Kid-friendly vacation rentals in Gloucester

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Top-rated kid-friendly rentals in Gloucester

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

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Guest favorite

Condo in Portsmouth

4.94 out of 5 average rating, 710 reviews

Downtown Gem |Group Getaway A+ Locale Free Parking

AMAZING LOCATION This downtown gem has 2 floors (1200sf) of living space, steps away from restaurants, theater, jazz club, bars, music hall, shopping + waterfront concerts. Luxe linens + modern décor. Full kitchen, 3 bedrooms, 1.25 baths, central air + hardwood floors. Private yard + 2 FREE parking spots. MUST be 24+ to reserve. Parents+kids < 24 is permitted. No 3rd party bookings. If you book, you must be staying. NO PETS. MOBILITY issues?? PLEASE take note of STEEP+NARROW staircase. Sleeps 8.

Guest favorite

Cottage in Kittery Point

4.95 out of 5 average rating, 154 reviews

Cozy Maine Cottage by the Sea

Cozy one bedroom beach cottage for rent in picturesque Kittery Point, ME. The cottage is located in a quiet coastal community over looking Chauncey Creek, but is just minutes to all the seacoast has to offer. Short drive to many area beaches (Hampton, NH; York, Ogunquit, Wells, ME). Better yet, walk to Kittery's own quiet Seapoint Beach, paddle at the bottom of the hill in the two kayaks provided or just relax on the peaceful deck with a book, a beverage and the gas fire pit for ambience...

Superhost

Rental unit in Amesbury

4.86 out of 5 average rating, 112 reviews

Private, 2bd, 1st floor unit in historic Amesbury

Your family will be close to everything when you stay at this centrally-located Antique New England getaway . Recently renovated, but tastefully original. Everything you need is within walking distance; shopping, grocery, dining, lake, short drive/ride to beach. The space is about 900sqft; 1 bathroom, king bedroom, queen bedroom, queen pull-out couch, and an additional room in which a twin bed can be put (upon request). It will comfortably hold 4 adults, but will accommodate up to 7.

Guest favorite

Cottage in Newbury

4.83 out of 5 average rating, 109 reviews

Sunset Bliss Beach 3 min + wood burning fireplace

Peaceful Plum Island cottage, renovated fall of 2018 and 2023 with New England coastal charm. Open floor plan and water views of the marsh, a short 3 minute walk to the beach. Watch the sun rise over the Atlantic and enjoy the spectacular sunset directly in front of the house for a nightly show. Walk to Plum Island Grill and the Sunset Club for cocktails and dinner. Beach, boating, fishing, wildlife sanctuary, and the historic downtown Newburyport all just 40 miles from Boston!

Guest favorite

Guest suite in Kittery Point

4.95 out of 5 average rating, 265 reviews

Enjoy Warm Autumn Days; Cool Hot Tub Nights!

Just 10-minutes from charming Portsmouth! Enjoy the crystal-clean hot tub on your private patio. Feet-up pampering and special gifts throughout this adorable Maine coastal getaway. Drive into Portsmouth, or stay-in and pamper yourselves. Walk to the Kittery Point town wharf, historical sites, the Bistro and Wharf Restaurant, and catch views of the lighthouse and spectacular sunsets. 5-minute drive to a beach or world-class restaurants, 10-min to the famous Kittery Outlets.

Guest favorite

Cottage in Newburyport

4.92 out of 5 average rating, 104 reviews

Sunset Waterfront Privacy Beach

Newly renovated waterfront with private beach and panoramic views. Enjoy the private pool (heated June through September). Unmatched privacy and large outdoor living. Front row wildlife views of marsh. Bikes to venture out and discover the island. Evenings by the firepit watching the tides roll in. Amazing sunsets! Private sleeping loft in bedroom 3 perfect for older kids. Modern kitchen with a washer/dryer combo. Wake up to a fresh Tea or Coffee.

Guest favorite

Home in Kittery

4.98 out of 5 average rating, 280 reviews

Family Friendly 2BR 1 BA Coastal Kittery Home

Welcome to our cozy family guest home in beautiful Kittery, just 2 miles from downtown Portsmouth. Nearby are beaches, great restaurants, historic sites, boutique shopping, shopping outlets and Portsmouth Naval Shipyard. This home has 2 bedrooms, 1 bathroom, a fenced in yard for up to 4 adults with their children. This house is set up nicely for families of all ages. Dogs welcomed with permission from the owner. STR License # ABNB-22-50

Guest favorite

Home in North Andover

4.95 out of 5 average rating, 149 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!

Superhost

Home in Hampton Beach

4.8 out of 5 average rating, 181 reviews

Steps to Beach | Fireplace | Pat's Porch

Pat's Porch, the sister cottage of Lorraine's Landing and a professionally managed beach getaway - Just a 5-minute stroll from the sun-kissed shores and bustling boardwalk of Hampton Beach, this 3-bedroom, 1-bath abode boasts a queen master bedroom and newly updated kitchen. Relax on the expansive porch equipped with a picnic table, lounge chairs, and grill, or unwind indoors with fast wifi and a Samsung Smart TV.

Guest favorite

Guesthouse 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

Guest favorite

Cottage in Stow

4.95 out of 5 average rating, 149 reviews

White Pine Cottage

Cozy 1930s cottage in Stow, MA with modern amenities. Great landing pad if you are visiting the area. Located in quiet neighborhood with very little traffic. Convenient to local farms, orchards, golfing, parks and more. Hudson, Sudbury and Maynard's restaurants and shops 15 minutes away and big city Boston / Cambridge only 40 minutes.

Guest favorite

Cottage in Gloucester

4.86 out of 5 average rating, 169 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.