. The town of Becket is very rural and food options can be somewhat limited but the house has a full kitchen and grill to use if that's more your style. Overall 5 stars would stay here again.

Victorian house near Smith college and downtown
This was the absolute perfect place for our family to celebrate our daughter’s college graduation with 3 generations of family. The hang out space and kitchen were excellent for our family and friends. The house is old and charming with some quirks that we chose to love. Highly recommend and grateful for the memories made. Jeff couldn’t have been a better host.

Moonstone Lake House – romantic, serene, fun!
Mighty is fantastic! Her place is brimming with art and comfort, soft colorful rugs, creativity and spirit in every nook and cranny. So many thoughtful details from the toilet seat warmer to the lavender sachets. Just everything. But that lake that meets the back deck. It is magical. What a place and what a kind and caring host.

An 18th century farmhouse
What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!

Lovely 2BR Home Close to Downtown
I've stayed at many air bnb's and this is my favorite. The house is inviting, warm, beautiful and comfortable. It provided a wonderful environment to rest and renew. The kitchen is filled with light and looks out onto the yard which is green and host to lovely birds and bird song. The patio was also inviting and comfy for a meal or to sit with a cup of tea/glass of wine and unwind or read a book. The neighborhood is vibrant, safe and within easy walking distance to downtown. The host Louisa has paid attention to every detail to ensure an easy and very comfortable stay. i highly recommend!!!

Magical, Rural Getaway in the Berkshires
This place was great, I was a little concerned it may be too rustic based on the pictures, but the place was fabulous. No problems with wifi, access, sleeping arrangements. The open space for the kitchen/tv room were so great for our large family. Everything is well appointed, there are clear instructions everywhere on how to use anything in the house. It was really nice for our short weekend stay for graduation. I felt the kitchen was better stocked than most places I've stayed. They had everything we needed. I wish we could have used the fireplace on this rainy cold weekend, but heard maybe it's an Airbnb thing not an owner thing. If you want to head to this area, this was a great place to stay.

Real Estate:Therapy - Lake, Laundry, Love it
Edson’s place was perfect for my family of 4 for a long weekend, could have easily stayed for a week. Weather was rainy and chilly but the house had everything we needed to cook and play and chill. when the sun came out we really enjoyed paddle boarding and walking around the lake. Would definitely come again

Stone n' Sky Lodge
Sarah and her place were absolutely wonderful!! There are not enough great things to say about Stone n’ Sky Lodge. Our big group of 9 fell in love with cabin immediately, and Sarah was very responsive and made us feel so at-home. As past umass grads, we were familiar with the area, but the cabin gave us a new place to make memories in western Mass. Thank you so much Sarah, you made our trip unforgettable and we can’t wait to come back!
Apartment rentals with outdoor seating

Sunny, light filled loft in 1873 Colonial
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.

Cozy, Private, Central 1 Bdrm, Large Yard
Rebecca's rental was extremely comfortable and cozy. And the beautiful garden and plants only made it even more so. The apartment is stocked with everything you could possibly imagine which made the stay very convenient. I highly recommend.

Experience Three Sisters Sanctuary
Amazing stay at Richards. It is like the photographs and so much more. Richard was friendly and helpful and enjoyed sharing his home, sculptures and gardens with others. The apartment is beautiful and peaceful and a great getaway. He has put so much love and energy into his home and property and we are so lucky to be able to enjoy it also. I look forward to returning. A nice escape into the country side of western mass but still close to so many adorable small towns, farms, Northampton and fun little back roads.!!!

Historic Richardson House, 1873 farmhouse
Excellent stay! Michael's place had everything we needed for our family visiting the area for graduation. Well-appointed kitchen and strong shower were highlights Restaurants, coffee shops, and stores all within walking distance. Would highly recommend.

Sunny carriage house apartment
Beautiful home, many thoughtful touches to make traveling easy and comfortable! Thank you!

Woodsy hideaway apartment
This was a very nice stay. Deborah was very responsive to our needs without being intrusive.

Florence ctr 1br apt near town, trails, river!
The super host Bruno was “super”! He was a pleasant timely communicator. My partner and I stayed for one night. We were very pleased with the space. It was clean and spacious. The queen bed was very comfortable. The living room had cozy furniture. The shower had amazing water pressure and plenty of hot water. I suggest you read the instructions of how to turn the shower on and set the temperature in the listing. The location was perfect. It was only an 8 minute drive to Northampton center which offers a wealth of restaurants and unique shops. Also it was only a 2 minute drive or 20 minute walk to Florence center. Definitely check out the Florence Pie Bar, Miss Florence Diner and Coopers Market. Just a 10 minute walk from the apartment is Masa Mexicana- a great Mexican restaurant. The apartment was in a very quiet neighborhood and set in back, on the second floor. It was private and looked out onto some pretty greenery. It had all the amenities. We would definitely stay here again!

Tree Top Suite, cozy downtown apartment
Very comfortable apartment that provided that small things you sometimes forget.
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- Six Flags New England
- Monadnock State Park
- TPC River Highlands
- Jiminy Peak Mountain Resort
- Bushnell Park
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Dinosaur State Park
- Brimfield State Forest
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Naumkeag
- Brignole Vineyards
- The Shattuck Golf Club