
Family-friendly vacation rentals in Westwood
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Top-rated family-friendly rentals in Westwood
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Westwood family-friendly rentals
Family-friendly home rentals with a hot tub

New Seabury pool/hot tub near beach,Popponesett
We stayed here for a bachelorette party and the house exceeded our expectations. Sherri was responsive and quick to answer all of our questions before and during the stay.

Hopkinton Mass 3+ Bedrooms - Great location!
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.

Waterside Guest House
The view out the window to the ocean was spectacular and the accommodations were very pet friendly, my two dogs were very happy hanging out on the two couches in the living room. Perfect place to serve as a home base for exploring the quaint restaurants and shops in downtown Falmouth. Full kitchen if you want to cook, and plenty of furniture to have guests for dinner with a good size kitchen table. Ron, was very available and friendly, and I will definately go back!

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.

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!
Family- and pet-friendly home rentals

Welcoming 7-room house <15 miles to Boston & Salem
Karen was absolutely incredible. She was very responsive, respectful, and accommodating. We very much enjoyed our stay as my team and I were there on business. She was able to take care of us even on short notice. I really couldn’t be happier with her communication, the quality of their home, and the entire experience. Thank you so much Karen for inviting us into your home. This was truly a 12/10 experience. 😃😃

The Solar Powered Dogtown Cabin at Applecart Farm
Our stay at Dogtown Cabin was absolutely wonderful! Julie was consistently available for any questions or concerns and she was kind and welcoming and made sure we had everything we needed. The cabin itself was cozy yet spacious. Plus it was equipped with everything we needed to help make our stay comfortable. They had some great trails on the property and my family had a great time exploring them. The beautiful property is serene and private but close enough to a lot of tourists destinations. And let’s not forget the animals! My son had a great time meeting the horses and chickens. But I will say hands down the best part of our stay were our adorable furry hosts, Darwin and Azore! They greeted us every morning! Hanging out with them made our stay even more special! We honestly can’t wait to come back.

Family Home + Near Downtown + Cool Backyard!
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.

Charming South End Duplex (Pets Ok)
We just a wonderful few days in Boston for the marathon. Maude was the perfect host… we really appreciated the flexibility with check-in and check-out and were so grateful for the provisions left for us, particularly as we arrived late! The location is perfect, it meant that we could explore everywhere in the City on foot. The neighbourhood is particularly great for restaurants and when the sun came out and the temperature rose, the vibe was fabulous. As a previous review mentioned, if you’re looking for a pristine, freshly painted apartment then it’s not for you, but if you like ‘quirky’ and a house with bags of character, (I especially loved the art), then I’d highly recommend.

Sparkling Condo With Modern Amenities
Michelle was very responsive and great at communicating leading up to our stay. The house was easy to find, good neighborhood, perfectly clean and had everything we needed. Parking was included which was awesome. The T was easy to walk to so we could go downtown every day easily. The host recommendation for Lulu’s Allston was spot on, it was nearby and great. We felt right at home and had a wonderful stay and check out was also easy. Thank you Michelle for hosting a wonderful place!

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
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!

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!
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
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!

Affordable In-Law Apartment in Brooklyn, CT
I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!

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.

ShoestringBayHouse, waterfront & pool in Cotuit
Perfect stay - just be sure to bring or order sheets and towels!

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.ﺇ294 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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- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- Brown University
- New England Aquarium
- Sandwich Glass Museum
- Sagamore Beach
- Faneuil Hall Marketplace
- New Silver Beach
- Freedom Trail
- Onset Beach
- Prudential Center
- Symphony Hall
- Roger Williams Park Zoo
- Oakland Beach
- Boston Public Library
- Crane Beach
- Scusset Beach
- Pinehills Golf Club
- Aaronap Cellars
- South Shore Beach
- John Hancock Tower
- Boston Children's Museum