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Family-friendly vacation rentals in Chelmsford

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 20 vacation rentals in Chelmsford

  • Nightly prices starting at

    Chelmsford vacation rentals start at G$10,457 GYD per night before taxes and fees

  • Verified guest reviews

    Over 760 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chelmsford vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chelmsford rentals

  • 4.5 Average rating

    Chelmsford stays receive an average rating of 4.5 out of 5 from guests

Top-rated family-friendly rentals in Chelmsford

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious home sits on a manicured lot, featuring a well-kept garden and an expansive driveway. The two-story structure boasts large windows and a welcoming entrance, with outdoor lighting enhancing its features during twilight. The attached garages are visible on the right.
Guest suite in Windham

Sunny, private and peaceful apartment!

Our home sit in a private and peaceful setting. It is perfect for the business travelers looking for a place to relax at the end of the day or anyone looking for a quiet place. Close to Castleton Banquet and Conference Center, Searles Castle, Canobie Lake Park, walking & biking trails, shopping and restaurant. Centrally located between Boston, beaches and mountain and lake region. Only 16 miles from Manchester Boston Regional Airport, 36 miles from downtown Boston, 3.5 miles from Interstate 93.

FamilyKitchenHiking

4.99 out of 5 average rating, 319 reviews
Top guest favorite
Apartment in Woburn

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple, small family or groups of 4. Just minutes from Boston or the North Shore. Travel by car, Uber, or local train to enjoy Boston excursions, Salem witches, Cape Ann antiquing, sand beaches, fall leaf peeping, skiing, historical sights, sporting events, graduations, and retail therapy at nearby malls, outlets, or ionic Newbury St. A multitude of local and city restaurants and breweries provide an array options for your pleasure. YMCA next door!

Indoor spacesFamilyCondition

4.94 out of 5 average rating, 253 reviews
Top guest favorite
A modern kitchen is presented with white cabinets and stainless steel appliances, including a refrigerator and oven. Granite countertops provide ample workspace, with a sink beneath a window. Natural light fills the area, enhancing the open and inviting atmosphere.
Apartment in Windham

The Cozy Corner Apartment

Cozy up during your next trip to the southern New Hampshire area! The Cozy Corner is a combination of style and comfort in so many ways from the double windows and sliding glass doors that flood the space with light to the airy and peaceful design that makes it feel like home. The Cozy Corner is a short drive to Canobie Lake Park and Manchester Airport, 45 minutes to Boston and NH Seacoast, close to Lakes Region, White mountains, and great skiing spots. 10 minutes from major shopping centers!

FamilyIndoor spacesHeating

4.89 out of 5 average rating, 374 reviews
Guest favorite
A wooden staircase leads to a blue front door, framed by two hanging planters filled with vibrant flowers. A large, decorative white pot sits at the base, featuring a lush green plant surrounded by smaller potted plants, enhancing the entrance's welcoming appearance.
Condo in Chelmsford

The Art Experience

The Art House at the Ellison Building was built in 1878. This unit was renovated in 2004 and 2022. It is walking distance to both Freeman lake beach and also a boat launch for the Merrimack River. It's situated between Lowell and Nashua NH. 40 minute drive to Boston or Manchester. This 2 bedroom condo was renovated by artist/architect Daniel Forcier. All of the artwork hanging is for sale and Daniel has his art studio on site where classes are available for the complete art experience.

Indoor spacesKitchenAmenities

4.88 out of 5 average rating, 124 reviews
Top guest favorite
A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.
Home in Chelmsford

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Indoor spacesFamilyView

5.0 out of 5 average rating, 259 reviews
Top guest favorite
A spacious exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.
Apartment in Groton

Farmhouse Guest Apartment

Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, gardens, and a pond. You will enter through a shared entrance & stairway to the second floor in our home, but have an entire 725 sq. ft. guest apartment all to yourself that includes a living room, full kitchen, bathroom, and large bedroom with a desk. It has ample light with views of fields, stone walls, Christmas trees and our barn. Out back we have a pool, table & chairs you may use.

Indoor spacesFamilyAccess

5.0 out of 5 average rating, 108 reviews
Guest favorite
Farm stay in North Andover

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

Vineyard Retreat. Stay at the newly remodeled Ice House, a luxury farmhouse at historic Marble Ridge Farm (est. 1680). This light-filled 3-bedroom home is perfect for bachelorette weekends, bridal party get-ready, or group getaways. Enjoy the private hot tub, beautiful natural light, and a peaceful winery setting just minutes from top-rated restaurants, shopping, and major highways. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases.

FamilyKitchenPets

4.97 out of 5 average rating, 132 reviews
Top guest favorite
A cozy living area features a red sofa and a round wooden table with two chairs. A small bedside table is positioned nearby. The kitchen is visible with wooden cabinets and appliances, and natural light highlights the space through a skylight.
Apartment in Westford

Furnished Cozy Apartment in quiet neighborhood

Come stay in this great place with nice cozy apartment features in a quiet neighborhood. Are you looking to getaway for a few days, relax, rejuvenate and get back to your everyday hustle? Are you looking for a perfect place to work remotely at shoe string budget? Conveniently located this place offer these and more including recreational activities all year long - NE beaches in summer, fishing, leaf peeping in Fall, skiing in winter etc Close to UMass Lowell

Indoor spacesKitchenSleep quality

4.92 out of 5 average rating, 103 reviews
Top guest favorite
A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.
Guest suite in Lexington

Modern Farmhouse Suite in Historic Lexington

Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

KitchenIndoor spacesAir conditioning

4.97 out of 5 average rating, 183 reviews
Top 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

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!

Indoor spacesKitchenLong stay

4.95 out of 5 average rating, 184 reviews
Top guest favorite
A serene lake view is captured at sunset, showcasing soft hues of orange and pink illuminating the sky. The frozen surface of the water reflects the colors, while distant houses are faintly visible along the shoreline, framed by tree branches in the foreground.
Home in Westford

Lakefront House with breathtaking sunsets!

Enjoy a breathtaking view and sunsets by the water! This is a lovely ground-level cottage by Nabnasset Lake in a quiet neighborhood. Close to Route 40, Route 3, and Route 495. 15 minutes drive to Nashua NH, and 45 minutes from Boston/Logan Airport. Newly renovated. Brand wood floors, appliances, windows etc... Rental discounts are offered for 8+ weeks bookings and automatically calculated when you put in your dates.

FamilyKitchenWalkability

4.77 out of 5 average rating, 105 reviews
Top guest favorite
A private entrance to a charming home is framed by well-maintained landscaping and a gravel driveway. Decorative flower boxes adorn the windows of the light-colored exterior, while surrounding trees provide a natural backdrop, creating a serene environment.
Apartment in Concord

Mema's Place --Lovely apartment in private home

This private apartment in a lovely home in historic Concord, Massachusetts features one bedroom with queen bed, living room, kitchen, bathroom, and porch. Your apartment is locked off from the rest of the home and you have your own entrance. We are within 4 miles of Concord Academy, Middlesex School, the North Bridge, Sleepy Hollow Cemetery (where Alcott, Thoreau, Emerson, and Hawthorne are buried).

FamilyIndoor spacesOutdoor spaces

4.96 out of 5 average rating, 243 reviews

Popular amenities for Chelmsford family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
An open living area is presented, featuring a dark leather sofa facing a circular dining table with wooden chairs. A well-equipped kitchen, complete with modern appliances, is visible in the background. Natural light enters through large windows, illuminating the wood flooring.
Apartment in Windham

The Estate Escape with Hottub

Indoor spacesKitchenParking

4.86 out of 5 average rating, 256 reviews
Top guest favorite
A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.
Farm stay in Hopkinton

1790 Stone Manor Farm

Indoor spacesKitchenWifi

4.96 out of 5 average rating, 166 reviews
Top guest favorite
A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.
Home in Jaffrey

Willow Falls Home ~Hot tub & Waterfront

KitchenFamilyBackyard

4.98 out of 5 average rating, 106 reviews
Top 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

Hopkinton Mass 3+ Bedrooms - Great location!

KitchenIndoor spacesOutdoor spaces

4.95 out of 5 average rating, 179 reviews
Guest favorite
A spacious bedroom features a large bed adorned with a patterned green and white quilt. Natural light floods the room through multiple windows, highlighting a small desk and ergonomic chair. Soft lighting is provided by sconces on the walls.
Guesthouse in Worcester

Quiet Oasis In The City

Indoor spacesFamilyComfort

4.82 out of 5 average rating, 115 reviews
Top guest favorite
Cottage in Mendon

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Indoor spacesKitchenHot tub

4.95 out of 5 average rating, 154 reviews
Top guest favorite
The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.
Farm stay in Thompson

Rustic Farmette Studio w/yearround Hot Tub

KitchenIndoor spacesPets

5.0 out of 5 average rating, 263 reviews
Top guest favorite
An open living space features a modern kitchen island with blue cabinetry and a white countertop. A sofa is situated nearby, adorned with colorful cushions. Large windows showcase scenic views of nature, while natural light brightens the room.
Home in Mont Vernon

Private Waterfront • Views, Hot Tub, King Bed

KitchenIndoor spacesGetting around

4.95 out of 5 average rating, 239 reviews

Family- and pet-friendly home rentals

Guest favorite
A serene view of the lake is framed by two bright blue chairs and a small white table topped with a pot of yellow flowers. Lush greenery surrounds the water, with residential homes visible in the distance.
Home in Salem

Quaint Little New Hampshire Lake House Getaway!

Indoor spacesKitchenHospitality

4.94 out of 5 average rating, 194 reviews
Guest favorite
Home in Wayland

Spacious 4 bedroom home with large yard

FamilyKitchenPets

4.9 out of 5 average rating, 132 reviews
Top guest favorite
A stylish living room features a green sectional sofa complemented by colorful throw pillows. A round coffee table rests on a patterned area rug. Art pieces adorn the walls, and natural light enters through windows, illuminating the warm wooden flooring and brick fireplace.
Home in Arlington

The Brickhouz at Arlington !

Indoor spacesFamilyAccess

4.99 out of 5 average rating, 117 reviews
Guest favorite
A spacious yard is surrounded by tall trees, showcasing a playground with a slide and swings. A garden area is interspersed with colorful flowers and is set against the backdrop of lush greenery. A trampoline is visible in the distance, along with a greenhouse.
Farm stay in Rutland

Farm Living

KitchenFamilyAir conditioning

4.95 out of 5 average rating, 423 reviews
Top guest favorite
A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.
Home in Framingham

Cozy en suite w/ high ceilings

Indoor spacesFamilyDecor

4.98 out of 5 average rating, 137 reviews
Top guest favorite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston

Flower Farm Getaway 2BR, 20 Min To Boston

KitchenIndoor spacesHospitality

5.0 out of 5 average rating, 209 reviews
Superhost
The spacious living area features warm wooden flooring and a central table with seating. Natural light enters through a nearby door, complemented by modern pendant lighting. A kitchenette is visible with a stylish shelf displaying decorative items, creating a functional yet inviting environment.
Apartment in Arlington

Dixie’s House, 1BD in Arlington

Indoor spacesKitchenAccess

4.88 out of 5 average rating, 234 reviews
Guest favorite
The image displays a modern, two-story home with a brown exterior featuring horizontal siding. A unique sculpture is situated on the front lawn, surrounded by landscaped greenery. A stone pathway leads to the entrance, which is framed by tall trees and shrubs.
Guesthouse in Lexington

Unique Loft/ Studio Guesthouse (super convenient)

Indoor spacesKitchenAccess

4.74 out of 5 average rating, 272 reviews

Family-friendly home rentals with a pool

Top guest favorite
A spacious outdoor area features a dining table surrounded by chairs, complemented by loungers and a hot tub. An umbrella provides shade over the seating area, while lush greenery and well-maintained landscaping create a peaceful environment. The in-ground pool is visible in the foreground.
Guesthouse in Newton

Charming 2-story private Guesthouse

KitchenFamilyLayout

4.94 out of 5 average rating, 254 reviews
Top guest favorite
A cozy living area is featured with a brown sofa adorned with patterned cushions. A small coffee table sits on a patterned rug, and a lamp is positioned beside a side table. In the background, the kitchen is visible, showcasing stainless steel appliances and additional cabinetry.
Guest suite in Hubbardston

In-law Apartment, Full Kitchen, Near Mt Wachusetts

KitchenIndoor spacesPets

4.98 out of 5 average rating, 221 reviews
Guest favorite
A cozy living area features a spacious daybed flanked by decorative pillows. Two armchairs are positioned across from a coffee table, enhancing the seating arrangement. A decorative vase adds charm beside the fireplace, while natural light filters through the window, illuminating the wood flooring.
Guest suite in Revere

Amazing studio

Indoor spacesFamilyCondition

4.88 out of 5 average rating, 206 reviews
Top guest favorite
Cottage in Marblehead

Pool Is Open in Sept! Steps from Harbor + Old Town

Indoor spacesFamilyLong stay

4.99 out of 5 average rating, 167 reviews
Top guest favorite
A washing machine and dryer are positioned side by side against a wall. A small dining table with white chairs is situated near a window, while a desk and chair are also present in the space. Light-colored walls and a nautical-themed clock add to the room's design.
Apartment in Waltham

Cozy Private Studio Unit w/ Laundry and Parking!

KitchenIndoor spacesDecor

4.97 out of 5 average rating, 445 reviews
Top guest favorite
The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.
Home in Weston

Spacious vacation unit in premium suburban town

Indoor spacesFamilyCheck-in

4.97 out of 5 average rating, 120 reviews
Guest favorite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury

Country Cottage in the City

FamilyKitchenNearby

4.95 out of 5 average rating, 217 reviews
Guest favorite
A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.
Apartment in Brighton

The Murthy : Bright • Spotless • W/D

Indoor spacesFamilyHospitality

4.96 out of 5 average rating, 159 reviews

When is the best time to visit Chelmsford?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,954 GYDG$31,163 GYDG$31,163 GYDG$31,163 GYDG$29,908 GYDG$37,019 GYDG$33,463 GYDG$33,463 GYDG$38,483 GYDG$33,673 GYDG$29,281 GYDG$31,372 GYD
Avg. temp-2°C-1°C3°C9°C15°C20°C23°C22°C18°C11°C6°C1°C

Destinations to explore