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Windsor

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Windsor Flights as Low as $425

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

JetBlue Airways
Fri, Mar 27 - Mon, Apr 6
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$425 Roundtrip, found 1 day ago
$425
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 6, priced at $425 found 1 day ago
Delta
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$435 Roundtrip, found 19 hours ago
$435
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $435 found 19 hours ago
JetBlue Airways
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$435 Roundtrip, found 2 days ago
$435
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $435 found 2 days ago
JetBlue Airways
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$440 Roundtrip, found 19 hours ago
$440
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $440 found 19 hours ago
American Airlines
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$444 Roundtrip, found 19 hours ago
$444
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $444 found 19 hours ago
Delta
Tue, Mar 24 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$445 Roundtrip, found 1 day ago
$445
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 24 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $445 found 1 day ago
American Airlines
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$455 Roundtrip, found 19 hours ago
$455
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $455 found 19 hours ago
Delta
Fri, Mar 27 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$455 Roundtrip, found 1 day ago
$455
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $455 found 1 day ago
JetBlue Airways
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$461 Roundtrip, found 19 hours ago
$461
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $461 found 19 hours ago
JetBlue Airways
Thu, Mar 26 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$461 Roundtrip, found 3 days ago
$461
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $461 found 3 days ago
United
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$462 Roundtrip, found 19 hours ago
$462
Roundtrip
found 19 hours ago
Select United flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $462 found 19 hours ago
Delta
Fri, Mar 27 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$465 Roundtrip, found 1 day ago
$465
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $465 found 1 day ago
Delta
Fri, Mar 27 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$466 Roundtrip, found 1 day ago
$466
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $466 found 1 day ago
Delta
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$468 Roundtrip, found 19 hours ago
$468
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $468 found 19 hours ago
JetBlue Airways
Thu, Mar 26 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$476 Roundtrip, found 4 days ago
$476
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $476 found 4 days ago
JetBlue Airways
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$488 Roundtrip, found 19 hours ago
$488
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $488 found 19 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 VSF 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 March, 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 Lebanon 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 $425, 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 $425 right now, why wait?

Windsor Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$348

Last Minute Hotel Deals in Windsor

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Book a stay at this ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (1,000 reviews)
Room was clean. Hotel was clean. Enjoyed my stay

Reviewed on Mar 2, 2026

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Killington Mountain Lodge, Tapestry Collection by Hilton
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,131 reviews)
Perfection in every way

Reviewed on Mar 1, 2026

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Align Inn Vermont
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Book a stay at this business-friendly hotel in West Lebanon. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the pool in ...
8.2/10 Very Good! (1,006 reviews)
False Advertising. There was no breakfast

Reviewed on Mar 2, 2026

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Fireside Inn & Suites West Lebanon
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (998 reviews)
Excellent for a family stay

Reviewed on Mar 1, 2026

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Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (565 reviews)
Very clean, high end, friendly staff

Reviewed on Feb 20, 2026

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Woodstock Inn & Resort
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
121 Ballardvale Dr White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,004 reviews)
My second stay this season. it`s newly renovated, its nice.

Reviewed on Mar 2, 2026

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Holiday Inn Express Hotel & Suites White River Junction by IHG
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff ...
8.6/10 Excellent! (1,004 reviews)
Bar and restaurant close really early and a group of guys checked in at 1am and were so loud woke us up till 3am. Flew all the from phoenix Arizona and ruined our ski trip to Killington we were so tired.

Reviewed on Feb 28, 2026

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North Star Lodge and Resort
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7/10 Good! (1,003 reviews)
The staff was good the room was clean had a couple of issues but nothing major we try to come here once a year to celebrate our anniversary and the pool is a plus but not sure if they had issues with the heating system for the pool it was kinda cold and stores and restaurants are close by to go ...

Reviewed on Mar 1, 2026

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White River Inn and Suites
See all 2,693 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.