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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! (759 reviews)
The costumer service was more than great! Everyone was very friendly, easy to communicate with and helped me set up the sauna. Thank you for all the great work. Can’t wait to visit again.

Reviewed on Feb 7, 2026

Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located ...
8.6/10 Excellent! (92 reviews)
This place is GREAT!! Outstanding room, top notch service, cool staff, and good food!! Mmm mm!! I'm ready to go again!!

Reviewed on Jan 10, 2026

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 ...
9/10 Wonderful! (88 reviews)
Remarkably comfortable clean AND warm (sooo cold outside). Fun and warm poncho robes. Nice little seating area by the window. Very happy to have stayed here.

Reviewed on Feb 8, 2026

Eastwind Windham
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3 out of 5
5220 NY-23 Windham NY
Book a stay at this 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! (347 reviews)
Great staff, shuttle to mountain

Reviewed on Jan 27, 2026

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
Book a stay at this 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! (273 reviews)
Lovely hotel and a friendly welcome by the owners. Some small issues arose which we were not affected by, but we were always kept informed. Sadly, we couldn't enjoy the breakfast due to a bereavement in the family but am looking forward to it on our next visit. Thank you and here's hoping to come ...

Reviewed on Jan 29, 2026

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 ...
7.6/10 Good! (23 reviews)
Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access.

Reviewed on Dec 30, 2025

The Haüs Windham
Antique Rose Inn Windham

Antique Rose Inn Windham

3 out of 5
326 State Route 296 Windham NY
Book a stay at this 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! (127 reviews)
Cool historic home with a nice host. Great breakfast.

Reviewed on Jan 29, 2026

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! (138 reviews)
friendly host. Clean room basic breakfast

Reviewed on Feb 5, 2026

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.