Motel Windham - Find the Best Motels for 2026

Q: What are the best motels in Windham?

Jimmy OConnors Windham Mountain Inn : Stay within a 30-minute drive of Hunter Mountain and Kaaterskill Falls. Enjoy access to the free Wi-Fi and free parking. Cave Mountain Motel : A 24-hour front desk along with freebies such as breakfast, WiFi and self-parking are available during your stay. You'll be located within 24 minutes of Hunter Mountain by car.

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

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 prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Windham motels

A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

1. Cave Mountain Motel

Windham

Nancy

includes taxes & fees

4 Oct - 5 Oct

2. Jimmy OConnors Windham Mountain Inn

Windham

"This is an old-school fifties-style motel (looking at it makes one think of "Shady Rest Inn" ), with a central building that serves simple dinner and beer (did not avail). The room is very old-fashioned and mine had two very solid double beds. Have to admit that my sheet had a rather prominent red (blood?) spot that was near my head and hard to ignore. Otherwise, the room was comfortable, had a small air conditioner that worked, a nice shower, and old-style but very nice furnishings. I would...

Jeffrey

includes taxes & fees

15 Sept - 16 Sept

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

3. SunView Motel

Tannersville

Victoria

includes taxes & fees

1 Oct - 2 Oct

A swimming pool with lounge chairs and potted plants.

4. Moore's Motel

Prattsville

Cory

includes taxes & fees

15 Sept - 16 Sept

A covered porch with outdoor seating, a staircase, and potted plants.

5. The Colonial Motel

Grand Gorge

Eric

includes taxes & fees

27 Sept - 28 Sept

A river flowing through a forested area with rocks and autumn-colored trees.

6. Black Bear Lodge

Prattsville

Gerald

includes taxes & fees

15 Sept - 16 Sept

A living room with a leather sofa, a wooden coffee table, a TV on a wooden stand, and a window with curtains.

7. Red Ranch Motel

Catskill

Dhan

includes taxes & fees

15 Sept - 16 Sept

A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

8. The Graham & Co.

Phoenicia

Daniel

includes taxes & fees

29 Sept - 30 Sept

A wooden deck with a flower pot and a view of a playground area with picnic tables and a small shed.

9. Four Seasons Motel

Catskill

Jeremy

includes taxes & fees

16 Sept - 17 Sept

A forested area with tall trees and a grassy field.

10. Catskill Motor Court Motel

Catskill

Ella

includes taxes & fees

13 Sept - 14 Sept

A living room with a fireplace, a television, a sofa, and a coffee table.

11. Margaretville Motel

Margaretville

Donna

includes taxes & fees

14 Sept - 15 Sept

A bedroom with a bed, a sliding door, a TV, a shelf, and a clock.

12. The Vine on main

Stamford

Dana

includes taxes & fees

28 Sept - 29 Sept

A cozy room with wooden walls, a dining table with chairs, a fireplace, and a staircase.

13. The Leeway

Mount Tremper

Shih-Chun

includes taxes & fees

14 Sept - 15 Sept

A residential area with a driveway leading to a house with a porch.

14. Peloke's Motel

Catskill

Julian

includes taxes & fees

11 Oct - 12 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Windham Hotel Reviews

The Winwood Condominiums

10/10 Excellent

"I came here thirty years ago. And I came here thirty years later, and it's still run by a wonderful proprietor and it's a beautiful place to unwind, and enjoy breakfast in the morning will be a wonderful host if she's not busy. That is taking care of this amazing place. I very much enjoyed my stay"

Hunter Lodge, a Bluebird by Lark

8/10 Good

"Our stay started with an open door, food in the fridge and a trip to reception to make sure the room was not already occupied. We stayed in the room. The rooms seemed to be recently renovated, new AC systems, spacious, etc. so the accommodations were very nice. Biggest problem is the lighting is terrible and the room is very dark (paint, decorations, etc.), a bulb went out and one of the two light fixtures would not work. The fridge needed defrosting badly; we could not use the freezer. The next day they moved us to a suite and refunded a $40 activity fee (not sure what this additional fee was for; there were no activities, pool, etc.). The suite had lots of natural light, but again, not much light after dark. The glass shower door was off the track, but there was no handyman there that day. The bathroom sink is separate from the very tiny bathroom; there were no towel hooks or towel bars in the sink area. In the prior room there were two hooks in the sink area. Owners should live in these rooms for a night. We appreciated the upgrade; the fridge was in much better shape. The public rooms were very nice."

Jimmy OConnors Windham Mountain Inn

10/10 Excellent

"Jimmy Conner Inn is truly one of the best places to stay if you’re looking for somewhere quiet, peaceful, and surrounded by nature. Everything is so convenient you have a bar and restaurant right on the property, so you don’t even need to leave. It’s incredibly peaceful and the perfect place to decompress from all the noise and craziness of the city. The service was excellent, and the whole experience made us feel so welcomed and taken care of. They even have a beautiful fire pit where you can relax and enjoy the evening. Highly recommend this place if you’re looking to disconnect, reconnect with nature, and just enjoy some peace and quiet! 🔥🌲"

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10/10 Excellent

"This house was great! We had 20 people stay here comfortably and never really left the house! Greg was very responsive to all of my messages and the house was equipped with a lot of things!"

Find out more about Windham

Windham Motels information

Number of reviews	1,850
Accommodation	16 Motels
Lowest Price	NZ$163
Highest Price	NZ$454

Frequently asked questions

What can I expect from a motel trip to Windham?

If you're having trouble locating a motel in Windham, consider some of the motels we suggest around the area or let Expedia help you find something similar from over 270 hotels and other lodging options. Simply filter using our search tools by nightly room rate or cost-effective amenities such as free breakfast and free airport transport.

What are motels like?

At many motels, you'll often find a free parking spot and an outdoor pool. When you stay at a motel property, you'll usually access your room from an outside corridor overlooking the car park. Beginning in the early 1950s, eye-catching neon signs enticed road-weary travellers, and examples can still be seen today along historic US Route 66.

What are the best motels in Windham?

Jimmy OConnors Windham Mountain Inn: Stay within a 30-minute drive of Hunter Mountain and Kaaterskill Falls. Enjoy access to the free Wi-Fi and free parking. Cave Mountain Motel: A 24-hour front desk along with freebies such as breakfast, WiFi and self-parking are available during your stay. You'll be located within 24 minutes of Hunter Mountain by car.

What can I do in Windham?

In this relaxing area, you can explore the ski slopes and enjoy the coffee shops while you're sightseeing. Those who've visited Windham like the mountain landscape. Enjoy nature with a stop at Elm Ridge Wild Forest and Ashland Park. You'll find these family-friendly sights in the area: Zoom Flume, Empire State Railway Museum and Pine Hill Community Center. During your trip, here are some other places to visit: Windham Country Club, Windham Mountain Resort and Catskill State Park.

What's the weather like in Windham?

Weather can make or break a road trip, so here's some data about year-round temperatures in Windham to help you plan yours: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.

What are my options for getting around Windham while staying in a motel?

We've gathered some information about local transportation options in Windham to help you navigate your stay: Fly into Hudson, NY (HCC-Columbia County), which is located 27.6 mi (44.4 km) from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia

More ways to book

Book Motels in Windham on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates