Find hotels in Ashland, NY from Rp1.644.146

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24 Dec - 25 Dec
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25 Dec - 26 Dec
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26 Dec - 28 Dec
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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)
Experience the charm of this mountain retreat just minutes from Windham Mountain Resort. Enjoy complimentary WiFi and parking while exploring nearby skiing and snowboarding trails. Windham Country Club awaits after a day of alpine adventure.
"Very good"
United States
Sophia
The price is Rp2.834.317
Rp4.420.810 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)
Stay steps from Windham Mountain Resort with this hotel's free ski shuttle and WiFi. After hitting the slopes, unwind in the outdoor pool. Windham Country Club is nearby, and free parking adds convenience to your mountain getaway.
"Cozy and warm. I think it would be better to visit during the winter season"
United States
TAEJUN
The price is Rp4.196.750
Rp4.532.490 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)
Tranquil retreat near Windham Mountain Resort and Country Club. Enjoy rejuvenating massages and manicures after a day outdoors. Free WiFi and parking enhance your stay, with garden and terrace spaces for relaxation.
"Great spot for a weekend getaway"
United States
Bertrand
The price is Rp3.164.142
Rp3.417.139 total
includes taxes & fees
5 Jan - 6 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)
Embrace alpine charm at this motel with complimentary buffet breakfast, WiFi, and parking. Just 5 minutes from Windham Mountain Resort, it offers easy access to hiking trails, vineyards, and winery attractions.
"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 Rp2.332.003
Rp2.518.563 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cave Mountain Motel
Exterior
Fairlawn Inn

Fairlawn Inn

Fairlawn Inn
3.0 star property
Hunter
8.8 out of 10, Excellent, (436)
Wake up to free breakfast at this cosy B&B, just minutes from Hunter Mountain. Winter sports enthusiasts will find prime skiing nearby, while summer offers mountain biking adventures. Convenient free parking enhances your Catskills escape.
"Lovely stay"
United States
Deborah
The price is Rp4.345.243
Rp4.692.862 total
includes taxes & fees
10 Jan - 11 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)
Ski enthusiasts will love this charming bed & breakfast, offering free perks like a daily full breakfast, WiFi, and parking. The Victorian property includes a terrace and garden, with ski passes available. Located near Windham Country Club.
"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 Rp2.264.895
Rp2.446.087 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)
Surrounded by outdoor adventure, this charming B&B offers free WiFi and parking just 5 minutes from skiing. Hiking trails, kayaking, and mountain biking await, while the garden, terrace, and bike cleaning station welcome you back after exploring.
"Nice people and great breakfast. "
United States
Remelin
The price is Rp2.245.937
Rp2.425.786 total
includes taxes & fees
5 Jan - 6 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)
Set in Cornwallville, this hotel provides easy access to Windham Mountain Resort, just a 15-minute drive away. Guests enjoy premium bedding, free WiFi, and complimentary parking, with Zoom Flume and Durham Centre Museum nearby.
"Lovely stay"
United States
Barry
The price is Rp9.776.749
Rp10.558.889 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)
Peaceful lodging surrounded by nature, where complimentary parking and WiFi enhance your stay. Close to Ashland Park and Bearpen Mountain State Forest, this tranquil motel offers daily housekeeping for a refreshing mountain getaway.
"A great place to stay in the Catskills at a reasonable price point. "
United States
Peter
The price is Rp2.499.773
Rp2.699.755 total
includes taxes & fees
5 Jan - 6 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)
Mountain views surround this cosy B&B with local cuisine breakfast included daily. Guests praise the helpful staff and proximity to hiking trails, mountain biking, and skiing at Belleayre. Delaware & Ulster Railway offers nearby scenic adventures.
"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 Rp3.171.692
Rp3.425.360 total
includes taxes & fees
5 Jan - 6 Jan 2026
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)
Splash in the outdoor pool at this mountain getaway, just 5 minutes from Windham Mountain Resort. Enjoy refreshments at the coffee shop or bar after a day of adventure. Free WiFi and parking add convenience to your stay.
"Spotless room and great staff "
United States
Josue
The price is Rp3.454.513
Rp4.570.223 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)
Surrounded by scenic beauty, this hotel offers easy access to Windham Mountain Resort and Country Club. Enjoy relaxation with free WiFi and parking while unwinding with a drink at the welcoming bar after an adventurous day.
"I loved our stay!"
United States
Erika
The price is Rp4.072.694
Rp4.903.483 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)
Tranquil accommodation provide a restful atmosphere at this Prattsville motel. Take a refreshing dip in the outdoor pool after exploring nearby Pratt Museum. Free WiFi and parking add value to this peaceful getaway.
"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 Rp2.013.240
Rp2.174.299 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)
Discover the charm of this countryside motel with free WiFi and parking. Enjoy easy access to Hudson's attractions while exploring the beautiful falls nearby. Daily housekeeping ensures a comfortable and refreshing stay in the Catskills.
"."
United States
Jennifer
The price is Rp1.817.508
Rp1.962.908 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)
Tucked away in the Catskills, this charming inn offers a seasonal outdoor pool and tennis courts. Just minutes from Belleayre Mountain Ski Centre with free breakfast, WiFi and parking for a relaxing mountain retreat.
"Great Stay would definitely recommend "
United States
Jay
The price is Rp2.499.773
Rp2.799.746 total
includes taxes & fees
5 Jan - 6 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)
Unwind at this mountain retreat featuring an indoor pool and complimentary breakfast. Borrow free bikes to explore nearby trails or take a 5-minute drive to hit the slopes at Windham Mountain Resort. Guests rave about the helpful staff and prime location.
"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)
Free perks elevate this mountain retreat. The hotel offers complimentary WiFi and parking, with Belleayre Mountain Ski Centre and Pine Hill Community Centre just moments away for outdoor adventures.
"Great host, large and cozy rooms."
United States
Mohamed
The price is Rp1.509.930
Rp1.691.122 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 Rp2.717.874
Rp2.989.661 total
includes taxes & fees
3 Jan - 4 Jan 2026
Shadowcrest
Reception
Margaretville Motel

Margaretville Motel

Margaretville Motel
2.5 star property
Margaretville
6.8 out of 10, (187)
Located in Margaretville, this motel offers free continental breakfast, WiFi, and parking. Explore nearby East Branch Delaware River or take a scenic ride on the Delaware & Ulster Railway. Perfect for a tranquil mountain getaway.
"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 Rp1.426.045
Rp1.837.082 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

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

10/10 Excellent
"Clean rooms"
Christopher 1-night trip
Posted 3 months ago
Winwood Condominiums by Windham Mountain Club
Phoenicia Lodge

Phoenicia Lodge

10/10 Excellent
"Nice service and nice room. Exactly what you pay for!"
Adam 1-night trip
Posted 3 months ago
Phoenicia Lodge

More cheap stays in Ashland

The Colonial Motel

The Colonial Motel

37283 NY-23 Grand Gorge NY
The price is Rp1.494.831 per night from 28 Dec to 29 Dec
Rp1.494.831
Rp1.644.146 total
28 Dec - 29 Dec
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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