Flights To Middlesex County - Cheap Flights Starting at CA $89

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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.

Thu, Nov 5 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $275 Roundtrip, found 1 day ago
CA $275
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 5 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at CA $275 found 1 day ago
Thu, Sep 24 - Mon, Sep 28
MCO
Orlando Intl.
PVD
T.F. Green
CA $275 Roundtrip, found 5 days ago
CA $275
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 24 from Orlando Intl. to T.F. Green, returning Mon, Sep 28, priced at CA $275 found 5 days ago
Thu, Nov 5 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $282 Roundtrip, found 1 day ago
CA $282
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 5 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at CA $282 found 1 day ago
Thu, Oct 1 - Sun, Oct 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $285 Roundtrip, found 3 hours ago
CA $285
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Oct 1 from Orlando Intl. to Portsmouth Intl., returning Sun, Oct 4, priced at CA $285 found 3 hours ago
Thu, Sep 24 - Mon, Sep 28
MCO
Orlando Intl.
PVD
T.F. Green
CA $289 Roundtrip, found 5 days ago
CA $289
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 24 from Orlando Intl. to T.F. Green, returning Mon, Sep 28, priced at CA $289 found 5 days ago
Thu, Oct 1 - Sun, Oct 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
CA $290 Roundtrip, found 3 days ago
CA $290
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Oct 1 from Orlando Intl. to Portsmouth Intl., returning Sun, Oct 4, priced at CA $290 found 3 days ago
Wed, Jul 22 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
CA $298 Roundtrip, found 12 hours ago
CA $298
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Jul 22 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at CA $298 found 12 hours ago
Wed, Aug 19 - Sun, Aug 23
YYZ
Pearson Intl.
BOS
Logan Intl.
CA $314 Roundtrip, just found
CA $314
Roundtrip
just found
Select Porter Airlines flight, departing Wed, Aug 19 from Pearson Intl. to Logan Intl., returning Sun, Aug 23, priced at CA $314 just found
Tue, Aug 11 - Wed, Aug 19
MCO
Orlando Intl.
BOS
Logan Intl.
CA $326 Roundtrip, found 5 days ago
CA $326
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Orlando Intl. to Logan Intl., returning Wed, Aug 19, priced at CA $326 found 5 days ago
Sat, Sep 19 - Wed, Sep 23
YYC
Calgary Intl.
BOS
Logan Intl.
CA $384 Roundtrip, found 1 hour ago
CA $384
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Sat, Sep 19 from Calgary Intl. to Logan Intl., returning Wed, Sep 23, priced at CA $384 found 1 hour ago
Thu, Aug 27 - Sun, Aug 30
YYZ
Pearson Intl.
PVD
T.F. Green
CA $400 Roundtrip, found 16 hours ago
CA $400
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Aug 27 from Pearson Intl. to T.F. Green, returning Sun, Aug 30, priced at CA $400 found 16 hours ago
Price found within the past 48 hours. Click for updated prices.
Good Hotels Boston
2.0-star property

Good Hotels Boston

Jul 23 - Jul 27

4 night stay

Buffalo (BUF) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was CA $1,668, price is now CA $1,109 per person
CA $1,109
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Aug 20 - Aug 23

3 night stay

Buffalo (BUF) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was CA $2,223, price is now CA $1,321 per person
CA $1,321
per person
found 1 day ago
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
3.0-star property

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

Aug 14 - Aug 19

5 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $7,549, price is now CA $4,962 per person
CA $4,962
per person
found 5 hours ago
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Travelers ❤️ These Middlesex County 🏨

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! (2,425 reviews)
"The location was great and the staff were amazing. I enjoyed the free shuttle that takes you to local areas."

Reviewed on Jul 7, 2026

Opens in a new windowHyatt Regency Boston/Cambridge
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! (3,929 reviews)
"Hotel is nice, our room had things that were broken. Toilet did not flush. Shades would not close. The front desk charged me 2 times different prices for the same room. I’m still trying to get one charge credited back. Valet was terrible waited almost 30 min I. The front to get my car after handing ..."

Reviewed on Jul 7, 2026

Opens in a new windowEncore Boston Harbor
The Charles Hotel

The Charles Hotel

5 out of 5
One Bennett Street Cambridge MA
Book a stay at this luxury hotel in Cambridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Harvard Square and Fenway Park are located nearby.
9.4/10 Exceptional! (1,006 reviews)
"Great location"

Reviewed on Jul 7, 2026

Opens in a new windowThe Charles Hotel
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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.
7.6/10 Good! (3,403 reviews)
"Good Breakfast and I will come back to stay this hotel"

Reviewed on Jul 7, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Boston Somerville
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 $275 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 20 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, November 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 $275. 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 $275 and CA $400 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.