
Family-friendly vacation rentals in Chelmsford
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Top-rated family-friendly rentals in Chelmsford
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Popular amenities for Chelmsford family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy private apt 8 mins from UCONN - solar powered
The place was quiet, surrounded by beautiful woods, and truly relaxing—it was exactly what I needed. The bed was incredibly comfortable, and I slept so well each night. I also appreciated how responsive the host was to my questions via text. I would love to stay there again in the future. Thank you so much!

Nana-tucket Inn
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.

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.

Coastal Maine & 10 Min to Portsmouth+ Hot Tub Too!
Really nice converted basement to studio. Large bedroom/living room combo. Through a door was a modern bathroom with stand up shower and a kitchenette. Well decorated and stocked. She is a terrific host. I never saw her but she pre answered any questions I may have had. Climate control was very efficient and hot tub was spotless and easy to access. I will add it is not a private atmosphere for the hot tub as it is open with no privacy screens. My only flex with this rental is that the bathroom and kitchenette area does not feel private due the lack of a wall and instead the use of a privacy screen, to block off the rest of the basement and being able to see her basement stairs (I don’t think she uses them while hosting) but for me the fact that someone could walk down from the main house and be there is uncomfortable. This part is not to complain but inform. It is costly to rent and I always like to know exactly what I’m walking into.

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

Seacoast Oasis (NH & ME)
We stayed with Robin and Peter for a night and had a great time. The place was just as described, and is located only a stone’s throw from Portsmouth. We loved the convenient location, and local recommendations we found in the apartment.

Home On The Hill
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!

awesome private cabin
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
Family- and pet-friendly home rentals

Clear Pond Pet Friendly Inn
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.

Welcoming 7-room house <15 miles to Boston & Salem
We loved staying here! Plenty of space for our family of 6, including one little one. It was exactly as pictured and well-stocked with spices in the kitchen and shampoo etc in the bathroom! Beds were super comfy and we loved how close it was to the lake, restaurants, and a playground. Would definitely stay here again!!

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)
Absolutely amazing place to stay! The host is sweet and responsive and it's in a great area :) lots to do just by walking around. My groups and I had a great time here and would come back again!

Family Friendly 2BR 1 BA Coastal Kittery Home
Great place and such a great location!! Hosts were lovely and responsive, had everything you need for a lovely time at the beach!

Stone n' Sky Lodge
We celebrated our Thanksgiving at the lodge We drove down from Maine and we’re planning on arriving Thanksgiving day, the weather was not going to be great for driving and Sarah was kind enough to invite us to come down the night before. It was such a great relief to not have to drive Thanksgiving day! The lodge was so spacious and comfortable. We had plenty of room to play games and enjoy our meal with additional family that met us there to eat. Sarah was the a gracious host and very responsive. Definitely plan on returning again next year ❤️

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
We had a great stay! The space was nice, clean, and very quiet. Parking was convenient, and the location was fantastic— since it was just a short drive the Crane Estate (where we attended a wedding). Communication with the host was great—we received quick and helpful responses. Highly recommend to anyone looking for a peaceful, well-kept place in a great area!
Family-friendly home rentals with a pool

Our families slice of heaven
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

Two-Bedroom Condo on the Wells/Ogunquit town-line
We had a great time staying here for a nearby wedding. The location is convenient, the place is well maintained, and Christopher is responsive!

Cedar Ridge: House or House+Apartment
Very responsive hosts who helped us with restaurants. House was very clean, well appointed and had everything we needed. Great for families or a girls weekend!

Bright, Large, Spacious Family Home
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!!

Country Cottage in the City
What a perfect weekend in a private cottage by the pool. Although the weather did not cooperate for pool time, Mark & Susan’s cottage was a perfect place to have a central location outside of Boston. You would never know you were close to the city. Absolutely lovely! Their cottage was super clean and inviting and lacked nothing necessary for a long weekend away. They were very proactive in communicating with us about checking in and if we needed anything during our stay. Really terrific!

Beautiful Beach Studio
Good place to stay for Hampton Beach. Short walk to the water.

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

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 vacation rentals that are family-friendly in Chelmsford
Total rentals
20 properties
Nightly prices starting at
$50 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
Wifi availability
20 properties include access to wifi
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- Hampton Beach
- Boston Common
- Revere Beach
- Fenway Park
- TD Garden
- Harvard University
- Lynn Beach
- North Hampton Beach
- New England Aquarium
- Monadnock State Park
- Freedom Trail
- Faneuil Hall Marketplace
- Prudential Center
- Crane Beach
- Pats Peak Ski Area
- Canobie Lake Park
- Good Harbor Beach
- Rye North Beach
- Museum of Fine Arts, Boston
- MIT Museum
- Quincy Market
- Bunker Hill Monument
- Wentworth by the Sea Country Club
- Bear Brook State Park
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