A town with a prominent white church steeple, a snow-covered landscape, and a mix of residential and commercial buildings.

Chelmsford Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chelmsford holiday rentals

Exterior

1. ✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (36 reviews)
"Wonderful stay"
United States
Brent H.
The price is HK$941
HK$1,575 total
includes taxes & fees
20 Sept - 21 Sept
✨Private Studio w/ Loft Center Historic Carlisle✨
Coffee/tea maker, fridge, microwave, oven

2. Lake Access 4 Bed 3 Full Bath

Lake Access 4 Bed 3 Full Bath
Billerica
9.8 out of 10, Exceptional, (23 reviews)
"The house was perfect for us! Sparkling clean and comfortable. We really enjoyed staying here and would stay again for sure!"
United States
Diane B.
The price is HK$2,561
HK$6,113 total
includes taxes & fees
17 Sept - 18 Sept
Lake Access 4 Bed 3 Full Bath
Coffee/tea maker, fridge, microwave, oven

3. Lakeview Getaway with Hot Tub

Lakeview Getaway with Hot Tub
Billerica
9.0 out of 10, Wonderful, (2 reviews)
"Great stay!"
United States
KrackleJak
The price is HK$2,141
HK$4,841 total
includes taxes & fees
13 Sept - 14 Sept
Lakeview Getaway with Hot Tub
Interior

4. Bee-Themed Stay Near Boston – A Sweet and Unique Getaway

Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Billerica
10.0 out of 10, Exceptional, (17 reviews)
"It was a great stay. The place was cosy and had everything you need and stuff you forgot to bring . I will definitely be staying here again."
United States
Jonathan
The price is HK$1,076
HK$2,016 total
includes taxes & fees
21 Sept - 22 Sept
Bee-Themed Stay Near Boston – A Sweet and Unique Getaway
Dining

5. Cottage Suite "B" - Walk to Shops, Train, History

Cottage Suite "B" - Walk to Shops, Train, History
Concord
9.8 out of 10, Exceptional, (8 reviews)
"Convenient location and peaceful respite. "
United States
Maria S.
The price is HK$1,725
HK$3,259 total
includes taxes & fees
17 Sept - 18 Sept
Cottage Suite "B" - Walk to Shops, Train, History
Coffee/tea maker, fridge, microwave, oven

6. A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.

A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.
Nashua
9.6 out of 10, Exceptional, (21 reviews)
"My husband and I loved our visit to this charming home! We enjoyed the one level living, the simple yet perfect decor, and many great updates, which made this home perfect for us. Our dogs say it was their favorite backyard yet!!!"
United States
kelly N.
The price is HK$1,874
HK$3,361 total
includes taxes & fees
28 Sept - 29 Sept
A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.
Interior

7. SOFIMA-Cozy and Charming 2-bedroom apartment!

SOFIMA-Cozy and Charming 2-bedroom apartment!
Woburn
10.0 out of 10, Exceptional, (11 reviews)
"Great place close to everything we needed. Accomidations are nice and everything we needed was there. "
United States
Mark K.
The price is HK$1,623
HK$4,021 total
includes taxes & fees
22 Sept - 23 Sept
SOFIMA-Cozy and Charming 2-bedroom apartment!
Private kitchen

8. A Quintessential New England Historical Guesthouse

A Quintessential New England Historical Guesthouse
Groton
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful stay !!!!! Just perfect !!!"
United States
Sarah B.
The price is HK$7,841
HK$12,831 total
includes taxes & fees
14 Sept - 15 Sept
A Quintessential New England Historical Guesthouse
Smart TV

9. Spacious 4-bedroom unit in welcoming Nashua NH.

Spacious 4-bedroom unit in welcoming Nashua NH.
Nashua
8.4 out of 10, Very good, (9 reviews)
"Host is amazing and the space is beautiful location is very near the hospital which we needed for a family memeber having brain surgery... very close to restaurants etc"
United States
Riccie S.
The price is HK$2,423
HK$3,923 total
includes taxes & fees
5 Oct - 6 Oct
Spacious 4-bedroom unit in welcoming Nashua NH.
Coffee/tea maker, fridge, microwave, oven

10. Beautiful & Relaxing Nashua Home - Minutes from Downtown

Beautiful & Relaxing Nashua Home - Minutes from Downtown
Nashua
10.0 out of 10, Exceptional, (20 reviews)
"Great home that had everything we needed for our stay! Many great amenities close by. Amazing communication by host! "
United States
Kristina M.
The price is HK$1,770
HK$4,439 total
includes taxes & fees
14 Sept - 15 Sept
Beautiful & Relaxing Nashua Home - Minutes from Downtown
Smart TV

11. Enchanting Hidden Door Escape

Enchanting Hidden Door Escape
Stoneham
9.6 out of 10, Exceptional, (35 reviews)
"Everything was wonderful . The only suggestion would be to have a couple larger pans for cooking "
United States
John D.
The price is HK$2,124
HK$5,225 total
includes taxes & fees
17 Sept - 18 Sept
Enchanting Hidden Door Escape
Smart TV

12. Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston
stoneham
8.8 out of 10, Excellent, (11 reviews)
"Stayed at this property for a little over a week. Property is in good shape, location is convenient. Host is very responsive to questions. Highly recommend this property"
United States
Brendan D.
The price is HK$1,861
HK$4,226 total
includes taxes & fees
23 Sept - 24 Sept
Modern Three Bedroom Condo - Near Boston
Interior

13. Serene & Sleek Family Retreat w/ Office in Shirley

Serene & Sleek Family Retreat w/ Office in Shirley
3.0 star property
Shirley
The price is HK$2,376
HK$5,047 total
includes taxes & fees
24 Sept - 25 Sept
Serene & Sleek Family Retreat w/ Office in Shirley
Coffee/tea maker, fridge, microwave, oven

14. Stylish home next to train to Boston, near Salem

Stylish home next to train to Boston, near Salem
Wakefield
9.6 out of 10, Exceptional, (9 reviews)
"Great stay"
United States
Alex c.
The price is HK$2,329
HK$4,695 total
includes taxes & fees
20 Sept - 21 Sept
Stylish home next to train to Boston, near Salem
Coffee/tea maker, fridge, microwave, oven

15. Beautiful condo next to commuter rail into Boston

Beautiful condo next to commuter rail into Boston
Wakefield
9.6 out of 10, Exceptional, (27 reviews)
"The home was in a great neighborhood. The home is also super clean and hosts were responsive and helpful. "
United States
Melissa A.
The price is HK$3,192
HK$5,755 total
includes taxes & fees
28 Sept - 29 Sept
Beautiful condo next to commuter rail into Boston
Interior

16. 15 Min to Boston, Spacious 5BR Retreat on Road with Office Space & Comfortable Beds

15 Min to Boston, Spacious 5BR Retreat on Road with Office Space & Comfortable Beds
Stoneham
10.0 out of 10, Exceptional, (2 reviews)
"Very nice home with plenty of room for 2 grandparents, my son & his family & daughter & family. 10 total.Good location, easy to drive into Boston and other locations."
United States
Sam M.
15 Min to Boston, Spacious 5BR Retreat on Road with Office Space & Comfortable Beds
Exterior detail

17. Funky and cozy home ! A little bit of everything for everyone.

Funky and cozy home ! A little bit of everything for everyone.
Arlington
10.0 out of 10, Exceptional, (29 reviews)
"Our stay was lovely and we enjoyed everything! Our host are the awesome and we wanted for nothing. It was a great place to stay and highly recommend this home away from home!"
United States
Shellery R.
The price is HK$3,043
HK$5,449 total
includes taxes & fees
23 Sept - 24 Sept
Funky and cozy home ! A little bit of everything for everyone.
Exterior

18. Charming 1-bedroom well located Garden Apartment in Historic West Medford

Charming 1-bedroom well located Garden Apartment in Historic West Medford
West Medford
10.0 out of 10, Exceptional, (11 reviews)
"Will not be disappointed!"
United States
Dave O.
The price is HK$1,306
HK$2,405 total
includes taxes & fees
14 Sept - 15 Sept
Charming 1-bedroom well located Garden Apartment in Historic West Medford
Terrace/patio

19. Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1,265 reviews)
"Friendly staff. Bed was very comfortable and the kitchen was a plus!"
United States
Evelyn
The price is HK$1,263
HK$1,411 total
includes taxes & fees
13 Sept - 14 Sept
Crescent Suites Hotel
Dining

20. Relax with family or friends to this elegant apartment in the heart of Waltham

Relax with family or friends to this elegant apartment in the heart of Waltham
South Side
9.2 out of 10, Wonderful, (24 reviews)
"The location and parking were very convenient."
United States
Annie B.
The price is HK$3,105
HK$5,913 total
includes taxes & fees
21 Sept - 22 Sept
Relax with family or friends to this elegant apartment in the heart of Waltham
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.
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Top Chelmsford Hotel Reviews

enVision Hotel Boston Everett

enVision Hotel Boston Everett

10/10 Excellent
"Really enjoyed my stay! The hotel was great, parking is easy, and the location is super convenient."
Nadia 2-night trip
Posted 10 hours ago
enVision Hotel Boston Everett

Find out more about Chelmsford

Search for holiday rentals in Chelmsford on Expedia! You can easily find your home rentals, villas, holiday apartments in Chelmsford using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chelmsford!

Frequently asked questions

Can I find holiday rentals in Chelmsford?

Yes, there are holiday rentals close to the most popular sights in Chelmsford, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Chelmsford. While you're here, grab a bite or have a drink at the coffee shops.

What are some of the best holiday rentals that Chelmsford has to offer?

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking: This holiday home rental outside of Chelmsford offers a balcony, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Chelmsford?

Explore the area and family-friendly sights such as Kimball Farm, or get out into nature at a spot like Concord River. Great Brook Farm State Park and Cambodia Town are a couple of places you'll find in the wider area.

What are holiday rentals like in Chelmsford?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chelmsford. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips.