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

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

Our top choices for Windham motels

A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

1. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.2 out of 10, Wonderful, (10 reviews)
"We had a wedding in the area and this place was perfect for our needs. There’s a bar to the front of the property, which was fun to hang out and play pool. The beds were comfortable and the rooms were clean."
United States
Robin
The price is CA $189
CA $204 total
includes taxes & fees
Oct 19 - Oct 20
Jimmy OConnors Windham Mountain Inn
A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

2. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (150 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is CA $197
CA $212 total
includes taxes & fees
Nov 5 - Nov 6
Cave Mountain Motel
A covered porch with outdoor seating, a staircase, and potted plants.

3. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (498 reviews)
"Great place to stay!"
United States
Eric
The price is CA $112
CA $123 total
includes taxes & fees
Nov 16 - Nov 17
The Colonial Motel
A river flowing through a forested area with rocks and autumn-colored trees.

4. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (156 reviews)
"We had a nice stay at the Black Bear. Great location and Kim was very accommodating."
United States
Adam
The price is CA $211
CA $228 total
includes taxes & fees
Oct 19 - Oct 20
Black Bear Lodge
A swimming pool with lounge chairs and potted plants.

5. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (181 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
The price is CA $170
CA $183 total
includes taxes & fees
Oct 19 - Oct 20
Moore's Motel
A wooden deck with a flower pot and a view of a playground area with picnic tables and a small shed.

6. Four Seasons Motel

Four Seasons Motel
2.0 star property
Catskill
8.4 out of 10, Very good, (222 reviews)
"Great spot! Friendly and attentive staff, clean rooms, and reasonably priced!"
United States
Jabari
The price is CA $141
CA $153 total
includes taxes & fees
Oct 19 - Oct 20
Four Seasons Motel
A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

7. The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.6 out of 10, Exceptional, (64 reviews)
"Wonderful Stay"
United States
Daniel
The price is CA $221
CA $247 total
includes taxes & fees
Nov 15 - Nov 16
The Graham & Co.
A living room with a leather sofa, a wooden coffee table, a TV on a wooden stand, and a window with curtains.

8. Red Ranch Motel

Red Ranch Motel
2.5 star property
Catskill
7.4 out of 10, Good, (545 reviews)
"Older motel, room was clean, friendly staff, tv was good and working, shower and bathroom clean, beds could be better but ok."
United States
Oleg
The price is CA $151
CA $163 total
includes taxes & fees
Nov 16 - Nov 17
Red Ranch Motel
A living room with a fireplace, a television, a sofa, and a coffee table.

9. Margaretville Motel

Margaretville Motel
2.5 star property
Margaretville
7.0 out of 10, Good, (211 reviews)
"We checked in after hours, which was easy and all communication was excellent! The room is outdated but clean. The beds are comfortable. We stayed overnight to hike a trail earlier in the morning. Not far from places to eat."
United States
april
The price is CA $120
CA $155 total
includes taxes & fees
Oct 19 - Oct 20
Margaretville Motel
A forested area with tall trees and a grassy field.

10. Catskill Motor Court Motel

Catskill Motor Court Motel
2.5 star property
Catskill
6.0 out of 10, (140 reviews)
"Staff was very friendly."
United States
Allyson
The price is CA $166
CA $179 total
includes taxes & fees
Nov 8 - Nov 9
Catskill Motor Court Motel
A bedroom with a bed, a sliding door, a TV, a shelf, and a clock.

11. The Vine on main

The Vine on main
2.0 star property
Stamford
8.0 out of 10, Very good, (105 reviews)
"It was a very nice and clean room."
United States
Dana
The price is CA $264
CA $291 total
includes taxes & fees
Nov 16 - Nov 17
The Vine on main
A residential area with a driveway leading to a house with a porch.

12. Peloke's Motel

Peloke's Motel
2.0 star property
Catskill
6.4 out of 10, (182 reviews)
"The sheets and bathroom were clean. That's about it. I wasn't expecting amazing things since it's a motel, not hotel, but they definitely need some renovations. "New" paint stopped half way up the wall, paneling separating from the wall, curtains held up by a single nail. But it was clean where it counts and conveniently located."
United States
Jeanette
The price is CA $154
CA $173 total
includes taxes & fees
Nov 15 - Nov 16
Peloke's Motel
A motel with a prominent sign reading '21B MOTEL' on the roof.

13. 21B Motel

21B Motel
West Coxsackie
2.0 out of 10, (1 review)
"Expedia sold me this hotel room while it was still under construction. The hotel was barricaded around,"
United States
Onkar
The price is CA $170
CA $183 total
includes taxes & fees
Oct 21 - Oct 22
21B Motel
A cozy room with wooden walls, a dining table with chairs, a fireplace, and a staircase.

14. The Leeway

The Leeway
2.0 star property
Mount Tremper
10.0 out of 10, Exceptional, (24 reviews)
"Staff was helpful and friendly. Cabin was great"
Taiwan
Shih-Chun
The price is CA $324
CA $362 total
includes taxes & fees
Nov 16 - Nov 17
The Leeway
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.
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Top Windham Hotel Reviews

Urban Cowboy Lodge

Urban Cowboy Lodge

10/10 Excellent
"Overall fantastic stay. The property itself is beautiful and you can see it being upkept constantly, it is clear that they are taking great care of it while still maintaining the charm. The rooms were spotless both where we slept and the shared spaces like the Lodge. The staff was amazing, with kind responses and quick to answer/help out with any questions we had. One of the best properties I’ve ever stayed at, and the people here make it the 5 Star quality that it is."
Bryn 1-night trip
Posted 7 hours ago
Urban Cowboy Lodge

Find out more about Windham

Windham Motels information

Number of reviews
2,021
Accommodation
16 Motels
Lowest Price
CA $123
Highest Price
CA $362

Frequently asked questions

What can I expect from a motel trip to Windham?
If you can't find a motel in Windham, consider some of the motels we suggest around the area or let Expedia help you find something similar from more than 268 lodging options. Simply use our search tools to filter by nightly room rate or cost-saving amenities such as free breakfast and free airport transportation.
What are motels like?
When you stay at a motel, you'll often find free parking and an outdoor pool. With a stay at a motel, you'll usually access your room from an outside corridor overlooking the parking lot. Starting in the early 1950s, eye-catching neon signs enticed road-weary travelers, and today, examples of these can still be found along historic U.S. Route 66.
What are the best motels in Windham?
Jimmy OConnors Windham Mountain Inn: Stay within a quick 2-minute drive of Windham Mountain Resort. Enjoy access to the free WiFi and free parking. Cave Mountain Motel: A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. It's located within a quick 4-minute drive of Windham Mountain Resort.
What can I do in Windham?
In this relaxing area, you can check out the ski slopes and enjoy the coffeehouses 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 Windham Vineyards and Winery.
What's the weather like in Windham?
Weather can make or break a roadtrip, 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 temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.
What are my options for getting around Windham when 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 center. If you'd like to explore around the area, you may want a rental car for your journey.

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