Find hotels in Ashland, NY from ฿3,048

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24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for Ashland hotels

Interior
The Haüs Windham

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.6 out of 10, Excellent, (19)
"Very good"
United States
Sophia
The price is ฿5,252
฿8,192 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Haüs Windham
Classic Double Room, 1 King Bed with Sofa bed, Non Smoking | Iron/ironing board, free WiFi, bed sheets
The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club
2.5 star property
Windham
8.0 out of 10, Very good, (3)
"Cozy and warm. I think it would be better to visit during the winter season"
United States
TAEJUN
The price is ฿7,777
฿8,399 total
includes taxes & fees
25 Dec - 26 Dec
The Outpost by Windham Mountain Club
Porch
Beds on Clouds

Beds on Clouds

Beds on Clouds
3.0 star property
Windham
7.4 out of 10, Good, (68)
"Great spot for a weekend getaway"
United States
Bertrand
The price is ฿5,867
฿6,336 total
includes taxes & fees
6 Jan - 7 Jan 2026
Beds on Clouds
Front of property
Cave Mountain Motel

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (135)
"I enjoyed my stay here. I found the owner to have a good sense of humor. They have a light breakfast and coffee available. The room had everything I needed to have a comfortable stay. Check in went smoothly."
United States
Alexander
The price is ฿4,324
฿4,670 total
includes taxes & fees
12 Jan - 13 Jan 2026
Cave Mountain Motel
Exterior
Fairlawn Inn

Fairlawn Inn

Fairlawn Inn
3.0 star property
Hunter
8.8 out of 10, Excellent, (436)
"Lovely stay"
United States
Deborah
The price is ฿8,056
฿8,701 total
includes taxes & fees
24 Jan - 25 Jan 2026
Fairlawn Inn
Front of property
Antique Rose Inn Windham

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (125)
"Very entertaining owner, comfortable bed, quiet at night, bathroom shareable with the other two rooms, all very clean and cure for details. Great breakfast, not very far from Windham. "
United States
Simona
The price is ฿4,199
฿4,535 total
includes taxes & fees
25 Dec - 26 Dec
Antique Rose Inn Windham
Front of property
Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant
3.5 star property
Windham
9.6 out of 10, Exceptional, (270)
"Nice people and great breakfast. "
United States
Remelin
The price is ฿4,164
฿4,498 total
includes taxes & fees
4 Jan - 5 Jan 2026
Albergo Allegria Hotel & Breakfast Restaurant
Premium bedding, desk, cots/infant beds, rollaway beds
The Perch Hotel

The Perch Hotel

The Perch Hotel
2.0 star property
Cornwallville
9.4 out of 10, Exceptional, (22)
"Lovely stay"
United States
Barry
The price is ฿18,116
฿19,565 total
includes taxes & fees
26 Dec - 27 Dec
The Perch Hotel
View from property
Black Bear Lodge

Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (131)
"A great place to stay in the Catskills at a reasonable price point. "
United States
Peter
The price is ฿4,635
฿5,006 total
includes taxes & fees
11 Jan - 12 Jan 2026
Black Bear Lodge
Front of property
Meadowood Inn

Meadowood Inn

Meadowood Inn
3.0 star property
Arkville
9.6 out of 10, Exceptional, (266)
"I cant say enough positive things when it comes to the Meadowood Inn. Our hostess was informative, friendly, and cooked us up a gourmet breakfast each morning to get us on our way. The Inn itself was truly charming and we were excited to learn about the history of the house. I have stayed at a good amount of B&B's, and the cleanliness at the Inn was above excellent, spotless! "
United States
christoph
Meadowood Inn
Exterior
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.8 out of 10, Excellent, (344)
"convenient nice and clean residence with kitchen and market nearby."
United States
Jatin
The price is ฿5,881
฿6,351 total
includes taxes & fees
25 Dec - 26 Dec
Winwood Condominiums by Windham Mountain Club
Exterior
Wylder Hotel Windham

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.6 out of 10, Excellent, (89)
"Spotless room and great staff "
United States
Josue
The price is ฿6,401
฿8,469 total
includes taxes & fees
25 Dec - 26 Dec
Wylder Hotel Windham
Lushna Suite | Living area
Eastwind Windham

Eastwind Windham

Eastwind Windham
2.0 star property
Windham
9.4 out of 10, Exceptional, (76)
"I loved our stay!"
United States
Erika
The price is ฿7,547
฿9,086 total
includes taxes & fees
25 Dec - 26 Dec
Eastwind Windham
Outdoor pool
Moore's Motel

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (158)
"Stay here every time we are in the area. And its always a great stay and a good time down the street at the prattsville tavern. Moores is excellent"
United States
John
The price is ฿3,733
฿4,031 total
includes taxes & fees
25 Dec - 26 Dec
Moore's Motel
Property grounds
Catskill Motor Court Motel

Catskill Motor Court Motel

Catskill Motor Court Motel
2.5 star property
Catskill
5.8 out of 10, (124)
"."
United States
Jennifer
The price is ฿3,370
฿3,639 total
includes taxes & fees
25 Dec - 26 Dec
Catskill Motor Court Motel
Mountain view
Catskill Seasons Inn

Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.2 out of 10, Very good, (241)
"Great Stay would definitely recommend "
United States
Jay
The price is ฿4,635
฿5,191 total
includes taxes & fees
4 Jan - 5 Jan 2026
Catskill Seasons Inn
View from room
Hotel Vienna

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (726)
"Great service, nice and clean hotel."
United States
Mary
Hotel Vienna
Property grounds
The Wheelhouse Inn

The Wheelhouse Inn

The Wheelhouse Inn
2.5 star property
Pine Hill
8.6 out of 10, Excellent, (129)
"Great host, large and cozy rooms."
United States
Mohamed
The price is ฿2,801
฿3,137 total
includes taxes & fees
10 Jan - 11 Jan 2026
The Wheelhouse Inn
Front of property
Shadowcrest

Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (267)
"Room was clean and cozy, bathroom was very nice with heated floors. Comfy bed. Brendan was awesome! Very charming, would definitely stay again."
United States
Peter
The price is ฿5,039
฿5,543 total
includes taxes & fees
16 Jan - 17 Jan 2026
Shadowcrest
Reception
Margaretville Motel

Margaretville Motel

Margaretville Motel
2.5 star property
Margaretville
6.8 out of 10, (187)
"A little different than the normal hotel experience bu nice room very quiet and breakfast with a lot choice "
United States
William
The price is ฿2,644
฿3,406 total
includes taxes & fees
4 Jan - 5 Jan 2026
Margaretville 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.
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Stay near popular Ashland attractions

Ashland Town Hall

Ashland Town Hall is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels?
See properties

Top Ashland Hotel Reviews

The Haüs Windham

The Haüs Windham

10/10 Excellent
"Clean and excellent space. We love it."
Emanuel 2-night trip
Posted 3 weeks ago
The Haüs Windham

More cheap stays in Ashland

The Colonial Motel

The Colonial Motel

37283 NY-23 Grand Gorge NY
The price is ฿2,772 per night from 11 Jan to 12 Jan
฿2,772
฿3,048 total
11 Jan - 12 Jan 2026
includes taxes & fees
9.4/10 Exceptional! (406 reviews)

Frequently asked questions

What's the best place for a stay in Ashland?
Hunter Lodge, a Bluebird by Lark, located 11.5 mi (18.4 km) from the heart of Ashland, is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Hotel Vienna and Kaatskill Mountain Club & Condos by Vail Resorts. See all available top hotels, or vacation rentals in Ashland.
If I need to cancel my hotel reservation in Ashland, will I receive a refund?
Yes, most hotel room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Ashland.
What are some accommodation options with pools in Ashland?
Hotel Vienna: Hotel located near Windham Mountain Resort. Offers daily, an indoor pool and free self parking. Kaatskill Mountain Club & Condos by Vail Resorts and Emerson Resort & Spa are two additional hotels with an on-site pool. View all hotels with pools in Ashland.
What is staying in Ashland like?
Visitors to Ashland will definitely find plenty to explore and enjoy. A top sight in the area is Hunter Mountain. In Ashland, there are 8 hotels and other accommodation options to choose from. Find out more about Ashland.
What should I do while I'm visiting Ashland?
A favourite place to visit is Ashland Town Hall. Additionally, you'll find Hunter Mountain in the area. Take a look at what more there is to see and do in Expedia's Ashland guide.
What's the weather like in Ashland?
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 Ashland are January, March, December and November, with each month seeing an average of 18 cm of snowfall.

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