Family-friendly vacation 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

Guest favorite
A private backyard oasis is surrounded by lush greenery and blooming flowers. A swimming pool is featured in the foreground, reflecting blue skies. Outdoor seating areas are visible, providing space for relaxation and enjoyment.
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 favorite
Outdoor dining tables are set under large umbrellas, with guests enjoying a waterfront view. Sailboats are anchored in the calm water during sunset, creating a serene coastal atmosphere. The soft colors of the sky reflect on the water, enhancing the picturesque dining experience.
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 favorite
An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 stars1 week ago
Brad was very friendly and helpful. Beautiful home!
Guest favorite
A landscaped area features a rock border with colorful pink and purple flowers, providing an inviting approach to the property. A drive lined with pavers leads to the entrance of the house, surrounded by lush greenery and tall trees.
Home in Dunbarton
4.91 out of 5 average rating, 33 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 favorite
A spacious stone courtyard features a large stone fireplace surrounded by seating areas. Potted plants add greenery to the space, with outdoor furniture, including a table and chairs, positioned for relaxation. Strings of lights outline the patio, creating a welcoming ambiance.
Cabin in Rochester
4.94 out of 5 average rating, 230 reviews

awesome private cabin

JoshuaRating, 5 stars4 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 favorite
A spacious backyard is shown, featuring a wooden playset with a slide and swings. Lush greenery surrounds the yard, with tall trees providing shade and privacy. The grass is well-maintained, creating a suitable area for outdoor activities.
Guest suite in Canton
4.71 out of 5 average rating, 108 reviews

Newly renovated, close to Foxboro and Boston

StacyRating, 5 stars1 day ago
Smaranda was outside when we arrived, she greeted us and since it was around dinner time she offered some recommendations for dinner. It had been quite windy that day so the pool and hot tub had some leaves and debris in them. She was very apologetic (obviously not her fault, we can't control Mother Nature) and was very attentive and worked hard to get both the pool and hot tub ready for us to use. She showed us how everything worked and the instructions were clear and easy to follow. We used both the pool and hot tub after we got back to the space after dinner and they were both very nice and relaxing. We enjoyed our stay and everything went as planned. We would definitely stay again if Smaranda would have us! Stacy and Ray
Superhost
A charming two-story home is framed by lush greenery, featuring a sloped roof with solar panels. A driveway leads up to a spacious garage, while well-maintained gardens and neatly trimmed hedges enhance the inviting exterior.
Home in Plymouth
4.85 out of 5 average rating, 82 reviews

Amazing ocean front 3 bedroom

Neil and TerriRating, 5 stars4 weeks ago
Beautiful setting with ocean views and pretty landscaping and gardens view out every window. Easily accommodated six people in our party. Home was equipped with everything we needed. Outside seating, hot tub and grill area are lovely. We had a nor’easter arrive so didn’t get to enjoy outside too much but the little that we did was incredible! Gas fireplace in living room kept dampness at bay and was just lovely. Two inside eating areas were perfect! Would come back in a heartbeat!
Guest favorite
A vibrant sunset paints the sky with shades of orange, pink, and purple. Soft clouds stretch across the horizon, reflecting the warm tones on the calm surface of Sunset Lake, which is bordered by tree silhouettes in the distance.
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 favorite
A well-equipped kitchen presents stainless steel appliances and an island with seating for four. Natural light floods the space through large windows, creating a bright and inviting atmosphere. The adjacent sunroom is visible through an open entryway, enhancing the home’s spacious feel.
Home in Wakefield
4.96 out of 5 average rating, 265 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 favorite
A modern dining area features a glass table surrounded by upholstered chairs. A small potted plant adds a touch of greenery. The kitchen is visible in the background, showcasing dark cabinetry and stainless steel appliances, along with a bar area with sleek stools.
Townhouse in Everett
4.91 out of 5 average rating, 253 reviews

#9 Modern Home 15 min to Boston. Relax in Style!

DawnRating, 5 stars2 weeks ago
Great place. We loved the location and the surroundings. Wally was you receptive and proactive. Everything we needed was available. The instructions and local information was great and even though we had a plan of things to do, it provided us a couple of awesome ideas for our down time. Would definitely stay there again and would recommend. Thanks Wally.
Guest favorite
An outdoor space is presented, featuring a wooden picnic table surrounded by a sprawling lawn. A slide is integrated into the landscape, complemented by vibrant greenery and a nearby garden area. Outdoor seating is also visible in the background, enhancing the communal atmosphere.
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 favorite
A wooden cabin with a sloped roof is surrounded by a snow-covered landscape. The porch is visible, along with two friendly dogs playing in the snow. Tall trees, dusted with snow, create a serene, wintry atmosphere.
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.
Top guest favorite
A charming cottage is seen behind raised garden beds featuring green plants and flowering chives. The building's white exterior is complemented by wooden decking and natural surroundings of trees and greenery.
Tiny home in Kittery
4.95 out of 5 average rating, 516 reviews

water view property "The Little House"

RussellRating, 5 stars6 days ago
The home was very well maintained, clean and quiet neighborhood. Would highly recommend “the Little House”!
Guest favorite
A welcoming living room is equipped with two comfortable sofas, a wooden coffee table at the center, and a wall-mounted TV. Natural light enters through multiple windows, while a modern electric fireplace adds warmth to the space, enhanced by a vibrant area rug.
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 favorite
A cozy bedroom features a queen-sized bed with a patchwork quilt and coordinated pillows. Soft lighting is provided by two bedside lamps. The rich wood paneling and tile floor complement the warm atmosphere. A large window allows natural light to illuminate the space.
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 favorite
A newly remodeled kitchen features modern stainless steel appliances and ample counter space. White cabinetry contrasts with warm wood paneling and flooring. A dining area with a wooden table and chairs is visible, along with soft lighting from pendant fixtures above.
Cabin in Cohasset
4.92 out of 5 average rating, 336 reviews

Lionsgate at Cohasset

TerriRating, 5 stars2 weeks ago
Kao’s home worked great for us. His garden is absolutely beautiful and the area is quite serene. Would definitely stay there again.

Family-friendly home rentals with a pool

Top guest favorite
A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.
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 favorite
A large outdoor pool area is surrounded by lounge chairs in vibrant colors. The pool is complemented by neighboring buildings with multiple windows, providing a welcoming atmosphere. The concrete patio offers ample space for relaxation and sunbathing, with a barbecue area visible in the background.
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
Superhost
An indoor pool area features clear waters with a section for relaxation, complemented by a whirlpool. Large windows allow natural light to fill the space, while the entrance door and pool steps are visible in the background.
Apartment in Hampton Beach
5 out of 5 average rating, 5 reviews

Condo with pool sleeps 4

ChristopherRating, 5 stars11 months ago
Great stay. Nice clean place. Good view of fireworks from the balcony.
Guest favorite
A serene swimming pool is surrounded by well-maintained greenery, with lounge chairs placed along the deck. Large blue umbrellas provide shade, enhancing the outdoor space suitable for relaxation. A stone wall borders the area, adding a natural touch.
Home in Woodstock
4.94 out of 5 average rating, 239 reviews

Cedar Ridge: House or House+Apartment

AlissaRating, 5 stars1 week 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
Top guest favorite
A spacious backyard is visible, featuring a round swimming pool surrounded by lush green lawn. The charming barn-style buildings are framed by trees, and white fencing outlines the property. A basketball hoop and colorful landscaping add to the inviting outdoor space.
Farm stay in Rutland
4.96 out of 5 average rating, 374 reviews

Farm Living

GilsonRating, 5 stars1 week ago
Excellent place with beautiful surroundings! A great place to rest and be in contact with nature - trees and animals! Friendly hosts! Would love to come back!
Superhost
A spacious outdoor pool area is seen, surrounded by a paved deck. Sun loungers are positioned neatly along the perimeter, with blue umbrellas providing shade. A clubhouse with a large deck overlooks the pool, set against a backdrop of trees.
Cottage in Wells
4.88 out of 5 average rating, 42 reviews

Beach Dreaming

ArtemRating, 5 stars8 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 favorite
A light yellow cottage is positioned adjacent to a spacious swimming pool, surrounded by lush greenery. The pool features a diving board and a decorative tile border. Two lounge chairs sit nearby, while steps lead up to the entrance of the cottage.
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
An enclosed pool area features a clear water pool with a bubbling spa section. The pool is bordered by a smooth, tiled surface, and steps lead into the water. Large windows allow natural light to fill the space, and a door provides access to the exterior.
Apartment in Hampton Beach
4.74 out of 5 average rating, 122 reviews

Beautiful Beach Studio

AlexRating, 5 stars4 weeks ago
Good place to stay for Hampton Beach. Short walk to the water.

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    R891 ZAR 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

Destinations to explore