Deals on vacations and trips to Windham

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Windham flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $835, price is now $649 per person
$649
per person
Jan 7 - Jan 11
found 7 hours ago
Roundtrip flight included
Nassau (NAS) to Hudson (HCC)
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 express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.
Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

Mountainview - Guest House by Avantstay Heated Pool + Hot Tub + Games Lake + Cannoe Near Hunter Mountain

3 out of 5
Save 100% on your flight
Price was $3,886, price is now $3,113 per person
$3,113
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

Mountainview Estate - Main House by Avantstay Pool + Hot Tub + Canoe + Outdoor Dining + Game Room Near Windham Mountain

3 out of 5
Save 100% on your flight
Price was $4,019, price is now $3,264 per person
$3,264
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
An outdoor pool, free self parking, and barbecue grills are featured at this cottage. WiFi in public areas is free. A terrace is also provided.
Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $1,078, price is now $883 per person
$883
per person
Jan 7 - Jan 11
found 7 hours ago
Roundtrip flight included
Nassau (NAS) to Hudson (HCC)
This hotel features a restaurant and 2 bars/lounges. Enjoy the sauna and perks like free self parking and free WiFi. A lobby fireplace, a communal living room, and a picnic area are also on offer.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $871, price is now $734 per person
$734
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.

Top Windham hotels deals

Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
$141 nightly
The price is $152 total per night
$152 total
Nov 4 - Nov 5
Total with taxes and fees
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 express check-out. There's an indoor pool on site, and a terrace and a garden are also provided.
Pool
Breakfast included
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
$299 nightly
The price is $323 total per night
$323 total
Nov 4 - Nov 5
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a lobby fireplace, and a communal living room are also on offer.
Pool
Pet friendly
The Winwood Condominiums

The Winwood Condominiums

3 out of 5
5220 NY-23 Windham NY
$169 nightly
The price is $183 total per night
$183 total
Nov 4 - Nov 5
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Enjoy the free ski shuttle and onsite ski passes. Families will appreciate the arcade/game room and onsite laundry facilities.
Pool
Parking included
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
$295 nightly
The price is $318 total per night
$318 total
Nov 15 - Nov 16
Total with taxes and fees
This hotel features a restaurant and 2 bars/lounges. Enjoy the sauna and perks like free self parking and free WiFi. A lobby fireplace, a communal living room, and a picnic area are also on offer.
Pet friendly
Parking included
The Haüs Windham

The Haüs Windham

2 out of 5
218 NY-296 Windham NY
$306 nightly
The price is $330 total per night
$330 total
Nov 9 - Nov 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A 24-hour gym and barbecue grills are also provided.
Pet friendly
Parking included
Albergo Allegria Hotel

Albergo Allegria Hotel

3.5 out of 5
43 State Route 296 Windham NY
$174 nightly
The price is $188 total per night
$188 total
Nov 4 - Nov 5
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
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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.

Stay near popular Windham attractions

Windham Mountain Resort

9.0/10 (313 reviews)
Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area.
See properties

Frequently asked questions

How much are vacation packages to Windham?
Packages, which include hotels and flights in Windham, start from $649. 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 110 mi 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 40 mi from downtown, while Stewart Intl. Airport (SWF) is 55 mi 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

A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.
A canoe on a calm lake with a forested shoreline.
A river surrounded by autumn foliage.
A snowy ski slope with trees on either side and a view of the valley below.
Two skiers on a snowy slope with a valley and mountains in the background.

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