Family-friendly vacation rentals in Gloucester

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Gloucester family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars2 weeks ago
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.
Guest favorite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton
4.95 out of 5 average rating, 154 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars1 month ago
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.
Guest favorite
Outdoor dining tables are set under large umbrellas, with guests enjoying a waterfront view. Sailboats are anchored in the calm water during sunset, creating a serene coastal atmosphere. The soft colors of the sky reflect on the water, enhancing the picturesque dining experience.
Guest suite in Kittery Point
4.95 out of 5 average rating, 294 reviews

Coastal Maine & 10 Min to Portsmouth+ Hot Tub Too!

KyleRating, 5 stars5 days ago
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.
Superhost
An indoor pool area features clear waters with a section for relaxation, complemented by a whirlpool. Large windows allow natural light to fill the space, while the entrance door and pool steps are visible in the background.
Apartment in Hampton Beach
5 out of 5 average rating, 5 reviews

Condo with pool sleeps 4

ChristopherRating, 5 stars11 months ago
Great stay. Nice clean place. Good view of fireworks from the balcony.
Guest favorite
The image captures a two-story home nestled in a wooded area. A wooden deck adorned with a wreath and potted plants is visible, providing access to the upper level. Nearby, a brightly colored buoy adds a pop of color against the natural surroundings.
Guest suite in Kittery
4.91 out of 5 average rating, 845 reviews

Seacoast Oasis (NH & ME)

EmilyRating, 5 stars3 days ago
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!
Guest favorite
A landscaped area features a rock border with colorful pink and purple flowers, providing an inviting approach to the property. A drive lined with pavers leads to the entrance of the house, surrounded by lush greenery and tall trees.
Home in Dunbarton
4.91 out of 5 average rating, 32 reviews

Home On The Hill

JulieRating, 5 stars3 weeks ago
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!
Superhost
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars7 months ago
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.
Guest favorite
A vibrant sunset paints the sky with shades of orange, pink, and purple. Soft clouds stretch across the horizon, reflecting the warm tones on the calm surface of Sunset Lake, which is bordered by tree silhouettes in the distance.
Place to stay in Hampstead
4.88 out of 5 average rating, 92 reviews

Sunrise Sunset Lakefront Suite

AngelaRating, 5 stars2 weeks ago
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

Top guest favorite
A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.
Home in Wakefield
4.96 out of 5 average rating, 263 reviews

Welcoming 7-room house <15 miles to Boston & Salem

EmilyRating, 5 stars1 month ago
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!!
Superhost
The exterior of a spacious antique house is shown, featuring a yellow facade with green shutters. A large deck is visible in front, complemented by a white picket fence. The house is set against a clear blue sky, adding a bright and welcoming appearance.
Home in Lakeside Marblehead
4.76 out of 5 average rating, 169 reviews

Walk to Everything Great about Marblehead!

KatherineRating, 5 stars3 days ago
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!!
Top guest favorite
A wooden deck is situated in the foreground, featuring a small seating area and an umbrella. Lush greenery, including tall evergreen trees and colorful shrubs, creates a natural backdrop. A stone pathway leads into the garden area, enhancing the tranquil outdoor space.
Apartment in Lakeside Marblehead
4.94 out of 5 average rating, 194 reviews

Two bedroom Apt with a deck

CindieRating, 5 stars3 weeks ago
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.
Superhost
A cozy sleeping area showcases a spacious bed with light linens and a wooden headboard. A stylish lamp provides soft illumination. Adjacent, a well-organized entryway is visible, featuring a decorative storage unit and a door leading outside, with natural light streaming in from a skylight.
Barn in Essex
4.9 out of 5 average rating, 139 reviews

The Salt March Loft/Downtown Location/Views

JeriRating, 5 stars10 months ago
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.
Top guest favorite
A two-story house with a light grey exterior is framed by a manicured lawn. Bright green accents are present on the front door, which is complemented by a small porch and steps. Surrounding shrubs and trees enhance the outdoor setting.
Home in Kittery
4.96 out of 5 average rating, 105 reviews

Spacious 2 BR Kittery Home - Walk to Portsmouth!

CathyRating, 5 stars3 weeks ago
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...
Guest favorite
A coastal view is captured, featuring distant houses and the ocean merging into the horizon. Power lines stretch across the scene, while lush green foliage adds a natural frame to the image. The clear sky complements the tranquil atmosphere.
Home in Ipswich
4.89 out of 5 average rating, 109 reviews

Hillside Ocean View 2BR with Private Beach Access

NancyRating, 5 stars1 week ago
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
Top guest favorite
A private entrance to a charming home is framed by well-maintained landscaping and a gravel driveway. Decorative flower boxes adorn the windows of the light-colored exterior, while surrounding trees provide a natural backdrop, creating a serene environment.
Apartment in Concord
4.96 out of 5 average rating, 211 reviews

Mema's Place --Lovely apartment in private home

JackieRating, 5 stars3 weeks ago
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.
Guest favorite
A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.
Home in Salem
4.95 out of 5 average rating, 153 reviews

Quaint Little New Hampshire Lake House Getaway!

KevinRating, 5 stars2 weeks ago
We really enjiyed our stay and would recommend to anybody else.

Family-friendly home rentals with a pool

An open-concept kitchen and dining area features modern furnishings, including a long dining table surrounded by black chairs. Large windows offer views of greenery, allowing natural light to fill the space. A sleek kitchen island with bar stools complements the contemporary design.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars41 months ago
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!
An aerial view captures the nearby beach and ocean, with soft waves lapping at the shore. The beach is dotted with sunbathers and umbrellas, while roads lined with buildings provide access. The highlighted location is positioned across from the beach, showcasing a prime coastal setting.
Condo in Hampton Beach
4.85 out of 5 average rating, 27 reviews

Slice of Paradise at Hampton Beach!!

JohnRating, 5 stars11 months ago
Second time staying at Micheal’s place and it’s always a great time. Will be back
Guest favorite
Cottage in Rye
4.91 out of 5 average rating, 78 reviews

Seaside Cottage in Rye NH

HeidiRating, 5 stars9 months ago
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.
Guest favorite
An indoor swimming pool is visible, featuring clear water and a hot tub adjacent to it. Large windows allow natural light to fill the space, and a door leads outside. Poolside access is provided by a metal ladder.
Condo in Hampton Beach
4.89 out of 5 average rating, 36 reviews

Hampton 100 yards to beach

KrystinaRating, 5 stars10 months ago
Clean and good storage for a small space. Good location
Guest favorite
An in-ground pool is surrounded by a grassy area, providing a refreshing outdoor space. Light blue lounge chairs are arranged nearby, offering places to relax. A white house with black shutters is visible in the background, framed by trees under a clear blue sky.
Home in Kittery
5 out of 5 average rating, 23 reviews

Summer Hill: Sweet New Englander on Maine Coast

ElizabethRating, 5 stars12 months ago
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.
Top guest favorite
A light yellow cottage is positioned adjacent to a spacious swimming pool, surrounded by lush greenery. The pool features a diving board and a decorative tile border. Two lounge chairs sit nearby, while steps lead up to the entrance of the cottage.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

JulieRating, 5 stars1 week ago
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.
Superhost
An enclosed pool area features a clear water pool with a bubbling spa section. The pool is bordered by a smooth, tiled surface, and steps lead into the water. Large windows allow natural light to fill the space, and a door provides access to the exterior.
Apartment in Hampton Beach
4.74 out of 5 average rating, 122 reviews

Beautiful Beach Studio

AlexRating, 5 stars2 weeks ago
Good place to stay for Hampton Beach. Short walk to the water.
Superhost
The serene lake is framed by trees, reflecting the soft colors of the sunset sky. Gentle ripples disturb the water's surface, creating a tranquil atmosphere. In the distance, the silhouettes of trees and properties are visible along the shore, enhancing the peaceful landscape.
Home in Derry
4.82 out of 5 average rating, 135 reviews

Beautiful Lakefront Vacation

BobRating, 5 stars9 months ago
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

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