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Windsor

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Windsor Flights as Low as $647

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

Delta
Fri, Oct 23 - Sun, Nov 1
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$647 Roundtrip, found 5 days ago
$647
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Oct 23 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Sun, Nov 1, priced at $647 found 5 days ago
United
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$652 Roundtrip, found 5 days ago
$652
Roundtrip
found 5 days ago
Select United flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $652 found 5 days ago
JetBlue Airways
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$654 Roundtrip, found 10 hours ago
$654
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $654 found 10 hours ago
United
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$657 Roundtrip, found 5 days ago
$657
Roundtrip
found 5 days ago
Select United flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $657 found 5 days ago
Delta
Fri, Oct 23 - Thu, Oct 29
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$662 Roundtrip, found 6 days ago
$662
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Oct 23 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Thu, Oct 29, priced at $662 found 6 days ago
Delta
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$664 Roundtrip, found 10 hours ago
$664
Roundtrip
found 10 hours ago
Select Delta flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $664 found 10 hours ago
Delta
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$664 Roundtrip, found 1 day ago
$664
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $664 found 1 day ago
Delta
Tue, Oct 27 - Wed, Oct 28
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$668 Roundtrip, found 10 hours ago
$668
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Oct 27 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Wed, Oct 28, priced at $668 found 10 hours ago
Delta
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$670 Roundtrip, found 1 day ago
$670
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $670 found 1 day ago
Delta
Mon, Nov 2 - Tue, Nov 17
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$670 Roundtrip, found 2 days ago
$670
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Tue, Nov 17, priced at $670 found 2 days ago
American Airlines
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$674 Roundtrip, found 10 hours ago
$674
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $674 found 10 hours ago
Delta
Fri, Oct 23 - Sun, Nov 1
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$677 Roundtrip, found 5 days ago
$677
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Oct 23 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Sun, Nov 1, priced at $677 found 5 days ago
Delta
Tue, Oct 27 - Wed, Oct 28
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$678 Roundtrip, found 10 hours ago
$678
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Oct 27 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Wed, Oct 28, priced at $678 found 10 hours ago
United
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$679 Roundtrip, found 10 hours ago
$679
Roundtrip
found 10 hours ago
Select United flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $679 found 10 hours ago
Delta
Thu, Feb 18 - Mon, Feb 22
RDU
Raleigh - Durham Intl.
RUT
Rutland Southern Vermont Regional
$680 Roundtrip, found 1 day ago
$680
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Feb 18 from Raleigh - Durham Intl. to Rutland Southern Vermont Regional, returning Mon, Feb 22, priced at $680 found 1 day ago
Delta
Mon, Oct 26 - Mon, Nov 2
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$737 Roundtrip, found 2 days ago
$737
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 26 from Tampa Intl. to Rutland Southern Vermont Regional, returning Mon, Nov 2, priced at $737 found 2 days 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 October, 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 Hartness State 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 $647, 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 $647 right now, why wait?

Windsor Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$646

Last Minute Hotel Deals in Windsor

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd Windsor VT
Stay at this cabin in Windsor. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartland Public Library and Path of Life Garden are located ...
9.8/10 Exceptional! (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views!"

Reviewed on Jan 5, 2026

Get rates
Fat Sheep Farm & Cabins
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 ...
8.4/10 Very Good! (1,004 reviews)
"spa under construction poor output on fireplace in room-minimal flame poor food at breakfast"

Reviewed on Oct 21, 2026

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Fireside Inn & Suites West Lebanon
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,009 reviews)
"The quality of the this location was not what I expected. The heating unit was not working and they could not get it to work. We were not offered another room but we were given a fan to move the air. The place smelled of chemicals. The view was overlooking a small construction area and trashy barn. ..."

Reviewed on Oct 21, 2026

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The Mountain Inn at Killington
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)
"great price, great location, and very nice and clean for a "local" hotel."

Reviewed on Oct 21, 2026

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White River Inn and Suites
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. ...
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Woodstock Inn & Resort
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! (1,409 reviews)
"Everything was amazing. Best nights sleep my entire trip!"

Reviewed on Oct 21, 2026

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Align Inn Vermont
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in ...
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Jackson Gore Village, A Vail Resorts Property
Courtyard by Marriott Hanover Lebanon

Courtyard by Marriott Hanover Lebanon

3 out of 5
10 Morgan Drive Lebanon NH
Book a stay at this business-friendly hotel in Lebanon. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,000 reviews)
"This hotel was clean and recently updated, room spacious. The on ly negative I give and it seems to be all Marriott hotels I stay in lately the pillows are awful, squishy flat un comfortable. The rest of the property was perfect."

Reviewed on Oct 20, 2026

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Courtyard by Marriott Hanover Lebanon
See all 2,712 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.