Guesthouse vacation rentals in Massachusetts

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.

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

Joanna was a pleasure to work with—welcoming from our first exchange. She was also very accommodating when I asked about cleaning products, as I have some sensitivities. My mother and I especially enjoyed the fresh air afforded by the large sliding glass doors. We also enjoyed sitting on the porch to visit. The well stocked kitchen was so helpful, and Joanna even left a few high quality snacks on the counter for us to enjoy during our stay. Joanna was generous with her time, offering recommendations for sightseeing, shopping, and dining. She was personable but also very respectful. We felt we had privacy but could ask for assistance, if needed. My mother and I thoroughly enjoyed our stay. (The only thing I might mention is that the shower design can be challenging for some to navigate. My mother is 75—not frail but not as strong as she once was. She had difficulty getting in and out of the shower safely because of the depth/step height.)

Lovely cottage surrounded by countryside: there were ducks, wild turkeys, chipmunks and blue jays in the garden. 5 mins drive from the lovely town of Dedham and 30 mins into central Boston. Cottage is small but beautifully decorated and has everything you need. Mark was super helpful.

If you’re looking for a sublime, relaxing getaway, go to Erica’s cottage. Inside, it’s pretty, livable, with everything you need. Great sunlight. Wake up to a view of the woods. Beaches for long walks nearby, the local market across the street is amazing. Birds are up to their early spring singing. We were there off season and it was a perfect spot. Plus, Erica is fantastic. Just can’t do better than Thrasher cottage.

Super place! Wish we could’ve stayed longer. In town for one night. Very clean and beautifully decorated. Comfy and quiet. Close to everything. Great view! We watched the sun while having coffee on the little deck. Friendly and responsive host. Would stay again!

Very clean and comfortable, easy to access, and quiet. I would have preferred a small table in place of the loveseat, but that is just a preference, not a criticism. If we had been there during warmer weather, I would certainly have spent time at the table outside. It was a good location for our little dog as well. He enjoyed walking over to the beach and meeting some of the neighborhood dogs. The beach is accessible by a rather long staircase, which we felt uneasy about due to mobility issues. We did enjoy sitting on the benches above and just looking at and listening to the ocean. There are plenty of good restaurants nearby providing a wide variety of foods, as well as a grocery store. Perfect for our short stay, as cooking options were limited. Overall a very comfortable stay, good communication with the hosts, and I highly recommend!

Nice, private, large room. We loved the real flame of the franklin stove. Little mini-kitchen. Nice duvet on good queen-size bed. Very private, separate building. There is a swimming pool, but that's summer-months only. We liked that it was just a 5 minute drive to Williamstown and the Clark. Not really enough hot water for two showers in a row, but other than that, great. Well appointed, with shampoo, Q-Tips, salt, sugar, etc.

Great stay! Location was very good, central to everything but very private at the same time. Very nice host and really appreciated the goodies from Morning Glory Farm. Thank you!!

Most comfortable bed ever! The setting was beautiful, lush, green and relaxing. A perfect rejuvenation point for a busy Cape Cod sightseeing stay. The accommodations were well appointed. A great night sleep on a comfortable bed was a bonus!

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.

We really enjoyed being across the street from a beautiful clean beach. Many beach towels, boogie boards, and beach amenities provided at the home! They made sure to make us feel right at home. Very wonderful location and hosts.

Easy and responsive. The house was clean and well equipped.

This cottage was perfect me, my wife, and our dog! We like the quieter side of Martha’s Vineyard and we found it here. You feel like you’re tucked away, but it’s easy to get to, and you are still within walking distance to a wonderful restaurant, and a short drive to anything else you need. You can get to the most beautiful beaches in just a few minutes. I am so appreciative that Adam was an extremely helpful host and very easy to communicate with. Would love to stay here again!

Me and my family have stayed at Emma’s twice now, and we’ve loved it both times we’ve stayed here. I love how bright and clean the space is, and so functional for us to stay in as a family. The kids especially love the bunk bed, and the grandparents loved the comfy beds, and I loved getting some work done on the beautiful desk on the second floor. We love this place and can’t wait to come back in the summer to sit and eat meals on the front porch. The neighborhood is great! It’s so convenient to be able to walk to the playground and bike path, Common Pub, and package store.

Wonderful stay over Thanksgiving weekend. The space is very easy to keep clean and everything I needed or wanted was already there. Easy walk to the harbor and a Main Street full of restaurants and shops. Thank you Zarla!

Close to hike/bike path & easy to drive to other locations on island. Very clean! Firm foam mattress if you like that. Nice touches like soda water & chips & chocolate— sweet!

What a perfect, cozy space to spend our long weekend on Martha’s Vineyard! This place is better than the pictures. Beautifully decorated, well stocked, comfortable bed, so quaint, and peaceful location. This is an easy drive to all towns on the island. It comfortably fit two adults and our infant. We would hands down return!

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.

Jane and Michael’s Carriage House is truly breathtaking. It strikes the perfect balance of luxury and tranquility, creating a wonderfully romantic setting. If you’re looking for an intimate escape on the Cape, this place is an absolute must. The warm hospitality and seamless communication made our stay even more enjoyable. We can’t wait to return!

My daughter and I enjoyed our stay at Jean's charming cottage. Brewster was a great home base for a weekend on the Cape, we particularly enjoyed being able to walk to the beach. We found the cottage spotless and just as lovely as it appears online. The beds were very comfortable, and we both enjoyed the skylights while falling asleep and waking up. Jean was enthusiastic and quick to respond when we had a few questions. I do suggest you take note of the layout of beds/seating upstairs to be sure it works for your needs. We highly recommend Jean's cottage and would be very happy to stay there again in the future!

The well named enchanted cottage was fabulous. We had a lovely stay, lucky with the weather. Easy reach of Boston on the train. Whole foods just down the road - I cooked in most evenings- as the kitchen had everything we needed. We sat out on the deck chairs and contemplated the Universe over a bottle of wine, watching the birds, squirrels and fall colours. We did a couple of day trips- Concord (loved the antique shops), the Nashoba Winery (get some of the Northern Comfort Apple, Cranberry and Maple Brandy…. Wish I’d bought two, it goes great with Mince Pies). We did the Union Oyster Bar in Boston and Legal Seafood (the oysters were amazing). I would highly recommend The Enchanted Cottage (very comfy beds).

Had a wedding to attend and Brunas apartment was nearby. It was in a lovely neighborhood, kept impeccably clean and offered the privacy needed. On my way back to Maine I went to see the Scituate Lighthouse...close to Boston as well...

This is an ideal spot, centrally located. It felt as though every destination, from downtown to Skonset, was 7 minutes away. The home is quiet, comfortable, spacious. The hosts are 100 % responsive. There is a lovely sitting area outside, to catch your breath after touring the island, prior to your next adventure.