A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Find Hotels with Free Parking in Windham, NY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Hotels with Free Parking

Tonight
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Windham hotels with parking

A log cabin with a deck, outdoor seating, and a view of a forest.
A cozy cabin interior with a stone fireplace, wooden walls, a dining area with a red and black checkered tablecloth, and a television mounted above the fireplace.
A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.
A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

1. Hotel Vienna

Hotel Vienna
Windham
United States
Hongtao
NT$3,789
NT$4,656 total
includes taxes & fees
Nov 8 - Nov 9
Hotel Vienna
A rustic cabin with a stone foundation, a wooden roof, and a small porch.
A bar with wooden chairs, a bar counter, and various bottles and glasses.
A glass of beer with a logo on it, placed on a straw surface.
A wooden room with a bed, a nightstand with a lamp, and a wall with tree decorations.

2. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
United States
Robin
NT$4,334
NT$4,681 total
includes taxes & fees
Oct 25 - Oct 26
Jimmy OConnors Windham Mountain Inn
A two-story building with a balcony, surrounded by well-maintained lawns and trees.
A compact living space with a kitchen, dining area, and seating.
A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.
A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
United States
Zihe
NT$5,480
NT$5,919 total
includes taxes & fees
Nov 2 - Nov 3
The Winwood Condominiums
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.
A room with two blue armchairs, a small round table, a lamp, and a large window with curtains.
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

4. Wylder Hotel Windham

Wylder Hotel Windham
Windham
United States
Yassaman Modarres
NT$4,937
NT$6,953 total
includes taxes & fees
Oct 30 - Oct 31
Wylder Hotel Windham
A large, two-story house with multiple porches and string lights.
A building with a porch and outdoor seating area.
A room with a wooden wardrobe, a bed, a nightstand, a lamp, and a fireplace.
A room with a wooden floor, a chair, a lamp, and a view through a window with a decorative frame.

5. Albergo Allegria Hotel

Albergo Allegria Hotel
Windham
United States
Roy
NT$5,634
NT$6,085 total
includes taxes & fees
Oct 27 - Oct 28
Albergo Allegria Hotel
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.
A wooden staircase leading to a second floor, a red sofa with floral cushions, and a wooden floor.
A dining room with a wooden table, chairs, a chandelier, and a vase of flowers.
A garden with blooming pink flowers and green grass.

6. Antique Rose Inn Windham

Antique Rose Inn Windham
Windham
United States
David
NT$4,378
NT$4,728 total
includes taxes & fees
Oct 27 - Oct 28
Antique Rose Inn Windham
A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.
A white door with a sign reading "BREAKFAST" above it, a thermometer, and a drawing of stacked cups with steam.
A hotel room with two beds, wooden paneling on the walls, and two framed pictures.
A kitchen with wooden cabinets, a refrigerator, and a window overlooking greenery.

7. Cave Mountain Motel

Cave Mountain Motel
Windham
United States
Nancy
NT$4,507
NT$4,868 total
includes taxes & fees
Nov 2 - Nov 3
Cave Mountain Motel
A wooden cabin with a triangular roof, a wooden door, and a bench outside.
A triangular wooden room with a bed and pillows, a window, and a view of a forested hill.
A bar area with wooden beams, a bar counter, and four bar stools.
A round wooden table with a hanging light fixture, surrounded by four stools, set against a backdrop of a large window with a view of trees and a wooden deck.

8. Eastwind Windham

Eastwind Windham
Windham
United States
Danica
NT$7,232
NT$8,764 total
includes taxes & fees
Nov 22 - Nov 23
Eastwind Windham
A bedroom with a large window, a bed, and a view of a forest.
A wooden cabin with a door, surrounded by greenery and a stone pathway.
A modern bedroom with a large bed, a view of greenery through floor-to-ceiling windows, and a wooden ceiling.
A large, multi-story wooden house with a snow-covered roof and several lit windows, surrounded by bare trees and snow.

9. The Haüs Windham

The Haüs Windham
Windham
United States
Erica
NT$5,881
NT$11,246 total
includes taxes & fees
Nov 3 - Nov 4
The Haüs Windham
A restaurant with wooden floors, stone walls, and a fireplace. Tables and chairs are arranged for dining.
A cozy lounge area with a sofa, armchairs, a coffee table, and a bookshelf.
A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.
A modern living room with a large window, a blue sofa, a wooden coffee table, and a rustic wooden wall.

10. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
Hunter
United States
Marina
NT$3,831
NT$4,838 total
includes taxes & fees
Nov 12 - Nov 13
Hunter Lodge, a Bluebird by Lark
View all properties

Top Windham Hotel Reviews

The Winwood Condominiums

The Winwood Condominiums

8/10 Good
"Great spot to stay if you want to be within walking distance of the town. Limited breakfast, small rooms, not really many amenities….amazing market and gas station next door!"
Eliot 2-night trip
Posted 1 day ago
The Winwood Condominiums
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Traveling with my husband for NY Sheep and Wool Festival. Worked for what we needed. Could use updating."
Cheri 2-night trip
Posted 3 days ago
Howard Johnson by Wyndham Saugerties
SunView Motel

SunView Motel

10/10 Excellent
"There’s nothing about the hotel that I could complain about!"
Erick 2-night trip
Posted 4 days ago
SunView Motel
Albergo Allegria Hotel

Albergo Allegria Hotel

10/10 Excellent
"What a find!! Impeccably clean. Beautiful Victorian architecture, super friendly and helpful owners. So many cozy nooks to hang out and relax. Restaurants within walking distance. I wish we came this way more often so I could stay again."
Staci 1-night trip
Posted 13 days ago
Albergo Allegria Hotel

Explore a world of travel with Expedia