Flights To Middlesex County - Cheap Flights Starting at CA $256

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Middlesex County's top cities

An aerial view of a town with a central square, a church, and surrounding residential areas.

Marlborough

Flights
Marlborough

How Much Does it Cost To Fly To Middlesex County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 31 - Sun, Nov 1
YTZ
Billy Bishop Toronto City
BOS
Logan Intl.
CA $450 Roundtrip, just found
CA $450
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Oct 31 from Billy Bishop Toronto City to Logan Intl., returning Sun, Nov 1, priced at CA $450 just found
Tue, Nov 3 - Fri, Nov 6
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $462 Roundtrip, just found
CA $462
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Nov 3 from Pearson Intl. to Logan Intl., returning Fri, Nov 6, priced at CA $462 just found
Tue, Nov 17 - Tue, Nov 24
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $462 Roundtrip, found 13 hours ago
CA $462
Roundtrip
found 13 hours ago
Select Air Canada flight, departing Tue, Nov 17 from Pearson Intl. to Logan Intl., returning Tue, Nov 24, priced at CA $462 found 13 hours ago
Tue, Nov 3 - Fri, Nov 6
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $462 Roundtrip, just found
CA $462
Roundtrip
just found
Select Air Transat flight, departing Tue, Nov 3 from Pearson Intl. to Logan Intl., returning Fri, Nov 6, priced at CA $462 just found
Tue, Dec 8 - Wed, Dec 16
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $464 Roundtrip, found 22 hours ago
CA $464
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Dec 8 from Pearson Intl. to Logan Intl., returning Wed, Dec 16, priced at CA $464 found 22 hours ago
Tue, Nov 17 - Tue, Nov 24
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $467 Roundtrip, found 13 hours ago
CA $467
Roundtrip
found 13 hours ago
Select Air Canada flight, departing Tue, Nov 17 from Pearson Intl. to Logan Intl., returning Tue, Nov 24, priced at CA $467 found 13 hours ago
Wed, Nov 18 - Mon, Nov 23
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $470 Roundtrip, found 4 hours ago
CA $470
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Nov 18 from Pearson Intl. to Logan Intl., returning Mon, Nov 23, priced at CA $470 found 4 hours ago
Sat, Oct 31 - Sun, Nov 1
YTZ
Billy Bishop Toronto City
BOS
Logan Intl.
CA $475 Roundtrip, just found
CA $475
Roundtrip
just found
Select Porter Airlines flight, departing Sat, Oct 31 from Billy Bishop Toronto City to Logan Intl., returning Sun, Nov 1, priced at CA $475 just found
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

Nov 25 - Nov 28

3 night stay

Ottawa (YOW) to Boston (BOS)

Air Canada • Non-stop • Coach

Boston (BOS) to Ottawa (YOW)

United • Non-stop • Coach
Price was CA $1,358, price is now CA $882 per person
CA $882
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Nov 24 - Nov 27

3 night stay

Toronto (YTZ) to Boston (BOS)

Porter Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,115, price is now CA $1,330 per person
CA $1,330
per person
found 1 day ago
Raffles Boston
5.0-star property

Raffles Boston

Nov 25 - Nov 29

4 night stay

Calgary (YYC) to Boston (BOS)

Porter Airlines • Non-stop • Coach

Boston (BOS) to Calgary (YYC)

Delta • Non-stop • Coach
Save 100% on your flight
Price was CA $2,637, price is now CA $1,825 per person
CA $1,825
per person
found 11 hours ago
Don't see what you're looking for?
See all available trips from Ottawa to Middlesex County
View all trips

Travelers ❤️ These Middlesex County 🏨

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Book a stay at this luxury hotel in Everett. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
9.6/10 Exceptional! (4,229 reviews)
"It’s always a lovely stay at the encore but the rooms are showing wear and our shades didn’t shut. They came and got them shut but we couldn’t open them in the am. Ready for a facelift, but always a good time."

Reviewed on Oct 10, 2026

Opens in a new windowEncore Boston Harbor
La Quinta Inn & Suites by Wyndham Boston Somerville

La Quinta Inn & Suites by Wyndham Boston Somerville

3 out of 5
23 Cummings St Somerville MA
Book a stay at this business-friendly hotel in Somerville. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Encore Boston Harbor and TD Garden are located nearby.
Opens in a new windowLa Quinta Inn & Suites by Wyndham Boston Somerville
The Royal Sonesta Boston

The Royal Sonesta Boston

4 out of 5
40 Edwin H. Land Boulevard Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions TD Garden and Boston Common are located nearby.
Opens in a new windowThe Royal Sonesta Boston
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fenway Park and Harvard Square are located nearby.
9/10 Wonderful! (2,695 reviews)
"We enjoyed our trip to Boston!"

Reviewed on Oct 10, 2026

Opens in a new windowHyatt Regency Boston/Cambridge
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.

Frequently asked questions

How much is the cheapest flight to Middlesex County?
In the last seven days, the cheapest roundtrip flight to Middlesex County cost CA $450 on our site. Check out our incredible deals, book your tickets and start planning for your next exciting getaway. This price was available on Travelocity for flights to Middlesex County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Middlesex County?
With 15 airlines flying in and out of Middlesex County, finding your ideal flight should be a snap. If your destination is Marlborough, go for the popular carrier, Delta Air Lines. It operates about 3,059 services to this wonderful city a month.
What is the cheapest month to fly to Middlesex County?
If you're thinking of booking a vacation in Middlesex County, October is the cheapest period to take to the skies. This is according to Travelocity's direct return flight demand between January and December last year. Pick your travel dates and secure your seat today.
How can I check my flight status to Middlesex County?
Whether you'd like to check the status of your flight to Middlesex County or make some changes, you'll find all the details you need on our handy portal, Trips. Click on "Trips" at the top of our homepage, then sign in or open a new account. Another great way to manage and view your booking is with the Travelocity app. Get alerts about gate changes or flight delays and easily share updates with any friends or family flying with you.
How do I find the best deals on flights to Middlesex County?
It's better to book ahead, and if possible, avoid traveling during vacation periods. Another smart way to save is by clicking the "Flexible dates" box at the top of the page after searching for your flights. This will reveal ticket prices for surrounding days. In the last seven days, the lowest price for a return flight to Middlesex County was CA $450. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Middlesex County with Travelocity?
If you're looking for cheap flights to Middlesex County, you'll come across some enticing deals with Travelocity. From cheap family flights on low-cost airlines to flexible airfares, we've got it all. Experience a stress-free trip with our 24/7 Virtual Agent online chat, Price Match Guarantee and free cancellations with most hotels and activities. Start planning your schedule and prepare to jet off to this exciting destination.
How much is a flight to Middlesex County on average?
Roundtrip flights to Middlesex County were priced between CA $450 and CA $475 in the last seven days. If you see a plane fare you like, act quickly. Cheap deals don't last long! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.