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Family-friendly holiday rentals in Dorchester, Boston

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Dorchester, Boston family-friendly rentals

Family-friendly home rentals with a hot tub

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
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
Flat 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!
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

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
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
Flat in South End
4.96 out of 5 average rating, 381 reviews

Charming South End Duplex (Pets Ok)

StephanieRating, 5 stars1 day ago
This is such an amazing place. We arrived very late but the instructions to get in were great and there was stuff in the fridge to keep us going until the morning. Maude had left detailed instructions and tips to work the lights etc. We felt really comfortable and probably the most relaxed on our US trip. It is also a very walkable and safe area. Don't hesitate to stay here!
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.
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.
Guest favourite
Home in Coolidge Corner
4.79 out of 5 average rating, 120 reviews

Lovely sunny 2 BD home, great area. Free Parking

CarolRating, 5 stars3 weeks ago
We had a wonderful stay. The neighborhood was quiet and centrally located with restaurants and shopping within an easy walking distance. Plan to stay again the next time we are in Boston
Guest favourite
Flat in Cambridge
4.87 out of 5 average rating, 444 reviews

Cambridge Getaway @ Harvard & MIT

MarkRating, 5 stars1 day ago
We very much enjoyed our stay at Kevin’s place. Great location. Easy access to the train and the city. Lots of nearby restaurants. Kevin was friendly and accommodating and provided some nice treats to eat and drink. The apartment was very comfortable. We especially enjoyed sitting out on the rooftop patio. We will be sure to stay again when visiting the area.

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 stars4 days ago
Brad was very friendly and helpful. Beautiful home!
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.
Guest favourite
Flat in Holliston
4.96 out of 5 average rating, 121 reviews

Lake Link

MichaelRating, 5 stars5 months ago
Our second time, weeklong stay! And we hope to do it again next year. Just simply meets our needs very well. It's a joy to stay here!

Quick stats about holiday rentals that are family-friendly in Dorchester, Boston

  • Total rentals

    390 properties

  • Nightly prices starting at

    ₹2,596 before taxes and fees

  • Total number of reviews

    19K reviews

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with dedicated workspaces

    230 properties have a dedicated workspace

  • Wifi availability

    390 properties include access to wifi

Destinations to explore