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Windham

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Windham Flights as Low as $147

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

Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $147 found 1 day ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$148 Roundtrip, found 5 days ago
$148
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $148 found 5 days ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $152 found 1 day ago
Allegiant Air
Sun, Dec 13 - Sun, Dec 20
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Sun, Dec 13 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Dec 20, priced at $156 found 3 days ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $157 found 1 day ago
Breeze Airways
Thu, Sep 3 - Sat, Sep 5
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$158 Roundtrip, found 5 days ago
$158
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 5, priced at $158 found 5 days ago
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $167 found 1 day ago
Frontier Airlines
Mon, Sep 28 - Fri, Oct 2
MCO
Orlando Intl.
BOS
Logan Intl.
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Orlando Intl. to Logan Intl., returning Fri, Oct 2, priced at $170 found 5 days ago
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $172 found 1 day ago
Breeze Airways
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $173 found 6 days ago
Breeze Airways
Thu, Aug 27 - Sun, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Portsmouth Intl., returning Sun, Aug 30, priced at $177 found 6 days ago
American Airlines
Tue, Sep 22 - Tue, Sep 29
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 22 from Orlando Intl. to Logan Intl., returning Tue, Sep 29, priced at $199 found 1 day ago
Delta
Tue, Sep 22 - Tue, Sep 29
MCO
Orlando Intl.
BOS
Logan Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 22 from Orlando Intl. to Logan Intl., returning Tue, Sep 29, priced at $209 found 1 day ago
JetBlue Airways
Tue, Sep 22 - Tue, Sep 29
MCO
Orlando Intl.
BOS
Logan Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 22 from Orlando Intl. to Logan Intl., returning Tue, Sep 29, priced at $209 found 1 day ago
United
Tue, Sep 22 - Tue, Sep 29
MCO
Orlando Intl.
BOS
Logan Intl.
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 22 from Orlando Intl. to Logan Intl., returning Tue, Sep 29, priced at $229 found 1 day ago
Breeze Airways
Thu, Sep 3 - Thu, Sep 17
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$294 Roundtrip, found 5 days ago
$294
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Manchester-Boston Regional, returning Thu, Sep 17, priced at $294 found 5 days ago

Cheap Flights to Windham

Fall in love at first flight with your vacation to Windham by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windham on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windham, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windham

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windham with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the BOS airport.

What is the cheapest month to fly to Windham?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windham are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windham?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windham.

What airport is best to fly into Windham?

When you’re planning your trip to Windham, convenience is the name of the game. Luckily, Windham Nashua Municipal Airport is nearby so you can deplane and get going on checking off everything on your Windham must-do list.

How much are flights to Windham?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windham on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $147, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windham?

The trick to saving a stack of cash on your flight to Windham? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $147 right now, why wait?

Windham Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$224

Last Minute Hotel Deals in Windham

Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3 out of 5
4 Highwood Drive Tewksbury MA
Book a stay at this business-friendly hotel in Tewksbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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Hilton Garden Inn Tewksbury Andover
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.2/10 Very Good! (2,099 reviews)
"Clean rooms, friendly staff, breakfast is good"

Reviewed on Jul 24, 2026

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La Quinta Inn & Suites by Wyndham Boston-Andover
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,413 reviews)
"The hotel it self was very clean! Rooms were nice and maintained. Check in was pretty rough but I understand people starting out. Breakfast was a few fruits and cold sausages and pancakes, not very impressive. I stayed for an event in the area so if I ever needed to, I would stay here again but not ..."

Reviewed on Jul 23, 2026

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Best Western Plus Executive Court Inn & Conference Center
La Quinta Inn & Suites by Wyndham Salem NH

La Quinta Inn & Suites by Wyndham Salem NH

3 out of 5
8 Keewaydin Dr Salem NH
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
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La Quinta Inn & Suites by Wyndham Salem NH
Comfort Inn Manchester Airport

Comfort Inn Manchester Airport

2.5 out of 5
298 Queen City Ave Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,003 reviews)
"Had to check in at 3:00 in the morning and was concerned that nobody would be at the front desk, but they were there and helped me out."

Reviewed on Jul 23, 2026

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Comfort Inn Manchester Airport
DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St. Manchester NH
Stay at this hotel in Manchester. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,205 reviews)
"This was an amazing stay! Came up to Manchester for a weekend with my girlfriend and the stay was perfect! Room had great amenities and extremely clean! The hotel staff were super kind and informative. The restaurant they have here is also delicious! Everything within walking distance. Good bars, ..."

Reviewed on Jul 23, 2026

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DoubleTree by Hilton Manchester Downtown
Courtyard by Marriott Boston Billerica/Bedford

Courtyard by Marriott Boston Billerica/Bedford

3 out of 5
270 Concord Rd Billerica MA
Book a stay at this business-friendly hotel in Billerica. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
9/10 Wonderful! (1,000 reviews)
"Comfortable beds, wonderful bistro and staff, nice work out room and pool as well. Great gathering spaces for families we enjoyed each night."

Reviewed on Jul 21, 2026

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Courtyard by Marriott Boston Billerica/Bedford
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway Salem NH
Stay at this motel in Salem. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,871 reviews)
"I've stayed at the Inn once or twice a year for many years. It is set well back from the highway so traffic noise is not a problem. Staff is pleasant and polite. It's a good value, priced well. Nothing fancy but comfortable, clean, safe and the room was spacious with good lighting. There two sinks ..."

Reviewed on Jul 24, 2026

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Park View Inn - Salem
See all 448 properties in Windham
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.