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Our top choices for Ashland hotels

1. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (152 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is AU$219
includes taxes & fees
10 Nov - 11 Nov
Cave Mountain Motel

2. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (910 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is AU$202
includes taxes & fees
16 Nov - 17 Nov
Hotel Vienna

3. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (184 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
The price is AU$189
includes taxes & fees
10 Nov - 11 Nov
Moore's Motel

4. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (160 reviews)
"We had a nice stay at the Black Bear. Great location and Kim was very accommodating."
United States
Adam
The price is AU$234
includes taxes & fees
10 Nov - 11 Nov
Black Bear Lodge

5. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (377 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is AU$266
includes taxes & fees
10 Nov - 11 Nov
The Winwood Condominiums

6. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (289 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is AU$273
includes taxes & fees
10 Nov - 11 Nov
Albergo Allegria Hotel

7. 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 AU$223
includes taxes & fees
18 Nov - 19 Nov
Jimmy OConnors Windham Mountain Inn

8. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"A fantastic stay!"
United States
David
The price is AU$212
includes taxes & fees
11 Nov - 12 Nov
Antique Rose Inn Windham

9. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (504 reviews)
"Great place to stay!"
United States
Eric
The price is AU$124
includes taxes & fees
12 Nov - 13 Nov
The Colonial Motel

10. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,011 reviews)
"Always a nice stay."
United States
Marina
The price is AU$233
includes taxes & fees
10 Dec - 11 Dec
Hunter Lodge, a Bluebird by Lark

11. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 reviews)
"Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. "
United States
Erica
The price is AU$463
includes taxes & fees
17 Nov - 18 Nov
The Haüs Windham

12. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is AU$404
includes taxes & fees
2 Dec - 3 Dec
Wylder Hotel Windham

13. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (122 reviews)
"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."
United States
Danica
The price is AU$392
includes taxes & fees
10 Dec - 11 Dec
Eastwind Windham

14. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (307 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is AU$261
includes taxes & fees
15 Nov - 16 Nov
Mountain Treasure B&B

15. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (451 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is AU$295
includes taxes & fees
22 Nov - 23 Nov
Kaatskill Mountain Club & Condos by Vail Resorts

16. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (334 reviews)
"Beautiful Inn. Every detail was so well thought out!"
United States
Nancy Joan
The price is AU$232
includes taxes & fees
11 Nov - 12 Nov
Shandaken Inn

17. The Wheelhouse Inn

The Wheelhouse Inn
2.5 star property
Pine Hill
8.4 out of 10, Very good, (136 reviews)
"I have nothing negative to say about my stay! The inn was clean and safe and Cinthia was very responsive and accommodating. It is a perfect location to access various hikes and other interests in the Catskills area."
United States
Victoria
The price is AU$163
includes taxes & fees
4 Dec - 5 Dec
The Wheelhouse Inn

18. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (297 reviews)
"I had a wonderful stay at Shadowcrest! The aesthetic was incredibly nice and cozy, making it the perfect place to relax. The host was also super kind and helpful throughout my visit. I highly recommend staying here!"
United States
Andres
The price is AU$205
includes taxes & fees
10 Dec - 11 Dec
Shadowcrest

19. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (47 reviews)
"Mountain View and cozy vibes are on point."
United States
Pushpavalli
The price is AU$298
includes taxes & fees
12 Nov - 13 Nov
The Perch Hotel

20. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (321 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is AU$237
includes taxes & fees
10 Nov - 11 Nov
Starlite Motel
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.

Compare top hotels in Ashland

2.5 star property
Windham
3.0 star property
Windham
2.5 star property
Prattsville
2.5 star property
Prattsville
3.0 star property
Windham
9.4
Exceptional
152 reviews
9.4
Exceptional
910 reviews
8.6
Excellent
184 reviews
9.0
Wonderful
160 reviews
8.8
Excellent
377 reviews
The price is AU$219
includes taxes & fees
10 Nov - 11 Nov
The price is AU$202
includes taxes & fees
16 Nov - 17 Nov
The price is AU$189
includes taxes & fees
10 Nov - 11 Nov
The price is AU$234
includes taxes & fees
10 Nov - 11 Nov
The price is AU$266
includes taxes & fees
10 Nov - 11 Nov
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking

Stay near popular Ashland attractions

Top Ashland Hotel Reviews

Frequently Asked Questions

What is the best area to stay in Ashland?

The best area to stay in Ashland, New York, is near the village centre, particularly along Main Street and its immediate surroundings.


This area is the heart of Ashland, offering convenient access to local shops, eateries, and community events. Main Street itself is quite walkable, with a mix of historic buildings and modern conveniences. You'll find many of the town's amenities concentrated here, making it easy to get around on foot.


For couples seeking a relaxing getaway, staying near the village centre is ideal. You're close to local restaurants for evening meals and can easily explore the small boutiques and art galleries. The area also provides a good base for short scenic drives into the surrounding Catskill Mountains.


Families will also find this area convenient. With many local businesses within walking distance, it's easy to grab snacks or find activities without extensive travel.

When is the best time to go to Ashland?

The best time to visit Ashland, New York, is typically during the summer months, from June to August, or in the autumn, from September to October.


Summer offers warm weather, ideal for outdoor activities like hiking, fishing, and enjoying the natural beauty of the Catskill Mountains. Most local attractions and businesses are fully operational, and the area is lively with visitors. This is a great time for families looking for an active holiday with plenty of options for children.


Autumn is particularly stunning due to the vibrant fall foliage. The cooler temperatures are superb for scenic drives, exploring hiking trails, and attending local harvest festivals. Couples often find this season especially appealing for a romantic getaway, with cosy evenings and picturesque landscapes.


While winter brings opportunities for skiing and snowboarding at nearby resorts, and spring offers new growth, these seasons can be less predictable with weather and have fewer attractions open.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Ashland.

How can I save on a hotel booking in Ashland with Expedia?

One Key™—Expedia’s free travel rewards program—gives you instant access to discounts with Member Prices on Ashland hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Ashland?

Prices for hotels in Ashland often vary, but you can find a great deal from AU$124 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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