Search Cheap Flights to
Windsor

Photo by William E Berry Jr.

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Windsor Flights as Low as $280

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

JetBlue Airways
Tue, Sep 9 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $280 found 1 day ago
JetBlue Airways
Tue, Sep 9 - Thu, Sep 18
TPA
Tampa Intl.
LEB
Lebanon Municipal
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Thu, Sep 18, priced at $290 found 1 day ago
JetBlue Airways
Tue, Sep 9 - Sun, Sep 14
TPA
Tampa Intl.
LEB
Lebanon Municipal
$301 Roundtrip, found 1 day ago
$301
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Sun, Sep 14, priced at $301 found 1 day ago
JetBlue Airways
Tue, Sep 9 - Fri, Sep 19
TPA
Tampa Intl.
LEB
Lebanon Municipal
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Fri, Sep 19, priced at $318 found 1 day ago
JetBlue Airways
Tue, Sep 16 - Tue, Sep 23
TPA
Tampa Intl.
LEB
Lebanon Municipal
$321 Roundtrip, found 3 days ago
$321
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 23, priced at $321 found 3 days ago
JetBlue Airways
Tue, Sep 9 - Fri, Sep 19
TPA
Tampa Intl.
LEB
Lebanon Municipal
$326 Roundtrip, found 3 days ago
$326
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Fri, Sep 19, priced at $326 found 3 days ago
JetBlue Airways
Sat, Sep 6 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $326 found 1 day ago
JetBlue Airways
Wed, Sep 10 - Fri, Sep 19
TPA
Tampa Intl.
LEB
Lebanon Municipal
$329 Roundtrip, found 3 days ago
$329
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Fri, Sep 19, priced at $329 found 3 days ago
JetBlue Airways
Sat, Sep 6 - Wed, Sep 17
TPA
Tampa Intl.
LEB
Lebanon Municipal
$331 Roundtrip, found 1 day ago
$331
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Tampa Intl. to Lebanon Municipal, returning Wed, Sep 17, priced at $331 found 1 day ago
JetBlue Airways
Mon, Sep 8 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$331 Roundtrip, found 1 day ago
$331
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 8 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $331 found 1 day ago
JetBlue Airways
Wed, Sep 10 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$335 Roundtrip, found 1 day ago
$335
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $335 found 1 day ago
JetBlue Airways
Tue, Sep 9 - Sat, Sep 20
TPA
Tampa Intl.
LEB
Lebanon Municipal
$337 Roundtrip, found 3 days ago
$337
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 20, priced at $337 found 3 days ago
JetBlue Airways
Tue, Sep 16 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 16, priced at $339 found 4 days ago
JetBlue Airways
Sat, Sep 6 - Thu, Sep 18
TPA
Tampa Intl.
LEB
Lebanon Municipal
$341 Roundtrip, found 1 day ago
$341
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Tampa Intl. to Lebanon Municipal, returning Thu, Sep 18, priced at $341 found 1 day ago
JetBlue Airways
Wed, Sep 10 - Thu, Sep 18
TPA
Tampa Intl.
LEB
Lebanon Municipal
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Thu, Sep 18, priced at $345 found 1 day ago
JetBlue Airways
Tue, Sep 16 - Fri, Sep 19
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$350 Roundtrip, found 2 days ago
$350
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Tampa Intl. to Rutland Southern Vermont Regional, returning Fri, Sep 19, priced at $350 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 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 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 $280, 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 $280 right now, why wait?

Windsor Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$280

Last Minute Hotel Deals in Windsor

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! (1,000 reviews)
"The staff was the best part of this stay. They were friendly and welcoming. The room was very spacious and comfortable for the price."

Reviewed on Aug 13, 2025

Get rates
White River Inn and Suites
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! (1,002 reviews)
"My recent stay exceeded my expectations regarding hotel room prices, comfort of the bed and pillows, large breakfast and hot shower. Unfortunately most staff were not very friendly or accommodating minus the one sweet girl at the front desk who was able to allow us a late checkout time."

Reviewed on Aug 20, 2025

Get rates
Fireside Inn & Suites West Lebanon
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star 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! (532 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Get rates
Woodstock Inn & Resort
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. ...
9/10 Wonderful! (874 reviews)
We’ll be back.
"Beautiful area, outside of facility looks dated, but that’s not realistic to change. Inside has had a nice update. The staff is very friendly and helpful. We had an inconsiderate and noisy person upstairs over us, just a matter of who is there. We would surely stay here again."

Reviewed on Aug 23, 2025

Get rates
The Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (807 reviews)
"Forth time at The Shire, everything was wonderful!!"

Reviewed on Aug 21, 2025

Get rates
The Shire Woodstock
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 ...
9.2/10 Wonderful! (1,006 reviews)
"The service was outstanding! I stayed at the hotel because I had a back injury, and Chelsea at the front desk provided me a room on the first floor and offered to get me ice and help me out however she could. The facilities were clean and well appointed. It's a nice place to stay and there is a dinner ..."

Reviewed on Aug 22, 2025

Get rates
Align Inn Vermont
Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Book a stay at this business-friendly motel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
6.2/10 (1,008 reviews)
"Came in for the night to move family in school in northfield and it was a convenient stay just 40 minutes away from the school front desk was extremely nice and helpful stay was great"

Reviewed on Aug 16, 2025

Get rates
Super 8 by Wyndham White River Junction
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! (1,002 reviews)
"Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, ..."

Reviewed on Aug 22, 2025

Get rates
North Star Lodge and Resort
See all 2,574 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.