Family-friendly vacation rentals in Chelmsford

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Popular amenities for Chelmsford family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A cozy bedroom features a bed dressed in a floral comforter with a decorative pillow. A soft glow from a floor lamp illuminates the space, complemented by a window that offers natural light. A mini-fridge is present in the corner, adding convenience.
Guest suite in Mansfield
4.96 out of 5 average rating, 207 reviews

Cozy private apt 8 mins from UCONN - solar powered

ShinjiRating, 5 stars2 weeks ago
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!
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 stars1 week 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
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, 154 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars1 month 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 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, 292 reviews

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

ChristineRating, 5 stars1 week ago
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.
Guest favorite
A stone statue of a woman is depicted sitting gracefully, holding a wreath. An American flag flutters above, while a multi-story building is visible in the background, suggesting a seaside location.
Condo in Hampton Beach
4.89 out of 5 average rating, 36 reviews

Hampton 100 yards to beach

KrystinaRating, 5 stars10 months ago
Clean and good storage for a small space. Good location
Guest favorite
The image captures a two-story home nestled in a wooded area. A wooden deck adorned with a wreath and potted plants is visible, providing access to the upper level. Nearby, a brightly colored buoy adds a pop of color against the natural surroundings.
Guest suite in Kittery
4.91 out of 5 average rating, 844 reviews

Seacoast Oasis (NH & ME)

NadineRating, 5 stars1 week ago
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.
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, 32 reviews

Home On The Hill

JulieRating, 5 stars2 weeks 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, 229 reviews

awesome private cabin

JoshuaRating, 5 stars1 week 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

Family- and pet-friendly home rentals

Superhost
Condo in Plymouth
4.76 out of 5 average rating, 155 reviews

Clear Pond Pet Friendly Inn

NicklausRating, 5 stars6 months ago
Friendly host! Allowed us to bring our 4 little dogs! Hard to find a host that will allow this. Clean and peaceful property.
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, 263 reviews

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

EmilyRating, 5 stars3 weeks ago
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!!
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.
Guest favorite
A sitting area features a classic blue wall with two framed botanical prints above a marble fireplace. An orchid in a pink pot and a small potted plant add color. A comfortable armchair and a leather sofa complete the cozy layout, enhancing the inviting atmosphere.
Apartment in South End
4.96 out of 5 average rating, 378 reviews

Charming South End Duplex (Pets Ok)

KaitlynnRating, 5 stars1 week ago
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!
Guest favorite
A classic Cape Cod-style home is presented, featuring crisp white siding and a welcoming American flag displayed on the front porch. Lush green grass surrounds the house, complemented by mature trees and vibrant shrubbery, creating a serene outdoor setting.
Home in Kittery
4.98 out of 5 average rating, 290 reviews

Family Friendly 2BR 1 BA Coastal Kittery Home

GraceRating, 5 stars1 week ago
Great place and such a great location!! Hosts were lovely and responsive, had everything you need for a lovely time at the beach!
Top guest favorite
A view from above displays a cozy sitting area beneath exposed wooden beams. A rich, patterned rug covers the floor, while a plush armchair and a small table are positioned nearby. Natural light filters in through the adjacent windows, illuminating bookshelves filled with items.
Home in New Salem
4.89 out of 5 average rating, 216 reviews

Stone n' Sky Lodge

JoanneRating, 5 stars6 months ago
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 ❤️
Guest favorite
A charming pond-side house is nestled among well-manicured gardens, featuring colorful blooming azaleas. Large windows offer views of the surrounding landscape. A gravel driveway leads up to the property, with the water visible in the background under a clear, blue sky.
Home in Plymouth
4.96 out of 5 average rating, 157 reviews

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

WadeRating, 5 stars6 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
4.85 out of 5 average rating, 285 reviews

Comfortable house, close to beach and downton IPSW

MyLinhRating, 5 stars1 week ago
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

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, 55 reviews

Our families slice of heaven

MarkRating, 5 stars7 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 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, 185 reviews

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

NinaRating, 5 stars1 week ago
We had a great time staying here for a nearby wedding. The location is convenient, the place is well maintained, and Christopher is responsive!
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, 238 reviews

Cedar Ridge: House or House+Apartment

HilaryRating, 5 stars2 weeks ago
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!
Superhost
The exterior of the spacious house is shown, featuring a gray facade with multiple windows and a large front yard. Sunlight filters through the trees in the background, casting a warm glow over the lush green grass and surrounding plants.
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars7 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 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, 195 reviews

Country Cottage in the City

MariaRating, 5 stars1 week ago
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!
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 stars1 week ago
Good place to stay for Hampton Beach. Short walk to the water.
Guest favorite
The outdoor space features a landscaped yard with vibrant flowers and neatly arranged cobblestone paths. A crystal-clear pool is visible beyond a decorative black fence, surrounded by trees and greenery. A gazebo adds character to the serene environment, ideal for relaxation.
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
Superhost
The serene lake is framed by trees, reflecting the soft colors of the sunset sky. Gentle ripples disturb the water's surface, creating a tranquil atmosphere. In the distance, the silhouettes of trees and properties are visible along the shore, enhancing the peaceful landscape.
Home in Derry
4.82 out of 5 average rating, 135 reviews

Beautiful Lakefront Vacation

BobRating, 5 stars8 months ago
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

Destinations to explore