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 favourite

Home in Ipswich

4.89 out of 5 average rating, 100 reviews

Hillside Ocean View 2BR with Private Beach Access

Spacious and fun for families and small groups, you can walk right down to Pavilion Beach within 10 minutes and access to Clark Beach. While it is a small house, there is great space inside. The living area is open an has a nice view outside toward the ocean. The living area is comfy with nice sofas to really relax. Cable and high speed wifi are standard, of course. There is a master bedroom with a side view of the ocean, so you can see a beautiful sunrise from the queen sized bed in the morning. The other bedroom has also has a queen sized bed. Nice kitchen space with lots of cooking equipment needed to entertain or cook, including a lobster pot and a small dishwasher. There is also a windowed-in sitting room which faces the ocean and leads to the balcony where great views and barbecues can be had. You'll have permission to go to Clark Beach, a private beach for Great Neck residents and visitors. It's about a 15 minute walk to Clark or 10 minutes to public Pavilion Beach. Other Notes: For reservations 28 nights and over, the actual usage utility bills will be paid by the guest. A $500 utilities deposit will be taken for long term rentals of 2 months or more. WIFI SPEED TEST MARCH 4 2021; DOWNLOAD 17.4 MBPS UPLOAD 11.3 MBPS

Guest favourite

Home in Salisbury

4.9 out of 5 average rating, 129 reviews

NEW 3BR home, incredible views - Beach across St

Enjoy sunrises and sunsets with an expanse of windows that offer breathtaking views of the river and marsh in a new construction, BEAUTIFUL, single family home. Over 2000 Sq Ft wTile & hardwood floors. 1st level has Open living room/kitchen, half bath & 1 bedroom. 2nd Floor has 2 bedrooms, bath, laundry & Large outdoor deck. Beach is a 2 minute walk across the street. 10 minutes to Browns Seafood restaurant, Ice Cream, Groceries & more. 2+ Parking spots. We follow the Advanced Clean Protocol.

Guest favourite

Flat in Winthrop

4.96 out of 5 average rating, 302 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

Top guest favourite

Home in Hampton

4.9 out of 5 average rating, 132 reviews

Luxury Vacation House at North Beach

Beautiful family house located in a quiet residential neighborhood, just steps from North Beach comes with everything you need for a relaxing vacation! This 4BR, 4.5BA house with two living areas, spacious kitchen, & ocean views is the perfect location for a luxury getaway. Three bedrooms have queen beds, & 1 has 2 full beds. With two outdoor living spaces to enjoy the summer weather, this house also has a washer/dryer and wi-fi, dining table for 8, and 4 additional seats at the kitchen island.

Guest favourite

Home in Hampton Beach

4.94 out of 5 average rating, 105 reviews

Pearls on Perkins, Beautiful Condo!

The Pink Pearl is the downstairs 1100 sqft. condo unit! With 2 bedrooms (1 queen & 1 twin bedroom, includes sheets, blanket & comforter), 2 full baths, with towels for your convenience, there is also a comfortable pull out sleep sofa, TV, WIFI, central air, washer/dryer. A large front to back fully equipped kitchen/living room with pots, pans & dishes for home cooked meals. Large roof top deck to watch the sunset over the Hampton River. Fantastic location, only 1 street from the beach.

Superhost

Flat in Beverly

4.75 out of 5 average rating, 297 reviews

Salem/Beverly- Explore Boston's North Shore!

Winter deal- 125 pr night. 3 night minimum- stays through 3/15. Bringing the gang to Boston's North Shore? You'll love this unfussy, spacious, apartment in Beverly. Plenty of room for the family! College visits, holidays & more. 1st floor with spacious eat in kitchen. Centrally located on a quiet side street with parking. Walk to beaches, entertainment, a vibrant downtown with a great food scene and just steps from the commuter rail with trains to Boston, Salem or points north!

Top guest favourite

Home in Rockport

4.97 out of 5 average rating, 326 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.

Guest favourite

Apartment in Cambridge

4.89 out of 5 average rating, 138 reviews

#1A Harvard MIT Central location! in unit W/D

WALK to Harvard, MIT and steps to all public trans & blue bikes! Gorgeous fully furnished monthly stays! Great for tourists, visiting nurses, Harvard, MIT fellows, etc! In-unit w/d and full eat in kitchen (granite counters, dishwasher/disposal (all cooking utensils, etc.). Light filled large bay windows living room with custom built in bookshelves & picture book library. Wood floors, AC/WIFI/all utilities included! Pets (yes large dogs too) welcome w. preapproval.

Guest favourite

Home in North Andover

4.94 out of 5 average rating, 152 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Guest favourite

Flat in Salisbury

4.82 out of 5 average rating, 124 reviews

2BD Apt Steps to Ocean| Pet Friendly-Wkly Discount

Welcome to our newly renovated 2 bedroom, 1 bath beach getaway perfectly located one street back from the beautiful Salisbury beach and just two blocks away from the Salisbury Center, arcades, "beach pizza", restaurants, bars & attractions. With high speed internet, this beachfront condo is perfect for a staycation, work-from-home alternative or beach getaway with family and friends.

Superhost

Flat in West Newton

4.83 out of 5 average rating, 390 reviews

Airy, Sunny, CLEAN 2 BR in Waltham- 15 min BOS

CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College.

Guest favourite

Guest house in Hampton Beach

4.88 out of 5 average rating, 163 reviews

Cute Beach Cottage

Our updated cottage is located steps from the Beach, Boardwalk and beach activities. Quiet, safe street, AC, Smart TV, WIFI, Deck, BBQ grill. Why stay in a hotel room when you can vacation in our cozy cottage by the sea ! Nice updated kitchen. new paint and very clean. The boardwalk has many restaurants music, casino, gift shops Fireworks on Wednesday’s