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Windsor

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Windsor Flights as Low as $145

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

Breeze Airways
Sun, Sep 7 - Sun, Sep 14
MCO
Orlando Intl.
ALB
Albany Intl.
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Sep 7 from Orlando Intl. to Albany Intl., returning Sun, Sep 14, priced at $145 found 1 day ago
JetBlue Airways
Fri, Sep 26 - Sun, Sep 28
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$147 Roundtrip, found 22 hours ago
$147
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Fri, Sep 26 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 28, priced at $147 found 22 hours ago
JetBlue Airways
Mon, Sep 22 - Sat, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$150 Roundtrip, found 22 hours ago
$150
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Mon, Sep 22 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sat, Sep 27, priced at $150 found 22 hours ago
JetBlue Airways
Fri, Sep 26 - Mon, Sep 29
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$157 Roundtrip, found 22 hours ago
$157
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Fri, Sep 26 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Sep 29, priced at $157 found 22 hours ago
JetBlue Airways
Mon, Sep 22 - Mon, Sep 29
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$161 Roundtrip, found 22 hours ago
$161
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Mon, Sep 22 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Sep 29, priced at $161 found 22 hours ago
Breeze Airways
Thu, Nov 6 - Sun, Nov 9
MCO
Orlando Intl.
ALB
Albany Intl.
$163 Roundtrip, found 1 day ago
$163
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 6 from Orlando Intl. to Albany Intl., returning Sun, Nov 9, priced at $163 found 1 day ago
American Airlines
Wed, Sep 3 - Thu, Sep 4
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$164 Roundtrip, found 5 days ago
$164
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Sep 3 from Raleigh - Durham Intl. to Albany Intl., returning Thu, Sep 4, priced at $164 found 5 days ago
JetBlue Airways
Fri, Sep 26 - Sat, Sep 27
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$167 Roundtrip, found 22 hours ago
$167
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Fri, Sep 26 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sat, Sep 27, priced at $167 found 22 hours ago
Breeze Airways
Thu, Nov 6 - Sun, Nov 9
MCO
Orlando Intl.
ALB
Albany Intl.
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 6 from Orlando Intl. to Albany Intl., returning Sun, Nov 9, priced at $168 found 1 day ago
JetBlue Airways
Thu, Sep 25 - Mon, Sep 29
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$171 Roundtrip, found 22 hours ago
$171
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Thu, Sep 25 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Sep 29, priced at $171 found 22 hours ago
American Airlines
Tue, Sep 23 - Tue, Sep 30
MCO
Orlando Intl.
ALB
Albany Intl.
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Sep 23 from Orlando Intl. to Albany Intl., returning Tue, Sep 30, priced at $190 found 4 hours ago
American Airlines
Tue, Sep 30 - Tue, Oct 14
ORD
O'Hare Intl.
ALB
Albany Intl.
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Sep 30 from O'Hare Intl. to Albany Intl., returning Tue, Oct 14, priced at $192 found 2 days ago
United
Tue, Sep 30 - Tue, Oct 14
ORD
O'Hare Intl.
ALB
Albany Intl.
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select United flight, departing Tue, Sep 30 from O'Hare Intl. to Albany Intl., returning Tue, Oct 14, priced at $193 found 2 days ago
Delta
Tue, Oct 14 - Tue, Oct 21
MCO
Orlando Intl.
ALB
Albany Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 14 from Orlando Intl. to Albany Intl., returning Tue, Oct 21, priced at $197 found 1 day ago
Delta
Tue, Sep 30 - Tue, Oct 7
IAH
George Bush Intercontinental
ALB
Albany Intl.
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 30 from George Bush Intercontinental to Albany Intl., returning Tue, Oct 7, priced at $256 found 1 day ago
American Airlines
Tue, Aug 26 - Sat, Aug 30
SFO
San Francisco Intl.
ALB
Albany Intl.
$328 Roundtrip, found 12 hours ago
$328
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Aug 26 from San Francisco Intl. to Albany Intl., returning Sat, Aug 30, priced at $328 found 12 hours ago

Cheap Flights to Windsor

Fall in love at first flight with your vacation to Windsor 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 Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windsor 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 ALB airport.

What is the cheapest month to fly to Windsor?

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 Windsor are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

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 Windsor.

What airport is best to fly into Windsor?

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

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $145, 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 Windsor?

The trick to saving a stack of cash on your flight to Windsor? 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 $145 right now, why wait?

Windsor Flight Information
Destination airport
Albany Intl.
Destination airport IATA code
ALB
Roundtrip price
$145

Last Minute Hotel Deals in Windsor

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,940 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."

Reviewed on Aug 10, 2025

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Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (555 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."

Reviewed on Aug 11, 2025

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Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (766 reviews)
"The bathroom in our room looks like someone was murdered in the bathtub. There were stains on the bottom of the tub."

Reviewed on Aug 10, 2025

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FairBridge Inn Express
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (485 reviews)
"Beautiful hotel!"

Reviewed on Aug 10, 2025

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The Williams Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (668 reviews)
"The room was fine, quiet and clean. It was somewhat small. This is a nicely refurbished old standard motel. The lobby area was very nice but the location is high atop a hill off of a major road. You can’t walk anywhere from the hotel and it can be difficult making a left turn into it."

Reviewed on Aug 7, 2025

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Berkshires Untold
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,007 reviews)
"This is an old Holiday Inn that the new owners came and made all modern and fancy, including adding a couple of our calories downstairs. Ample parking, although it was full towards the end of the night. Safe location. They did a really good job revitalizing in this place."

Reviewed on Aug 11, 2025

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Hotel Downstreet, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (689 reviews)
"This was our third year of two summer weeks at Oak 'n' Spruce. The accommodations are comfortable and convenient, and the staff is wonderful. We hope to be back next summer."

Reviewed on Aug 10, 2025

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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,003 reviews)
We loved the sunny Stevens room
"We love the Red Lion. And had two excellent meals around our trips to Tanglewood concerts. We stayed at the Stevens house room 184. Sunny, sweet, fridge downstairs was helpful to store picnic items/wine. But the bed is soft and the bathtub was plastic insert which was unexpected for the cost per ..."

Reviewed on Aug 9, 2025

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The Red Lion Inn
See all 979 properties in Windsor
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.