
Family-friendly vacation rentals in Gloucester
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Top-rated family-friendly rentals in Gloucester
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Popular amenities for Gloucester family-friendly rentals
Family-friendly home rentals with a hot tub

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!

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.

South Boston. Minutes away from Convention Center
The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!

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.

Plum Island - Luxury Beach House
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!

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

Steps to Good Harbor Beach
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.

# 18 Large deluxe 3br, 2 1/2 bath condex sleeps 13
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
Family- and pet-friendly home rentals

Walk to Everything Great about Marblehead!
Great stay, house perfectly as advertised, super cute and great for a big group. John was easy to reach and was able to accommodate an early check-in and a late check-out. Would come back again!

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!!

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.

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

2BD Apt Steps to Beach|Pet Friendly| Wkly Discount
Amazing find! This is a perfect location. Salisbury is such a fun, cute, and affordable town. Lots to do and see and all super walkable from this house. You can get to beach in just a few steps. Take a walk down the beach to get some Beach Pizza at Cristy's (or Tripoli if you prefer) and enjoy one of the best arcades on the east coast at Joe's Playground. Host is super responsive and helpful. Beach gear being already there is a huge plus. Parking is easy. Love this place. Hope to be back some day.

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

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

100 yds/Hampton Beach Pool-4 guest
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!!

Another Slice of Paradise
Easy parking, clean, large balcony, view of the ocean and sunsets, lots of storage for clothes, easy quick communication with Michael. Ac units worked Amazing and very quiet. Tv in each room with a door for master bedroom privacy. Large public parking lot beside condo for family to park for the day. Quick mart with essentials and ice directly under rental. About 500 feet from condo to casino ballroom entrance. Great open clean space to make memories. Perfectly located between ocean, stores, shops and restaurants. Directly above busy street ( suggest ear plugs and eye mask if you are a light sleeper)

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
What a perfect weekend in a private cottage by the pool. Although the weather did not cooperate for pool time, Mark & Susan’s cottage was a perfect place to have a central location outside of Boston. You would never know you were close to the city. Absolutely lovely! Their cottage was super clean and inviting and lacked nothing necessary for a long weekend away. They were very proactive in communicating with us about checking in and if we needed anything during our stay. Really terrific!

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