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Windham County from $304

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Cheap round-trip flights to Windham County

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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

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (531 reviews)
Clean, quiet and safe. The only issue was finding parking spot in the premises at late night.

Reviewed on Oct 13, 2025

Opens in a new windowMountaineer Inn
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,020 reviews)
Very clean besides mold on shower, just needs to be scrubbed with bleach.

Reviewed on Oct 12, 2025

Opens in a new windowThe Covered Bridge Inn
Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
515 Canal St, Brattleboro, VT
Stay at this motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vermont Marketplace and Estey Organ Museum are located ...
5.4/10 (580 reviews)
Little disappointed
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

Opens in a new windowEcono Lodge Brattleboro
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Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (803 reviews)
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

Opens in a new windowLatchis Hotel
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.