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Hotels in Ashland

Choose from 1534 Ashland Hotel Deals

Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by Lark
3 out of 5
7433 Main St, Hunter, NY
  • 18 min drive from Ashland Town Hall
Stay at this 3-star hotel in Hunter. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.2/10 Wonderful! (639 reviews)
"Loved our stay. The rooms are large, freshly renovated, stylish and affordable. We loved being able to see the mountains directly from our window. They also have a lovely restaurant and library. I’m surprised they don’t host events."

Reviewed on May 4, 2025

Hunter Lodge, a Bluebird by Lark
The Roxbury at Stratton Falls
The Roxbury at Stratton Falls
2 out of 5
48 Co Rd 41, Roxbury, NY
  • 9 min drive from Ashland Town Hall
Stay at this hotel in Roxbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Plattekill State Forest and Plattekill Mountain are located ...
9.6/10 Exceptional! (24 reviews)
"One of the most unique lodging experiences you will ever have. 10/10, fantastic, blow your mind, etc. etc. Staff was great/friendly and very helpful. Pick your favorite theme and have a blast."

Reviewed on May 11, 2025

The Roxbury at Stratton Falls
Urban Cowboy Lodge
Urban Cowboy Lodge
5 out of 5
37 Alpine Rd, Big Indian, NY
  • 42 min drive from Ashland Town Hall
Stay at this 5-star luxury lodge in Big Indian. Enjoy free WiFi, free parking, and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (136 reviews)
"Beautiful property and amazing staff. We had a great time. Thank you"

Reviewed on May 11, 2025

Urban Cowboy Lodge
Eastwind Windham
Eastwind Windham
2 out of 5
5088 NY-23, Windham, NY
  • 16 min walk from Ashland Town Hall
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Windham Mountain Resort and Windham Country Club ...
9.2/10 Wonderful! (53 reviews)
"Very lo-fi and bare bones, but well-designed and properly thought-out. Just what city hipster ski bums are looking for."

Reviewed on Mar 16, 2025

Eastwind Windham
Hotel Mountain Brook
Hotel Mountain Brook
4 out of 5
57 Route 23c, Tannersville, NY
  • 19 min drive from Ashland Town Hall
Stay at this 4-star hotel in Tannersville. Enjoy free breakfast, free parking, and cable TV channels. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (476 reviews)
"great stay"

Reviewed on Apr 21, 2025

Hotel Mountain Brook
Wylder Hotel Windham
Wylder Hotel Windham
3.5 out of 5
19 New York 296, Windham, NY
  • 16 min walk from Ashland Town Hall
Stay at this 3.5-star hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club ...
8.2/10 Very Good! (55 reviews)
"All was nice, very nice staff esp the bartender Chris! We could not get the TV’s to work in either room with the required logins, and the water took a really long time to get warm for the showers. Otherwise, really all fine and bucolic."

Reviewed on May 11, 2025

Wylder Hotel Windham
Kaatskill Mountain Club at Hunter Mountain
Kaatskill Mountain Club at Hunter Mountain
2 out of 5
61 LIFTSIDE DR, Hunter, NY
  • 17 min drive from Ashland Town Hall
Stay at this hotel in Hunter. Enjoy free WiFi, a sauna, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Hunter ...
9/10 Wonderful! (233 reviews)
"I have read a lot of reviews on this property and I always try to steer clear of the bad reviews to let myself in on the experience so I can find out When you speak on “updating” and such, you must keep in mind the Nostalgia of this sport and what this mountain has down to maintain the East Coast ..."

Reviewed on Mar 21, 2025

Kaatskill Mountain Club at Hunter Mountain
Hotel Vienna
Hotel Vienna
2.5 out of 5
107 State Route 296, Windham, NY
  • 16 min walk from Ashland Town Hall
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.2/10 Wonderful! (557 reviews)
"It was beautiful stay nice clean and staff was very friendly and welcoming I would go again!"

Reviewed on May 12, 2025

Hotel Vienna
The Graham & Co.
The Graham & Co.
3 out of 5
80 Route 214, Phoenicia, NY
  • 37 min drive from Ashland Town Hall
Stay at this 3-star business-friendly motel in Phoenicia. Enjoy free breakfast, free parking, and an outdoor pool. Popular attractions Empire State Railway Museum ...
10/10 Exceptional! (3 reviews)
"The Graham is the place to stay in the Catskills!! I stayed in the Bunkhouse and my small room had everything I needed. It was a solo trip and my room had bunk beds. That twin bed was so comfy and cozy! There were 3 bathrooms to share and the bathroom was big and sparking clean. Amazing water pressure ..."

Reviewed on Apr 26, 2025

The Graham & Co.
Eastwind Oliverea Valley
Eastwind Oliverea Valley
2 out of 5
212 McKenley Hollow Rd, Big Indian, NY
  • 39 min drive from Ashland Town Hall
Stay at this hotel in Big Indian. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Belleayre Mountain Ski Center and Slide Mountain ...
9.4/10 Exceptional! (26 reviews)
"A beautifully located and thoughtfully designed property with a warm and welcoming atmosphere - especially from Brendan and Gillian, who were both loads of fun and full of insights into the local area. Highly recommended!"

Reviewed on May 9, 2025

Eastwind Oliverea Valley
The Colonial Motel
The Colonial Motel
2.5 out of 5
37283 NY-23, Grand Gorge, NY
  • 10 min drive from Ashland Town Hall
Stay at this motel in Grand Gorge. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9.4/10 Exceptional! (349 reviews)
Stepped back in time
"I had a room in the main house, built in the 1860s and loved it. They tried to keep some of the old world charm in the room with a huge tall queen size bed with a big pile of pillows, original cast iron radiator and even the slightly squeaky wood floors under the carpet. If you love old houses like ..."

Reviewed on May 13, 2025

The Colonial Motel
Catskill Seasons Inn
Catskill Seasons Inn
2.5 out of 5
178 Route 42, Shandaken, NY
  • 29 min drive from Ashland Town Hall
Stay at this hotel in Shandaken. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Belleayre Mountain Ski Center and Copperhood Retreat ...
8/10 Very Good! (215 reviews)
"Staff who greeted us was very nice and welcoming. Easy and fast check in."

Reviewed on May 11, 2025

Catskill Seasons Inn
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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