Family-friendly vacation rentals in Westwood

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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, 147 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

NandaRating, 5 stars1 month ago
Brad is a wonderful host. He checked in to make sure I was happy with everything and was quick to respond to my messages before I arrived. His house is very comfortable with everything my family needed for a relaxing stay. The view of the golf course from the bedroom was a nice plus. We felt right at home. Highly recommend!

Home in Essex

4.73 out of 5 average rating, 12 reviews

Rustic Lux Farm House with Simplistic Elegance

RobinRating, 5 stars7 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.
Superhost

Townhouse in Mashpee

5 out of 5 average rating, 3 reviews

4th July week! Cape Cod Townhome

DmitryRating, 5 stars80 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.

Home in Sandwich

5 out of 5 average rating, 6 reviews

40 Ploughed Neck Rd

FrankRating, 5 stars6 months ago
This was a first family vacation since the kids were little. 6 adults in a very spacious home ! Could not have been better. The living room, dining room and completely modern kitchen [fully capable of any meal preparations] made for family fun and connections. The patio and fenced in yard was supurb - and the complete kitchen BBQ set-up, fire pit, fenced in yard all made for the perfect vacation. A small slice of paradise. Thank you to the Chambers family for letting us stay in your home. We were delighted and felt safe and secure in all things. Hopefully we will be able to make next year happen - amongst the future wedding plans and such ! God Bless. Frank + Cathy and the family.
Guest favorite

Home in Barrington

4.9 out of 5 average rating, 41 reviews

Waterfront Home with Pool & Hot Tub in Barrington

PatrickRating, 5 stars6 months ago
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
Superhost

Guest suite in Canton

4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars3 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.
Superhost

Home in Plymouth

4.87 out of 5 average rating, 79 reviews

Amazing ocean front 3 bedroom

CrystalRating, 5 stars3 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 stars3 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

Guest favorite

Home in Wakefield

4.96 out of 5 average rating, 252 reviews

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

TheresaRating, 5 stars2 days ago
Would highly recommend! Karen is a fantastic host and very quick to respond. She is the friendliest host I’ve met yet and means it when she says, she wants her guests to enjoy their stay! Beds are super comfy, there’s lots of space and the house had everything we needed.
Guest favorite

Cabin in Rockport

4.97 out of 5 average rating, 438 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

JohnRating, 5 stars1 week ago
My girlfriend and I stayed at Dogtown cabin recently to celebrate her birthday. We loved how secluded it was and the cabin was just perfect. We went to a couple of different seafood restaurants near by and the food was amazing. We also made breakfast at the cabin each morning and they had plenty of cooking supplies available. We watched the beautiful sunrise through the dining area windows while sipping our morning coffee. We also took a long hike in the woods with many trails starting right outside the cabin. We enjoyed petting the 4 horses and watching the chickens scurry around. One major highlight was their 2 dogs. They greeted us upon arrival and we let them come inside the cabin to visit with us. They were both very well behaved and brought us much joy being dog lovers. I highly recommend staying at Dogtown cabin. I’m looking forward to staying there again in the future.
Superhost

Home in Cranston

4.92 out of 5 average rating, 131 reviews

Raised Ranch Retreat: Modern 3 BR/3 Bath w/ Office

GeorgeRating, 5 stars2 months ago
We loved our Thanksgiving stay at this home! Perfectly located and easy to get to from I-95 & I-295, future renters will easily see how great this place is…unless we rent it first! :)
Guest favorite

Apartment in South End

4.96 out of 5 average rating, 364 reviews

Charming South End Duplex (Pets Ok)

RuthRating, 5 stars3 weeks ago
We loved staying here! Beautiful apartment in a fantastic location. The communication with the hosts was excellent. Maude left a lovely hand written note, a stocked fridge and even a bottle of wine! Would definitely recommend staying here. Thank you so much for sharing your beautiful home!
Superhost

Home in Medford

4.84 out of 5 average rating, 135 reviews

Sunny home minutes from Boston. Free parking.

AllisonRating, 5 stars4 weeks ago
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.
Guest favorite

Home in Sandwich

4.93 out of 5 average rating, 211 reviews

Cottage in the heart of the village

JeffRating, 5 stars5 months ago
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.
Guest favorite

Apartment in Cambridge

4.87 out of 5 average rating, 434 reviews

Cambridge Getaway @ Harvard & MIT

CamilleRating, 5 stars2 months ago
We are repeat guest at Kevin's. We love the location near Inman and Harvard Square. We enjoy the rooftop deck, having a well stocked kitchen and he always leaves us with bagels, cookies, coffee and tea to make the transition easy. Having a Whole Foods minutes walk is very convenient. Will definitely be back.
Superhost

Apartment in Ipswich

4.85 out of 5 average rating, 273 reviews

Comfortable house, close to beach and downton IPSW

ChloéRating, 5 stars2 months ago
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

Guest favorite

Home in Plymouth

4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars3 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, 233 reviews

Cedar Ridge: House or House+Apartment

ElizabethRating, 5 stars1 month ago
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.
Guest favorite

Guest suite in Brooklyn

4.93 out of 5 average rating, 178 reviews

Affordable In-Law Apartment in Brooklyn, CT

CynthiaRating, 5 stars1 month ago
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.
Guest favorite

Farm stay in Rutland

4.96 out of 5 average rating, 357 reviews

Farm Living

ArdenRating, 5 stars1 month ago
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!
Guest favorite

Apartment in Brooklyn

4.85 out of 5 average rating, 217 reviews

8 Bedroom, 4 full bath residence with 40' pool

JudieRating, 5 stars3 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.
Guest favorite

Home in Cotuit

4.94 out of 5 average rating, 18 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

ZackRating, 5 stars3 months ago
Perfect stay - just be sure to bring or order sheets and towels!
Superhost

Apartment in North Falmouth

4.78 out of 5 average rating, 109 reviews

Falmouth, Cozy Studio Near Old Silver Beach

Anna GraceRating, 5 stars5 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!
Guest favorite

Guesthouse in West Roxbury

4.95 out of 5 average rating, 191 reviews

Country Cottage in the City

BeckyRating, 5 stars3 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

    $80 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

Destinations to explore