Family-friendly holiday rentals in Chelmsford

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chelmsford family-friendly rentals

Family-friendly home rentals with a hot tub

Top Guest favourite
Guest suite in Mansfield
4.96 out of 5 average rating, 208 reviews

Cozy private apt 8 mins from UCONN - solar powered

BillRating, 5 stars1 month ago
We have been staying here over the last 4 years, when we visit UConn, and will miss it now that our daughter has graduated. Keri is wonderful host, welcoming & accommodating. Her home in the woods is a refuge, comfortable, peaceful, and minutes from campus.
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
Guest suite in Kittery Point
4.95 out of 5 average rating, 294 reviews

Coastal Maine & 10 Min to Portsmouth+ Hot Tub Too!

KyleRating, 5 stars2 weeks ago
This is one of the best Air B&B experiences that we’ve had…beautiful place and surroundings, great amenities and personal touches, wonderful recommendations. Couldn’t have had a better time.
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!
Guest favourite
Home in Dunbarton
4.91 out of 5 average rating, 32 reviews

Home On The Hill

JulieRating, 5 stars1 month ago
Beautiful home! Thank you for sharing it with my family. We were in town for my daughter’s college graduation. This location was perfect for my family. Cozy. Family oriented. Clean. Well equipped. Highly recommend!
Guest favourite
Cabin in Rochester
4.94 out of 5 average rating, 230 reviews

awesome private cabin

JoshuaRating, 5 stars3 weeks ago
Dave was an amazing host and he provided the best possible get away for our first wedding anniversary. It was private there is so much beautiful outdoor art to look at and the hot tub was the perfect way to wind down after the day. If there was a 6 star option I would give it this was everything we wanted and needed and then some
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
Place to stay in Hampstead
4.88 out of 5 average rating, 93 reviews

Sunrise Sunset Lakefront Suite

LizRating, 5 stars1 week ago
So lovely at this awesome house right on the lake. The view is amazing, the place was spotlessly clean, and Tom and Donna are gracious hosts. I highly recommend this Airbnb, this was our second stay and we will be back. Highlights were enjoying the hot tub, a lovely sunset cruise with Tom and Donna and of course, hearing the loons on the lake at night.

Family- and pet-friendly home rentals

Top Guest favourite
Home in Wakefield
4.96 out of 5 average rating, 264 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
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.
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.
Superhost
Barn in Essex
4.9 out of 5 average rating, 139 reviews

The Salt March Loft/Downtown Location/Views

JeriRating, 5 stars11 months ago
This was absolutely perfect for our needs. The location was central to Salem, Gloucester, and not too far from Boston. Very close to wonderful local restaurants and Marla was very attentive to our requests.
Top Guest favourite
Tiny home in Kittery
4.95 out of 5 average rating, 516 reviews

water view property "The Little House"

RussellRating, 5 stars5 days ago
The home was very well maintained, clean and quiet neighborhood. Would highly recommend “the Little House”!
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
Guest suite in Charlton
4.86 out of 5 average rating, 418 reviews

Baker Pond Hideaway

JohnRating, 5 stars1 week ago
My friend and I always enjoy our time at this beautiful home. Appointed with everything we need for a fun weekend! Just wish we could of spent a little time with our amazing hosts!
Guest favourite
Cabin in Cohasset
4.92 out of 5 average rating, 335 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.

Family-friendly home rentals with a pool

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
Condo in Wells
4.85 out of 5 average rating, 187 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars2 weeks ago
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 239 reviews

Cedar Ridge: House or House+Apartment

AlissaRating, 5 stars6 days ago
We LOVED: 1) The location! The driveway is long & sand/gravel but you could drive it in a sedan fine. 2) The amenities! The pack n play was a HUGE lifesaver! 3) This location is mostly child friendly. 4) The view is phenomenal! When we woke up & opened the curtains for the first time, we were in awe! 5) The host was extremely helpful. The hot water went out once, but she was over in 5 minutes to fix it. Some feedback: 1) The windows in the ceiling in the master bed! They're HUGE and BRIGHT. 2) The bugs. Ants. Spiders. It was a struggle. NOW I WILL SAY - I brought this up to the host on day 3 and they were more than willing to come help how they could. The house is located in the middle of the forest, but it was a lot. If it weren't for an m&m left under the nightstand in the bedroom by a previous guest, it probably wouldn't have been so bad. 3) the coffee maker was pretty rough when we got there.. a simple over site by the crew. Overall, I would definitely consider this location again
Superhost
Apartment in Brooklyn
4.85 out of 5 average rating, 221 reviews

8 Bedroom, 4 full bath residence with 40' pool

Maria ChristinaRating, 5 stars2 weeks ago
The hosts Marybeth and Douglas were so welcoming to us and accommodated our request to check- in earlier than scheduled! They were very friendly and provided extra stuff to make our stay feel so homely and comfortable! Everyone of us (13 people) truly enjoyed our stay at their beautiful, spacious and historical home!
Superhost
Cottage in Wells
4.88 out of 5 average rating, 42 reviews

Beach Dreaming

ArtemRating, 5 stars7 months ago
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.
Top Guest favourite
Guesthouse in West Roxbury
4.95 out of 5 average rating, 196 reviews

Country Cottage in the City

JulieRating, 5 stars2 weeks ago
Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.
Superhost
Apartment in Hampton Beach
4.74 out of 5 average rating, 122 reviews

Beautiful Beach Studio

AlexRating, 5 stars3 weeks ago
Good place to stay for Hampton Beach. Short walk to the water.
Guest favourite
Home in Brimfield
4.88 out of 5 average rating, 73 reviews

Luxury Home * Pool * Fireplace

DanaRating, 5 stars4 months ago
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

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    $77 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

Destinations to explore