Family-friendly holiday rentals in Westwood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Westwood

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

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Guest favourite

Flat

4.96 out of 5 average rating, 301 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.

Superhost

Apartment

4.77 out of 5 average rating, 154 reviews

Clear Pond Pet Friendly Inn, Winter months 50% off

This pond front property offers a relaxing atmosphere with beautiful views of your private beach for swimming, kayaking and canoeing. You're a stone's throw from the Plymouth Rock, Plantation, and Plymouth Beach, along with all the restaurants and shops along the waterfront. Boston, Cape Cod, Nantucket, and Martha's Vineyard are only minutes from your doorstep. There is a walking trail for pets around an adjacent cranberry bog. Fire pits, private patio, and beach for your outdoor pleasure!

Guest favourite

Home

4.95 out of 5 average rating, 113 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

Guest favourite

Home

4.97 out of 5 average rating, 121 reviews

Charming 3 br apartment/East side

Beautiful 2 floor apartment/house (part of a duplex) with floral front yard and shady back garden. Close to Brown, RISD, downtown, etc. Fully furnished. Front and back private entrances. Kitchen stocked with cooking basics, including spices, and many utensils, small appliances and pots, pans, etc. Picnic basket, beach towels and mats, hand weights, yoga mat on premises. Suitable for entertaining indoors and out. Parking: 1 garage, 1 alley space. Can host 4 or 5 easily, but up to 6 is possible.

Guest favourite

Flat

4.91 out of 5 average rating, 124 reviews

Comfy, Cozy City flat

Location! Location! Location! Come stay with a super host! Best of the west side/Providence sweet quiet, safe street. Lovely 1st fl. Queen bedroom and 2nd twin bedroom. Fully equipped eat in kitchen. Big, bright living rm. w big sofa for great hang out area. All cotton linens, original art, hardwoods and oriental rugs! No need for a car, within walking distance to 20 eateries and restaurants and less than a mile to downtown. Liquor store, mini-mart, laundromat & bakery around the corner.

Guest favourite

Home

4.92 out of 5 average rating, 133 reviews

Cape Cod; John’s Pond beach w/2 kayaks -SuperHost!

Welcome to our Cape house! Amazing neighborhood & the perfect spot to explore the Cape. Located on fully recreational John's Pond with your private association beach at the end of the street. Large sandy beach, boat launch, float, playground and tennis courts - plus enjoy use of our two kayaks! Just 10 min to South Cape ocean Beach & Mashpee Commons. The house is FULLY updated with hardwoods throughout, AC's, laundry room, front deck with views, private back patio with fire pit and patio.

Guest favourite

Flat

4.75 out of 5 average rating, 297 reviews

Salem/Beverly Last minute Christmas opening!

Winter deal is a 3 night minimum. 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 plenty of kitchen space. Explore the area from this central location on a quiet side street with parking. Walk to beaches, entertainment and a vibrant downtown with a great food scene. Just steps from the commuter rail with trains to Boston, Salem or points north! Let's book!

Superhost

Cottage

4.83 out of 5 average rating, 210 reviews

Cottage by the Bay

Cottage in Fairhaven, perfect for a vacation for a small family, a romantic getaway or a home away from home if you are in the area for business. Enjoy all a vacation has to offer. During warmer weather, walk to the public beach and boat ramp - swim, sun, boat. Spend evenings by the outdoor fireplace. When it is cold out side, enjoy parks, museums, arts and cultural events, with evenings spent enjoying hot chocolate in front of the gas stove as the fire blazes providing a cozy warmth.

Guest favourite

Home

4.96 out of 5 average rating, 121 reviews

Private Family Friendly N Kingstown Guest House

Spacious, quiet, bright and private guest house in a beautiful family-friendly suburban neighborhood, halfway between Providence & Newport. Two-story residence with private entrance and on-site parking. First floor entrance into large master bedroom with ample closet space and full bathroom. Second floor walk up open concept living room, dining area, kitchen, TV, DVD player, AC, fireplace, washer/dryer and full bathroom. Tranquil views of backyard garden. Beach is minutes away.

Guest favourite

Home

4.93 out of 5 average rating, 126 reviews

Wachusett Mountain Get-Away

This family home is spacious and accommodating for those looking to relax while away from the ski slopes or simply wanting to get away from the city. Situated nearby a plethora of hiking and mountain biking trails, lakes for fishing and paddling, the home is perfect for those craving the great outdoors. The home is 6 min from Wachusett Mountain Ski Resort, 3 min from the Wachusett Brewery, and 1 min from the 1761 Old Mill Restaurant.

Guest favourite

Home

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

Guest suite

4.99 out of 5 average rating, 242 reviews

Liberty Street Guest Suite

Footsteps away from Sandwich Boardwalk , mini golf, Belfry Inn, Daniel Webster Inn, enchanting shops and eateries.. You’ll love this place because of the coziness, the light, the neighborhood, the kitchen, the comfy beds and the private deck. This guest suite is best for couples over 25, solo adventurers, and small families as it only sleeps four.