Kid-friendly holiday rentals in Middlesex County

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Middlesex County family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Wakefield
4.96 out of 5 average rating, 261 reviews

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

TyroneRating, 5 stars2 weeks ago
Karen was absolutely incredible. She was very responsive, respectful, and accommodating. We very much enjoyed our stay as my team and I were there on business. She was able to take care of us even on short notice. I really couldn’t be happier with her communication, the quality of their home, and the entire experience. Thank you so much Karen for inviting us into your home. This was truly a 12/10 experience. 😃😃
Guest favourite
Home in Reading
4.95 out of 5 average rating, 61 reviews

Charming Home in Reading with a Large Yard

T.J.Rating, 5 stars2 weeks ago
We thoroughly enjoyed our stay. The location was wonderful and the hosts were extremely easy to work with
Superhost
Home in Canton
4.83 out of 5 average rating, 170 reviews

3 bedroom impeccable private home, quiet street

PhilipRating, 5 stars3 days ago
We found the perfect spot to visit Trillium for the Boston Hot Sauce Party! The guys from Full Slice Podcast and Table Top Trio say thank you and hope to come back next year!
Guest favourite
Home in Worcester
5 out of 5 average rating, 9 reviews

Newly built Home fenced yard Pet & family friendly

LilyRating, 5 stars6 months ago
Great space with big kitchen and living room. Comfy beds and couches. Okk a very busy road but a fenced back yard. Would stay again
Top guest favourite
Home in Norwood
4.95 out of 5 average rating, 39 reviews

The Cozy Colonial - 4 BDRM house with parking

CalebRating, 5 stars3 weeks ago
What an absolutely lovely home that our family was thrilled to stay at! Very clean, quiet, and comfortable. Close to everything!! Certainly a 5 star stay!
Top guest favourite
Home in Sterling
4.94 out of 5 average rating, 205 reviews

Quiet country retreat with modern conveniences

JonRating, 5 stars3 weeks ago
Great getaway and tranquil place to retreat! Would definitely book again. Enjoyed the atmosphere.
Guest favourite
Home in Framingham
4.97 out of 5 average rating, 145 reviews

2BR—Charming 1900s Home—1st Floor—25min to Boston

NathanRating, 5 stars5 months ago
Amazing price and amazing place to spend Halloween! Great places to eat and adventure around! The house was peaceful but had very friendly atmosphere with the neighbors. If I could have Andrea be the host for every air bnb I would be greatful knowing I have someone that's reliable and great with communication. She will treat you right and has great recommendations!
Top guest favourite
Home in Melrose
4.96 out of 5 average rating, 105 reviews

Spacious 5BR Near Boston | Family-Friendly Stay.

KevinRating, 5 stars2 weeks ago
I really enjoyed the house very clean and classy, Big up Greg keep the great work See you next time because i won't hesitate to come back.🫡

Family-friendly apartment rentals

Top guest favourite
Flat in Medford
4.99 out of 5 average rating, 255 reviews

Charming Colonial Two BR Basement Apt with Parking

DouglasRating, 5 stars5 days ago
The host was excellent, accommodating, very quick to respond and helpful. The unit is a basement apartment but with large window wells so it does get light. The unit was totally remodeled recently, nice condition and spotless. The hosts live upstairs and as this is their home they take a great deal of pride in the property and it shows. We did not have a car and relied on Uber and transit which you can do but given the distance to services a car would be handy and they do have parking. Overall this is a highly recommend option, we would repeat.
Top guest favourite
Flat in Cambridge
4.87 out of 5 average rating, 660 reviews

Lovely East Cambridge Apartment

LaurenRating, 5 stars3 days ago
Jimmy was so helpful and clear with all information on how to get there, where everything was, and how to get in. Communication was fast and specific. I got to meet him and just loved that him and his family were close just incase we needed anything. The place was so clean and comfortable which was perfect for my 3 friends and I. The area was beautiful and everything was walkable for restaurants and bars around the area. It was rainy on our longest stay and we still had a great time. It was a home away from home and we are so grateful to find it and with a good price.
Superhost
Flat in Boston
4.88 out of 5 average rating, 600 reviews

3 bed apt next to T- fast wifi-off street parking

ValerieRating, 5 stars1 week ago
We were extremely satisfied with Jurak’s place. We were thankful for timely responses and the flexibility to use entryway space for our luggage as we had many hours in the city without a place for our luggage. Three very comfortable beds with great linens. Lots of comfortable space for three friends to catch up and have access to the city. We would definitely come to this space again!
Guest favourite
Flat in Boston
4.97 out of 5 average rating, 124 reviews

Quiet brownstone close to city

AndresRating, 5 stars2 weeks ago
Very quiet and walkable neighborhood away from downtown madness but still just one train stop away(Maverick Blue Line station is a 5 min safe walk) from everything. Communication with host was great.
Guest favourite
Flat in Boston
4.85 out of 5 average rating, 196 reviews

1st Flr 2BR unit with parking + steps from train

JessicaRating, 5 stars1 week ago
We came to Boston for the marathon and are so grateful we chose to stay at George and Ann-Marie's bnb in Jamaica Plain. It is super close to the train that zips you right into the heart of Boston and is far enough away we could get some peace and enjoy the beautiful neighborhood away from all the race chaos. The home itself was very comfortable. We slept great. We enjoyed having coffee and drinks on the patio and lounging on the giant couches. It felt spacious with the 4 of us. We really liked walking 10 minutes up to Central for ice cream and restaurants, or 5 minutes over to the Sam Adams brewery. The neighborhood has tons of trees and was really quiet. George and Ann-Marie were very responsive and checked in with us during the stay to make sure we had all we needed. They also were able to accommodate a later check out, which was really helpful. Awesome spot!! We highly recommend it :)
Guest favourite
Flat in Cambridge
4.87 out of 5 average rating, 438 reviews

Cambridge Getaway @ Harvard & MIT

LindaRating, 5 stars1 month ago
This is an authentic Cambridge home that has been owned by the host's family for multiple generations. Kevin is accommodating, and he generously left some snacks and drinks in the full kitchen for us. Well-stocked kitchen was super convenient for eating breakfasts. Note: there are significant stairs to get into the unit. Once there it's quite spacious. And I love the operable bathroom window. :) Thanks for a lovely stay in a convenient, walkable neighborhood!
Guest favourite
Flat in Cambridge
4.95 out of 5 average rating, 260 reviews

Walk to Harvard/MIT (unit 2) w/ parking

TomRating, 5 stars1 month ago
Thanks for the great weekend use of your place.
Superhost
Flat in Boston
4.86 out of 5 average rating, 424 reviews

3 Bedroom Apartment with Parking

PatrickRating, 5 stars3 weeks ago
What a fantastic spot in a great area. Kevin couldn't have been a better host, so good on communication. The apartment itself was absolutely spotless, very spacious with every amenity provided. The area of Allston is beautiful, clean and safe, two big grocery shops close by, lots of nice coffee shops and restaurants close aswell. Train station is only 10 minute walk, make sure and check the times of these as not as frequent as the T as this is a commuter rail. There are plenty of bus options aswell that will get you to downtown. All in all one of the nicest places I've stayed and really made our trip to Boston perfect 👌. Thanks for everything Kevin.

Family-friendly apartment rentals

Superhost
Apartment in Boston
4.89 out of 5 average rating, 107 reviews

Condo in downtown Boston

JonathanRating, 5 stars1 month ago
The spot was super clean and had everything you needed, the location of it was great, and Griffin was a responsive and helpful host.
Guest favourite
Apartment in Cambridge
4.91 out of 5 average rating, 191 reviews

Luxury 3BR near Harvard/MIT w/ King Bed+Parking!

GeoffreyRating, 5 starstoday
This Airbnb is truly a gem. The location is perfect, you can walk basically anywhere, metro around the corner. The apartment standard are crazy high, probably one of the best Airbnb we’ve been to.
Superhost
Apartment in Framingham
4.89 out of 5 average rating, 102 reviews

Boston Suburb Luxury condo

LynnRating, 5 stars1 month ago
The condo was the perfect size for 3 of us in separate rooms and two bathrooms. Condo was very clean, simple with comfortable space and we had everything we needed for the stay. Finding the place in the dark was a little tricky as the numbers are faded but overall 5 stars and I would book again if in the area and listing is available.
Guest favourite
Apartment in Boston
4.98 out of 5 average rating, 102 reviews

Spacious Dorchester Retreat | 2-bdrm condo

AmmaraRating, 5 stars2 days ago
We stayed at Marian & Avanish's place for a spring trip in Boston and it was a wonderful experience! We were 4 people and the unit felt incredibly spacious and comfortable, the kitchen and bathroom were sparkling clean, well-stocked and made you feel right at home! We would wholeheartedly recommend this place to future guests!
Guest favourite
Apartment in Dracut
4.85 out of 5 average rating, 116 reviews

Cozy Entire Unit Condo close to UMASS Lowell

GiselleRating, 5 stars1 month ago
Amir’s condo was perfect for what I was looking for. It had all the kitchen essentials for my month-long stay, and the place was neat, tidy, and perfect for studying or working during the day with little to no noise from outside. Parking was right out front with easy in/out. Amir was proactive whenever I had any questions, and he resolved things right away. I’d recommend it to anyone looking for a nice, quiet place in the area.
Guest favourite
Apartment in Boston
4.88 out of 5 average rating, 101 reviews

Transit friendly condo on quiet street

JaneRating, 5 stars2 weeks ago
The home was comfortable and clean. Bed was comfortable. We appreciated being able to stream our favorite shows on the TV and the Keurig in the kitchen.
Guest favourite
Apartment in Boston
4.93 out of 5 average rating, 409 reviews

Victorian Charm, Modern Style w/Private Entrance

RachelRating, 5 stars4 days ago
Great spot in the middle of a good area. The beds were some of the most comfortable we have slept in at any AirBnB spot!
Top guest favourite
Apartment in Boston
4.92 out of 5 average rating, 220 reviews

Spacious 5BR Condo w/parking near METRO

BenjaminRating, 5 stars1 month ago
Wonderful location, five minutes away from the train station perfect for getting to downtown Boston. Very clean home with lots of space and a nice communal area. The host was very responsive. 100% stay again when returning to Boston.

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