Guesthouse vacation rentals in Massachusetts

I was looking for a quiet place to stay a couple of days and Judy and Bob's place was the perfect place. Located in a very quiet neighborhood and near the town beach, it's a great to relax. Judy and Bob were very friendly and made me feel at home.

We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA

My first visit bk to the Valley after moving away last year- and I loved staying @Joanna’s! So peaceful and private but also easy walk into town. The space is very cool and also comfortable. I hope to be back!

Tomi and Jim warmly greeted us when we arrived, showed us the place and offered recommendations for restaurants etc. Beds comfortable, towels soft…..just a beautiful cottage as listed!!!

Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.

Perfect Location in North Truro!!! This classic country cape is tucked peacefully and privately in a quiet garden setting. The inside is bright, airy and open! The xtra large master bedroom has a comfortable mattress, sitting area and cathedral ceiling. It is a beautiful serene 10 minute stroll to Cold Storage Beach on the bay side and about a mile to the ocean. Salty’s Market is diagonally across the street for supplies with Provincetown just a 10 minute drive for all of the restaurants, movies, theater shows and shopping needed!! Erica the host gave instant responses to my text questions! We will definitely stay here again!!

A wonderful place in the country. A Berkshires hideaway. A close walk from the AirBnB is a great breakfast spot - The Store. tasty pastries, coffee and entrèes. It's the second Spring we have stayed there. We noticed that the bathroom was renovated from a tub to a walk-in shower. Good move! Weather this May was chilly and wet. We hiked Appalachian Trail anyway. One caution for seniors: the bedroom and bath are on the second floor up a narrow metal spiral starecase. Hard place to lug suitcases up the stairs. If you are seasoned backpackers, no problem.

We loved our stay at Stephanie’s place in Chilmark. Her place is in an amazing part of The Vineyard near to the best beaches on the Island. The listing accurately reflects the space and it was very clean and nice and just as we expected. Stephanie was also very accommodating, allowing us to check in early and check out late. In short, it made for a perfect island getaway and we will definitely be back.

Absolutely beautiful spot and hosts were wonderful. Access to the local beach was an awesome bonus to this adorable spot.

Had a delightful second stay at Carolyn and John's B&B...clean, beautiful, peaceful. They were responsive quickly, and made us feel at home. John met us as we arrived and we had a pleasant chat with him. We have stayed here before, and will stay again! Thank you!

Beautiful cottage! Thank you, Mary Ellen and Dan, for your attention to detail and the many thoughtful touches! Everything was at our fingertips…from robes and slippers to clean, crisp linens! The cottage is quaint, clean and comfortable! This little oasis is quietly tucked away, yet allows quick and easy access to all that the Upper Cape has to offer! Thanks again! Kevin and Nancy

This was amongst the best AirBnB experiences we’ve ever had. The home is absolutely charming, comfortable, and picturesque. The attention to detail by the hosts was apparent in their personalized communications and service offerings. And quite obviously, in all of their furnishings and artful selections throughout the house - and their choices were exceptional. Everything from the balanced weight of the flatware to the bedside pillow mist (and so many other amazing touches) were curated for the guest’s pleasure. It was incredible. Easy parking, private location in a beautiful neighborhood (an ice cream truck even rolled by the house in the afternoon with his summer tunes audible to all the nearby children). We easily rode the orange line into downtown Boston. So glad we didn’t stay in a hotel inside the city. This was so much better. Would highly recommend staying here. The hosts really make you feel welcomed and appreciated.

Fantastic stay! Elizabeth and Norman and wonderful hosts Absolutely gorgeous space. Thank you so much again for your warm hospitality 🙏❤️

We really enjoyed Rebekah and Tim's place. Right when we arrived, Rebekah made us feel very welcome and the place was just as the pictures showed: beautiful, peaceful and cosy. After a month working in the big city New York this place was perfect to wind down and relax. Rebekah has a list of all things to do and lots of great recommendations we tried and enjoyed. We already miss this place and would love to return on day!

Allison is a dream host. We stayed at the cottage for our engagement and proposal trip and couldn’t have picked a more perfect place for it. Allison created a magical Cape Cod experience full of beautiful details including fresh flowers, relaxing hammock, chill breakfast deck, whimsical treehouse, soft bedding and wonderful kitchen with views of nature. Everything is designed with fine taste and genuine care. Line of sights flow elegantly and framed beautiful views throughout the space. She left us handwritten notes and generously prepared the space for our engagement photoshoot. We had such a peaceful and romantic time at the cottage that it felt like a sweet home away from home. We left with lots of happy memories and inspirations. Thank you Allison. We truly loved the space and would come back again in a heartbeat!

Ryanne's guesthouse is beautifully decorated with quality furnishings and bedding, very comfortable and quiet for a relaxing getaway. There is plenty to do in the area and Ryanne made some excellent recommendations for dining. Ryanne is a friendly communicator and very quick to answer all of our messages, in advance of and during our stay. Check in was easy and all amenities we could have needed were available. I would highly recommend booking this cozy spot!

The house is very comfortable and feels like home. The kitchen is spacious and well-equipped — a great experience for cooking. There’s a peaceful courtyard that’s perfect for calming your mind or reading a book. One night, we even spotted a bear from the window! It’s a great location, and don’t worry — the bears are vegetarian. Elisa and Mickey are very kind and responsive. They’ll even create a personalized list to help you explore the town, even if you’re not familiar with the area. You can shop at Taft Farm — my favorite local farm. Cooking at the house really made it feel like home, and also “farm to table” experience. Thank you!

We came to Natalie’s place for a baby shower in a neighboring town and are so lucky we found such a homey place! The house is very kid friendly with lots of musical instruments and books around which helped our little one feel at home in a new place. The breakfast treats were tasty and thoughtful. The wood stove was the perfect cozy feature to end each night! Highly recommend!!

I had a great stay! The couches were especially comfortable and featured convenient power controls. The kitchen was a perfect size—well-equipped with all the appliances working flawlessly. I easily found all the utensils, plates, cups, and everything else I needed for cooking and dining. The variety of lighting options, including several lamps and switches, made it easy to create the right mood in every room. Would definitely stay again.

They were super friendly and kind to our kiddos. If we find ourselves traveling again we will think about staying there. We are so thankful for this stay.

The studio was beautiful and our stay there was amazing! The furnishings were lovely, was a perfect place for my husband and me with a comfortable large bed, wonderful amenities and beautiful surroundings. It was easy to find and get inside and was convenient to getting around the island. Carlo and Leah provided lots of local recommendations too which we appreciated. We highly recommend this wonderful studio and gracious hosts and will definitely stay there again should we return to Martha’s Vineyard!

The Barn is very cozy and has a well appointed kitchen - we enjoyed cooking most of our meals here and enjoying the views out the large windows facing the field! Ilana was super accommodating and communicative before & during our stay. The location is excellent, within minutes of most major Berkshires attractions.

Cottage was exactly as described. Great location. We loved spending time on the porch, enjoyed the outdoor shower and all the hydrangeas were so beautiful!

Lori’s place was wonderful. It is within walking distance to local shops and restaurants and has great views of the harbor. It is so calming and pleasant to sit and watch boats coming and going and knowing the local fish market has the freshest catch each day. She thought of everything you would need and it is also very tastefully decorated. We loved this place and will definitely return. Highly recommend !