Kid-friendly holiday rentals in Gloucester

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in Gloucester

Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.

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Guest favourite

Loft in Rockport

5.0 out of 5 average rating, 199 reviews

Chic Downtown Loft ☆ Private Parking ☆ Ocean View

Enjoy the coastal and seaside views from the renovated and bright "jewel" located in the charming seaside New England town of Rockport on Cape Ann. The loft is centrally located is literally steps to the beaches, the Bearskin Neck cafes, restaurants, boutiques, art shops, and the Shalin Liu. 1-min walk to Bearskin Neck & Motif No.1 5-min walk to Front Beach + easy access to many others 8-min drive to Halibut Point Park 25-min drive to Salem 1-hour drive to Boston 15-min walk MBTA Train Station

2–9 Jan

$210 SGD per night

Guest favourite

Flat in Beverly

4.92 out of 5 average rating, 449 reviews

Private apartment 10 min to Salem!

This private entrance basement apartment is within a 1/2 mile to several beautiful Beverly beaches. Downtown Beverly is about a 10 to 15 minute pleasant walk. It offers great restaurants and cafes. Live entertainment is happening almost nightly at the Larcom and Cabot theaters. Endicott College is 1 mile away. Downtown Salem is about a ten minute drive from here. The train to Boston, Salem, or Rockport is about a mile away. Plenty of safe street parking is available in front of my house.

1–8 Sep

$195 SGD per night

Superhost

Guest suite in Beverly

4.85 out of 5 average rating, 661 reviews

Historic North Shore, private suite & bathroom

Minutes from Salem! Relax in historic Beverly (walk to Beverly shops) in your private suite; bedroom, living room, and small bathroom, connected to our home, but private entrance. Just minutes from Salem. Commuter line to Boston and close to beautiful North Shore beaches and historic sites. Beaches within biking and driving distances, downtown, parks, hiking. Comfy, soft king bed, queen pull out couch, and plenty of linens. Great for couples, solo adventurers, business travelers, and families.

30 Aug – 6 Sep

$168 SGD per night

Guest favourite

Guest suite in Gloucester

4.98 out of 5 average rating, 377 reviews

SplashLanding Private Beach Getaway in Gloucester

Jan-March 2024 open for monthly rentals. Must Book Summer 2024 via Airbnb website not the APP! *Our 2nd unit SquishInn has openings beginning April 2024 airbnb.com/h/squishinn-gloucester-ma Long walks on a private beach. Get sun-kissed; toes in the sand. Romantic dinners on the deck. Cozy in Winter (Energy Star home and Radiant heat throughout). TRAVELING WITH ANOTHER COUPLE? Book Private Beach Getaway SquishInn. Our 2nd unit for adult couples. Now another 2 friends can join you!

26 Apr – 3 May

$397 SGD per night

Guest favourite

Loft in Gloucester

4.9 out of 5 average rating, 167 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Welcome 2024! We look forward to you visiting RockyNeck in Gloucester. You will be sure to enjoy various special activities and events this summer and fall. We are located in the "quiet end", on a private residential dead end street in a historic artist colony . Nearby public transportation, Audubon sites, cultural events, the Gloucester Stage Co and beaches . Parking is on street with a parking lot nearby, if needed. PLEASE NOTE: the yard is private Bring your passcodes for TV

11–18 Dec

$171 SGD per night

Guest favourite

Cottage in Gloucester

4.97 out of 5 average rating, 101 reviews

Sunny & private cottage in Lanesville Village

Sunny private 2 bedroom cottage with large garden, deck,and great Lanesville location near the ocean. In the off-season, a quiet escape -perfect for focused work, writing, painting or reading, Please contact host for discounts on longer stays (of a week or more) Living room with large flat screen smart TV with Roku, fast internet, and lounge with pull out couch and pocket door for privacy. Dogs under 55 lbs allowed (no more than 2 ) no cats. Yard is not fenced in.

30 Mar – 6 Apr

$239 SGD per night

Guest favourite

Flat in Gloucester

4.94 out of 5 average rating, 109 reviews

Walk to Good Harbor Beach

Newly renovated ground floor efficiency apartment with sliders/walkout to fenced backyard. Wifi and Netflix included. Most dogs okay, some breed restrictions apply. If you want to bring your dog please contact us prior to booking. Three night minimum for all stays. Space includes 1 bedroom with Queen size bed and Living Area with pull out couch. 2 adults will be most comfortable. 5 minute walk to Good Harbor Beach or Bass Rocks. 15 minute walk to Rocky Neck.

27 Sep – 4 Oct

$277 SGD per night

Guest favourite

Guest suite in Rockport

4.99 out of 5 average rating, 611 reviews

Halibut Point State Park. Nature Lovers Retreat

"Tween Coves Cottage" lies nestled next to breathtaking Halibut Pt. State Park. A short walk along wooded paths will lead to the ocean where you can picnic by the water, explore tidal pools, and enjoy a variety of wildlife and vegetation. Distance to the center of Rockport by car is under 10 minutes/ walking is approx. 50 minutes. Distance to the railway station is approx. 5 minutes by car/ walking is approx. 40 minutes.

6–13 Nov

$175 SGD per night

Guest favourite

Guest suite in Rockport

4.87 out of 5 average rating, 197 reviews

Charming Studio in the Pines

This is a first floor, above ground, garden apartment in a private home and is located in a quiet neighborhood with the backyard nestled in the woods, just out side your sliding door. Flower gardens and bird feeders adds ambiance for relaxing in a private setting. The studio offers a kitchenette, dining nook, a full bathroom, a queen bed, plus a sofa. Also available is CableTV, Netflix and Wi Fi.

3–10 Jan

$165 SGD per night

Guest favourite

Guest house in Gloucester

4.94 out of 5 average rating, 143 reviews

Jestina's Cottage - Next to Rocky Neck

Jestina's Cottage is walking distance to the Rocky Neck Art Colony, Gloucester Stage, restaurants, Niles Beach and a short bike ride to Good Harbor Beach. You’ll love the cottage because of the ambience and the location; you feel like you are lost in the woods of Maine but you are close to everything. The cottage is great for couples, solo adventurers, business travelers, and pet-friendly.

10–17 Oct

$222 SGD per night

Guest favourite

Flat in Gloucester

4.97 out of 5 average rating, 103 reviews

The Gilbert: 1-Bed downtown suite, walk to beach.

Come stay in Gloucester’s historic downtown district, in St. Peter’s Square, just one block from Pavilion Beach, Stacey Boulevard and the historic West End of Main Street. The Gilbert sleeps two (up to 3 with an air mattress). A perfect getaway for those in love with history and seaside living. The unit has a private entrance, king sized bed, kitchenette and private bath.

31 Mar – 7 Apr

$302 SGD per night

Guest favourite

Guest suite in South Hamilton

4.96 out of 5 average rating, 240 reviews

It’s better to wake at the Lake 2BR guest suite

Overlooking Chebacco Lake, your rooms are downstairs in a private level. There are 2 bedroom available for use downstairs along with a big living area a coffee/tea bar and a bathroom with shower on this level. You can access to the lake for swim, kayak, canoe or if you come in the winter you can icefish, ice skate, cross country ski or snowshoe too.

12–17 May

$230 SGD per night