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Check prices for these dates

Tonight
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

Presidential Duplex, Fireplace, Mountain View
The Haüs Windham

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.6 out of 10, Excellent, (19)
"Great service with the front desk calls and extra towels provided no problem!"
United States
Deana
Travelling with family
The price is AU$390
includes taxes & fees
13 Jan - 14 Jan 2026
The Haüs Windham
Lobby sitting area
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 AU$403
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 AU$304
includes taxes & fees
25 Dec - 26 Dec
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)
"The location was pretty convenient as well!"
United States
Tanya
Travelling with partner
The price is AU$224
includes taxes & fees
4 Jan - 5 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 Bed and Breakfast in convenient picturesque location in Hunter, NY."
United States
Sudhanshu
The price is AU$417
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)
"Lastly, the landlord/hostess, Laureen, always had positive vibes and friendly at all times."
United States
DAWN
Travelling for leisure
The price is AU$218
includes taxes & fees
25 Dec - 26 Dec
Antique Rose Inn Windham
Room 15
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)
"Beautiful, unique hotel with comfortable bed and delicious breakfast."
United States
Sue
The price is AU$216
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)
"Beautiful weekend here at this hotel with great views from our room."
United States
Ryan
Travelling for leisure
The price is AU$938
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)
"The room was very clean and well appointed with a fridge and microwave."
United States
kathleen
Travelling for leisure
The price is AU$240
includes taxes & fees
4 Jan - 5 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)
"The location was extremely convenient."
Canada
Karl
Travelling with partner
The price is AU$311
includes taxes & fees
26 Dec - 27 Dec
Meadowood Inn
Seasonal outdoor pool
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)
"And excellent room (clean linen) and big windows in thr dinning area."
United States
Megha
Travelling with small children
The price is AU$305
includes taxes & fees
25 Dec - 26 Dec
Winwood Condominiums by Windham Mountain Club
The Windham Mountain View King with Balcony
Wylder Hotel Windham

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.6 out of 10, Excellent, (89)
"Our room was comfortable, views were amazing and we really enjoyed the amenities."
United States
Nicole
Travelling for leisure
The price is AU$406
includes taxes & fees
25 Dec - 26 Dec
Wylder Hotel Windham
Pet-friendly
Eastwind Windham

Eastwind Windham

Eastwind Windham
2.0 star property
Windham
9.4 out of 10, Exceptional, (76)
"Loved drinking mulled wine by the window after long ski day at Windham."
United States
David
Travelling with family
The price is AU$417
includes taxes & fees
28 Dec - 29 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)
"20 minutes to ski slopes, otherwise excellent."
United States
Geoffrey
Travelling with family
The price is AU$193
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 AU$175
includes taxes & fees
4 Jan - 5 Jan 2026
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)
"Room was clean and well appointed."
United States
Sarah
Travelling for leisure
The price is AU$249
includes taxes & fees
4 Jan - 5 Jan 2026
Catskill Seasons Inn
Exterior
Hotel Vienna

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (726)
"Our room was spacious and clean."
United States
Tsafrir
Travelling with family
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)
"room was nice and big for the fam"
United States
richard
Travelling for leisure
The price is AU$150
includes taxes & fees
10 Jan - 11 Jan 2026
The Wheelhouse Inn
The Turquoise Room | Bathroom
Shadowcrest

Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (267)
"Room was very quiet and clean"
United States
William
Travelling for business
The price is AU$266
includes taxes & fees
3 Jan - 4 Jan 2026
Shadowcrest
Room, 2 Queen Beds
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 AU$163
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

Recent Reviews in Ashland

Eastwind Windham

Eastwind Windham

10/10 Excellent
"Beautiful property , friendly staff, felt like a home "
DAndra 1-night trip
Posted 11 hours ago
Eastwind Windham

More cheap accommodation in Ashland

The Colonial Motel

The Colonial Motel

37283 NY-23 Grand Gorge NY
The price is AU$146 per night from 28 Dec to 29 Dec
AU$146
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.
What are some of the best holiday rentals that Ashland has to offer?
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend: This holiday home rental outside of Ashland is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. See all 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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