Photo by Mark D

Search Vacation Homes in Chelmsford

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chelmsford

Union Square House

9.6 out of 10, Exceptional, (75)
"Good vibe, comfy stay, fine location. No complaints. Host was responsive and on top of the care of the place."
Union Square House

Lake Access 4 Bed 3 Full Bath

10.0 out of 10, Exceptional, (17)
"What a great place to cook dinner and have a night with the girls! "
The price is AED 1,446
AED 3,151 total
includes taxes & fees
22 Jul - 23 Jul
Lake Access 4 Bed 3 Full Bath

Beautifully Renovated Cozy Home

Beautifully Renovated Cozy Home

Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

2.0 star property
9.8 out of 10, Exceptional, (6)
"Lived the location and light!!Thanks!!"
Charming 2 bedroom house 5 miles from Logan Airport/ Boston. Walking to train.

Historic and Charming Brownstone

9.8 out of 10, Exceptional, (53)
"We stayed for a week with extended family to celebrate Thanksgiving in Boston. This property was great! We served many big meals, had a very well equipped kitchen. One thing to note is the upstairs room with the futon in it is a pass-through room that two other bedrooms open into, we had a teenager sleeping in there, and it was fine, but not much privacy. Compared to many other Boston properties, the stairs are not too steep, and not too narrow, which was great for my in-laws. Would love to...
Historic and Charming Brownstone

Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

10.0 out of 10, Exceptional, (4)
"We could accomodate all 11 of us comfortably with four levels of house. "
Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

Spacious vacation townhome unit with a pool

10.0 out of 10, Exceptional, (12)
"Traveled to Boston for the A250 and this place was perfect to travel between Boston, Concord and Lexington. Excellent walking trails next to the property. Nicely furnished, clean, overall relaxing environment."
Spacious vacation townhome unit with a pool

Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

9.6 out of 10, Exceptional, (4)
"Responsive owner, noce clean quiet property. "
The price is AED 951
AED 1,329 total
includes taxes & fees
11 Aug - 12 Aug
Newly Renovated Luxury 3-Bed 2-Bath House with Easy Airport Access

Classic New England Bunkhouse- Home for the whole family!

10.0 out of 10, Exceptional, (4)
"Very good place to stay. Quiet community and lovely home. Clean and bright. Would stay again for a homecoming."
The price is AED 777
AED 1,299 total
includes taxes & fees
21 Jul - 22 Jul
Classic New England Bunkhouse- Home for the whole family!

Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

8.8 out of 10, Excellent, (25)
"Excellent property; easy to work with owners."
The price is AED 1,104
AED 2,117 total
includes taxes & fees
21 Jul - 22 Jul
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

Majestic lakefront 3-bedroom with pool, hot tub, water sports and birdwatching

10.0 out of 10, Exceptional, (5)
Majestic lakefront 3-bedroom with pool, hot tub, water sports and birdwatching

Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

10.0 out of 10, Exceptional, (16)
"The home is well cared for and beautiful. The beds were very comfortable. It was the perfect spot for our family getaway, very close to Boston. Would stay here again in a heartbeat if we are ever in the area again!"
Family-Friendly Rose Cottage | Near Encore | 4 Beds 3 Baths

Tuscan Village Charming Home Steps From it All

7.4 out of 10, Good, (3)
"This house has two bedrooms downstairs and two upstairs. One bathroom (one of the listings stated 1). The outside of the house needs work. It would have been nice to be out on the deck enjoying the weather but needs updating. Beds are comfortable and linens seem new. Spacious inside. The location is next to EVERYTHING. Restaurants, music, shopping. Some items were broken and I did let the owners know. They were easy to contact. "
The price is AED 4,796
AED 6,172 total
includes taxes & fees
21 Jul - 22 Jul
Tuscan Village Charming Home Steps From it All

Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem

9.0 out of 10, Wonderful, (26)
"Everything was as expected. Convenient location. Would recommend."
Cozy 3bdr Free parking/Wifi, 5 min to Encore Close to Boston,Cambridge ,Salem

Charming home with deck- walkable to transit, shops & restaurants

10.0 out of 10, Exceptional, (5)
"Everything was great! Our host was very quick to respond if there was a question. Plenty of room for all 5 adults (and then some). The only negative about the location is pulling out of the driveway. Easy enough to deal with though. For us, the proximity of this location to our family and friends for this visit was great. 20-25 minutes at most whether going into Boston or heading out to family in the suburbs."
Charming home with deck- walkable to transit, shops & restaurants

Wellesley Spacious and Modern

2.0 star property
Wellesley Spacious and Modern

Deluxe Spacious 2-bedroom 2-story with gas fireplace Guest House

10.0 out of 10, Exceptional, (1)
"The property was beautiful and spacious. Everything was very clean. The host was friendly and responsive. Definitely recommend! "
Deluxe Spacious 2-bedroom 2-story with gas fireplace Guest House

3-bedroom house in Malden with WiFi, 10 minutes from the Casino

8.0 out of 10, Very Good, (1)
"Checking is was no issue. Driveway was tight. Happened to stay when temperature was above 100 degrees for 2 days. Was told that to not turn on all of the a/c units as it would pop a breaker. In retrospect, I should have asked which units to NOT turn on as we did pop a breaker and has no A/c. Took a while bit they did send a representative to reset and then had no issues. Bathtub in 2nd floor bathroom doe not drain while taking a shower. Other than these issues, the property itself was awesome."
3-bedroom house in Malden with WiFi, 10 minutes from the Casino

The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston

10.0 out of 10, Exceptional, (2)
"I only had the issue about my code not working to enter and i couldnt get a hold of anyone in the moment and it was raining, haha. But they responded and let me in! House is very nice!! The only issue is my kids are older, majority of cabinets were childlock and i have NO IDEA how to unlock. So we couldn’t access cabinets and wasnt able to find a broom to clean up. I like to keep clean. But. Othererwisd, it was super nice inside, super responsive, and close to 8min drive to a wegmans! Not bad!...
The Niche: A cozy perfection! Newly Renovated Family Friendly! Near Boston

Perfect Getaway in Historic NewtonHighland (CDC Safe)

8.8 out of 10, Excellent, (18)
"We absolutely loved this place. The beds were very comfortable and the location was great. Being able to park in the driveway was a great bonus!"
Perfect Getaway in Historic NewtonHighland (CDC Safe)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in