
Family-friendly holiday rentals in Chelmsford
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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.

Air Bee-n-Bee Hive– Unique Themed Creative Retreat
Plan a unique and memorable stay at the Hive, a bee-themed apartment in a Boston suburb 21.1 miles from the city. Delight in the charming honeybee-inspired décor. Relax on the patio and enjoy the nearby chickens and geese – and especially their fresh eggs. You’ll love the entertainment options – 100s of free movies plus cable TV and access to streaming channels. Everything you need is here, from a full kitchen with a coffee bar to EV charger. Got work? A workspace and super-fast Wi-Fi await you.

Comfy-Spacious-private 1BR conveniently located
This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

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.

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.

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.

Farm stay in a Historic Ski Lodge turned Barn
Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

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

Professional Accommodations!
Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

Private guest house on beautiful country road
Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

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.
Popular amenities for Chelmsford family-friendly rentals
Family-friendly home rentals with a hot tub

Nana-tucket Inn

Your Cozy 1 BR Apt & Relaxing Retreat

Pond-Front Passive Solar Architectural House

Haven by the Lake

Private Waterfront! Views, Hot Tub, King Bed

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

Lakeside apartment, patio, hot tub, outside shower

Little Lake House, the Bungalow
Family- and pet-friendly home rentals

Winnie's Place - Freshly Renovated 1800s Farmhouse

Cheerful 1-bedroom New England Ranch

Sylvan White Pine Cottage – Cozy 3BR w/ Fireplace

Flower Farm Getaway 2BR, 20 Min To Boston

AKBrownstone: cozy private studio by T

New Super Modern 2 bed in Waltham

Vaughn Hill Hideaway & Sauna

Charming House on 7 Acres in Rural New Hampshire
Family-friendly home rentals with a pool

Peaceful suite in Boston with city views

Hopkinton Mass 3+ Bedrooms - Great location!

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Spacious vacation unit in premium suburban town

Modern Space With Pool Close To Singing Beach

Country Cottage in the City

Private Suite with Hot Tub

Antique Home - Steps from Harbor - Private Pool
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 $89 NZD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Chelmsford holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Fenway Park
- TD Garden
- Boston Common
- Harvard University
- Revere Beach
- Lynn Beach
- Monadnock State Park
- New England Aquarium
- MIT Museum
- Good Harbor Beach
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Jenness State Beach
- Quincy Market
- Pats Peak Ski Area
- Rye North Beach
- North Hampton Beach
- Prudential Center
- Salem Willows Park
- Franklin Park Zoo
- Symphony Hall




