
Family-friendly holiday rentals in Chelmsford
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Top-rated family-friendly rentals in Chelmsford
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Chelmsford family-friendly rentals
Family-friendly home rentals with a hot tub

Hopkinton Mass 3+ Bedrooms - Great location!
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.

Hampton 100 yards to beach
Clean and good storage for a small space. Good location

Seacoast Oasis (NH & ME)
Logement spacieux et fonctionnel. 2 grandes chambres et un petit séjour, plus une cuisine. Au calme. Quelques bruits à l’étage mais rien de très gênant.

Home On The Hill
We enjoyed the our stay. The house has unique design, kids love it! A very relaxing home like place. Bryan is super responsive and friendly. The house is well equipped with everything we need. Can’t ask for more. Thank you!

awesome private cabin
Gorgeous grounds and location for a quiet peaceful weekend getaway! David was very responsive and personable. The cabin is eclectic with something new and interesting in every corner.

Newly renovated, close to Foxboro and Boston
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.

Amazing ocean front 3 bedroom
We had a wonderful stay! The house was great! Views were awesome from the top balcony! We wished the bushes and shrubs had been trimmed a little to have a better view from the main level but it was still a nice view from the one area there. House was quite roomy and had everything we needed in the kitchen. There are not tvs in the two spare rooms which would have been good after dinner for our teenagers while winding down after family time. The host is wonderful and communicated great. Overall we had a great family vacation and a good time. The house is nice. Would recommend!

Sunrise Sunset Lakefront Suite
In the area for work. Absolutely loved the place. Would absolutely stay again for work or vacation.
Family- and pet-friendly home rentals

Welcoming 7-room house <15 miles to Boston & Salem
We really enjoyed our stay here! Karen was very quick to respond to any of our questions. The house is spacious and clean. We especially enjoyed the kitchen and dining room. I’d recommend this place to anyone staying in the area!

The Solar Powered Dogtown Cabin at Applecart Farm
We loved our stay at Dogtown cabin. The cabin is in the middle of the woods and is also close to everything. Azure and Darwin are excellent hosts. Thank you Eric and Julie for sharing your home!

Family Home + Near Downtown + Cool Backyard!
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.

Charming South End Duplex (Pets Ok)
We just a wonderful few days in Boston for the marathon. Maude was the perfect host… we really appreciated the flexibility with check-in and check-out and were so grateful for the provisions left for us, particularly as we arrived late! The location is perfect, it meant that we could explore everywhere in the City on foot. The neighbourhood is particularly great for restaurants and when the sun came out and the temperature rose, the vibe was fabulous. As a previous review mentioned, if you’re looking for a pristine, freshly painted apartment then it’s not for you, but if you like ‘quirky’ and a house with bags of character, (I especially loved the art), then I’d highly recommend.

Family Friendly 2BR 1 BA Coastal Kittery Home
This house was perfect for our weekend getaway. Not only was the location close to everything, it was cozy and pet-friendly. The fenced in backyard was the perfect touch for our fur friend. The house itself was very clean and stocked with all the essentials. Rebecca and Jeff were very responsive hosts in the case we needed anything. Highly recommend staying here as you won’t be disappointed.

Cambridge Getaway @ Harvard & MIT
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!

1 of a Kind Pond-Front Home, Minutes from Downtown
We loved staying at this lakeside cabin for thanksgiving with family. Beautiful sunsets, great location, charming house. Loved it!

Comfortable house, close to beach and downton IPSW
This is our 3rd stay at one of their Airbnb’s and they are always so accommodating. Places are always clean and well stocked. Communication is great! Will Be staying again on our next visit!
Family-friendly home rentals with a pool

Two-Bedroom Condo on the Wells/Ogunquit town-line
Had a wonderful stay at Christophers place. He is a great host, always responsive with clear instructions. Place was peaceful, private and is exactly same as it was in the pictures. Will come soon!

Cedar Ridge: House or House+Apartment
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!

Beach Dreaming
A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

Country Cottage in the City
Lovely cottage surrounded by countryside: there were ducks, wild turkeys, chipmunks and blue jays in the garden. 5 mins drive from the lovely town of Dedham and 30 mins into central Boston. Cottage is small but beautifully decorated and has everything you need. Mark was super helpful.

Beautiful Beach Studio
Rita was responsive, friendly, and accommodating. Place was clean and inviting, close to the strip. Would definitely stay again!

Luxury Home * Pool * Fireplace
We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything

Spacious 3-BR Furnished Beach Home
We had a wonderful stay. Perfect place for families with children. So close to the beach with all the beach and home necessities you need while on vacation! Quaint town that was quiet but still has plenty of restaurants to visit. Overall, a great place!

Beautiful Lakefront Vacation
Donna is fantastic and if your looking for a charming New England spot this is it! We Are very satisfied with this home.
Quick stats about holiday rentals that are family-friendly in Chelmsford
Total rentals
20 properties
Nightly prices starting at
$78 AUD before taxes and fees
Total number of reviews
610 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
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- Hampton Beach
- Boston Common
- Revere Beach
- TD Garden
- Fenway Park
- Lynn Beach
- Harvard University
- North Hampton Beach
- New England Aquarium
- Monadnock State Park
- Pats Peak Ski Area
- Freedom Trail
- Faneuil Hall Marketplace
- Prudential Center
- Crane Beach
- Rye North Beach
- Symphony Hall
- Boston Public Library
- Quincy Market
- Water Park of New England
- Good Harbor Beach
- Museum of Fine Arts, Boston
- Aaronap Cellars
- John Hancock Tower