Windham Vacation Packages 2026 from $651

Windham flight + hotel vacation packages

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

Hotel Vienna

$651

per person

Aug 23 - Aug 29

found 3 hours ago

Roundtrip flight included

Houston (IAH) 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.

Eastwind Windham

$868

per person

Aug 23 - Aug 29

found 3 hours ago

Roundtrip flight included

Houston (IAH) 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.

Red Feather Lodge

Save 100% on your flight

$3,875

per person

Aug 23 - Aug 29

found 3 hours ago

Roundtrip flight included

Houston (IAH) to Hudson (HCC)

This vacation home features a seasonal outdoor pool and a hot tub. Enjoy the sauna and perks like free self parking and free WiFi. A picnic area is also provided.

The Haüs Windham

$1,148

per person

Aug 23 - Aug 29

found 3 hours ago

Roundtrip flight included

Houston (IAH) 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

107 State Route 296 Windham NY

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$157 total

Jun 15 - Jun 16

Total with taxes and fees

Pool

Breakfast included

Wylder Hotel Windham

19 New York 296 Windham NY

$305 nightly

$329 total

Jun 15 - Jun 16

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

5088 NY-23 Windham NY

$209 nightly

$225 total

Jun 15 - Jun 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

218 NY-296 Windham NY

$223 nightly

$241 total

Jun 15 - Jun 16

Total with taxes and fees

Pet friendly

Parking included

The Winwood Condominiums

5220 NY-23 Windham NY

$169 nightly

$183 total

Jun 15 - Jun 16

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

Albergo Allegria Hotel

43 State Route 296 Windham NY

$163 nightly

$176 total

Jun 15 - Jun 16

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.

Frequently asked questions

How much are vacation packages to Windham?

Packages, which include hotels and flights in Windham, start from $651. 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.