
Holiday rentals with outdoor seating in Hampshire County
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Top-rated Holiday Houses with Outdoor Seating in Hampshire County
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

Moonstone Lake House – romance and serenity
A wonderful stay — Moonstone is charming and full of soul, with a deck right up on the lake’s edge. Beautiful scenery and a quick drive to many places. Woods nearby to walk in and provided kayaks make this spot great for nature lovers. Mighty was communicative and responsive, the cottage was filled with handwritten notes giving us any info we needed. Lots of personal touches and plants made it cozy. Good amenities and a little bigger than I thought from the pictures!

Lovely 4 bedrooms home with huge backyard to enjoy
Aung is a very helpful gentleman, after I left my personal stuff in the house he’s still very helpful to get everything back for me!

Historic Williams House
This house is drop dead gorgeous, clean, comfortable, and anything else you could ask for in an Airbnb. They do not supply coffee but they do have a French press and drip coffee machine - the only piece of info I wish I knew before coming. 10/10 experience would love to stay again.

Happy Valley getaway
Really lovely place. Spacious and super comfortable, stocked with helpful sundries and techy items in every room. Beautiful kitchen and downstairs bathroom! TV projector and screen a blast. While unexpected lawn maintenance limited some outside time, was otherwise a fantastic rental.

An 18th century farmhouse
I stayed for 3 nights. Bed was comfortable and sheets were great. Kitchen was fully stocked with food and beverages, even a bottle of wine. Very special place to stay in gorgeous part of rural Western Mass. Close to drive to colleges, delicious food and museums. I love the gorgeous roads, barns, trees. It was early Spring and little flowers were just popping up. I cannot recommend this stay more highly.

True Shangri-la, Country Retreat
Mary’s place is absolutely beautiful, inside and out - a gem of peace off the beaten path. There is a big kitchen that was great to cook in, the beds were big and comfortable, and the house is full of beautiful art. Mary was super helpful, and while she lives on the property, we still felt that we had complete privacy during our stay. We hope we can go back and stay again someday soon!

Lovely 2BR Home Close to Downtown
Louisa was a wonderful and accommodating host. The space was beautiful and perfect for our quick visit to Western MA to see family friends. It was clean, quiet, and homey and had lovely design touches that made it an even more enjoyable stay. We would definitely stay here again. Highly recommend!

Relax & Enjoy it all to yourself
Grest house. Would highly recommend to anyone with young kids - playhouse & trampoline and other fun for little ones.
Apartment rentals with outdoor seating

Charming & Quiet, walk to colleges
Bridget’s place is charming and close to downtown Amherst. She’s also a very responsive and accommodating host. 5 stars all around!

Warm & Stylish Apartment w/laundry - walk to DT
Heather's place is amazing...very spacious and was great for my two week stay for work. It really great it is so close to the highway and also local restaurants and shopping. Will definitely stay again if I am in the area.

Sunny, light filled loft in 1873 Colonial
I needed a local getaway while some work was being done on my house, and Peter's place was perfect. Comfortable, quiet, clean, and in a beautiful, rural location. Served my needs perfectly, and I will definitely recommend it to visiting friends and family.

Light filled three bedroom apartment DT Florence!
I chose to stay at Donna's a second stay because I appreciate the quiet neighborhood and very, clean comfortable home. Communication with Donna is easy and friendly.

Historic Richardson House, 1873 farmhouse
The apartment was perfect for our trip. We were there visiting my niece at Hampshire. It is well kept and Michael’s instructions for getting in were very clear. The place was clean and comfortable. It is close to town and was easy to get around. The game selection was amazing!! And there was enough space to lounge around. We will be back!!

Sunny Peaceful Home
My daughter and I were seeking a basecamp to explore nearby colleges but also had one day where we needed to connect to our computers for work. We slept well, had peaceful morning walks in the neighborhood, took advantage of the sunshine on the lovely deck, and enjoyed making meals in the kitchen that had more than all the essentials.

Sunny carriage house apartment
Erin is lovely and so is her carriage house. A huge winter storm came in just before my arrival--lots of snow and many trees down, lost power, etc. In spite of all this, Erin had cleared a parking space for me, shoveled and sanded both driveway and walk ways. The kitchen area was a bit hard to heat but the upstairs bedroom and beautiful sitting area were toasty warm, spacious and very comfortable. I hope one day I'll return in the warmer months when I can be out in the beautiful countryside all around. It's a gorgeous area!

Florence ctr 1br apt near town, trails, river!
We had a great stay. Bruno’s place is quiet and very comfortable. It worked very well for us during our Northampton trip. Host is communicative and accommodated our needs.
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Monadnock State Park
- Six Flags New England
- TPC River Highlands
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Snow Ski Resort
- Bushnell Park
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Hartford Golf Club
- Beartown State Forest
- Naumkeag
- Pineridge Cross Country Ski Area
- Otis Ridge
- WIckham Park
- Rockledge Golf Club
- Keney Park Golf Course
- Talcott Mountain State Park
- Brignole Vineyards