Book Exclusive Windham Vacation Packages

Choose one or more items to build your trip:

Top Windham hotels deals

Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
The price is CA $195 per night
CA $195
CA $234 total
May 18 - May 19
includes taxes & fees
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. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Pool
Breakfast included
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
The price is CA $225 per night
CA $225
CA $281 total
May 18 - May 19
includes taxes & fees
Book a stay at this golf hotel in Windham. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Pet-friendly
Parking included
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
The price is CA $304 per night
CA $304
CA $397 total
May 22 - May 23
includes taxes & fees
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Pool
Pet-friendly
The Haüs Windham

The Haüs Windham

2 out of 5
218 NY-296 Windham NY
The price is CA $165 per night
CA $165
CA $290 total
May 17 - May 18
includes taxes & fees
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Pet-friendly
Parking included
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham NY
Get rates
Book a stay at this family-friendly vacation home in Windham. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Hot tub
Kitchen
Antique Rose Inn Windham

Antique Rose Inn Windham

3 out of 5
326 State Route 296 Windham NY
The price is CA $185 per night
CA $185
CA $200 total
May 18 - May 19
includes taxes & fees
Book a stay at this ski B&B in Windham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Windham Country Club and Windham Mountain Resort are located nearby.
Breakfast included
Parking included
Don't see what you're looking for?
See all available properties in Windham
View all properties
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.

Popular places to visit

Windham Mountain Resort

Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area.

Windham Mountain Resort

Windham Country Club

Enjoy a round of golf in Windham at Windham Country Club. Discover the mountain views in this relaxing area.

Windham Country Club

Windham Vineyards and Winery

You can enjoy a tasting or tour at Windham Vineyards and Winery during your travels to Windham. Discover the mountain views in this relaxing area, or seek out the ski slopes.

Windham Vineyards and Winery

Windham Vacations

Get your vacation off to an awesome start by knowing a thing or two about Windham before you head off.

You'll find this Kingston neighborhood 30 miles (48 kilometers) to the northwest of the downtown action.

Last time they counted, the population of Kingston was 24,000.

Places to visit in Windham

Escape into the wider Kingston area and get closer to nature with activities like snowboarding. After you've ticked that off your list, make some more unforgettable memories by taking yourself skiing.

Where do you fly into for Windham?

If you're journeying to Windham, the closest major terminal is Albany International Airport (ALB). It's roughly 35 miles (56 kilometers) to the northeast from the central area. Choose an in-flight film, sit back and you'll be landing in no time at all.

Frequently asked questions

How much are vacation packages to Windham?
Packages, which include hotels and flights in Windham, start from . Turn your travel fantasies into reality and secure your vacation with Travelocity today.
How long should my Windham vacation be?
About 2 nights is what many tourists book for their Windham trip. That's a great guide, but there's loads more to discover if you give yourself a little more time.
Where can I get the best vacation package deals for Windham?
For an amazing package deal to Windham, head straight to Travelocity. Take your pick of 400 partner airlines and 1,000,000 properties worldwide to create your ideal escape — it's as easy as that.
Why should I book my Windham vacation bundle via Travelocity?
We offer 24/7 support, top-notch service and a Price Match Guarantee. Life is one big journey — and we have alluring destinations for you to journey to all over the world. Wander with us and make your hip pocket happy.
Will I save money on my Windham car rental if I book it with my hotel or flight?
Sure can — combine your car, flight and hotel into a Windham vacation package and you'll save a tidy sum. With so many places to explore in and around Windham, that rental car will make it easy to explore. Once you're in the driver's seat, turn up the stereo and find your way to Times Square, a well-known attraction about 177 kilometers from Windham.
Which airport is best for Windham?
There are two choices for flying into Windham, the first one being Albany Intl. Airport (ALB). It's around 64 kilometers from downtown, while Stewart Intl. Airport (SWF) is 88 kilometers away from central Windham.
Where should I stay when visiting Windham?
The Hammo's Lodge is the first choice of many visitors. Book soon before it's too late.

Photos of local treasures

Browse Windham vacation photos for more inspiration

Beautiful Fall colors
A pair of skis looking over the dege of a snow covered trail, Windham, NY, USA
Overlooking the valley with skiers going downhill, Windham, New York, USA
Catskill Mountain Autumn: A scenic view through Autumn trees foliage to the Catskill Mountains beyond
Amazing foliage upstate New York. Morning sunlight spills over the golden foliage. Windham NY is one of the most popular destination for scenic drives, bike trails, foliage and nature lovers.