Kid-friendly vacation rentals in Gloucester

Oh my goodness. This place was a DREAM. Such a beautiful home with a view you can’t top. My husband and I stayed with our children and two friends for an east coast summer getaway and we could not have found a better place. Awesome setup, view, and Gaby could not have been more helpful. We would love to stay here again.

This was the perfect home to host us as we got ready for my sister's wedding in Gloucester. It was close enough to all of the activities we had planned, and large enough to host a large bridal party as we got ready. I loved that Patrick sent clear and informative instructions before our arrival. That made check-in a breeze. The driveway was a bit treacherous, but that's no ones fault! We didn't get to spend much time at the house, since most of our stay was spent running around. It was a beautiful home, in a very quiet neighborhood. Luckily, we didn't need to reach out to Patrick at all during our stay since everything went smoothly, and again he covered everything ahead of time. He provided everything we needed to follow his check-out instructions efficiently. It was a bit expensive for just a couple of nights, but it was a very spacious and accommodating home.

Beautiful spacious home, tucked away by in quiet cove. The home was clean, comfortable and the kitchen was well stocked. Communication with the host was very easy and pleasant.

Peter's spot is walking distance to many restaurants and little shops. The pictures are accurate- and the place is just as cute as it looks in the photos ! Very comfortable sleeping arrangements and great shower. Was nice to have the washer and dryer to do a quick load of laundry. I would definitely recommend this spot to others !

Cozy & comfortable house & convenient location for our visit to Gloucester for family wedding. Loved that it was walkable to market for coffee or lunch AND the beach. Weather not great while we were there but lots of games, puzzles, etc in the house to keep us entertained. Diane was very attentive, offered early check-in which we took advantage of. Highly recommend.

Fantastic spot! Incredibly clean, homey, and has everything you need. Her backyard was a gem to get some needed R&R. Highly recommend!

Look no further for a central spot to enjoy everything Gloucester has to offer! Cozy home with the quintessential fishing port views. Short walk to shops, restaurants and many historical sites to enjoy. This home is perfect for families to gather and feel comfortable, safe and comfortable. Excellent value for location, amenities, walkable, and quiet!!! Beautiful home. Our family had our best Christmas Holiday ever. Kathy is an exceptional host.

This house has an exquisite view and setting - so picturesque, one of us who’s an amateur watercolor painter sat in the sunroom one day and painted the harbor channel scene right out the large bay windows! Ray was a helpful, responsive host and the house was clean and well-appointed. A beautiful, quiet, relaxing stay!

Great place to stay, and hosts were very friendly and responsive. One note.. not related to the unit or the hosts but to navigation to the unit ... our GPS had us drive right past it and then drive around the block and attempt to pull in from behind which is impossible. So if you choose to stay here, and you should :-) , be aware..

Tina’s place is on a great location for walking to shops, art galleries and dining. Scenic views surround you at every turn. Located on a Main Street across from the beach it was remarkably quiet. Definitely stay!

We had such a wonderful stay at the Crows Nest! We used Carl & Julie's beautiful home as a "home base" during our adventures through Salem and greater Boston and it was such a wonderful place to come back to. Everything was easy to find, the place was very clean and accommodated myself and my friends perfectly! Rockport is also very cute with a generous beach. Cannot recommend enough!

Look no more! Winter Island Retreat is a seaside oasis that creates an atmosphere of tranquility and peace. From the moment I arrived I was struck by it's beauty captivated by the stunning sunrises to start each day The retreat is charming and a place of solace. The beautifully manicured lawn and gardens filled with lush floral designs adds to its magic. while the front porch with its rocking chairs, invite you to slow down and savor your morning coffee or lose yourself in a good book. Evenings are equally special walking the path to the beach and settling into the adriondack chair with a glass of wine It's a peaceful ritual that grounds you in gratitude. The home itself is cozy, comfortable and thoughtfully decorated with calming beachy touches that make you feel at ease. It's perfectly located just minutes from downtown Salem. I'm grateful to be one of the lucky guests to stay in David's home. He was a kind and gracious host. A truly memorable retreat I will be back

This was the perfect place to stay in Ipswich! Clean, beautifully furnished, and easy walking distance to town. Will definitely stay here again!

Robin’s home was beautiful and the directions to get there were very clear and explicit. She was adorable and wrote us a personalized note. Rockport is a beautiful little town with gorgeous views and great individuals. We ate at a small cafe with views of the ocean. Would stay again if we ever revisit the area!

My husband and I booked with Gina for a weekend getaway with our 2 dogs. Gina was not only accommodating with us, she also put so much thought in our pups as well, setting up gates around the deck so they could run around without a worry. The space was beautiful, quaint, quiet, and out right beautiful. We can’t wait to come back!

A lovely place that was charming and comfortable. Location was great for sightseeing locally and eating out

The unit was exactly as advertised. Spotless and well kept with modern amenities. Chris is a great communicator…never waited more than a few minutes for a response. All in all a great stay. Thanks, Chris!

Kelly's place was pristine and perfectly comfortable. Everything was as advertised and Kelly was a super responsive and helpful host. Would highly recommend this spot to anyone looking for a peaceful home base in Salem, a little apart from the chaos.

We loved our stay! Christina’s condo was comfortable, peaceful and perfectly located. We were walkable to the entire downtown area, museums, the concert venue, walking paths, shopping and restaurants. But the best thing was sitting outside on our private deck overlooking the harbor, with Motif #1 just across the inlet. We almost didn’t want to leave the condo…so gorgeous! And Christina is lovely, making sure we were okay, had everything we needed, so responsive. After the condo coffeemaker stopped working, she kindly offered a gift card to a nearby coffee shop, and before night fell, a new coffeemaker was delivered to the condo! Such a thoughtful host… we will be back!

If you’re looking for a place to stay in Marblehead, this is it. The house exceeded our expectations—it was quaint, cozy, and offered a stunning view overlooking the bay. It had everything we needed for a relaxing family getaway, and was within a perfect walking distance to all the best shops and restaurants. We couldn’t have asked for a better spot!

Had a wonderful one night stay at Bryan’s place while visiting family. Home was extremely clean and quiet and had everything we needed. The provided snack basket/water was a nice touch. Would definitely stay again.

Great location, walked everywhere, did not take the car out once during our stay. Onsite parking which is a big plus for the area. Historic home updated beautifully. Unit was very clean, would give cleanliness ten stars!! Matty responded quickly throughout the rental process. Would definitely recommend to anyone looking to stay in the area.

We had a great stay in Boston. We really appreciated being able to drop our luggage off in locked storage since our flight got in early. There are many great restaurants, coffee shops, and convenience stores just a short walk away. Additionally, it took us about 3 minutes to walk to the closest T station for easy access to the airport and downtown. The Airbnb was very well equipped, spotless, and thoughtfully laid out. Thank you Ali for a fantastic stay!

Diane’s condo was a wonderful choice! Her place is clean and spacious and she left very clear helpful instructions for an easy stay. It comes with everything you need and anything you’d want to do in walking distance, highly recommend this spot!