Family-friendly holiday rentals in Gloucester

Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!

Clean and good storage for a small space. Good location

We rent a house on PI every year and this house was perfect for us. We could walk to the basin with our SUP’s, easy walk to beach and stores and ice cream! We loved the double outdoor shower option for the kids after a long sandy day at the beach and they supplied all the beach toys, umbrellas and chairs! The rooftop deck was our favorite part we watched the sunset every night. We would rent this house again if the dates line up!

Great stay. Nice clean place. Good view of fireworks from the balcony.

Kate's house in Gloucester is an ideal place to experience one of the best beaches on the North Shore. Kate's home accommodated the eight of us very comfortably; the proximity to the beach was second to none and Kate and Michelle's response to a couple of minor issues we had was expeditious and friendly. There aren't enough superlatives I could use to recommend Kate's place.

Spacious and functional accommodation. 2 large bedrooms and a small living room, plus a kitchen. Quiet. A few noises upstairs but nothing very inconvenient.

Our short stay was needed and this location was exactly what we was looking for! Very accommodating, private. Made us feel right at home. Our one complaint would just be the wifi. We struggled to get connected even with simple instructions. All in all, I would DEFINITELY reserve this location for our travels/vacations in the future! Thanks, Rick

The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.

We really enjoyed our stay here! Karen was very quick to respond to any of our questions. The house is spacious and clean. We especially enjoyed the kitchen and dining room. I’d recommend this place to anyone staying in the area!

We loved our stay at Dogtown cabin. The cabin is in the middle of the woods and is also close to everything. Azure and Darwin are excellent hosts. Thank you Eric and Julie for sharing your home!

We just a wonderful few days in Boston for the marathon. Maude was the perfect host… we really appreciated the flexibility with check-in and check-out and were so grateful for the provisions left for us, particularly as we arrived late! The location is perfect, it meant that we could explore everywhere in the City on foot. The neighbourhood is particularly great for restaurants and when the sun came out and the temperature rose, the vibe was fabulous. As a previous review mentioned, if you’re looking for a pristine, freshly painted apartment then it’s not for you, but if you like ‘quirky’ and a house with bags of character, (I especially loved the art), then I’d highly recommend.

Michelle was very responsive and great at communicating leading up to our stay. The house was easy to find, good neighborhood, perfectly clean and had everything we needed. Parking was included which was awesome. The T was easy to walk to so we could go downtown every day easily. The host recommendation for Lulu’s Allston was spot on, it was nearby and great. We felt right at home and had a wonderful stay and check out was also easy. Thank you Michelle for hosting a wonderful place!

My husband and I were getting married and in his mind it is customary to not see the bride until she walks down the aisle! On my mind…I didn’t just want to come home, as we live together, just like any other night. I took my mother with me the night before our wedding and fell in love with this cute, quiet place with a gorgeous view, again nothing too far from our venue. We had worked out a little confusion on communication, we were great and going to have the cutest little house overlooking a pond/lake! My mother loved it and my husband loved it as well. It was very well kept, gorgeous view out the ceiling to floor windows! Private, quaint, easy to get to, quiet….just super cute all around! My husband and I do Airbnb‘s a couple times a year….if we were to look for some place close to home, we would definitely love to stay here again! Everything was great!

This Airbnb was one of the best we ever had stayed in! Her house was beautiful, cozy and clean! Johanna was a great host and would definitely love to stay here again!!

We spent 3 nights at Elizabeth’s place. We were 5 adults and had enough space for us all! The house is well located, easy to go to the center of Boston to visit. Beds are confortable and neighborhood really calm. Highly recommended!

This is an authentic Cambridge home that has been owned by the host's family for multiple generations. Kevin is accommodating, and he generously left some snacks and drinks in the full kitchen for us. Well-stocked kitchen was super convenient for eating breakfasts. Note: there are significant stairs to get into the unit. Once there it's quite spacious. And I love the operable bathroom window. :) Thanks for a lovely stay in a convenient, walkable neighborhood!

Second time staying at Micheal’s place and it’s always a great time. Will be back

We love coming here. The beach is right across the street for me to look for rocks and sea glass and then right down the road is the beach for swimming. Perfect little getaway. Rachel is an amazing hostess.

This was our first time at Hampton Beach and we couldn’t ask for a better host or place to stay. If felt like our home away from home. The location was perfect to everything and we didn’t need to use our car. The place was nice, clean and exactly as described and our host was so responsive and helpful! Thank you for making our first experience to the area a great one!!

This was the perfect place for a girl's weekend. Very close to Kittery and Portsmouth shops, great seafood restaurants and State Park beaches. We were lucky the temperature was cool, as a lot of the windows didn't have screens and were too hard to open. I assumed maybe the owners haven’t fully switched over to summer mode as it's been cold up till recently. Wonderful decor, very whimsical.

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.

Rita was responsive, friendly, and accommodating. Place was clean and inviting, close to the strip. Would definitely stay again!

We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!