Search Cheap Flights toWindham County from $304
Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Cheap round-trip flights to Windham County
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
















Flights to Windham County starting at $304
Have you been telling yourself, “2025 is the year I travel more and sit less”? Well, here we are and there you are. So, where are you going? Looks like a flight to Windham County is calling. Good thing we can help you bag that flight out of town for cheap, so you can get your resolutions resolved.
Travel like you mean it
When you land it’s not straight to the tourist traps for you. You have things to do and see in Windham County that aren’t on a map or in the “Best of. . .” guides. You know this region is filled with hidden haunts, locals-only know favorites, and the off-beat-so-weird-it’s-amazing places. And you plan to find every last one of them. Good thing you’ll save a grip of cash on your flight so you can daytrip far and wide.
You won’t have to wing it
So how do you score that killer deal on a flight to Windham County? Easy, go through us. These aren’t pie in the sky deals, but ones you can actually score. Filter flights to Windham County by:
- Hotwire Hot Rate: Do you have a flexible schedule? Hit up the Hotwire Hot Rate and land a super cheap flight to Windham County. We’ll reveal the airline and exact time after you book.
- Price: How low can we go? Find out. We have prices from $304 to $488.
- Duration: Want to get to Windham County as fast as you can? Or maybe you don’t mind taking your time to save a few bucks here and there.
- Departure or Arrival: Like to arrive in the a.m. to get your day going? Or are you a night owl that knows the best fun happens late night? The choice is yours.
So are you going to live up to those travel plans or kick the can to next year? Book your flight to Windham County today and get going.
Last Minute Hotel Deals in Windham County

Mountaineer Inn
Clean, quiet and safe. The only issue was finding parking spot in the premises at late night.
Reviewed on Oct 13, 2025

The Covered Bridge Inn
Very clean besides mold on shower, just needs to be scrubbed with bleach.
Reviewed on Oct 12, 2025

Econo Lodge Brattleboro
The staff was nice and helpful. We checked in ok. I was told the room was ready, but it wasn't. Tv didn't work right, needed help getting the fridge running, had to ask for more towels because we only had a hand towel in the room, the mattress was a 2 out 5 at best and finally, had to give them the ...
Reviewed on Oct 11, 2025

Latchis Hotel
Very cool historical hotel and friendly staff. I want to see a movie in the theater next time. Some details were off, such as no working needle on the record player and tv display settings were messed up, and a broken marble top on the radiator.
Reviewed on Oct 13, 2025
Top Destinations in Windham County
- Flights to Brattleboro
- Flights to Bennington
- Flights to West Dover
- Flights to Stratton
- Flights to Wilmington
- Flights to Appalachian Mountains
- Flights to Londonderry
- Flights to Chester
- Flights to Springfield
- Flights to Peru
- Flights to Western Massachusetts
- Flights to Putney
- Flights to Bondville
- Flights to Southern Vermont
- Flights to Jamaica
- Flights to Grafton
- Flights to Central Vermont
- Flights to Newfane
- Flights to Bellows Falls
- Flights to Wardsboro
Top Flight Destinations In World
- Flights to Spain
- Flights to United States of America
- Flights to Canada
- Flights to India
- Flights to Thailand
- Flights to Italy
- Flights to Indonesia
- Flights to Greece
- Flights to Sweden
- Flights to Brazil
- Flights to Germany
- Flights to United Kingdom
- Flights to South Korea
- Flights to Philippines
- Flights to Australia
- Flights to Argentina
- Flights to Colombia
- Flights to Türkiye
- Flights to China
- Flights to Switzerland