
Family-friendly vacation rentals in Gloucester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Gloucester
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Gloucester family-friendly rentals
Family-friendly home rentals with a hot tub

Nana-tucket Inn
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.

Hopkinton Mass 3+ Bedrooms - Great location!
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.

Coastal Maine & 10 Min to Portsmouth+ Hot Tub Too!
This is one of the best Air B&B experiences that we’ve had…beautiful place and surroundings, great amenities and personal touches, wonderful recommendations. Couldn’t have had a better time.

Condo with pool sleeps 4
Great stay. Nice clean place. Good view of fireworks from the balcony.

Seacoast Oasis (NH & ME)
Convenient location and easy to find. Great for an overnight stay like we needed. If you needed to cook at all, it would be tight but we didn’t need to. I highly recommend Bob’s Clam Hut while you are in the area!

Home On The Hill
Beautiful home! Thank you for sharing it with my family. We were in town for my daughter’s college graduation. This location was perfect for my family. Cozy. Family oriented. Clean. Well equipped. Highly recommend!

Newly renovated, close to Foxboro and Boston
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.

Sunrise Sunset Lakefront Suite
This was my second time staying here, and it will not be my last. This little peaceful place is beautiful, and the view is gorgeous. The hosts are very kind and responsive.
Family- and pet-friendly home rentals

Welcoming 7-room house <15 miles to Boston & Salem
We loved staying here! Plenty of space for our family of 6, including one little one. It was exactly as pictured and well-stocked with spices in the kitchen and shampoo etc in the bathroom! Beds were super comfy and we loved how close it was to the lake, restaurants, and a playground. Would definitely stay here again!!

Walk to Everything Great about Marblehead!
Beautiful home in quiet area that's only a 13 minute drive to Salem. It was perfect for my Bachelorette (9 people), we each had our own bed with plenty of room to spread out. Awesome host, very responsive with all of our questions and super nice. Thanks John!!

Two bedroom Apt with a deck
This was the cutest place! We all loved the garden space. The deck was very inviting. Rhona was kind enough to leave English muffins and butter for us. The selection of tea was fabulous! The bouquet and house plants made it feel very homey. There was an area close by that had a convenience store, a Dunkin Donuts, and a few decent restaurants. We would stay here again if we come back.

The Salt March Loft/Downtown Location/Views
This was absolutely perfect for our needs. The location was central to Salem, Gloucester, and not too far from Boston. Very close to wonderful local restaurants and Marla was very attentive to our requests.

Spacious 2 BR Kittery Home - Walk to Portsmouth!
We instantly felt at home! Everything we needed was there, including things that I often bring with me because they aren't usually provided. Erin has set up this house the way you would if you lived there yourself--extra pillows, blankets, bathroom and kitchen towels, kitchen and laundry detergent. Basic spices, coffee and tea, sugar and creamer, every kitchen gadget and utensil. Bath products, night lights, beach chairs and towels. Even a bluetooth speaker and use of their Netflix account! All we needed were a few groceries and some sunshine to enjoy the outdoor spaces and seasonal game room. The house is spacious and charming! Their check-in and check-out methods are easy and they left ample info on how things work in the house and local restaurant and activity recommendations. This is a great location and home. I almost wish we had brought the kids...

Hillside Ocean View 2BR with Private Beach Access
Great location to getaway. Short walk to two different beaches as well as parking pass for great neck beach. Lots of room for two people to spread out. Lots of games to play. Living room was very comfortable, kitchen well stocked. Easy check-in and checkout

Mema's Place --Lovely apartment in private home
Ellen is an excellent host and her apartment was spacious, clean and in a peaceful setting. We always enjoy staying at her place when we have the opportunity to be in the area.

Quaint Little New Hampshire Lake House Getaway!
We really enjiyed our stay and would recommend to anybody else.
Family-friendly home rentals with a pool

Luxury Ultra Modern House in Newton ; Boston
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!

Slice of Paradise at Hampton Beach!!
Second time staying at Micheal’s place and it’s always a great time. Will be back

Seaside Cottage in Rye NH
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.

Hampton 100 yards to beach
Clean and good storage for a small space. Good location

Summer Hill: Sweet New Englander on Maine Coast
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.

Country Cottage in the City
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.

Beautiful Beach Studio
Good place to stay for Hampton Beach. Short walk to the water.

Beautiful Lakefront Vacation
Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.
Quick stats about vacation rentals that are family-friendly in Gloucester
Total rentals
380 properties
Total number of reviews
13K reviews
Pet-friendly rentals
110 properties allow pets
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Wifi availability
380 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- Boston Vacation rentals
- The Hamptons Vacation rentals
- Hudson Valley Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Montreal Vacation rentals
- Jersey Shore Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- Philadelphia Vacation rentals
- Beach house rentals Gloucester
- Apartment rentals Gloucester
- Fitness-friendly rentals Gloucester
- Pet-friendly rentals Gloucester
- Rentals with beach access Gloucester
- Rentals with a patio Gloucester
- Waterfront rentals Gloucester
- Beachfront rentals Gloucester
- Rentals with a fireplace Gloucester
- Rentals with a washer and dryer Gloucester
- Rentals with breakfast Gloucester
- Rentals with an EV charger Gloucester
- Rentals with a fire pit Gloucester
- Kid-friendly rentals Gloucester
- House rentals Gloucester
- Private suite rentals Gloucester
- Condo rentals Gloucester
- Rentals with outdoor seating Gloucester
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Boston Common
- Revere Beach
- Fenway Park
- TD Garden
- Harvard University
- Lynn Beach
- Duxbury Beach
- York Harbor Beach
- North Hampton Beach
- New England Aquarium
- Long Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Crane Beach
- Canobie Lake Park
- Prudential Center
- Long Sands Beach
- MIT Museum
- Good Harbor Beach
- Rye North Beach
- Museum of Fine Arts, Boston