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Windham Vacations

Pack those stellar shades. We have Windham vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Windham – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Windham vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Windham

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Windham vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Windham well.

Top Hotel Deals

See all 178 Hotels in Windham
Winwood Inn & Condominiums

Winwood Inn & Condominiums

5220 NY-23, Windham
3.5 out of 5.0

Conveniently located near the ski slopes, this Windham resort is in the mountains, within 2 mi (3 km) of Windham Country Club and Windham Mountain Resort, and ...

Beds on Clouds

Beds on Clouds

5320 Main Street, Windham
3.5 out of 5.0

Situated in Windham, this bed & breakfast is 0.8 mi (1.3 km) from Windham Mountain Resort and 1.3 mi (2.1 km) from Windham Country Club. Windham Vineyards and ...

The Thompson House

The Thompson House

19 Rt. 296, Windham
2.5 out of 5.0

Situated in a state park, this hotel is 0.4 mi (0.6 km) from Windham Country Club and 1.7 mi (2.7 km) from Windham Mountain Resort. Windham Vineyards and Winery ...

Albergo Allegria Bed and Breakfast Hotel

Albergo Allegria Bed and Breakfast Hotel

43 State Route 296, Windham
4.0 out of 5.0

Situated in the historical district, this bed & breakfast is 0.3 mi (0.4 km) from Windham Country Club and 1.6 mi (2.6 km) from Windham Mountain Resort. Windham ...

Hotel Vienna

Hotel Vienna

107 State Route 296, Windham
3.0 out of 5.0

Situated in Windham, this hotel is 0.5 mi (0.8 km) from Windham Country Club and 1.8 mi (3 km) from Windham Mountain Resort. Windham Vineyards and Winery and ...

$130

$130
Georgian Garden Inn

Georgian Garden Inn

5159 state route 23, Windham
3.5 out of 5.0

This beachfront bed & breakfast is located in Windham, close to Windham Country Club and Windham Mountain Resort. Area attractions also include Windham Vineyards ...

Antique Rose Inn Windham

Antique Rose Inn Windham

326 State Route 296, Windham
3.5 out of 5.0

Situated in Windham, this bed & breakfast is 1.1 mi (1.8 km) from Windham Country Club and 2.4 mi (3.9 km) from Windham Mountain Resort. Mountain Top Arboretum ...

Catskill Lodge

Catskill Lodge

350 NY State Route 296, Windham
3.5 out of 5.0

Situated in Windham, this bed & breakfast is close to Windham Country Club and Windham Mountain Resort. Area attractions also include Windham Vineyards and Winery ...

Cave Mountain Motel

Cave Mountain Motel

10978 STATE RTE 23, Windham
2.5 out of 5.0

Situated in Windham, this motel is close to Windham Mountain Resort, Windham Vineyards and Winery, and Windham Country Club. Regional attractions also include ...

Copper Kettle Cottages

Copper Kettle Cottages

5098 Main Street, Windham
2.5 out of 5.0

Situated in Windham, this motel is 0.5 mi (0.8 km) from Windham Country Club and 1.8 mi (2.9 km) from Windham Mountain Resort. Windham Vineyards and Winery and ...