Family-friendly holiday rentals in Weymouth

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Weymouth family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Gloucester
4.91 out of 5 average rating, 11 reviews

Steps to Good Harbor Beach

EllenRating, 5 stars46 months ago
This beach house worked perfectly for our stay!! The access to the beach is easy and the accommodations perfectly welcoming! The co-host could not have been more welcoming and helpful!!
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.
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!
Superhost
Home in Plymouth
4.85 out of 5 average rating, 82 reviews

Amazing ocean front 3 bedroom

Neil and TerriRating, 5 stars1 month 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!
Guest favourite
Home in Brighton
4.96 out of 5 average rating, 267 reviews

Spacious 3 bed, in unit laundry, central Air

ErikaRating, 5 stars5 days ago
Great location and nice and clean apartment. Host was also really great, provided good instructions and answered quickly to any questions we had. Overall, great place and great host - highly recommend!
Superhost
Apartment in Roxbury
4.78 out of 5 average rating, 330 reviews

Modern, Spacious 1BR for 4 - Easy Marathon Access!

TanjaRating, 5 stars2 weeks ago
Alex placed us in another, upgraded apartment of his due to a last minute water issue. It’s clear he went above and beyond so we didn’t have to scramble for another place to stay.

Family- and pet-friendly home rentals

Top Guest favourite
Home in Wakefield
4.96 out of 5 average rating, 266 reviews

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

tinamarieRating, 5 stars3 days ago
I had a wonderful stay at this Airbnb! The place was incredibly clean and well-maintained. The space was even more spacious than it looked in the photos! The host was communicative and made check-in easy, and the home had all the essentials my friends and I needed for a smooth stay! I would absolutely stay here again and recommend it to anyone looking for a clean, spacious, comfortable place to stay!
Guest favourite
Apartment in Lakeside Marblehead
4.94 out of 5 average rating, 197 reviews

Two bedroom Apt with a deck

AndrewRating, 5 stars3 days ago
Apartment was clean, comfortable and priced well. It was the perfect size for family of three. Loved the outdoor space and great location. Marblehead is stunning. Host is excellent
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 stars1 month 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
Townhouse in Everett
4.91 out of 5 average rating, 253 reviews

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

DawnRating, 5 stars2 weeks 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 stars8 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 Holbrook
4.93 out of 5 average rating, 121 reviews

Charming Townhouse near Boston. Free Parking. WiFi

KenRating, 5 stars3 weeks ago
Staying at Paul’s house was like staying at a close friend’s. The extra touches of wine, eggs, and simple things that made this house feel like you are cared for as more than just a guest. I cannot possibly say enough about this wonderful home
Top Guest favourite
Home in Melrose
4.96 out of 5 average rating, 110 reviews

Upscale 5BR Family Home Near Boston

DaleRating, 5 stars1 month ago
The home was in a very nice and quiet area of town with groceries, gas and restaurants a short walk or drive away even in during busy hours of Boston traffic. The home was actually larger than expected with two full bathrooms, one on each floor. Everything was clean and ready for us with a well equipped kitchen and filtered water. There was a nice booth area to eat as well as counter seating and a dining room. We only had three in our party, but you could comfortably house a much larger family in the rental. We have a few more trips planned to Boston this year and will book this first if it is available, would like to stay again.

Family-friendly home rentals with a pool

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, 158 reviews

Nana-tucket Inn

SamRating, 5 stars3 weeks ago
We had a great time - beautiful house in a terrific location. Super convenient for Phillips Academy if that's why you're in the area. Nancy was very attentive (and actually lives in an apartment downstairs) so was able to do lots of nice things for us like bake us a coffee cake and make floral centerpieces. Thank you!
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars1 week ago
Brad was very friendly and helpful. Beautiful home!
Top Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 57 reviews

Our families slice of heaven

RileyRating, 5 stars2 weeks ago
Beautiful house, with quiet pond in the back. Most days had the whole pond to ourselves. Perfect spot for a weekend fish trip.
Guest favourite
Guest suite in Canton
4.71 out of 5 average rating, 108 reviews

Newly renovated, close to Foxboro and Boston

StacyRating, 5 stars3 days ago
Smaranda was outside when we arrived, she greeted us and since it was around dinner time she offered some recommendations for dinner. It had been quite windy that day so the pool and hot tub had some leaves and debris in them. She was very apologetic (obviously not her fault, we can't control Mother Nature) and was very attentive and worked hard to get both the pool and hot tub ready for us to use. She showed us how everything worked and the instructions were clear and easy to follow. We used both the pool and hot tub after we got back to the space after dinner and they were both very nice and relaxing. We enjoyed our stay and everything went as planned. We would definitely stay again if Smaranda would have us! Stacy and Ray
Guest favourite
Apartment in Winthrop
4.96 out of 5 average rating, 313 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

BethRating, 5 stars2 weeks ago
We had a wonderful stay! It's very close to Boston, and other area attractions like Salem and beaches, but still peaceful. We enjoyed sitting at the pool. Kathy was very responsive and checked in with us to make sure we had everything we needed. They provided clear instructions for getting into the space and I had no issues navigating in and out of the neighborhood or to the basement apartment. I would definitely stay again if I'm needing a place in the area!
Superhost
Cottage in Westford
4.92 out of 5 average rating, 39 reviews

Beach & pond cottage ! Westford MA and Boston!

KatherineRating, 5 stars1 month ago
We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.
Home in Plymouth
4.9 out of 5 average rating, 190 reviews

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

IsraelRating, 5 stars1 week ago
Birgit was one of the best hosts I’ve ever met. Amazingly accommodating, kind and did everything she can to make our stay enjoyable. I can’t say enough great things about her. My family and friends were very impressed with the house.

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

  • Total rentals

    50 properties

  • Nightly prices starting at

    $66 NZD before taxes and fees

  • Total number of reviews

    2.7K reviews

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 properties include access to Wi-Fi

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