Pet-friendly holiday rentals in Massachusetts

Karen was absolutely incredible. She was very responsive, respectful, and accommodating. We very much enjoyed our stay as my team and I were there on business. She was able to take care of us even on short notice. I really couldn’t be happier with her communication, the quality of their home, and the entire experience. Thank you so much Karen for inviting us into your home. This was truly a 12/10 experience. 😃😃

The Wishbone was lovely, comfortable and charming. It was within a very easy walk to the beach. There were games, beach towels and flip flops on the porch for guests which I thought was a wonderful idea. Sean, always responded very quickly to every inquiry. A great place to stay!

We rented both apartments for a multigenerational family get together. Everyone found something they loved-walking to the beach, biking to Parker River refuge for hiking/birding, loads of restaurants and shopping nearby. Glorious sunsets!

Maria's place was so nice and cozy, very easy to check in, and everything was well organized, clean, and makes you feel like home! Had a winter storm on the day we went there so we had to stay inside and spend our time there. She and her team were there the next morning to clear up the snow from the driveway so we could leave and gave us 2 extra hours to check out free of charge!

A wonderful place that felt even larger than in the pictures, surrounded by beautiful scenery, offering complete privacy, and the perfect touch of a delicious hot tub experience under a snowy night.

Very quiet spot. Felt comfortable staying here. very good communication, very welcoming. Thank You Craig

Sue’s place was great for my family and dog. The 2 apartments give a nice separation when staying with a group. Very clean and comfortable. We paid the extra fee to not worry about linens and felt It was worth it. It is on a busy road and you can definitely hear the traffic when the windows are open as the house is pretty close to the road but it wasn’t an issue for sleeping. Location is great for many restaurants and beaches. 20-25 minutes to Hyannis or Chatham

We loved staying at this lakeside cabin for thanksgiving with family. Beautiful sunsets, great location, charming house. Loved it!

Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!

We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.

We have stayed at Carol’s other campers but this was our first time at Trigger’s cabin. Great rustic accommodations and a beautiful spot right on the pond. It is such a peaceful spot to disconnect and enjoy nature. Carol is a great host and we plan to be back again.

Perfect stay. Pool was amazing. Host was very responsive to everything. Great for families, Just bring socks with friction pads on the bottom so you don’t slide .

This property was precisely as advertised, ideally located for my needs, and Ian was a very responsive host. I would recommend the property and the host without reservation.

wonderful stay thank you

The house was clean and comfortable. I loved the coffee bar:) my kids loved the pool and hot tub. And it was especially great to be able to bring my dog! We will definitely rent again.

Our stay at this beautiful home in the Berkshires was nothing short of fantastic! Even in the winter, the house was warm, inviting, and perfectly set up for a relaxing getaway. The wood-burning fireplace in the living room made for the perfect cozy atmosphere, whether we were reading a book, watching a movie on the large TV, or just enjoying the peaceful mountain views. The house was well-insulated and heated, keeping us comfortable even on the coldest nights. The kitchen was modern and fully stocked, making it easy to cook meals instead of going out in the snow. The beds were incredibly comfortable, and the primary bedroom with its own ensuite bathroom was a great touch. The downstairs living area gave us plenty of space to spread out, making it a great option for groups or families.

I spent another spectacular week at Paradise Found. The cottage is peaceful and private with beautiful surroundings and an ideal location on the Cape. My dogs enjoy themselves in the large yard and going on neighborhood walks. Jayne and Steven are so friendly and always make me feel at home. My third year in a row and I can't wait to come back!

We would definitely recommend Deb’s and Sharon’s cottage as a place to stay. The location is great, as it is within walking distance to shopping, restaurants, and the water, but is tucked away in a quiet little neighborhood so it still also offers plenty of privacy. They were wonderful and responsive hosts and checked on us throughout our stay, though we didn’t end up needing a thing. They were gracious enough to allow our dog Bella join for the weekend too, which we appreciated very much as she goes everywhere with us. Overall, we had a lovely stay and would definitely look to book again if we make our way back to the beautiful island!

The Swiss House is an ideal retreat for families seeking a harmonious blend of comfort and connection. The expansive open-concept living area downstairs fostered a sense of togetherness, while the well-appointed kitchen made preparing family meals a breeze. Nestled away from the hustle, yet conveniently close to amenities, the house offers a perfect balance of privacy and accessibility. A quick drive to Mayflower Beach added to the allure, making our stay nothing short of delightful.

This home is amazing. It’s close to so many things to do. Within a few minutes drive of the beach and Provencetown. The yard is large and spacious for pups and there are so many board games and places to sit. The kitchen is amazing and the location feels private despite being in a small neighborhood. Would highly recommend this as the perfect get away!

The cottage is cozy and comfortable, including the beds. It's in a quiet neighborhood yet very accessible to hiking trails, beaches, restaurants, and shops. Fiona was extremely friendly and helpful. She is definitely a Super Host! We would happy have stayed longer if we could have! For those who like to ride your bike: Rt. 127, the main road that goes around Cape Ann, is very narrow and has no shoulder, so I don't recommend planning to bike there.

Private and serene is spot on! Adam and Ben are incredible hosts, very responsive to questions/needs, and their rental has everything you need. The rental itself is very cute and spacious, and was very clean upon arrival. We had the best week closing out summer vacation with our kids and pups. Looking forward to returning!

This was an amazing choice for our New Year’s Eve celebration getaway. It was perfect in every way. A warm welcome first of all and very informative and accommodating after that. The location is hard to describe because it’s SO beautiful!! You can’t go wrong here. Perfection in every way. That we can assure. The winter is especially awesome- so we recommend you go for it. We absolutely loved it.

Great and peaceful stay, good communication and perfect location.