
Holiday rentals in Chelmsford
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Top-rated holiday rentals in Chelmsford
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Cute & Cozy Groton apartment w/private patio
Cozy apartment with your own private patio; 5-min walk to downtown, shops, cafes, library & restaurants; hop on the Nashua River Rail trail where you can walk/bike to neighboring towns. Enjoy all Groton has to offer, miles of hiking trails, rent a canoe or kayak, golf, horse riding, fishing, apple, pumpkin & berry picking; walk up to Bancroft Castle on Gibbet Hill where “Little Women" was filmed & enjoy the view. Don’t miss a visit to Groton Hill Music, our world class music performance venue 🎶

All New Private Country Setting (2 Level-No Share)
We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

Private & Remote, Enjoy Outdoors, Sleep in Luxury
Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Comfort Oasis with Private Garage | Steps from UML
Welcome to our Tulum-inspired 2-bed, 1-bath townhouse with a private garage in Lowell! Earthy tones and Tulum charm define this two-level retreat. Proximity to Umass Lowell, a 35 min drive to Boston makes it ideal for commuters. Hospitals like Lowell General and Lawrence General are nearby. Only 15 minutes from southern New Hampshire, our townhouse offers style, comfort, and accessibility for academics, healthcare, or a serene escape. Book now for a perfect blend of relaxation and convenience

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.

Winery Studio w/ Private Hot Tub & Wine Tasting
Private Hot Tub, Vineyard Guesthouse at Winery. This former art studio is a true getaway to relax & feel at peace. Filled with natural light, it sits beside one of our historic 1800s barns on the winery property with vineyard views. Perfect for a romantic retreat or the traveling professional seeking a peaceful home away from home. Located in an affluent neighborhood minutes from shopping & restaurants. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases

Lakefront Suite Two-Room, Comfy, Tranquil
Located on a lovely small lake, the upstairs suite has a panoramic view from the bedroom, a private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room - it feels like an apartment, but no kitchen. Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants, a casino, or tax-free shopping. We are one hour from Boston.

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.

The Cozy Den
Welcome to your home away from home! This cozy and stylish apartment is thoughtfully designed with families in mind, offering a peaceful retreat where you can truly relax. Soft, comfortable furnishings and a calm color palette create a welcoming atmosphere, perfect for unwinding after a day of exploring. Within a walking distance to the MBTA (the T) and close to UMASS Lowell and Tsongas Center. Not to mention close to restaurants, museums, grocery stores and gas stations.

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 horses and ponies and see the 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

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!
Popular amenities for Chelmsford holiday rentals
Other great holiday rentals in Chelmsford

Family-Friendly Townhouse on the Merrimack River

* * Crooked_Spring_Colonial * *

Cozy Lake Cottage

Exclusive Stay: Entire Unit by UMASS

Family Retreat | Huge Yard, Playground & 5BR Home

Furnished Cozy Apartment in quiet neighborhood

Sleep Well, Walk Everywhere | Private & Spacious

Balsam Retreat
When is the best time to visit Chelmsford?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £48 | £48 | £48 | £47 | £48 | £50 | £52 | £48 | £48 | £50 | £51 | £51 |
| Avg. temp | -2°C | -1°C | 3°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 6°C | 1°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Chelmsford?
Chelmsford has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in hotel rentals in Chelmsford?
Experience the best of Chelmsford with our hotel rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Chelmsford?
Four-legged friends are welcome in Chelmsford. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Chelmsford?
Yes! Work meets play with ease at over 80 vacation rentals in Chelmsford featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Chelmsford?
Make yourself at home in Chelmsford by choosing from our most frequently booked neighborhoods. We have over 150 vacation rentals in Pawtucketville, over 100 vacation rentals in Heart Pond, and over 180 vacation rentals in North Chelmsford.
Do hotel rentals in Chelmsford have air conditioning?
Absolutely! We offer over 10 hotel rentals with air conditioning in Chelmsford. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Chelmsford have a kitchen?
Absolutely! We offer over 20 bed and breakfast rentals with a kitchen in Chelmsford. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chelmsford have wifi?
Absolutely! We offer over 20 apartment rentals with wifi in Chelmsford. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Chelmsford have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Chelmsford. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Hotel Rentals in Chelmsford?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Chelmsford

Total holiday rentals
Explore 110 holiday rentals in Chelmsford

Nightly prices starting at
Chelmsford holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 3,600 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
110 of Chelmsford holiday rentals include wifi access

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

4.7 Average rating
Chelmsford stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
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- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Common
- Boston Seaport
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- New England Aquarium
- Freedom Trail
- Pats Peak Ski Area
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Monadnock State Park
- Boston College
- North Hampton Beach
- Roxbury Crossing Station
- Northeastern University
- Quincy Market
- Tufts University
- Prudential Center





