Family-friendly holiday rentals in Weymouth

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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!!
Flat 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
Flat 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 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!
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!
Superhost
Flat in Roxbury
4.78 out of 5 average rating, 329 reviews

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

YsamarRating, 5 stars2 weeks ago
Very quiet area. Close to the orange Line and multiple busses. Check In/out was easy. Apt room temp was good. Hot water was extra hot, so also a plus. Cable TV was nice.

Family- and pet-friendly home rentals

Top guest favourite
Home in Wakefield
4.96 out of 5 average rating, 265 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!
Guest favourite
Flat in Lakeside Marblehead
4.94 out of 5 average rating, 196 reviews

Two bedroom Apt with a deck

EmilyRating, 5 stars1 week ago
We had a great stay here! Very flexible check in, the comfiest beds and a variety of incredible books to choose from if you’re staying in!! The host was very sweet and even gave us a recommendation for a great spot to watch the full moon that evening. Gorgeous gardens in the back. Highly recommend this stay!
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 stars4 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
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
Apartment 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
Flat 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 stars2 weeks 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.
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

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, 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
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars6 days ago
Brad was very friendly and helpful. Beautiful home!
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
Guest suite in Canton
4.71 out of 5 average rating, 107 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars8 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.
Guest favourite
Flat 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, 189 reviews

The Secret Garden 4 Bedroom, 7 Bed 3 Baths

IsraelRating, 5 stars6 days 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

    ₹3,462 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

  • Wifi availability

    50 properties include access to wifi

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