Search Cheap Flights to
Windham

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

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! (749 reviews)
We love this hotel. We come back every year. It is clean, friendly, good breakfast, extraordinary baking goods and various coffee from the coffee machine. They also offered free hot wine, very thoughtful after a day on the slopes. On the critical side I would note small towels, a bit too firm mattress, ...

Reviewed on Jan 28, 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 ...
9.2/10 Wonderful! (86 reviews)
Great time, Candace was AWESOME! This hotel is super lucky to have her. The entire crew took great care of the hotel and guests during a wild snow storm. Was our second time staying and even more blown away this time but how cozy and special this little place can be.

Reviewed on Jan 28, 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! (346 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! (271 reviews)
Such a lovely bed and breakfast. The bed was unbelievably comfortable we didn’t want to leave. Would absolutely return!

Reviewed on Jan 11, 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
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! (137 reviews)
Clean roomns helpful staff and close to the mountain and town

Reviewed on Jan 18, 2026

Cave Mountain Motel
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
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.