Windham Vacation Packages

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Top Windham hotel deals

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Free Cancellation
Reserve now, pay when you stay
The price is $139 per night
$139
per night
May 27 - May 28
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an indoor pool on site, and a terrace and a garden are also provided.
Pet friendly
Breakfast included
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.

SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.

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A water park and a spa tub are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A gym and a garden are also provided.
Hot Tub
Fireplace
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
The price is $230 per night
$230
per night
May 29 - May 30
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A bar/lounge is also provided.
Pet friendly
Breakfast available
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter

The price is $1,095 per night
$1,095
per night
May 27 - May 28
A water park and a gym are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and barbecue grills. A garden is also provided.
Fireplace
Pet friendly
Winwood Inn & Condominiums

Winwood Inn & Condominiums

3 out of 5
5220 NY-23, Windham, NY
The price is $185 per night
$185
per night
May 27 - May 28
This hotel features a full-service spa and a restaurant. There's a free ski shuttle, and ski passes and ski storage are available on site. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities.
Pool
Spa
Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

3.5 out of 5
43 State Route 296, Windham, NY
The price is $125 per night
$125
per night
May 27 - May 28
A restaurant, free self parking, and a terrace are among this bed & breakfast's amenities. WiFi in public areas is free. A business center, a garden, and a lobby fireplace are also on offer.
Breakfast available
Parking included
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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 in Windham

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Windham Mountain Resort

4.5/5(89 reviews)

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

Windham Mountain Resort
Image for Windham Country Club

Windham Country Club

4.5/5(3 reviews)

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

Windham Country Club
Image for Windham Vineyards and Winery

Windham Vineyards and Winery

5/5(2 reviews)

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

Frequently asked questions

How much are vacation packages to Windham?
You can find a great hotel and flight bundle from just . With a Travelocity vacation package, a getaway to Windham has never looked more irresistible! Save some time and money and then get a head start on packing those bags.
How long should my Windham vacation be?
Typically, 2 nights is how long most travelers spend checking out Windham. Wondering whether that’ll be enough time to get to everything on your bucket list? Stay another night or two and experience everything this place has to offer.
Where can I get the best vacation package deals for Windham?
It’s difficult to beat Travelocity when it comes to piecing together your Windham package deal. There are as many as 400 partner airlines and 1,000,000 properties worldwide to choose from. Book your trip now and get ready to cross another destination off your bucket list.
Why should I book my Windham vacation bundle with Travelocity?
Because life is one big journey, and we offer all you need to help you on the way. With our first-rate service and Price Match Guarantee, you can book your trip with confidence. And you can sleep easy on the road knowing we’ve got you covered with our 24/7 support.
Will I save money on my Windham car rental if I book it with my hotel or flight?
Sure can — combine your flight, hotel and car into a Windham vacation package and you can save loads. With so much to uncover in Windham, that rental vehicle will come in handy. Once you’re behind the wheel, hit the wide open road and find your way to Times Square, a well-known attraction approximately 110 mi from Windham.
What is the best time of year to go to Windham?
That all depends on whether you’d prefer to save cash or visit Windham at its most exciting. The quietest time to see this part of the world is April, May and October. If you want to experience this destination at its busiest, consider November, December and January. More interested in saving your hard-earned cash? The most affordable month is . typically has the most expensive prices.
Which airport is best for Windham?
There are two options for jetting to Windham, the first being Albany Intl. Airport (ALB). It’s situated 40 mi from the center of the city, while Stewart Intl. Airport (SWF) is 55 mi away from central Windham.
Where should I stay when visiting Windham?
If you’re after someplace comfortable to lay your head, have a look at the Hammo’s Lodge. It’s the top pick for many visitors.