Search Ashland hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Ashland hotels

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
Property grounds
Emerson Resort & Spa

Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.2 out of 10, Wonderful, (46)
"The resort is very clean and quiet."
United States
Bianca
The price is AU$426
includes taxes & fees
6 Jan - 7 Jan 2026
Emerson Resort & Spa
Interior detail
Urban Cowboy Lodge

Urban Cowboy Lodge

Urban Cowboy Lodge
5.0 star property
Big Indian
9.2 out of 10, Wonderful, (189)
"Room with hot tub outside was amazing especially in the winter !"
United States
Maria
The price is AU$317
includes taxes & fees
4 Jan - 5 Jan 2026
Urban Cowboy Lodge
Property entrance
The Colonial Motel

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.4 out of 10, Exceptional, (406)
"Best shower head, comfy beds and great pool!"
United States
paula
Travelling for leisure
The price is AU$146
includes taxes & fees
28 Dec - 29 Dec
The Colonial Motel
Exterior
Mountain Treasure B&B

Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (287)
"Our room was clean and tastefully decorated."
United States
Megan
The price is AU$231
includes taxes & fees
25 Dec - 26 Dec
Mountain Treasure B&B
Front of property
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
Exterior
Deer Mountain Inn

Deer Mountain Inn

Deer Mountain Inn
2.0 star property
Haines Falls
9.2 out of 10, Wonderful, (5)
"I loved the guest room with the pool table and self attend bar."
United States
Chavez
The price is AU$624
includes taxes & fees
6 Jan - 7 Jan 2026
Deer Mountain Inn
Exterior
Kaatskill Mountain Club & Condos by Vail Resorts

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, (323)
"Our room was very spacious, comfortable and clean."
United States
Lauren
Travelling for leisure
The price is AU$389
includes taxes & fees
6 Jan - 7 Jan 2026
Kaatskill Mountain Club & Condos by Vail Resorts
Exterior
Hotel Mountain Brook

Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
Tannersville
9.8 out of 10, Exceptional, (516)
"Fire pit in the garden was great."
United Kingdom
Patricia
Travelling for leisure
The price is AU$240
includes taxes & fees
6 Jan - 7 Jan 2026
Hotel Mountain Brook
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
6 Jan - 7 Jan 2026
Antique Rose Inn Windham
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
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
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
31 Dec - 1 Jan 2026
Moore's Motel
Dinner served
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (828)
"Room was very clean and fresh."
United States
Ronald
The price is AU$281
includes taxes & fees
8 Jan - 9 Jan 2026
Hunter Lodge, a Bluebird by Lark
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$313
includes taxes & fees
26 Dec - 27 Dec
Meadowood Inn
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)
"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
Free self-parking
Xenia Resort

Xenia Resort

Xenia Resort
2.5 star property
Jewett
9.0 out of 10, Wonderful, (56)
"Family friendly resort with great optional dinner and breakfast. The owner is very friendly and accommodating to guest's need. Great location for ski trip. "
United States
Eastlyn
The price is AU$242
includes taxes & fees
25 Dec - 26 Dec
Xenia Resort
Lushna Suite | Living area
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
Fireplace
The Graham & Co.

The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.6 out of 10, Exceptional, (22)
"the bathroom was big and sparking clean"
United States
Erika
Travelling for leisure
The price is AU$259
includes taxes & fees
4 Jan - 5 Jan 2026
The Graham & Co.
Dining
Phoenicia Lodge

Phoenicia Lodge

Phoenicia Lodge
2.0 star property
Phoenicia
9.2 out of 10, Wonderful, (32)
"Had a great stay! "
United States
Lace
The price is AU$177
includes taxes & fees
6 Jan - 7 Jan 2026
Phoenicia Lodge
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Great Spacious Room. The Front Desk Staff were super welcoming and very helpful. Highly Recommended. "
Arthur 1-night trip
Posted 2 days ago
Hotel Vienna

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.

Explore a world of travel with Expedia