Chelmsford Vacation Packages

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Your Chelmsford Vacation

When a city getaway is calling, answer it with a vacation package to Chelmsford. The neighborhood of Ballardvale, which is good for watersports, nature and history, makes a wonderful base for your adventures. If taking in sights is part of the program during your trip to Chelmsford, stop by major attractions like University of Massachusetts Lowell, Tsongas Arena and Lowell Memorial Auditorium. Expedia is here to help you escape the everyday. Tailor your vacation to Chelmsford to match your travel style, whatever that may be.

Top Chelmsford Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (2,039 reviews)
Excellent hotel with friendly staff, clean and comfortable rooms with a Starbucks! We love the cookies at check in. always a winner. It is in a weird location but for our one night it was great.

Reviewed on Jul. 14, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
Great hotel terrific staff

Reviewed on Jul. 12, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 4
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Embassy Suites Boston Logan Airport

Embassy Suites Boston Logan Airport

3.5 out of 5
East Boston
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (2,001 reviews)
Not bad at all, but nothing special

Reviewed on Jul. 13, 2025

Ready to book your vacation to Chelmsford?

 

Choose your dates

Chelmsford Hotel Deals

Hyatt Regency Boston/Cambridge
Hyatt Regency Boston/Cambridge
4 out of 5
575 Memorial Drive, Cambridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Aug 10 to Aug 11
CA $197
CA $260 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,976 reviews)
"Fantastic location for 4th of July weekend as fireworks were set off on the nearby Charles."

Reviewed on Jul. 10, 2025

Hyatt Regency Boston/Cambridge
Encore Boston Harbor
Encore Boston Harbor
5 out of 5
1 Broadway, Everett, MA
Fully refundableReserve now, pay when you stay
The price is CA $344 per night from Jul 28 to Jul 29
CA $344
CA $384 total
Jul 28 - Jul 29
includes taxes & fees
9.6/10 Exceptional! (3,103 reviews)
"Encore is awesome!"

Reviewed on Jul. 13, 2025

Encore Boston Harbor
The Arcadian Hotel
The Arcadian Hotel
3.5 out of 5
1200 Beacon St, Brookline, MA
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Jul 29 to Jul 30
CA $206
CA $276 total
Jul 29 - Jul 30
includes taxes & fees
8/10 Very Good! (3,178 reviews)
"It was an interior room with no windows, didn’t care for that. And the breakfast was mostly bread and yogurt."

Reviewed on Jul. 13, 2025

The Arcadian Hotel
See all 1,478 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chelmsford vacation package cost?
You'll find cheap prices from CA $631 on Expedia for your Chelmsford getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Chelmsford costs.
What are the cheapest months to go to Chelmsford?
You can generally find lower prices and better availability in January, February and November. Explore our cheap Chelmsford vacation packages and you could land some great off-season discounts.
How many days is enough for Chelmsford?
We recommend booking a Chelmsford vacation for around 2 days. This gives you time to visit top attractions such as Clara Sexton House and Westford Town Common, as well as check out neighbourhoods like South Lowell and Highlands. You might even be able to squeeze in a day trip outside of Chelmsford.
How to find the best Chelmsford package deals?
Begin your search for a Chelmsford package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Chelmsford package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chelmsford adventure underway.
Is it cheaper to book a Chelmsford vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Chelmsford vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Chelmsford?
If you're considering an impromptu Chelmsford adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chelmsford?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Chelmsford.
  2. Set a budget: Consider expenses such as flights, food and transportation when working out how much to set aside for your trip to Chelmsford. Then, choose a hotel that works with your budget, whether that's an affordable stay or a more upscale retreat.
  3. Decide how many days away: Start by listing all the attractions you'd like to experience in Chelmsford. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the right Chelmsford vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.