Family-friendly holiday rentals in Westwood

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Westwood family-friendly rentals

Family-friendly home rentals with a hot tub

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 stars1 week 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 stars3 days ago
Brad was very friendly and helpful. Beautiful home!
Cabin in Falmouth
4.66 out of 5 average rating, 596 reviews

Waterside Guest House

AidenRating, 5 stars2 weeks ago
Super responsive, great host. Very friendly, offered us the local newspaper with deals on places to go and everything. incredible space, right along the water. Thank you, Ron!
Guest favourite
Apartment in Oak Bluffs
4.93 out of 5 average rating, 137 reviews

Victorian Oasis: Driveway, hot tub, grill & more

SaraRating, 5 stars3 days ago
My husband and I and our small dog had a fantastic stay. Sharon accommodated a (very!) early morning checkin time and was very responsive and clear throughout our stay. The unit suited our needs well and we absolutely loved spending time in the back patio/garden area.
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
4.88 out of 5 average rating, 81 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!
Superhost
Condo in Newport
4.87 out of 5 average rating, 31 reviews

Newport Ocean Rentals 1

JanineRating, 5 stars9 months ago
Very convenient in town location. Easy property for parking. Friendly and helpful staff.

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 stars2 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!
Top Guest favourite
Cabin in Rockport
4.97 out of 5 average rating, 454 reviews

The Solar Powered Dogtown Cabin at Applecart Farm

JasonRating, 5 stars3 weeks ago
Wonderful getaway in the woods, but close to restaurants and shop in Rockport. We loved being greeted by the dogs and the hiking trails right outside the front door are amazing.
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
Guest suite in Charlton
4.86 out of 5 average rating, 417 reviews

Baker Pond Hideaway

JohnRating, 5 stars4 days ago
My friend and I always enjoy our time at this beautiful home. Appointed with everything we need for a fun weekend! Just wish we could of spent a little time with our amazing hosts!
Guest favourite
Cabin in Cohasset
4.92 out of 5 average rating, 334 reviews

Lionsgate at Cohasset

PritiRating, 5 stars2 weeks ago
Our stay in Lionsgate cabin in Cohasset was heavenly abode for a week during our stay in the last week of May. The cabin is located in peaceful surroundings with beautiful bird watching areas. The bird feeder outside our cabin kept me and my toddler daughter occupied throughout our stay here. The lawn areas and seating outside are great areas to take a stroll and listen to nature’s music. The cabin is comfortable and cozy with enough provided even for a long stay. It is located within short travel distance from many good restaurants, grocery shops and metro. Very close to the beach, we visited Nantasket and Hull many times during our stay. We loved our stay here and will stay here again. Highly recommend this cabin.
Superhost
Home in Medford
4.85 out of 5 average rating, 142 reviews

Sunny home minutes from Boston. Free parking.

NanditaRating, 5 stars2 weeks ago
We really enjoyed our stay. Such a Warm and cozy home. Elizabeth was easily reachable whenever we had a question. Would highly recommend her cozy home. Thanks Elizabeth
Guest favourite
Barn in Carlisle
4.88 out of 5 average rating, 421 reviews

✨Private Studio w/ Loft Center Historic Carlisle✨

RyanRating, 5 stars5 months ago
Spotlessly clean, quiet, and a warm, comfortable bed. Everything I needed and nothing I didn't.
Guest favourite
Apartment in Ipswich
4.87 out of 5 average rating, 295 reviews

Ipswich Apartment

FelixRating, 5 stars6 days ago
Molly's home was the perfect pick. From the second we walked in, we knew we made the right choice. Before even arriving, Molly reached out & made us feel welcome. Her place truly felt like a home away from home. It was comfortable and cozy. Worried that you forgot something? I guarantee she has an extra there waiting for you. Truly the little things that made a huge difference.

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 stars7 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
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.
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 238 reviews

Cedar Ridge: House or House+Apartment

HilaryRating, 5 stars1 month ago
Very responsive hosts who helped us with restaurants. House was very clean, well appointed and had everything we needed. Great for families or a girls weekend!
Superhost
Townhouse in Middletown
4.97 out of 5 average rating, 36 reviews

Townhouse Close to Downtown Newport & Beaches

LydiaRating, 5 stars4 days ago
Absolutely beautiful space! Very comfortable and cozy! We enjoyed every bit of our visit and felt so at home. It's also in the perfect location: close enough to downtown Newport that everything is very accessible and it's also in a quiet, peaceful neighborhood for a good night's rest. But wait--there's more! Kristin was by far one of the most proactive, friendly, and helpful host I've ever experienced with Airbnb! I highly recommend this listing!
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.
Guest favourite
Home in Middletown
4.92 out of 5 average rating, 63 reviews

Private POOL, Central AC, Walk to beach, king MBR

MarciRating, 5 stars1 month ago
This place was beautiful! The kitchen was spacious and accommodated our larger group nicely. Hosts left clear instructions and proactively checked in. They were even nice enough to open their pool a little earlier so we could enjoy it. Highly recommend staying here if you are planning a girls’ weekend. Bedrooms were comfy, and everyone in my group had a lovely time. Thank you!
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

    $133 NZD 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

Destinations to explore