Chelmsford Vacation Rentals

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Our top choices for Chelmsford vacation rentals

Idyllic Small-Town Stay

Idyllic Small-Town Stay
Derry
10.0 out of 10, Exceptional, (8)
"Liked the stay, thank you"
United States
Ciria
$119 nightly
The price is $129
Dec 29 - Dec 30
Total with taxes and fees
Idyllic Small-Town Stay

Furnished Apartments near Encore Boston

Furnished Apartments near Encore Boston
2.5 star property
Everett
8.4 out of 10, Very Good, (8)
"Great place. Very clean. Great communication."
United States
Michele
$245 nightly
The price is $274
Dec 27 - Dec 28
Total with taxes and fees
Furnished Apartments near Encore Boston

Cozy 2BR-Walk to Tufts & Green Line, Near Boston!

Cozy 2BR-Walk to Tufts & Green Line, Near Boston!
Medford
9.4 out of 10, Exceptional, (22)
"Great, will come back again."
United States
Dushyant V.
$220 nightly
The price is $246
Dec 29 - Dec 30
Total with taxes and fees
Cozy 2BR-Walk to Tufts & Green Line, Near Boston!

NEW Modern Apartment Near Boston & Harvard Square.

NEW Modern Apartment Near Boston & Harvard Square.
Watertown
10.0 out of 10, Exceptional, (48)
"Pefect location for us to be near family. Hosts were extremely accomodating and apartment had every little detail provided for. We would absolutely stay again!"
United States
Sherry K.
NEW Modern Apartment Near Boston & Harvard Square.

Spacious Private Entrance Master Bedroom/Bath

Spacious Private Entrance Master Bedroom/Bath
Wellesley
10.0 out of 10, Exceptional, (89)
"Great place to stay. "
United States
Alexa
$142 nightly
The price is $156
Dec 28 - Dec 29
Total with taxes and fees
Spacious Private Entrance Master Bedroom/Bath

Cozy Large House close to TUFTS/Harvard/MIT 4BR

Cozy Large House close to TUFTS/Harvard/MIT 4BR
South Medford
9.6 out of 10, Exceptional, (8)
"Very nice house check in was easy there was parking and the beds were comfortable. Shower with great water pressure and a well stocked kitchen for making and eating food! "
United States
Ronan B.
$387 nightly
The price is $411
Dec 28 - Dec 29
Total with taxes and fees
Cozy Large House close to TUFTS/Harvard/MIT 4BR

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.

Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.
Medford
10.0 out of 10, Exceptional, (4)
"Very well appointed, fully stocked with everything we needed during our stay. Clean and comfortable as well. Convenient location to T station and shopping. Quick train ride or drive into downtown. "
United States
Krissy V.
$276 nightly
The price is $308
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beautiful 3BR+Office+Parking+Backyard near Boston-Cambridge.

✨Private Studio w/ Loft Center Historic Carlisle✨

✨Private Studio w/ Loft Center Historic Carlisle✨
Carlisle
9.4 out of 10, Exceptional, (33)
"We had a great stay! The place was perfect for our weekend trip. We were able to hit all of the spots we planned, with the central location!"
United States
C Z.
$149 nightly
The price is $157
Dec 28 - Dec 29
Total with taxes and fees
✨Private Studio w/ Loft Center Historic Carlisle✨

Nothing Fancy Older Pet Friendly Home – near I-95

Nothing Fancy Older Pet Friendly Home – near I-95
Georgetown
9.4 out of 10, Exceptional, (3)
"Came for a short stay and had absolutely no complaints. Easy entry, great communication and an amazing home to stay in. Would highly recommend:)"
United States
Fedalis R.
$302 nightly
The price is $319
Jan 20 - Jan 21, 2026
Total with taxes and fees
Nothing Fancy Older Pet Friendly Home – near I-95

Great Apartment on River/ Harvard Square two blocks

Great Apartment on River/ Harvard Square two blocks
2.0 star property
West Cambridge
8.6 out of 10, Excellent, (29)
"Everything was great! We had a really fun stay and the place was perfect for what we needed! "
United States
millie p.
$206 nightly
The price is $236
Dec 28 - Dec 29
Total with taxes and fees
Great Apartment on River/ Harvard Square two blocks

Boston Cozy 4BD/15min to Downtown/Airport + Backyard and Parking

Boston Cozy 4BD/15min to Downtown/Airport + Backyard and Parking
Revere
$243 nightly
The price is $271
Dec 29 - Dec 30
Total with taxes and fees
Boston Cozy 4BD/15min to Downtown/Airport + Backyard and Parking

Charming 1BR Near Encore 8483

Charming 1BR Near Encore 8483
2.0 star property
Everett
Charming 1BR Near Encore 8483

Bright & Cozy Entire Apartment - Your New England Hub

Bright & Cozy Entire Apartment - Your New England Hub
Haverhill
9.8 out of 10, Exceptional, (6)
"Check in was easy! Nice apartment that has been updated. It was great for my family while we were in the area visiting multiple locations."
United States
Erin W.
$383 nightly
The price is $428
Dec 28 - Dec 29
Total with taxes and fees
Bright & Cozy Entire Apartment - Your New England Hub

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston
stoneham
9.0 out of 10, Wonderful, (9)
"We enjoyed our stay and would definitely stay here again. It was clean, cute, very cute area, safe, and very short drive to Boston. We really loved the area and the people we interacted with were all so friendly! The beds were very comfy too!!"
United States
Meghan D.
Modern Three Bedroom Condo - Near Boston

Sunny Dog Friendly Union Sq 1brm

Sunny Dog Friendly Union Sq 1brm
Spring Hill
9.6 out of 10, Exceptional, (20)
"his unit fit all of our needs regarding location, cleanliness, and amenities. I would 100% recommend this property to my friends and family and will revisit this if I'm in town in the future!"
United States
Reservations G.
$263 nightly
The price is $294
Jan 11 - Jan 12, 2026
Total with taxes and fees
Sunny Dog Friendly Union Sq 1brm

Crescent Suites Hotel

Crescent Suites Hotel
3.0 star property
South Side
9.6 out of 10, Exceptional, (1145)
"Lovely, quiet place."
United States
Fatu
$131 nightly
The price is $147
Jan 17 - Jan 18, 2026
Total with taxes and fees
Crescent Suites Hotel

Cottage Suite "A" - Walk to Shops, Train, History

Cottage Suite "A" - Walk to Shops, Train, History
Concord
9.8 out of 10, Exceptional, (7)
"It was easy to find close to the main road and centrally located close to the commuter rail."
United States
Marilyn J.
$202 nightly
The price is $226
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cottage Suite "A" - Walk to Shops, Train, History

On River/Harvard Sq. two blocks

On River/Harvard Sq. two blocks
2.0 star property
West Cambridge
8.0 out of 10, Very Good, (32)
"Great place to stay! We loved our time there!"
United States
Melody
$200 nightly
The price is $229
Dec 28 - Dec 29
Total with taxes and fees
On River/Harvard Sq. two blocks

Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay

Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay
Everett
9.4 out of 10, Exceptional, (28)
"It worked perfect for me and my friends and was a nice distance from the city. Amenities were nice and the whole process was super easy!"
United States
Brendan D.
$385 nightly
The price is $430
Jan 12 - Jan 13, 2026
Total with taxes and fees
Stylish Boston-Area Duplex - Free Parking, Yard, Comfortable Stay

Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq

Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq
North Cambridge
$215 nightly
The price is $246
Jan 3 - Jan 4, 2026
Total with taxes and fees
Charming 2-bedroom apartment in Cambridge with AC near Harvard Tufts porter sq
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

Find out more about Chelmsford

Everything you need to know about Chelmsford vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chelmsford vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chelmsford vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chelmsford vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chelmsford. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chelmsford in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chelmsford rentals

At Expedia, we put the best Chelmsford vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chelmsford rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chelmsford vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chelmsford. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Chelmsford?

Yes, we give you a choice of vacation rentals close to top sights in Chelmsford, or you can select a more secluded option if you want a relaxing place to 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 coffeehouses.

What are some of the best vacation rentals in Chelmsford?

Historic house renovated for modern convenience: This vacation home rental near Chelmsford is located near skiing and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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 Tsongas Arena are a couple of places you'll find in the larger area.

What are vacation rentals like in Chelmsford?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Chelmsford. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for small groups.