Windham Vacation Packages 2026 from $605

Windham flight + hotel vacation packages

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

Hotel Vienna

$605

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Boise (BOI) 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

$3,342

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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

$3,472

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Wylder Hotel Windham

$805

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Boise (BOI) 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.

Windham NY Escape

$1,194

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip non-stop flight included

Boise (BOI) to Hudson (HCC)

Luggage storage is available at this cabin. Take advantage of the free self parking.

Top Windham hotels deals

Hotel Vienna

107 State Route 296 Windham NY

Free Cancellation

Reserve now, pay when you stay

$141 nightly

$152 total

Nov 4 - Nov 5

Total with taxes and fees

Pool

Breakfast included

Wylder Hotel Windham

19 New York 296 Windham NY

$299 nightly

$323 total

Nov 4 - Nov 5

Total with taxes and fees

Pool

Pet friendly

The Winwood Condominiums

5220 NY-23 Windham NY

$169 nightly

$183 total

Nov 3 - Nov 4

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

5088 NY-23 Windham NY

$254 nightly

$273 total

Dec 1 - Dec 2

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

218 NY-296 Windham NY

$301 nightly

$325 total

Nov 3 - Nov 4

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

43 State Route 296 Windham NY

$174 nightly

$188 total

Nov 3 - Nov 4

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 $605. 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.