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Family-friendly holiday 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.

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Guest suite in Beverly

4.85 out of 5 average rating, 660 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 Sept

$1,535 AUD total

Guest favourite

Apartment in Ipswich

4.88 out of 5 average rating, 228 reviews

Ipswich Apartment

The apartment, with a private entrance is located in downtown Ipswich. We are within walking distance to restaurants and the commuter rail, which services Salem, Boston etc. May - September, the CATA shuttle stops at the commuter rail station, a 3 minute walk. Some CATA services include Cranes Beach, and the town of Essex (famous for its clams and antique shops). You can also enjoy a river cruise down the Essex River there. Kayaking, canoeing, and fishing are also available in Ipswich.

6 – 13 Dec

$1,428 AUD total

Guest favourite

Apartment in Beverly

4.94 out of 5 average rating, 617 reviews

Beverly Farms Apartment “Homeport”

"Homeport" - A nautical themed apartment, nestled in the small coastal village of Beverly Farms. The village has cafes, restaurants, beaches and nearby to “Witch City” Salem MA. Homeport has a private entrance, den, two bedrooms, 1.5 baths with essential amenities and guest parking. The local area is famous for beaches, museums, galleries, eateries and many historic attractions. Explore the North Shore or take a commuter train to explore Boston, saving time and expense of driving.

18 – 25 Jan

$2,001 AUD total

Guest favourite

Home in Rockport

4.97 out of 5 average rating, 282 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

Toe-Hold is a wonderful year-round 1846 home with plenty of rooms, reading nooks and quiet spaces for family and friends of all backgrounds to eat and play together. The gorgeous beaches and picturesque downtown, great restaurants, art galleries and shops for the whole family, are within 10-15 minute walk. Rockport is one of the oldest art colonies in the US, and home to generations of fishermen. Day trips by car or train to Boston and other beautiful historic towns.

26 Jan – 2 Feb

$3,116 AUD total

Guest favourite

Cabin in Rockport

4.97 out of 5 average rating, 406 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

Beautiful hand built very private cabin with master bedroom and large loft located deep in the woods of Cape Ann. Walking distance to down town Rockport and waterfront. Friendly miniature horses just 200 feet away that children love to visit. Applecart Farm is happy to have guests of diverse backgrounds and interests. Pets are allowed only with advanced request to ensure safety of guest and residents pets. NEM 1450 plug for EV charging.

13 – 20 Sept

$3,948 AUD total

Guest favourite

Apartment in Salem

4.95 out of 5 average rating, 602 reviews

Historic Salem Oceanfront 2 Rm Apt

Enjoy beautiful vistas and the sounds of the ocean from this oceanfront 2 room apt in a quaint Victorian seaside neighborhood. This basement apt has full sized windows with ocean views that make it bright and cheerful. It offers a full kitchen, bath and a good sized bedroom w/queen bed & comfy chairs. Relax in our Adirondack chairs beside the ocean! NOTE: YOU CAN ONLY BOOK UP TO 6 MONTHS FROM TODAY RATES FLUCTUATE SEASONLY

5 – 10 May

$1,664 AUD total

Guest favourite

Cottage in Manchester-by-the-Sea

4.94 out of 5 average rating, 346 reviews

Singing Beach Cottage in Manchester by the Sea

Beach is .9 tenths of a mile, Gordon College 5.1 miles, Endicott College 4.6 miles, Salem 14 miles (23 min train ride), Boston is 30.6 miles (53 min train ride). No visitor parking at the beach during the summer. Shops, restaurants, groceries & train are .2 tenths of a mile away. Town limit = 4 guests. Off-street parking for 1 car. Super clean unit however not hypoallergenic (known scam to get refund).

24 – 31 Aug

$2,870 AUD total

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.

24 – 31 Oct

$1,532 AUD total

Apartment in Rockport

4.87 out of 5 average rating, 163 reviews

"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven

Experience the beauty of Rockport's waterfront at this 2 bed/1 bath oceanfront haven. Located on Bearskin Neck, this historic building was once the Sail Loft and is now your perfect getaway. Enjoy the convenience of being close to the ocean, restaurants, shops, and beaches. Come and make lasting memories at this charming Rockport escape. Don't forget to take advantage of the small patio and kitchen.

18 – 25 Nov

$2,304 AUD total

Guest favourite

Guesthouse 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

$2,025 AUD total

Guest favourite

Townhouse in Gloucester

5.0 out of 5 average rating, 153 reviews

Between 2 Beaches

This 3 level, 3 bedroom, 2.5 baths, recently renovated beach themed, fully stocked condo, has 2 unique outdoor spaces, and is located within walking distance right in between 2 of the most amazing beaches in Cape Ann: Good Harbor Beach in Gloucester, and Long Beach in Rockport. Take your pick, no need to drive and pay to park, it's just a short to walk to either.

11 – 18 Apr

$6,458 AUD total

Guest favourite

Cottage in Gloucester

4.86 out of 5 average rating, 157 reviews

Bright & Cheerful 3BR+den, Gloucester Cottage

Quiet 3BR + den, 2BA cottage sits on a creek with a lovely deck overlooking the tidal marsh which opens up to Essex Bay. Comfy beds, light and airy space. Quiet neighborhood surrounded by nature. Train to Boston is 2 miles from the house, local hikes, bike rides and beaches all a short walk, drive or bike ride away.

28 Sept – 5 Oct

$4,976 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Gloucester family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Guest suite in Kittery

4.9 out of 5 average rating, 744 reviews

Seacoast Oasis (NH & ME)

$153 AUD per night

Guest favourite

Guest suite in Kittery Point

4.94 out of 5 average rating, 232 reviews

Hot Tub & Spa-Like! Pamper Yourself This Spring!

28 Mar – 4 Apr

$2,224 AUD total

Apartment in Boston

4.77 out of 5 average rating, 277 reviews

Modern, Spacious 1BR for 4 - Easy Marathon Access!

12 – 19 Dec

$2,926 AUD total

Townhouse in Newton

4.8 out of 5 average rating, 218 reviews

Airy 3 BR House w/ Outdoor Sauna Hot Tub EV Charge

2 – 9 Aug

$3,637 AUD total

Guest favourite

Farm stay in Eliot

4.97 out of 5 average rating, 99 reviews

Shilo Farmhouse: Goats & Hot Tub! Near Portsmouth

23 – 30 Jan

$3,411 AUD total

Condo in Hampton

4.68 out of 5 average rating, 76 reviews

# 18 Large deluxe 3br, 2 1/2 bath condex sleeps 13

31 Oct – 7 Nov

$3,184 AUD total

Home in Newton

4.75 out of 5 average rating, 52 reviews

Beautiful 6000 sq ft home 7 miles to Copley Sq.

3 – 10 Dec

$13,108 AUD total

Home in Salisbury

4.83 out of 5 average rating, 104 reviews

Namaste at the Beach

2 – 9 Nov

$5,130 AUD total

Family- and pet-friendly home rentals

Guest favourite

Apartment in Marblehead

4.93 out of 5 average rating, 155 reviews

Two bedroom Apt with a deck

11 – 18 Nov

$1,830 AUD total

Guest favourite

Apartment in Natick

4.98 out of 5 average rating, 332 reviews

Scandi-Modern Apartment

9 – 16 Sept

$1,588 AUD total

Guest favourite

Apartment in Ipswich

4.86 out of 5 average rating, 229 reviews

Comfortable house, close to beach and downton IPSW

20 – 27 Nov

$2,657 AUD total

Guest favourite

Home in Kittery

4.95 out of 5 average rating, 432 reviews

water view property "The Little House"

30 Mar – 6 Apr

$1,863 AUD total

Guest favourite

Guest suite in Salem

4.83 out of 5 average rating, 588 reviews

Salem House

1 – 8 July

$1,534 AUD total

Guest favourite

Cabin in Cohasset

4.92 out of 5 average rating, 284 reviews

Lionsgate at Cohasset

13 – 20 Oct

$1,990 AUD total

Guest favourite

Guesthouse in Lee

4.98 out of 5 average rating, 128 reviews

Mousetrap - a Cozy Cottage near the Lamprey River

26 Apr – 3 May

$1,969 AUD total

Guest favourite

Apartment in Concord

4.94 out of 5 average rating, 207 reviews

Bishop Suite - Private suite in historic Concord

1 – 8 Apr

$1,424 AUD total

Family-friendly home rentals with a pool

Guest favourite

Guesthouse in Dedham

4.95 out of 5 average rating, 171 reviews

Country Cottage in the City

24 June – 1 July

$1,877 AUD total

Guest favourite

Home in North Andover

4.94 out of 5 average rating, 127 reviews

Nana-tucket Inn

24 Nov – 1 Dec

$10,828 AUD total

Guest favourite

Apartment in Holliston

4.95 out of 5 average rating, 110 reviews

Lake Link

14 – 21 Sept

$1,914 AUD total

Guest favourite

Apartment in Winthrop

4.96 out of 5 average rating, 275 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

26 Mar – 2 Apr

$2,586 AUD total

Guest favourite

Villa in Cambridge

4.99 out of 5 average rating, 187 reviews

Phil's Harvard & MIT Home

18 – 25 Aug

$4,357 AUD total

Guest suite in Canton

4.7 out of 5 average rating, 89 reviews

Newly renovated, close to Foxboro and Boston

28 Oct – 4 Nov

$1,991 AUD total

Guest favourite

Condo in Hampton

4.93 out of 5 average rating, 28 reviews

Hampton 100 yards to beach

5 – 12 Oct

$3,223 AUD total

Home in Seabrook

4.9 out of 5 average rating, 42 reviews

Family friendly beach house

28 Sept – 5 Oct

$1,555 AUD total

Quick stats about holiday rentals that are family-friendly in Gloucester

Total rentals
340 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
330 properties include access to Wi-Fi
Rentals with dedicated workspaces
180 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Total number of reviews
10K reviews

Destinations to explore