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.
The Hidden Inn

The Hidden Inn

4 out of 5
Price was $582, price is now $436 per person
$436
per person
Oct 10 - Oct 13
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.
Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

Game Farm Villa by Avantstay 10bdr, Private Pond, Spa, Pool Family-friendly

3 out of 5
Save 100% on your flight
Price was $4,377, price is now $3,259 per person
$3,259
per person
Oct 10 - Oct 13
found 12 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are provided for your convenience.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Save 100% on your flight
Price was $753, price is now $566 per person
$566
per person
Oct 10 - Oct 13
found 11 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

3 out of 5
Save 100% on your flight
Price was $1,144, price is now $903 per person
$903
per person
Oct 10 - Oct 13
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace and barbecue grills are also provided.
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
Price was $602, price is now $485 per person
$485
per person
Oct 10 - Oct 13
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Hudson (HCC)
A restaurant and an outdoor pool are featured at this hotel. Enjoy the sauna and perks like free WiFi. A lobby fireplace, a picnic area, and luggage storage are also on offer.

Top Windham hotels deals

Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296, Windham, NY
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $150 total per night
$150 total
Sep 21 - Sep 22
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
$260 nightly
The price is $281 total per night
$281 total
Aug 31 - Sep 1
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
Eastwind Windham

Eastwind Windham

2 out of 5
5088 NY-23, Windham, NY
$195 nightly
The price is $210 total per night
$210 total
Sep 23 - Sep 24
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A bar/lounge is also provided.
Pet friendly
Parking included
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

3 out of 5
5220 NY-23, Windham, NY
$189 nightly
The price is $204 total per night
$204 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free ski shuttle. Take advantage of ski passes on site, and enjoy sledding. Families will appreciate the arcade/game room and onsite laundry facilities.
Pool
Parking included
The Haüs Windham

The Haüs Windham

2 out of 5
218 NY-296, Windham, NY
$214 nightly
The price is $232 total per night
$232 total
Sep 9 - Sep 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Parking included
Free WiFi
Cave Mountain Motel

Cave Mountain Motel

2.5 out of 5
10978 STATE RTE 23, Windham, NY
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $150 total per night
$150 total
Sep 1 - Sep 2
Total with taxes and fees
This motel features free WiFi in public areas, barbecue grills, and free self parking. Free buffet breakfast is served. A garden and a picnic area are also provided.
Breakfast included
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

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

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

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

Frequently asked questions

How much are vacation packages to Windham?
Packages, which include hotels and flights in Windham, start from $436. 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

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