Family-friendly vacation rentals in Westwood

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Westwood family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Hopkinton
4.95 out of 5 average rating, 151 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

KevinRating, 5 stars1 week ago
We had an excellent time at Brad’s beautiful home. Beds were very comfortable, enough hot water for several showers, and all of the cooking ware you would need! Well these things are what catch our attention when traveling for work. Brad is an awesome guy and fantastic host. He was there from time to time, and there was never an awkward moment. He is very personable and easy going. I would stay here 10 out of 10 times when passing through.
Superhost
Home in Essex
4.73 out of 5 average rating, 12 reviews

Rustic Lux Farm House with Simplistic Elegance

RobinRating, 5 stars9 months ago
This is a wonderful place for a family gathering. There can't be too many 17th century rentals (1686?) with amazing original fireplace and wood. We enjoyed exploring the house - 3 staircases, many fireplaces, surprising rooms and passageways. Very nicely decorated rooms. Large kitchen and pantry, comfortable seating in living area, on screen porch, outside on large lawn.
Top guest favorite
Home in West Barnstable
4.98 out of 5 average rating, 63 reviews

West Barnstable Resort

ShaneRating, 5 stars1 week ago
Beautiful home. One of the best master suites I’ve stayed in. Great outside amenities and a really nice floorplan for large groups. We had a great trip and would stay here again.
Superhost
Townhouse in Mashpee
5 out of 5 average rating, 3 reviews

4th July week! Cape Cod Townhome

DmitryRating, 5 stars82 months ago
The place is great if you don't mind having to drive to a beach or to town. It's spacious and clean. And Ruth is a great host. She was very responsive.
Superhost
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars5 months ago
The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.
Guest favorite
Home in East Falmouth
4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

ConorRating, 5 stars8 months ago
We stayed at this home with a group of five people and the home fit everyone great. The view from the home of the marsh is beautiful and we spent Saturday hanging out on the dock. It is really peaceful and we had an amazing time. Michele was a pleasure to work with and was very accommodating with being flexible for check in and check out times. Thank you again!
Superhost
Home in Plymouth
4.87 out of 5 average rating, 79 reviews

Amazing ocean front 3 bedroom

CrystalRating, 5 stars5 months ago
We had a wonderful stay! The house was great! Views were awesome from the top balcony! We wished the bushes and shrubs had been trimmed a little to have a better view from the main level but it was still a nice view from the one area there. House was quite roomy and had everything we needed in the kitchen. There are not tvs in the two spare rooms which would have been good after dinner for our teenagers while winding down after family time. The host is wonderful and communicated great. Overall we had a great family vacation and a good time. The house is nice. Would recommend!
Guest favorite
Home in Newton
4.77 out of 5 average rating, 61 reviews

Beautiful 6000 sq ft home 7 miles to Copley Sq.

MatiasRating, 5 stars5 months ago
We rented Veronika's home for a work related trip to Boston. The home was great, perfectly located for our needs. Thoroughly enjoyed our stay in Neeton. Hope to be back next year.

Family- and pet-friendly home rentals

Top guest favorite
Home in Wakefield
4.96 out of 5 average rating, 257 reviews

Welcoming 7-room house <15 miles to Boston & Salem

ChrisRating, 5 stars3 weeks ago
I’ve stayed at Karen’s Airbnb multiple times while traveling for work, and it’s always been a fantastic experience. Karen is a great host—she’s quick to respond to messages and makes sure everything is just right. The home itself is clean, comfortable, and in a great location, making it perfect for both work trips and relaxing stays. I always look forward to returning and highly recommend this Airbnb to anyone visiting the area!
Top guest favorite
Cabin in Rockport
4.97 out of 5 average rating, 443 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

TatianaRating, 5 stars3 weeks ago
Had a great experience staying at Dogtown, will absolutely love to go back there again. The host was wonderful and very kind. The animals were beautiful and nice. Location was peaceful. Everything you may need was just 10/15mins away. We got all of our questions answered and more! Will be looking to book for the near future. We went for just a weekend and it truly was worth it.
Guest favorite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars4 weeks ago
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.
Top guest favorite
Apartment in South End
4.96 out of 5 average rating, 371 reviews

Charming South End Duplex (Pets Ok)

AmyRating, 5 stars4 days ago
We arrived in the evening after a long plane ride and there was wine and cheese and crackers for us. Maude stocked the food so well we hardly neede to buy anything. This was such a bonus because we were at the World Figure Skating Championship all day and evening. It was a great stay! Thank you Maude!
Guest favorite
Home in Newport
4.91 out of 5 average rating, 161 reviews

⚓️ Top Notch Newport Location! SuperHost! 🏡

DemitriRating, 5 stars4 months ago
Lovely trip to Newport. Location of this house is perfect. Everything was clean and nice and super super easy communication. We forgot some small items and the hosts went above and beyond to mail them back to us.Great stay.
Guest favorite
Apartment in Cambridge
4.87 out of 5 average rating, 437 reviews

Cambridge Getaway @ Harvard & MIT

LindaRating, 5 stars1 week ago
This is an authentic Cambridge home that has been owned by the host's family for multiple generations. Kevin is accommodating, and he generously left some snacks and drinks in the full kitchen for us. Well-stocked kitchen was super convenient for eating breakfasts. Note: there are significant stairs to get into the unit. Once there it's quite spacious. And I love the operable bathroom window. :) Thanks for a lovely stay in a convenient, walkable neighborhood!
Guest favorite
Home in Plymouth
4.96 out of 5 average rating, 157 reviews

1 of a Kind Pond-Front Home, Minutes from Downtown

WadeRating, 5 stars4 months ago
We loved staying at this lakeside cabin for thanksgiving with family. Beautiful sunsets, great location, charming house. Loved it!
Superhost
Apartment in Ipswich
4.85 out of 5 average rating, 275 reviews

Comfortable house, close to beach and downton IPSW

BryanRating, 5 stars1 month ago
Very pleasant stay! The place was clean, comfortable, and exactly as described. The host was helpful and responsive, making the whole experience smooth and enjoyable. Would definitely stay here again — highly recommend!

Family-friendly home rentals with a pool

Top guest favorite
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars5 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Guest favorite
Home in Woodstock
4.94 out of 5 average rating, 235 reviews

Cedar Ridge: House or House+Apartment

SuzanneRating, 5 stars2 weeks ago
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!
Top guest favorite
Guest suite in Brooklyn
4.93 out of 5 average rating, 180 reviews

Affordable In-Law Apartment in Brooklyn, CT

EricaRating, 5 stars3 weeks ago
Nice, comfortable stay. Bonus accessible washer and dryer.
Superhost
Townhouse in Middletown
4.97 out of 5 average rating, 35 reviews

Townhouse Close to Downtown Newport & Beaches

WillaRating, 5 stars19 months ago
My family had a great weekend at Kristin’s house. I love this Beautiful, clean, well maintained property. The fire pit is great for marshmallow. We did not get to use the lovely pool because it got really cold at night. Bonus: filtered water from fridge, blinds + curtain, skylight in bathroom.
Top guest favorite
Farm stay in Rutland
4.96 out of 5 average rating, 361 reviews

Farm Living

ShawnRating, 5 stars1 week ago
Beautiful location! Our hosts were very friendly and responsive. We would love to come back and enjoy more of the farm!
Superhost
Apartment in Brooklyn
4.85 out of 5 average rating, 217 reviews

8 Bedroom, 4 full bath residence with 40' pool

JudieRating, 5 stars5 months ago
This was our first time at the Barn. There were 8 of us. We had plenty of room. Plenty of parking. MaryBeth and Doug are extremely friendly. We enjoyed hearing about the history of the Barn. Will definitely book there again next year.
Superhost
Apartment in North Falmouth
4.79 out of 5 average rating, 108 reviews

Falmouth, Cozy Studio Near Old Silver Beach

Anna GraceRating, 5 stars7 months ago
We had a wonderful weekend stay! The house is located in a quiet neighborhood and the upstairs apartment was very clean. There is quick access to local beaches and restaurants. We would stay again!
Top guest favorite
Guesthouse in West Roxbury
4.95 out of 5 average rating, 191 reviews

Country Cottage in the City

BeckyRating, 5 stars5 months ago
Lovely place to stay, very peaceful. Mark and Merry were great hosts! Thank you very much!

Quick stats about vacation rentals that are family-friendly in Westwood

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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