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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, 205 reviews

Cozy private apt 8 mins from UCONN - solar powered

TerryRating, 5 stars1 month ago
This is a wonderful place to stay if you are visiting UConn or the surrounding area. Keri and Jason were fabulous hosts and very responsive to my needs. Keri even anticipated needs by offering to have a fresh cup of coffee ready for me on the AM. Everything was perfect for my stay and there was definitely a comfortable feel. I will definitely be staying here in the future.
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars2 weeks ago
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.
Guest favourite
Condo in Hampton Beach
4.89 out of 5 average rating, 36 reviews

Hampton 100 yards to beach

KrystinaRating, 5 stars9 months ago
Clean and good storage for a small space. Good location
Guest favourite
Guest suite in Kittery
4.91 out of 5 average rating, 836 reviews

Seacoast Oasis (NH & ME)

GeoffroyRating, 5 stars4 days ago
Spacious and functional accommodation. 2 large bedrooms and a small living room, plus a kitchen. Quiet. A few noises upstairs but nothing very inconvenient.
Guest favourite
Home in Dunbarton
4.9 out of 5 average rating, 31 reviews

Home On The Hill

QiRating, 5 stars2 months ago
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!
Guest favourite
Cabin in Rochester
4.94 out of 5 average rating, 228 reviews

awesome private cabin

IlonaRating, 5 stars7 months ago
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.
Superhost
Guest suite in Canton
4.72 out of 5 average rating, 106 reviews

Newly renovated, close to Foxboro and Boston

MeganRating, 5 stars6 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.
Superhost
Home in Plymouth
4.87 out of 5 average rating, 79 reviews

Amazing ocean front 3 bedroom

CrystalRating, 5 stars6 months ago
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!

Family- and pet-friendly home rentals

Top Guest favourite
Home in Wakefield
4.96 out of 5 average rating, 262 reviews

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

MorganRating, 5 stars1 week ago
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!
Guest favourite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars2 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
Apartment in South End
4.96 out of 5 average rating, 375 reviews

Charming South End Duplex (Pets Ok)

HelenRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Kittery
4.98 out of 5 average rating, 287 reviews

Family Friendly 2BR 1 BA Coastal Kittery Home

ChristineRating, 5 stars2 weeks ago
I booked the house as a place for my family of 6 (4 adult children) and our black lab, to come together for Easter weekend. Since my boys live in Portsmouth we only needed 2 bedrooms and this house made the perfect getaway and place to host dinners. The house was spacious and very comfortable. We enjoyed the enormous fenced in yard all weekend. The host had many yard games which we played and our lab was so happy too. The fire pit was an added bonus for a night of s’more making. We truly had a wonderful time and the house really felt like home. Ps the stairs are fine once you get used to them. Rebecca was responsive and a wonderful host.
Top Guest favourite
Home in New Salem
4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

JasonRating, 5 stars5 months ago
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.
Guest favourite
Apartment 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
Home in Plymouth
4.96 out of 5 average rating, 157 reviews

1 of a Kind Pond-Front Home, Minutes from Downtown

WadeRating, 5 stars5 months ago
We loved staying at this lakeside cabin for thanksgiving with family. Beautiful sunsets, great location, charming house. Loved it!
Superhost
Apartment in Ipswich
4.84 out of 5 average rating, 281 reviews

Comfortable house, close to beach and downton IPSW

Zachary AndrewRating, 5 stars3 weeks ago
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

Top Guest favourite
Home in Plymouth
4.96 out of 5 average rating, 55 reviews

Our families slice of heaven

MarkRating, 5 stars6 months ago
Marla's vacation home was very lovely. We liked the pictures of her place, but once we arrived we realized that she had remodeled a number of rooms. Each room was updated, very clean and cozy. Marla has made sure that her place is stocked with all of the large and small conveniences that guests would want in a home away from home. The location and the surroundings are stunning, especially with the Fall foliage. One can tell that Marla takes great pride in her beautiful rental. -Mark & Susan G
Guest favourite
Condo in Wells
4.84 out of 5 average rating, 179 reviews

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

RichardRating, 5 stars5 days ago
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!
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 235 reviews

Cedar Ridge: House or House+Apartment

SuzanneRating, 5 stars1 month ago
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!
Guest favourite
Guest suite in Brooklyn
4.92 out of 5 average rating, 183 reviews

Affordable In-Law Apartment in Brooklyn, CT

OmarRating, 5 stars1 month ago
I fell in love with this apartment, the living room, kitchen, bathroom and bedroom were excellent, very cozy and endless amenities, the only complaint I have is the ceiling of the room but it is understandable and is not a big deal and they did not tell us where to put the garbage so we had to leave it in front of the door in the garage but other than that a very good experience in this beautiful place, I recommend it!
Superhost
Apartment in Brooklyn
4.85 out of 5 average rating, 217 reviews

8 Bedroom, 4 full bath residence with 40' pool

JudieRating, 5 stars6 months ago
This was our first time at the Barn. There were 8 of us. We had plenty of room. Plenty of parking. MaryBeth and Doug are extremely friendly. We enjoyed hearing about the history of the Barn. Will definitely book there again next year.
Superhost
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars6 months ago
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!
Top Guest favourite
Guesthouse in West Roxbury
4.95 out of 5 average rating, 193 reviews

Country Cottage in the City

GarryRating, 5 stars1 week ago
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.
Superhost
Apartment in Hampton Beach
4.74 out of 5 average rating, 121 reviews

Beautiful Beach Studio

AngelaRating, 5 stars8 months ago
Rita was responsive, friendly, and accommodating. Place was clean and inviting, close to the strip. Would definitely stay again!

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