Family-friendly holiday rentals in Westwood

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Popular amenities for Westwood family-friendly rentals

Family-friendly home rentals with a hot tub

Apartment in Fenway-Kenmore
4.73 out of 5 average rating, 83 reviews

Renovated 2Bed, 0.5 mile to Longwood Med Hospital

AmyRating, 5 stars1 month ago
This condo was perfect for what we needed. Just two bedrooms, a kitchen and living room, so we could relax in between walking adventures. I wish I had come across this back in the fall when my daughter was playing soccer for Northeastern because the soccer field is literally across the street. There is a nice walking trail about a quarter of a mile away. We really liked Coolidge Corners. Easy to get Ubers. The place was perfect and comfortable and easy to get in/out.
Home in West Roxbury
4.71 out of 5 average rating, 7 reviews

Luxury Ultra Modern House in Newton ; Boston

Ryan MRating, 5 stars42 months ago
Excellent location! Great stay for a family away from home! House was magnificent and modern. Beautiful upstairs with an open layout and a downstairs living room. Plenty of space to relax and enjoy each other’s company. Close to the Newton center to access the (T)rain so Boston is easily accessible. Great communication with Amir! He responded quickly with any questions I had! Would definitely come back for another family vacation!
Guest favourite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars3 weeks ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Guest favourite
Apartment in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars2 weeks ago
The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars5 days ago
Brad was very friendly and helpful. Beautiful home!
Guest favourite
Home in Brighton
4.96 out of 5 average rating, 266 reviews

Spacious 3 bed, in unit laundry, central Air

BillRating, 5 stars3 weeks ago
We had a great stay! This house was in a great location, and very nice/spacious. We also appreciated the very thorough and clear communication regarding check-in etc, before the stay. I highly recommend Joel as a host!
Guest favourite
Home in East Falmouth
4.9 out of 5 average rating, 60 reviews

Peaceful waterfront home with dock/ hot tub

ConorRating, 5 stars10 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
4.85 out of 5 average rating, 82 reviews

Amazing ocean front 3 bedroom

Neil and TerriRating, 5 stars3 weeks ago
Beautiful setting with ocean views and pretty landscaping and gardens view out every window. Easily accommodated six people in our party. Home was equipped with everything we needed. Outside seating, hot tub and grill area are lovely. We had a nor’easter arrive so didn’t get to enjoy outside too much but the little that we did was incredible! Gas fireplace in living room kept dampness at bay and was just lovely. Two inside eating areas were perfect! Would come back in a heartbeat!

Family- and pet-friendly home rentals

Top Guest favourite
Home in Wakefield
4.96 out of 5 average rating, 264 reviews

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

NancyRating, 5 stars3 weeks ago
We enjoyed staying at Karen’s! It was a super clean space which we really, really appreciated. The neighborhood is peaceful and quiet. Super easy to check-in and check-out. Karen is also super responsive and proactive which was great! Only bump in the road was that we unfortunately had to deal with a water leak issue which was stressful but Karen did what she could to be as helpful as possible. It was fixed shortly after reporting. We appreciated that Karen coordinated maintenance so quickly in a way that was accommodating to our schedule. Overall we are very pleased and would definitely recommend!
Superhost
Cottage in Sandwich
4.86 out of 5 average rating, 401 reviews

Oceanfront Cottage w/Private Beach ~ Lil’ Sea Sass

EricRating, 5 stars2 weeks ago
This place is great. The house is very nicely decorated and clean. Everything one needs is there. We could wind down within a day of the total of three days. Susan was very responsive, which made our stay simple and easy.
Guest favourite
Townhouse in Everett
4.91 out of 5 average rating, 253 reviews

#9 Modern Home 15 min to Boston. Relax in Style!

DawnRating, 5 stars1 week ago
Great place. We loved the location and the surroundings. Wally was you receptive and proactive. Everything we needed was available. The instructions and local information was great and even though we had a plan of things to do, it provided us a couple of awesome ideas for our down time. Would definitely stay there again and would recommend. Thanks Wally.
Guest favourite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 months 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.
Guest favourite
Apartment in Milton
4.85 out of 5 average rating, 119 reviews

Retreat Milton/Boston line (transit close) Pets

GeraldineRating, 5 stars7 months ago
We were a group of four guys on a sports-trip to Boston. The location was perfect, 30 minute drives from Downtown, Foxborough and Boston College. Lovely neighbourhood, quiet and nice walks nearby. The house was as described in the listing, plenty of space for four, clean and comfortable with a well-equipped kitchen.
Guest favourite
Townhouse in Allston
4.93 out of 5 average rating, 189 reviews

Sparkling Condo With Modern Amenities

MelissaRating, 5 stars1 week ago
Had a wonderful stay with my friends in Boston. The rooms and living spaces were very comfortable and clean. Michelle was very reachable and responded quickly. Would recommend this home to anyone.
Top Guest favourite
Apartment in Concord
4.96 out of 5 average rating, 214 reviews

Mema's Place --Lovely apartment in private home

MiebethRating, 5 stars3 days ago
We loved Ellen's place from the minute we walked in. It was warm, welcoming and had everything that we needed for a week's stay. The house/apartment is set on a quiet street set in the woods but a very close drive to Concord where we spend most of our time sightseeing. Helen's is the best restaurant to try in town. Ellen and her husband Kevin were there to welcome us and answered any concerns we had about the place. Her place is very comfortable with a large living room to relax in, a kitchen to cook in and a very comfortable bed to sleep in. I give her place 10 stars and more and I recommend it to anyone who is staying in Concord. Thank you Ellen for the wonderful stay and we look forward to seeing you again
Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 159 reviews

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

AngelaRating, 5 stars2 weeks ago
The house is amazing! It has everything that you would need and is so comfortable. The property is peaceful, and it feels like you’re on your own little island while still being minutes from stores and restaurants. We had a perfect weekend celebrating some milestone birthdays in our family.

Family-friendly home rentals with a pool

Top Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 56 reviews

Our families slice of heaven

EmilyRating, 5 stars8 months ago
This place was INCREDIBLE!! Marla and her family were so responsive and so welcoming!! This house was the cleanest I have ever stayed in. The furniture was so comfortable and cozy. I would HIGHLY recommend staying here! I hope to come back in the near future!! Thank you Marla and family for being such amazing hosts!!
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 239 reviews

Cedar Ridge: House or House+Apartment

AlissaRating, 5 stars5 days ago
We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again
Guest favourite
Guest suite in Brooklyn
4.93 out of 5 average rating, 190 reviews

Affordable In-Law Apartment in Brooklyn, CT

LyndaRating, 5 stars3 weeks ago
Thank you so much! Really enjoyed my time in brooklyn.
Top Guest favourite
Farm stay in Rutland
4.96 out of 5 average rating, 373 reviews

Farm Living

JenniferRating, 5 stars1 week ago
It's a beautiful back yard and working farm. It's peaceful & fun to hear the animals ( peacock & donkey). There is lots to do for kids. The place was clean with roomy main bedroom & livingroom. The kitchen had everything needed but lacked ample counter space or room to store unrefrigerated food. The dehumidifier ran all the time & had to be emptied every day. The patio has couch & chairs looked comfy but got wet in rain. The picnic table was nice & coukd be dried off. My grandkids had a blast using the pool, trampoline, hammock, see-saw & climbing structures. It's a very peaceful place. We hiked on 2 different Mass Rail Trails near by.
Superhost
Apartment in Brooklyn
4.85 out of 5 average rating, 221 reviews

8 Bedroom, 4 full bath residence with 40' pool

Maria ChristinaRating, 5 stars1 week ago
The hosts Marybeth and Douglas were so welcoming to us and accommodated our request to check- in earlier than scheduled! They were very friendly and provided extra stuff to make our stay feel so homely and comfortable! Everyone of us (13 people) truly enjoyed our stay at their beautiful, spacious and historical home!
Superhost
Condo in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.
Chalet in Killingly
4.86 out of 5 average rating, 22 reviews

Lake House in North Eastern CT

BarbaraRating, 5 stars8 months ago
Our family had a very nice time! Kids loved it. I definitely recommend it.
Top Guest favourite
Home in Cotuit
4.95 out of 5 average rating, 115 reviews

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

JorgeRating, 5 stars1 week ago
Beautiful house. Kid friendly Really close to the beach Amazing hosts

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    $124 AUD before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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