Waterfront holiday rentals in Massachusetts

You could not select a better location than this, with access to the Cape, beaches, and the Canal road for biking and walking. The apartment is modern and immaculate with a nice deck on which to relax. To top it off you could not find more pleasant hosts than Diane and Barry. We will surely visit again!

Gigi's place was clean and in a great location.

Visiting a large family for Thanksgiving can always be hectic but staying at Anna's and Milan's house provided that 'calm base camp' it is always nice to come home too. Since the T stops literally at the front door you really don't need a car. But if you do have one there is parking spot in the driveway so what more can you ask for in Boston in regards to transportation. The view is beautiful from the second floor apartment and I literally only had to go across the street to gather my most important collectible on each trip, native beach stones. there's no better place to stay in Winthrop

Stayed overnight on a visit to family in February. Fantastic place for the two of us and our dogs. Excellent walking area even in winter with snow. Thank you!

We had a very comfortable relaxed stay! The space was clean and well equipped. The beds were soooo comfortable as was all the living room furniture! Craig was very responsive and accommodating to our schedule. We lived the location and made two visits to the close by Big Red slide and walked the beach! So close! I highly recommend this place and can’t wait to return.

This place was great! Elyse was a wonderful communicator, flexible and responsive. The unit was just what we were hoping for- clean, ocean views, comfy furniture and the fact that they accept pets was a major plus. There are narrow stairs that you have to navigate but otherwise this place was perfect.

Great place. I’m from Shelburne Falls so it was nice to be “home”. The place was extremely clean and cozy. Everything was super easy. I would highly recommend this place. It’s a beautiful setting with great views of the mountains, bridge of flowers and quaint little village.

Carol and John’s home is a hidden gem! It is located right on the beach and you can wake up every morning to the most beautiful sight. My husband and I wanted to go away from the weekend but not have to travel too far. This was the perfect place to allow us to relax and unwind for an extended weekend. The hot tub and fire place made everything even better! We’ll certainly be back! :)

We had a wonderful stay at Colleen's place. The views were spectacular and we enjoyed the cozy living room, big dining table, and comfortable beds. We walked to the beach and enjoyed the sunsets from the porch. Everything was clean and the house had everything we needed. Wonderful weekend!

Great house for families, lots of room to spread out and enjoy. The location is terrific. The host and his family are nice and friendly. Communication with the host was excellent.

We were all very happy at Martin's place for a long weekend. The location on the lake is stunning with beautiful sunsets every night. The loft area in the house enchanted the 2 and 4 year olds among us as did the many interesting toys left behind for guests. Our dog adored the dog bed and treats left for him. The place also has many really interesting relics from times past. There were several state of the art appliances. The host/s were totally responsive, and we would go back and rent this house again!

This property was stunning! As described. Brenda was extremely responsive to messages. My family appreciated the labeling she had done, it made everything very easy to find. Anything you could want this place has it, from super comfortable beds, tons of space, clean, and beautiful views! We will definitely be back!

Beautiful home! Stunning view. The house was spotless and extremely comfortable. The area was very nice and quiet.

We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!

We had a lovely multigenerational stay at Rina's place: three bedrooms are upstairs, with one on the main living level (which was great for elderly grandparents). Watching the view change as the tide came in and out was fantastic, and the kitchen was well appointed with everything we needed to cook our meals. Sound travels easily upstairs (not an issue for us, but something to be aware of when planning who sleeps where, if children have varying bedtimes). Rina and her local aunt were very responsive and helpful. It was a fantastic winter getaway!

The house is wonderful. It has everything you need. The view of the water and access to the beach is the best. We truly enjoyed having our family there.

We had a wonderful time at Rob's place in Provincetown this February. If you are looking for a quiet place on the East End in the off season this is an exceptional spot. Beautiful water views from the condo. A gorgeous beach with some of the best views in Provincetown is right across the street. Condo was perfectly cleaned upon arrival and exactly as described. Couldn't ask for more.

An amazing beachfront getaway! The property was clean, well-maintained, and offered breathtaking views of the ocean. Waking up to the sound of waves and enjoying sunsets from the patio was a dream. The host was responsive and made everything seamless. Perfect for a relaxing stay—can’t wait to come back!

Christina's property was a wonderful place to escape to for a few days! It is the perfect size for 1-2 people, has everything you need, and the view is unbeatable. The parking space is incredibly convenient and the location of the property provides easy access to the rest of Bearskin Neck and Rockport proper. I hope to stay here again in the future!

Stayed for 2 nights in December with 5 guests. Very clean and spacious, great location. In unit laundry and good temperature controls for the bedrooms. Make sure to read instructions for turning on hot water heater. The apartment is on the third floor with stair access around the back of the building. Pull out couch bed in the living room is fairly comfortable but living room is colder than in the bedrooms. TV is small but has an Amazon fire stick. We would stay here again!

Chris’s place was exactly as described and depicted. Immaculately clean and very comfortable. Great location…..just steps to all of our favorite spots! Chris was also very responsive…. we hope to return again sometime!

Great space, close walk to all the places we needed to go. Loved the open layout of the kitchen and living room areas, awesome to lounge around during our downtimes. Bathrooms fit our needs and beds were comfortable. Nice and thoughtful amenities such as the Dove body soap and toothpaste. TV cable was much appreciated as well as the electric piano! Thanks for a great stay, would book again.

Fantastic North End Location. 3BR condo is perfect for 3-4 people — kitchen and bathrooms are fully updated and well appointed. Spacious Open plan living room and dining space allow friends or family to easily hang out together — with nice views of the Boston Harbor activity. The building itself is older and there’s a steep two flight walk up to the condo. Beds were comfortable and owners are super communicative and really make sure your visit is successful!

Great apt in the center of it all! Very clean and modern. Highly reccomend!