
Guesthouse vacation rentals in Western Massachusetts
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Top-rated guesthouses in Western Massachusetts
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Western Massachusetts guesthouses
Family-friendly guesthouses

Light-filled guest cottage
A very cute and rustic cottage stay for a weekend get away. It is perfectly located just minutes away from Tivoli, and feels private enough. Yuko & Ethan were super easy to communicate with and check in + check out was super smooth!

Amherst Area Studio Apartment
Judy could Jay have been a better host. My children and I were in town for a family function and couldn’t be happier with the stay.

Cozy Catskill Cottage Perfect Getaway for Two
I just want to say that this is a very beautiful place. Julian & Karen were extremely nice to us and to have us there. Karen made sure we were comfortable with the stay, and was very respectful and the place was very cozy and inviting. The place is beautiful and warm. Her recommendations were very helpful and we truly enjoyed ourselves! I will come back again! Thank you so much for your wonderful hospitality!

Moon Valley Country Retreat no clean fee pets yes
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

Hudson Valley Cottage with Pond Access
If you're looking for a private retreat in a gorgeous setting, this is your place. The property is stunning, super walkable grounds, and a gorgeous back patio. S.A. is a super host, and when we ran into an issue, he was quick to respond and help. We recommend this place, and intend to stay again in the future.

Historic Carriage House-20 Min to Okemo-Magic MTN
We enjoyed our stay at the Carriage House very much. Jennifer is a great host - very attentive with excellent communication.

Quiet and Cozy Country Cottage
The location was perfect for our needs. Samantha greeted us when we arrived and responded to our texts. This the second time we’ve stayed here and loved it.

House on Little River / Writer Retreat
Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!
Guesthouses with a patio

Brookside Cottage
The cabin was a peaceful respite. Cozy, comfy, and the stream was so calming. Sophie's restaurant recommendations were excellent, the Korean restaurant is a hidden gem.

Sherwood Barn - close to ski mountain
Beth was very kind and responsive. Great place to stay!

Red Barn Retreat - Shawangunk Mountains Getaway
This place was a perfect weekend get away for myself and husband. Plenty of space for the two of us. The place was nicely, decorated and fully furnished with accessories if you wish to cook. I enjoyed the spaces between the outside patio as well as the hot tub. Bill was great with giving suggestions of local places, even though I was a local myself.. if you’re looking for a quiet getaway this is your place.

Timber Cottage -studio guest house, pet friendly.
We had an amazing stay at Kristin and Dave’s cottage and cannot wait to return. The cottage was spotless, very well equipped, and supremely comfortable. Both Kristin and Dave were very responsive, extremely helpful, and provided great instructions and assistance. The location was beautiful and so peaceful. The outdoor space was such a nice option, and the porch and pool were so nice to relax in. We wholeheartedly recommend the cottage!

Wake up at the Track on Historic Union Ave!!!
John's place is in a great location. Walking distance to downtown Saratoga. Very close to the track. A couple of good Restaurant's near by. Pictures and description of property were perfect. Place was spacious and very clean. Perfect for a couple or 2 couples. We would definitely stay there again.

Cottage with a Waterfall View
The cottage is beautiful and such a surprise when you open the front door - the magical stream is right out the window. Although the cottage is close to the road you would never know it - the back patio is just perfect!! An easy drive to a a number of small and lovely quintessentially New England villages. We would highly recommend Jeff and Elizabeth's cottage!

Tiny Horse Barn
We felt very comfortable here but missed having a few amenities, especially a toaster oven, a dishwasher, and a laundry. If you’re not staying for more than a few days these items would not be important. We were staying for 8 days and planned to do a fair amount of cooking which made these items more desirable. However, none of this was a dealbreaker. The overall coziness, comfort, and attention to detail and decorative touches were more important to us and appreciated!

Serene one bedroom guest house with fireplace.
One of the best Airbnbs we've stayed at. We loved the interior design and how cozy the space was. The location is beautiful and peaceful. Highly recommend.
Guesthouse rentals with a washer and dryer

Bear Brook Trail Side Getaway & RV Park
The unit and property are very nice. It was super convenient for the event I was attending and price and accommodations was a great value. I will certainly return again if available as my event is twice a year. Thank you Bill and Kimberly, you have a great home and rental.

The Inn at Quail Run- Guest House
We were in town for a family wedding and this was the perfect place for 20 or so of us to spend the weekend. Everything was great. We were so comfortable and had so much fun! Thank you to Meiling, Martin, Mayra, and all the folks who assist them with housekeeping and logistics. Hope to find an excuse to return, as everyone was sorry when our stay came to an end. Highly recommend without hesitation.

Adorable one bedroom cottage
Our experience at Heidi’s place was amazing. The location is peaceful, beautiful and private. The place was clean and had all the amenities listed. Would definitely come again and recommend it to others!

Carriage house apartment
Poppy went above-and-beyond to make us feel welcome and make sure we had everything we needed. She also generously accommodated an unexpected change, the space was cozy and comfortable. Really looking forward to staying again soon!

Whitetail Deer Cabin #16 at the Adirondack Lodge
Beautiful cabin with authentic Adirondack furniture in great location!

Cozy Mountainside Suite - Minutes from Beacon
My boyfriend and I booked last minute trip! That turned out magical ! The view was priceless, the hot tub was large and had message features, hammock was great. Suite is adorable and very clean. You’re literally on top of a mountain with no neighbors and surrounded by nature. Very private ! We caught an amazing view day and night on a clear sunny day and then a lightning storm in the mist! We missed our farm friends as soon as we left. Accurate listing ! Highly recommend 4wheel drive !

Eco Cottage in the Woods
Upon entry, my architect husband said "Cute Cottage; Susan you did it again." Plenty of room for a couple in their mid-seventies, and a Millennial daughter. The cottage is very well insulated such that I didn't have to run the heat except for fifteen minutes at bedtime in mid-October, yet there is a big south-facing sliding door in each of the rooms where the sun and moon shines through. Beautiful woodland falls away from the cottage and small patio beyond the sliding doors, and moonlight is magic on all the leaves. If we had more time we would have investigated the many books in the shelving. We will find excuses for coming back to the area and will stay here again.

Spilt Milk Cottage - Hudson Valley, NY
We loved the cottage. If anything it was even cuter in person than in the pictures. Communication was perfect and the place was very well thought out. We enjoyed our stay, I’d recommend it and come back here in the future!
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Six Flags New England
- Albany Center Gallery
- 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
- Kent Falls State Park
- Pineridge Cross Country Ski Area
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Rockledge Golf Club
- WIckham Park
- Keney Park Golf Course
- Talcott Mountain State Park
- Bigelow Hollow State Park
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