Kid-friendly holiday 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.

My son was graduating from Landmark High School. He is a boarding student so we needed a place close by. There was room for his extended family. The kids loved the games and activities.

Property was just as pictured, which I find extremely important. This spot is off the beaten path and quiet with a nice little walking bridge for a stroll. Close enough by car, to all the attractions of Glouchester when your ready to get out and about.

Harbor House is a great place, conveniently located near downtown, shops, restaurants, and bars are walkable, nice ocean view from the upstairs living room, its an excellent choice for your visit to Gloucester

Great location and beautiful views. We will for sure look to stay here again on any future visits to Gloucester.

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.

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

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!

Comfortable, well-appointed, and in a great location. Maria was very nice and easy to work with. Thanks!

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

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!

We stayed at home port for a quick trip home to visit family and loved it! The softest towels of any Airbnb or hotel I’ve ever stayed in, super cute and charming decor, the property is beautifully landscaped with easy parking. We walked to get dinner our first night and were grateful for the air conditioning as it was very hot out our second day. This is a great Airbnb!

We had a great time and the house was local and convenient to beaches and restaurants

Perfect for our needs. Comfortable, convenient — exactly as described. The location was perfect, with so many great restaurants, shops, and attractions within walking distance. Easy to get around without a car. Would definitely stay here again!

We had a great stay! The space was nice, clean, and very quiet. Parking was convenient, and the location was fantastic— since it was just a short drive the Crane Estate (where we attended a wedding). Communication with the host was great—we received quick and helpful responses. Highly recommend to anyone looking for a peaceful, well-kept place in a great area!

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!

This was the second time we had stayed at Kristin’s. We loved it so much last year we had to come back! Nothing beats the view from the rooftop deck. Everything you need, to include ample public water access, is just a short walk. We plan on making this a yearly stay. The fact you can bring your pup is an added bonus!

Charming old home; clean and well maintained. A little smaller than we expected, but it served our needs. Shila was incredibly helpful and accommodating. Would recommend!

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.

Loved our stay! Marty’s place was spacious but still very homey! Perfect location to everything in Salem!

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!

This AirBnB was perfect for the six of us in town for a wedding. Not only was it clean, but having access to the kitchen and two full bathrooms was incredibly helpful. Interior was beautifully decorated and well maintained without feeling too stuffy or sterile. Very cozy and felt at home while traveling. Even though we had to take a few flights of stairs to access, it didn’t feel like a burden. Host was extremely communicative and helpful the whole weekend. Even though it is a condo, you feel like it is truly a private residence the whole time.