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Windham

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Cheap Flights to Windham

Fall in love at first flight with your vacation to Windham 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 Windham on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windham, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windham

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windham 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 HCC airport.

What is the cheapest month to fly to Windham?

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 Windham are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windham?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Windham.

What airport is best to fly into Windham?

When you’re planning your trip to Windham, convenience is the name of the game. Luckily, Windham Columbia County Airport is nearby so you can deplane and get going on checking off everything on your Windham must-do list.

How much are flights to Windham?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windham on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , 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 Windham?

The trick to saving a stack of cash on your flight to Windham? 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  right now, why wait?

Windham Flight Information
Destination airport
Windham
Destination airport IATA code
HCC

Last Minute Hotel Deals in Windham

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (600 reviews)
"Property was clean and updated. The location is perfect and we loved that it is dog friendly!"

Reviewed on Jul 22, 2025

Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296, Windham, NY
Stay at this 3.5-star hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club ...
8.6/10 Excellent! (65 reviews)
"We LOVED staying at Wylder. The staff was super friendly and helpful. Our room was comfortable, views were amazing and we really enjoyed the amenities. Highly recommend!"

Reviewed on Jul 21, 2025

Wylder Hotel Windham
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Windham Mountain Resort and Windham Country Club ...
9.2/10 Wonderful! (57 reviews)
"Friendly staff, accommodating and clean Some of it under construction"

Reviewed on May 23, 2025

Eastwind Windham
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3 out of 5
5220 NY-23, Windham, NY
Stay at this 3-star ski hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country ...
8.6/10 Excellent! (325 reviews)
Go for the views and town, stay for the pool
"Interesting place. Obviously a ski condo, so not too busy in the summer. Top-notch pool in a gorgeous setting. Rest of the complex was surprisingly ramshackle and of motel-like construction, unusual for a condo."

Reviewed on Jul 7, 2025

Winwood Condominiums by Windham Mountain Club
Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

3.5 out of 5
43 State Route 296, Windham, NY
Stay at this 3.5-star golf B&B in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (265 reviews)
Wonderful stay!
"We enjoyed our stay, the room was very comfortable, the bathroom very clean and convenient to town."

Reviewed on Jul 7, 2025

Albergo Allegria Hotel & Breakfast Restaurant
The Haüs Windham

The Haüs Windham

2 out of 5
218 NY-296, Windham, NY
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Windham Mountain Resort and Windham Country Club are ...
8.6/10 Excellent! (6 reviews)
"Great place nice and clean"

Reviewed on Jul 20, 2025

The Haüs Windham
Antique Rose Inn Windham

Antique Rose Inn Windham

3 out of 5
326 State Route 296, Windham, NY
Stay at this 3-star ski B&B in Windham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Windham Mountain Resort and Windham Country Club ...
9/10 Wonderful! (121 reviews)
"We did not expect to share a bathroom. We should of done our homework on the place. Its a lovely place to stay. Owner is very friendly, breakfast was accommodating to our wishes."

Reviewed on Jun 29, 2025

Antique Rose Inn Windham
Cave Mountain Motel

Cave Mountain Motel

2.5 out of 5
10978 STATE RTE 23, Windham, NY
Stay at this motel in Windham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Windham Mountain Resort and Windham Vineyards and Winery ...
9.2/10 Wonderful! (127 reviews)
"Beautiful view in The Catskills."

Reviewed on Jul 21, 2025

Cave Mountain Motel
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.