Photo by Mark D

Search Chelmsford Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 15 Cottages in Chelmsford with updated reviews, rates, and availability.

The PondeRosa cottage at Cobbett's pond
10.0 out of 10, Exceptional, (10)
"The weekend that my girlfriend and I spent here was fantastic. Ana was very helpful and the cottage was beautiful and cozy. Hiking trails, food, bars, and stores all in 10 minutes or less driving range. Would easily stay here again, nothing negative to say at all!"
The PondeRosa cottage at Cobbett's pond
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
10.0 out of 10, Exceptional, (8)
"A short walk to the lake where we enjoyed kayaking and were the first to use the new firepit. Great location with all the amenities you would need."
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
10.0 out of 10, Exceptional, (2)
"Third time staying here we love everything the place has to offer. It’s great for my family. Also can’t beat the location."
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.
Cozy 3 bedroom seasonal cottage with very short walk to private community beach
9.8 out of 10, Exceptional, (7)
"This house has a big kitchen/living room and comfy beds. Not drinking the well water was odd-would be nice if the water provided was in glass and more plentiful. Also the paddle board was broken which was a bummer but the owner was very responsive and worked with us to make up for that. It’s a sweet cottage."
Cozy 3 bedroom seasonal cottage with very short walk to private community beach
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
10.0 out of 10, Exceptional, (2)
"The home had everything we needed. The amount of activities made it that we didn’t even have to leave the community if we didn’t want to. We spent three days relaxing at the pool and pond. The restaurant on site is exceptional. The location is perfect! We were able to take day trips to Cape Cod, Salem, Boston and Gloucester for whale watching. Pam, the host is very helpful and attentive. We were very happy with our experience and would recommend to friends and family! 10/10"
Clean Cottage w/Heated Pools - Hot Tub - Playground - Golf Cart: Family Retreat
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
10.0 out of 10, Exceptional, (1)
"This cottage, in Summer Village, was modern and comfortable, with a sunny front room, whose loungers we enjoyed! The resort community was fairly quiet, since it was after Labor Day. There were an active group of older adults who were quite friendly. The fact that the community was gated made it a little harder to have visitors. We really liked taking walks in the morning--some good hills! We were sorry the beach and pond were closed due to high algae levels--were told that it was not uncommon at...
Cottage at Summer Village Gated Waterfront Resort Community-20 Miles from Boston
Enchanted Cottage on 5 Acres
Enchanted Cottage on 5 Acres
Bright & Pet-friendly Home: 2 Mi to Harvard Square
3.0 star property
Bright & Pet-friendly Home: 2 Mi to Harvard Square
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
Remodeled Cottage retreat on the Lake, close to Boston but nestled in the woods
Beautiful waterview and water access from adorable cottage
Beautiful waterview and water access from adorable cottage
Entire near Boston Cottage House: MBTA, T, all major roads, parking
Entire near Boston Cottage House: MBTA, T, all major roads, parking
Inviting Summer Village Cottage: Golf Cart & More!
Inviting Summer Village Cottage: Golf Cart & More!
Gated Resort Community
Gated Resort Community
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
3.0 star property
Waltham Vacation Rental ~ 12 Mi to Downtown Boston
Inviting Summer Village Cottage: Golf Cart & More!
3.0 star property
Inviting Summer Village Cottage: Golf Cart & More!
Summer Village Family Cottage w/ Community Perks!
2.0 star property
Summer Village Family Cottage w/ Community Perks!
Don't see what you're looking for?
See all available properties in Chelmsford
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.

Other property types in Chelmsford

HYATT house Boston/Burlington
3.0 star property
9.2 out of 10, Wonderful, (2225)
"The size of the room was really nice. Full kitchen, nice size living space with L shaped couch and large bed room. My only negative point was the only way into the bathroom was through the actual bed room. I had my niece with me who slept on the couch and she had to go through my bedroom area to get to the bathroom. Other than that very nice place! We unfortunately were traveling at busy times and if you are looking to get to downtown Boston it will take you a solid hour to get there during...
The price is $161
$180 total
includes taxes & fees
Jul 5 - Jul 6
HYATT house Boston/Burlington
Sonder 907 Main
4.0 star property
8.0 out of 10, Very Good, (344)
"Nice kettle and fragrant soap"
The price is $206
$239 total
includes taxes & fees
Jul 2 - Jul 3
Sonder 907 Main
Crescent Suites Hotel
3.0 star property
9.6 out of 10, Exceptional, (835)
"We only stayed one night but would absolutely book this place again. Rooms are spacious and clean. Dana is professional and friendly. Highly recommend the Crescent hotel "
The price is $161
$180 total
includes taxes & fees
Jul 1 - Jul 2
Crescent Suites Hotel
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.

Chelmsford Cottages information

Number of reviews
30
Accommodation
15 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Chelmsford with Expedia?
Expedia has some terrific cottages in Chelmsford, so start packing for an unforgettable vacation on nature’s doorstep. If you have a budget in mind, select how much you’re willing to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a hot tub or free WiFi. We’ll help you find a suitable place whatever your escape looks like.
How can I find cheap cottages in Chelmsford?
With Expedia’s useful filter tool, booking cheap cottages in Chelmsford is a cinch. To discover accommodations that’ll make your wallet happy, tailor your search results by amenities, star rating and budget.
What is there to do in Chelmsford near my cottage?
Chelmsford has enough experiences and activities to keep you busy for weeks, beginning with Nashoba Valley Ski Area. MIT Haystack Observatory, Fruitlands Museums and Westford Museum and Historical Society are other awesome attractions. If you’re staying a while longer, Butterfly Place and Mascuppic Lake Beach will cap off your itinerary nicely.

Recent reviews of Chelmsford hotels
Expedia verified reviews