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.
The Verb Hotel

The Verb Hotel

3.5 out of 5
Fenway–Kenmore
Price was CA $1,632, price is now CA $1,150 per person
CA $1,150
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (2,164 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $4,439, price is now CA $2,149 per person
CA $2,149
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
All the staff was very helpful and responsive I would recommend this hotel to everyone planning to stay in Boston.

Reviewed on Nov 9, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was CA $1,959, price is now CA $1,244 per person
CA $1,244
per person
Jan 12 - Jan 19
found 8 hours ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was CA $2,360, price is now CA $1,524 per person
CA $1,524
per person
Jan 29 - Feb 1
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)
The best location and the beat service! The best swimming pool

Reviewed on Nov 9, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $2,311, price is now CA $1,580 per person
CA $1,580
per person
Jan 29 - Feb 1
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)
Great place to stay!!

Reviewed on Nov 9, 2026

Ready to book your vacation to Chelmsford?

 

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Chelmsford Hotel Deals

Holiday Inn Express Chelmsford by IHG

Holiday Inn Express Chelmsford by IHG

2.5 out of 5
8 Independence Drive Chelmsford MA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Dec 10 to Dec 11
CA $128
CA $143 total
Dec 10 - Dec 11
includes taxes & fees
Holiday Inn Express Chelmsford by IHG
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 $404 per night from Nov 30 to Dec 1
CA $404
CA $452 total
Nov 30 - Dec 1
includes taxes & fees
9.6/10 Exceptional! (4,354 reviews)
"good"

Reviewed on Nov 10, 2026

Encore Boston Harbor
Arcadian Hotel

Arcadian Hotel

3.5 out of 5
1200 Beacon St Brookline MA
The price is CA $117 per night from Dec 6 to Dec 7
CA $117
CA $178 total
Dec 6 - Dec 7
includes taxes & fees
8.2/10 Very good! (4,488 reviews)
"Had to wait in check in line to purchase snacks."

Reviewed on Nov 10, 2026

Arcadian Hotel
See all 1,594 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.
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What to do in Chelmsford

Battle of Lexington and Concord Self-Guided Driving Audio Tour

Battle of Lexington and Concord Self-Guided Driving Audio Tour

CA $21
per traveller
90% of travellers recommend
Battle of Lexington and Concord Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)

CA $71
per adult
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
Lexington & Concord Self-Guided Driving & Walking Audio Tour

Lexington & Concord Self-Guided Driving & Walking Audio Tour

CA $21
per traveller
Lexington & Concord Self-Guided Driving & Walking Audio Tour
See all activities in Chelmsford

Frequently asked questions

How much does a Chelmsford vacation package cost?
You'll find cheap prices from CA $1,150 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.