
Family-friendly holiday rentals in Chelmsford
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chelmsford
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

Cozy Entire Unit Condo close to UMASS Lowell
My place is close to restaurants, UMASS. Lowell, and almost anything you need. You’ll love my place because instead of having a spare room in someone's house, you get an entire condo and privacy available to you (owner lives in separate unit). The unit includes basic amenities included (toiletries, bedding etc). In addition, the unit comes with a PlayStation 4 for the kids (or the husband/boyfriend) to keep them busy :) My place is good for couples, solo adventurers, and business travelers.

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.

New England Village Luxury Studio
Kick back and relax in this stylish studio! Our house is in a quiet neighborhood of older homes surrounded by woodlands yet conveniently located downtown, a half mile from our village green (Milford Oval). A short stroll over the river will take you to cafes, restaurants, pubs with live music, post office, library, shops & useful stores such as CVS. Whatever brings you…business, skiing, hiking, antiques, a family celebration or a romantic weekend away…we are looking forward to hosting you!

Large One Bedroom Apartment
1,100 square feet, completely renovated, 1 bedroom with a walk-in closet. Large bathroom with two sinks and walk-in shower. Open concept living, dining and kitchen area with vaulted ceiling. Hardwood floors throughout. Central air. Apartment is connected to a main house but with no interior access between house and apartment whatsoever. (No interior connecting doors at all) It has its own private driveway and side yard. Reef tank will no longer be in the apartment after May 20th.

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.

Water front cabin-like guest suite on a quiet pond
Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

Newly Built En Suite
Accommodations by Veteran Airbnb Hosts, we present An En suite in a new construction townhome. On the fringe of the suburbs, This special place is close to everything, making it easy to plan your visit. You have your own Entrance/exit into your space. 12 1/2 foot High cielings in your dedicated Level of the building gives this space a very West Coast feel. Walk out to your own Private patio for dining or relaxing as well as some shared greenspace to walk your fury friend.

Historic Loft with bathroom & kitchenette
A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

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

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).

Entire guest suite in Stoneham
Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.
Popular amenities for Chelmsford family-friendly rentals
Family-friendly home rentals with a hot tub

Hopkinton Mass 3+ Bedrooms - Great location!

Your Cozy 1 BR Apt & Relaxing Retreat

Luxurious Oceanfront Property

Pond-Front Passive Solar Architectural House

Boulder House - Extraordinary Luxury in the Woods!

Little Lake House, the Bungalow

Lakeside apartment, patio, hot tub, outside shower

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views
Family- and pet-friendly home rentals

New Super Modern 3 Bed in Waltham

White Pine Cottage – Cozy 3BR w/ Fireplace

Large, Comfortable & Conveniently located Home

Charming Downtown Gem ~ 2min to Salem ~ Workspace!

Vaughn Hill Hideaway & Sauna

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Ipswich Apartment

Quiet country apartment in farmland setting.
Family-friendly home rentals with a pool

Nana-tucket Inn

Spacious vacation unit in premium suburban town

Stylish and Cozy at Revere Beach

Modern Space With Pool Close To Singing Beach

Country Cottage in the City

Cozy Private Studio Unit w/ Laundry and Parking!

Antique Home - Steps from Harbor - Private Pool

In-law Apartment, Full Kitchen, Near Mt Wachusetts
Quick stats about holiday rentals that are family-friendly in Chelmsford

Total holiday rentals
Explore 20 holiday rentals in Chelmsford

Nightly prices starting at
Chelmsford holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 730 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Chelmsford holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chelmsford rentals

4.6 Average rating
Chelmsford stays receive an average rating of 4.6 out of 5 from guests
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- Family-friendly rentals Middlesex County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Hampton Beach
- TD Garden
- Fenway Park
- Boston Common
- Harvard University
- Revere Beach
- Pats Peak Ski Area
- New England Aquarium
- MIT Museum
- Freedom Trail
- Monadnock State Park
- Boston University
- Canobie Lake Park
- Boston Seaport
- Crane Beach
- Boston Convention and Exhibition Center
- Quincy Market
- Museum of Fine Arts
- North Hampton Beach
- Prudential Center
- Gillette Stadium
- Roxbury Crossing Station
- Boston Children's Museum
- Salem Willows Park




