
Family-friendly vacation rentals in Westwood
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Top-rated family-friendly rentals in Westwood
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Popular amenities for Westwood family-friendly rentals
Family-friendly home rentals with a hot tub

Hopkinton Mass 3+ Bedrooms - Great location!
Great stay for a last minute stay I needed. Brad was super responsive and accommodating. Place feels very homey, you can tell he's a family guy! Can only imagine how nice the pool is in the summer. Would've tried the hot tub if we had more time. 3 beds with varying firmness.

Rustic Lux Farm House with Simplistic Elegance
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.

4th July week! Cape Cod Townhome
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.

Waterfront Home with Pool & Hot Tub in Barrington
Robertas’s property was incredible. It’s everything you need and more. From the back deck, to the pool/hot tub, and of course the beautiful dock on the river. She was very communicative throughout the process and was helpful in any question I had. I would recommend everybody to check this spot out, you won’t regret it

Newly renovated, close to Foxboro and Boston
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.

Peaceful waterfront home with dock/ hot tub
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!

Amazing ocean front 3 bedroom
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!

Beautiful 6000 sq ft home 7 miles to Copley Sq.
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

Welcoming 7-room house <15 miles to Boston & Salem
We planned a trip to Boston and had to leave early to avoid a snow storm. Karen was extremely flexible, made it so that we could extend our stay but arriving early at her inconvenience. This is going above and beyond for clients. The house was very clean and the beds were very comfortable. A lot of good restaurants and quaint stores nearby. This was a memorable trip for us. Thank you Karen for making that happen for us.

The Solar Powered Dogtown Cabin at Applecart Farm
This was our third stay at Dogtown cabin and we hope it’s not our last! We were iced/snowed in all week, but we had our pup, plenty of food, tea, and books. I can’t think of a better place to be “stuck.” The cabin is so comfortable and our guide (Azore) arrived each day to accompany us and our dog on walks in the beautiful woods. Delightful. Thanks for a great visit!

Charming South End Duplex (Pets Ok)
Really comfortable, great location, great hosts. If you're sick of soulless passive income properties, decorated in shades of grey and taupe, that no person ever actually lives in, then this is a place for you. It's fun, it's comfortable, it's worn in a good way, it's decorated in glorious eclectic clutter. It has *soul*. Practicalities: Super comfortable mattress, really generously and fully stocked kitchen with good pans and knives. (Tons of condiments and supplies). Neighborhood: Great bakery/coffee shop on the block and tons of really good restaurants within a 5 minute walk. Traffic starts early but I didn't really hear it in the front bedroom. Quirks: Bathroom is downstairs with the bedrooms. 1850 architecture, so a serious lack of outlets and the space can be drafty. The various space heaters more than did the job though. Host: Great communication and they seem like genuinely awesome folks. Very welcoming!
Sunny home minutes from Boston. Free parking.
We stayed at 8 Lambert Street for nearly a month while visiting relatives in Medford. The house is cozy and well furnished. Did a lot of cooking in the kitchen, which had plenty of cooking equipment, the basics of salt, pepper, olive and vegetable oil, and even a set of seasonings. Because we were staying over Christmas, Beth had done some holiday decorating before we arrived, which was wonderful and made the house very cheery. She was a responsive host and kept us stocked with the basics like paper towels and toilet tissue. She even included a baby gift for our new grandson on one occasion. The house was great for our stay - the steam heat combined with the modern thermostat kept us warm and cozy, even on some very cold nights. It's an older house, yes, but full of charm and warmth. The neighborhood is quiet and there are lots of food choices nearby if you don't want to cook. Highly recommend Nappi's Restaurant (cash only) and Fioritaly Trattoria. Off street parking a plus.

Cottage in the heart of the village
Great location away from all the hustle and bustle of the Cape, but close enough to see it all. Highly recommend staying here, very relaxing, quiet, and walkable to a few restaurants and bars to unwind after a long day of exploring the Cape. Cute and cozy! Do yourself a favor and get up for Sunrise at Sandwich Boardwalk during your stay.

Cambridge Getaway @ Harvard & MIT
Excellent place to stay in Cambridge. Walkable but offers parking. Kevin's left treats were perfect. Highly recommend.

1 of a Kind Pond-Front Home, Minutes from Downtown
We loved staying at this lakeside cabin for thanksgiving with family. Beautiful sunsets, great location, charming house. Loved it!

Comfortable house, close to beach and downton IPSW
Great stay at Osvaldo’s! The place is well situated, good size for two couples. Will definitely be coming back!
Family-friendly home rentals with a pool

Our families slice of heaven
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

Cedar Ridge: House or House+Apartment
Arno and Susan were excellent hosts and incredibly responsive. We had a few glitches due to last minute requests that I made with the rental, and host was responsive and kind. The location is remote and private, right in the heart of nature.

Affordable In-Law Apartment in Brooklyn, CT
It was so nice to return to this place during a visit with my family in Connecticut. As always, it was comfortable and clean. We enjoyed cooking in the spacious kitchen each night.

Farm Living
We had a wonderful stay at the farm while visiting family for the holidays. The value was wonderful and it was a perfect place for our active toddler to have a safe sleep spot with very little baby proofing needed which is a key for young families. The beautiful farm was a great bonus and we loved seeing the animals on our way in and out. We hope to return in the summer to enjoy the amenities even more. Thank you Roger!

8 Bedroom, 4 full bath residence with 40' pool
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.

Falmouth, Cozy Studio Near Old Silver Beach
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!

Country Cottage in the City
Lovely place to stay, very peaceful. Mark and Merry were great hosts! Thank you very much!

Spacious 3-BR Furnished Beach Home
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!
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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