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Windham flight + hotel vacation packages

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Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Price was $1,384, price is now $1,214 per person
$1,214
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) 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.
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 $6,209, price is now $4,909 per person
$4,909
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) 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.
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 $5,947, price is now $4,707 per person
$4,707
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Hudson (HCC)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

Luxury Chalet, Firepit, Sauna, Pet Friendly, 5 mins to Windham Mtn resort

3 out of 5
Price was $3,326, price is now $3,054 per person
$3,054
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Hudson (HCC)
This chalet features a hot tub and a sauna. Free self parking and a terrace are also offered on site.
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,654, price is now $1,332 per person
$1,332
per person
Oct 14 - Oct 20
found 8 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Hudson (HCC)
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.

Top Windham hotels deals

Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $151 total per night
$151 total
Sep 1 - Sep 2
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
$305 nightly
The price is $330 total per night
$330 total
Aug 30 - Aug 31
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.
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
$247 nightly
The price is $266 total per night
$266 total
Aug 30 - Aug 31
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.
Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

141 South St Windham NY
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $146 total per night
$146 total
Sep 29 - Sep 30
Total with taxes and fees
Free WiFi in public areas is available at this motel. Take advantage of ski passes on site, and enjoy snowboarding. Take advantage of the free self parking.
The Haüs Windham

The Haüs Windham

2 out of 5
218 NY-296 Windham NY
$329 nightly
The price is $356 total per night
$356 total
Sep 1 - Sep 2
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.
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
Aug 30 - Aug 31
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.
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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 $1,214. 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.
Aluminum canoe on a mountain lake upstate New York. Camping. outdoors and adventure concept. Faded, vintage color post processed
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.
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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