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!

This was such a a delightful place to stay. The surroundings were so beautiful and calm. We were greeted by turkeys, and a mother and newborn deer crossed our path as we left. The hosts, Susan and Mark, were friendly, attentive and accommodating. I would certainly come back in a heartbeat.

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.

This was my third trip to the Cap Cod & my first Air B&B experience. I am so pleased that I may never go back to hotels. The cottage was cheerful. The pathway from the car to the cottage had breathtaking landscaped gardens. The bed was super comfy & the pillows were amazing. I cannot believe I had no neck or back pain! The TV had Roku & Hulu which was nice since I had a child with me. The kitchen nook was super cute & great use of space. Just enough dishes, & utensils. The coffee machine, stocked with coffee, tea, & sugar was much appreciated. The refrigerator had water bottles, condiments, & ice. The shower was the best part. A huge walk in shower with 2 options of shower heads. It was much appreciated after a 6 hour drive! The only issues were the broken celling fan-the first night it was hot, but the host made arrangements to install a window A/C unit the next morning while we were out. The door was hard to open as the key would get stuck. Overall, this was a great place to stay!

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.

We had a wonderful stay at this cozy guest house! Kat & Lucy send us different messages regarding check-in, things to do, best restaurants etc. which made our process easy and our time in Gloucester much more enjoyable. We will definitely be back!

We had a wonderful stay! The place is very peaceful and quiet with a firm king bed and a separate living room/kitchen. The unit featured one of the best bathrooms with a luxuriously large shower. Our hosts were kind, hospitable and had wonderful dogs that I loved to play with. We hope to come back again!

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

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 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!

Lovely aesthetics, close to many GB treasures. Wonderful kitchen space, with stocked pantry. Would recommend!

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.

We have stayed here before and it’s always been wonderful! Truly is an enchanted cottage where you can watch the bunnies in the garden and be secluded from the hustle and bustle of Framingham even tho it’s right in town! Decorated comfortably with antiques and kitchen well stocked! Walkable or easy drive to amenities downtown. Close enough to travel to Brimfield Antique Markets. Barry is so friendly and will do whatever is needed for his guests to be happy and communicates readily! We love it!

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 cottage was adorable. It was close walking distance to the shops and grocery store yet in a quiet peaceful neighborhood. Very centrally located for traveling about the island.

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 !

I spent 3 weeks at Christine’s fabulous cottage while working in the area. I felt a pang of sadness as I closed the door for the last time…this comfortable, charming little retreat had become home! It is airy and bright, the full kitchen is well-appointed and functional, the bathroom is clean and well-designed, and the sleeping loft is cozy and breezy at the same time! Christine is a responsive and pleasant host, check-in is easy. I will be back!