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$10,462 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.

KitchenFamilyBreakfast

4.99 out of 5 average rating, 319 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!

KitchenIndoor spacesParking

4.89 out of 5 average rating, 375 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 spacesKitchenLong stay

4.88 out of 5 average rating, 126 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 spacesFamilyWalkability

5.0 out of 5 average rating, 260 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 spacesFamilyValue

5.0 out of 5 average rating, 110 reviews
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

KitchenIndoor spacesLocation

4.92 out of 5 average rating, 105 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

FamilyKitchenHospitality

4.97 out of 5 average rating, 189 reviews
Top guest favorite
A cozy living area features a dark gray sofa adorned with patterned cushions. A wooden coffee table sits centrally on a textured rug, complemented by a small black chair. Natural light streams in from a nearby window, enhancing the calming decor.
Apartment in Andover

The Historic Bell House Hygge Retreat

Nestled in the picturesque New England town center of Andover, minutes from gourmet dining, coffee shops, a Whole Foods supermarket, the Addison Art Gallery, Merrimack College and Phillips Andover we present the new: Bell House "Hygge" Retreat. It's a 200 year old structure that was completely rebuilt and remodeled by a highly skilled design team. Interior Design: Nirma Raffi Raffi Design Lab Photography: Linda Holt Linda Holt Creative

FamilyKitchenGetting around

4.98 out of 5 average rating, 121 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!

KitchenIndoor spacesLaundry

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.

KitchenFamilyCheck-in

4.77 out of 5 average rating, 105 reviews
Guest favorite
Barn in Carlisle

Private Studio w/ Loft Center Historic Carlisle

Charming private studio in the heart of Carlisle, perfect for 2 adults (up to 4 guests). Completely separate with no shared spaces. Close to Routes 128, 495, 35min to Boston, 10 min to historic Concord. Outdoor lovers enjoy nearby hiking, biking, and Great Brook Farm State Park. Easy access to Lowell, Nashoba Valley Ski Area, shops, and restaurants.

KitchenFamilyCleanliness

4.89 out of 5 average rating, 485 reviews
Top guest favorite
An inviting open-concept living area features a brown sectional sofa with a chaise, accented by throw pillows. A round coffee table sits in front, surrounded by a welcoming atmosphere of honeybee-themed decor, such as hexagon shelves on the wall. A workspace with a chair is positioned nearby.
Apartment in Billerica

Bee-Themed Retreat Near Boston - Unique Stay

Experience a one-of-a-kind stay at the Bee Hive in Billerica, a delightful apartment uniquely themed around honeybees. Located just 21 miles from vibrant Boston, enjoy close proximity to city attractions while relaxing in a charming, peaceful garden setting. Perfect for couples, families, or remote workers seeking inspiration and tranquility.

FamilyKitchenCondition

4.99 out of 5 average rating, 222 reviews

Popular amenities for Chelmsford family-friendly rentals

Family-friendly home rentals with a hot tub

When is the best time to visit Chelmsford?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,967 GYDG$31,177 GYDG$31,177 GYDG$31,177 GYDG$29,921 GYDG$37,035 GYDG$33,478 GYDG$33,478 GYDG$38,500 GYDG$33,687 GYDG$29,293 GYDG$31,386 GYD
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