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Guesthouse vacation rentals in Western Massachusetts

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Western Massachusetts guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Tivoli
4.94 out of 5 average rating, 248 reviews

Light-filled guest cottage

ElyseRating, 5 stars2 weeks ago
Gorgeous place in a beautiful town. About a thirty minute walk (or 4 minute drive!) right into downtown with cute shops and restaurants. The cottage is beautiful, clean and so cozy. Highly recommend.
Guest favorite
Guesthouse in Belchertown
4.93 out of 5 average rating, 169 reviews

Amherst Area Studio Apartment

PeterRating, 5 stars5 months ago
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.
Guest favorite
Guesthouse in Mount Tremper
4.92 out of 5 average rating, 352 reviews

Cozy Catskill Cottage Perfect Getaway for Two

JessicaRating, 5 stars2 months ago
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!
Guest favorite
Guesthouse in Granville
4.9 out of 5 average rating, 896 reviews

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 stars1 week ago
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.
Superhost
Guesthouse in Stormville
4.98 out of 5 average rating, 172 reviews

Hudson Valley Cottage with Pond Access

JamieRating, 5 stars6 months ago
This bungalow was a magical place to spend an autumn weekend visiting family and the beautiful Hudson valley area. We enjoyed morning walks around the pond with our pup and our coffee. Wish we had time to use the fire pit! Hammocks and bed was comfy, shower and kitchen were clean and lovely! Thanks so much a for a great stay! Would certainly recommend!
Guest favorite
Guesthouse in Chester
4.92 out of 5 average rating, 177 reviews

Historic Carriage House-20 Min to Okemo-Magic MTN

ToddRating, 5 stars2 weeks ago
We enjoyed our stay at the Carriage House very much. Jennifer is a great host - very attentive with excellent communication.
Superhost
Guesthouse in Cambridge
4.93 out of 5 average rating, 181 reviews

Quiet and Cozy Country Cottage

Eugenia Rating, 5 stars2 months ago
Great and very cute place, perfect location for skiing
Guest favorite
Guesthouse in Sprague
4.96 out of 5 average rating, 201 reviews

House on Little River / Writer Retreat

PamelaRating, 5 stars8 months ago
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!

Guest house rentals with a patio

Top guest favorite
Guesthouse in Williamstown
4.96 out of 5 average rating, 180 reviews

Brookside Cottage

DannerRating, 5 stars1 month ago
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.
Top guest favorite
Guesthouse in Gardiner
4.99 out of 5 average rating, 174 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

PatriciaRating, 5 stars1 month ago
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.
Top guest favorite
Guesthouse in Saratoga Springs
5 out of 5 average rating, 20 reviews

Timber Cottage -studio guest house, pet friendly.

BrettanRating, 5 stars7 months ago
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!
Top guest favorite
Guesthouse in High Falls
4.97 out of 5 average rating, 31 reviews

Modern and warm guesthouse

EstefaniaRating, 5 stars3 months ago
Denise’s place was an amazing gateway from the craziness of the city. If somebody wants to escape and feel the quiet of the nature please book this right away. My boyfriend and me enjoyed this place a lot for the only two days we stay. Thanks Denise’s ❤️✨
Top guest favorite
Guesthouse in Saratoga Springs
4.96 out of 5 average rating, 183 reviews

Wake up at the Track on Historic Union Ave!!!

PatRating, 5 stars1 month ago
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.
Top guest favorite
Guesthouse in Sharon
4.94 out of 5 average rating, 107 reviews

Cottage with a Waterfall View

JeffreyRating, 5 stars1 week ago
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!
Guest favorite
Guesthouse in Accord
4.92 out of 5 average rating, 121 reviews

Tiny Horse Barn

WendyRating, 5 stars2 weeks ago
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!
Top guest favorite
Guesthouse in Hudson
5 out of 5 average rating, 27 reviews

Serene one bedroom guest house with fireplace.

AllisonRating, 5 stars6 months ago
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.

Guest house rentals with a washer and dryer

Top guest favorite
Guesthouse in Accord
5 out of 5 average rating, 20 reviews

Game House in Historic Accord

SusieRating, 5 stars5 months ago
This was the perfect place for us to stay for Thanksgiving in Accord with family. Although attached to Jolle's house, it was entirely private with its own entrance and parking area. The cottage is pristine, very nicely put together and so very comfortable. Underfloor heating made it even cosier on a very wintery snowy Thanksgiving Day! Jolle's very welcoming gift of local chocolates, a bottle of wine and coffee in the freezer made us feel welcome. All the local recommendations were helpful and we all decided that this was the place to come back to next time we return to Accord! Highly recommended.
Superhost
Guesthouse in Wilmington
4.96 out of 5 average rating, 24 reviews

The Inn at Quail Run- Guest House

MargaretRating, 5 stars22 months ago
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.
Top guest favorite
Guesthouse in Henniker
5 out of 5 average rating, 102 reviews

Adorable one bedroom cottage

VirginiaRating, 5 stars3 weeks ago
Absolutely perfect! I was traveling by myself to visit my son, so safety and privacy were important to me. Heidi's place exceeded expectations. The surroundings were so peaceful and the cottage was exactly what I was looking for. Heidi was very responsive and accommodating. The lines of communication were always open. I will definitely be back!
Guest favorite
Guesthouse in Worcester
4.81 out of 5 average rating, 264 reviews

Carriage house apartment

RickRating, 5 stars1 day ago
Carriage House apartment was very comfortable and quiet in a historic setting in Worcester. Poppy was a wonderful host who communicated well with us from the beginning. Enjoyed our stay very much.
Superhost
Guesthouse in Lake George
4.73 out of 5 average rating, 22 reviews

Whitetail Deer Cabin #16 at the Adirondack Lodge

JanisRating, 5 stars7 months ago
Beautiful cabin with authentic Adirondack furniture in great location!
Guest favorite
Guesthouse in Beacon
4.94 out of 5 average rating, 397 reviews

Cozy Mountainside Suite - Minutes from Beacon

DwainRating, 5 stars3 weeks ago
This is a beautiful place and exactly what my wife and I needed for a long weekend away! The barn is so cozy and we felt right at home . The hot tub was a nice treat on the cool evenings and the beautiful view. But by far the best part was the animals living below us that we could give snacks to throughout the day and see through the living space windows. Would definitely recommend this to anyone that loves horses and donkeys!
Superhost
Guesthouse in Lake George
4.91 out of 5 average rating, 23 reviews

5 Bedroom House Lake George Views and Beach Access

MelanieRating, 5 stars2 weeks ago
Tom was great, he delivered messages for check in and check out on time. Made sure we didnt have any questions and everything was perfect. The place was exactly what we saw in the pictures. The place was clean. Had everything we needed. everything was perfect Thanks for a great stay.
Guest favorite
Guesthouse in Stanfordville
4.93 out of 5 average rating, 179 reviews

Eco Cottage in the Woods

SusanRating, 5 stars6 months ago
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.

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