Search Ashland hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
9 Aug - 10 Aug
Tomorrow
10 Aug - 11 Aug
Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug

Filter by

Guest rating
Guest rating
Property class

Top hotels and accommodation in Ashland

Catskill Motor Court Motel
Enjoy a refreshing swim in the pool with a designated shallow area marked for safety.

Catskill Motor Court Motel

2.5 star property
5.8 out of 10, (105)
"Pool was filled in years ago not like the picture on Expedia. Smells like sewage. I didn’t stay. I left. Place was disgusting "
The price is NZ$172
includes taxes & fees
13 Aug - 14 Aug
Catskill Motor Court Motel
Wylder Hotel Windham
Relax in this stylish room with two armchairs and a round table, offering a view of the outdoors through the large window.

Wylder Hotel Windham

3.5 star property
8.6 out of 10, Excellent, (67)
"We LOVED staying at Wylder. The staff was super friendly and helpful. Our room was comfortable, views were amazing and we really enjoyed the amenities. Highly recommend! "
The price is NZ$523
includes taxes & fees
31 Aug - 1 Sept
Wylder Hotel Windham
Hotel Vienna
Escape to a serene retreat amidst lush greenery, with a spacious deck perfect for relaxation or entertaining.

Hotel Vienna

2.5 star property
9.4 out of 10, Exceptional, (612)
"good place to stay at"
Hotel Vienna
Eastwind Windham
Two-story house with a front entrance, wooden deck, and potted plants on the steps.

Eastwind Windham

2.0 star property
9.2 out of 10, Wonderful, (57)
"excellent place to stay with great surrounding areas to explore and helpful friendly staff. "
The price is NZ$414
includes taxes & fees
1 Sept - 2 Sept
Eastwind Windham
The Graham & Co.
Relax by the serene pool surrounded by lush greenery and lounge on the wooden deck.

The Graham & Co.

3.0 star property
9.6 out of 10, Exceptional, (14)
"Everything was great! A wonderful spot off the main road - super quiet and relaxing. Loved the nightly fire pit and breakfast each am. Really nice people and staff. Will be back! "
The price is NZ$268
includes taxes & fees
2 Sept - 3 Sept
The Graham & Co.
Catskill Seasons Inn
Escape to a serene forested hillside, surrounded by lush greenery and diverse tree species.

Catskill Seasons Inn

2.5 star property
8.2 out of 10, Very good, (221)
"Great Stay would definitely recommend "
The price is NZ$280
includes taxes & fees
20 Aug - 21 Aug
Catskill Seasons Inn
Urban Cowboy Lodge
Enjoy a traditional dining experience in our rustic restaurant with a cozy ambiance, wooden beams, and a large chandelier.

Urban Cowboy Lodge

5.0 star property
9.4 out of 10, Exceptional, (155)
"Stunning/ tranquility "
The price is NZ$287
includes taxes & fees
13 Aug - 14 Aug
Urban Cowboy Lodge
Albergo Allegria Hotel & Breakfast Restaurant
Enjoy a meal at the dining table, with a view of the surrounding landscape through the large window.

Albergo Allegria Hotel & Breakfast Restaurant

3.5 star property
9.6 out of 10, Exceptional, (266)
"Friendly, clean, beautiful setting"
The price is NZ$284
includes taxes & fees
10 Aug - 11 Aug
Albergo Allegria Hotel & Breakfast Restaurant
Antique Rose Inn Windham
Stunning two-story house with a charming porch and tower, surrounded by a serene winter landscape.

Antique Rose Inn Windham

3.0 star property
9.0 out of 10, Wonderful, (121)
"We did not expect to share a bathroom. We should of done our homework on the place. Its a lovely place to stay. Owner is very friendly, breakfast was accommodating to our wishes."
The price is NZ$244
includes taxes & fees
14 Aug - 15 Aug
Antique Rose Inn Windham
The Roxbury
The Archaeologist's Digs | Private kitchen

The Roxbury

3.0 star property
9.6 out of 10, Exceptional, (117)
"Great stuff and location."
The Roxbury
Eastwind Oliverea Valley
Relax on the deck with lounge chairs and enjoy the view from the window.

Eastwind Oliverea Valley

2.0 star property
9.4 out of 10, Exceptional, (31)
"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!"
The price is NZ$694
includes taxes & fees
1 Sept - 2 Sept
Eastwind Oliverea Valley
Starlite Motel
Enjoy al fresco dining in a serene garden setting with picnic tables and benches surrounded by lush greenery.

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (261)
"Quaint little place in the mountains, quiet. Beds were comfortable."
The price is NZ$211
includes taxes & fees
18 Aug - 19 Aug
Starlite Motel
Mountain Treasure B&B
Explore the serene rolling hills and vibrant autumn foliage along winding paths.

Mountain Treasure B&B

3.0 star property
9.4 out of 10, Exceptional, (274)
"We were greeted by the owner with a smile and very helpful information to make our stay excellent. She sat down with us to help us plan our hiking experience. The room was extremely clean and set up nicely. The food was delicious and the homemade chocolate chip cookies were the best ever! A wonderful stay and I recommend it highly."
The price is NZ$275
includes taxes & fees
17 Aug - 18 Aug
Mountain Treasure B&B
The Queen of the Catskills B&B
Stunning two-story building with a central entrance and windows on both levels, offering a warm and inviting atmosphere.

The Queen of the Catskills B&B

3.0 star property
9.2 out of 10, Wonderful, (70)
"Rooms were good size and comfortable. Breakfast was delicious and any time from 6-11 am. Hosts were friendly and accommodating."
The price is NZ$364
includes taxes & fees
18 Aug - 19 Aug
The Queen of the Catskills B&B
Meadowood Inn
Stunning two-story house with a central entrance and gabled roof, set amidst a serene winter landscape.

Meadowood Inn

3.0 star property
9.6 out of 10, Exceptional, (250)
"excellent breakfast, friendly hostess, and clean facility. "
The price is NZ$225
includes taxes & fees
17 Aug - 18 Aug
Meadowood Inn
Beds on Clouds
Stroll through lush gardens surrounded by classic columns and vibrant flowers.

Beds on Clouds

3.0 star property
7.4 out of 10, Good, (67)
"Great spot for a weekend getaway"
The price is NZ$310
includes taxes & fees
19 Aug - 20 Aug
Beds on Clouds
The Perch Hotel
1 bedroom, premium bedding, desk, cots/infant beds

The Perch Hotel

2.0 star property
9.2 out of 10, Wonderful, (11)
"Wonderful hotel i will recommend "
The price is NZ$294
includes taxes & fees
21 Aug - 22 Aug
The Perch Hotel
The Haüs Windham
Cozy attic bedroom with a large bathroom, bathtub, and comfortable bed.

The Haüs Windham

2.0 star property
8.0 out of 10, Very good, (10)
"Great place nice and clean"
The Haüs Windham
River Run Bed and Breakfast
Step into the charm of Kroer Ruin bed & breakfast, where a traditional porch invites relaxation amidst a serene garden setting.

River Run Bed and Breakfast

3.0 star property
9.2 out of 10, Wonderful, (192)
"Ben is a great host! Has a wealth of information about the area. Breakfast is yummy."
The price is NZ$275
includes taxes & fees
20 Aug - 21 Aug
River Run Bed and Breakfast
Shadowcrest
Enjoy a refreshing bathroom experience with a glass-enclosed sink and large mirror.

Shadowcrest

3.5 star property
9.8 out of 10, Exceptional, (252)
"Brendan was very friend. We had a very relaxing stay. We felt like we had the place to ourselves, it was so quiet. Bed was very comfortable so slept very well. Bath was nicely remodeled. It was the perfect location for us to attend a local wedding."
The price is NZ$241
includes taxes & fees
18 Aug - 19 Aug
Shadowcrest
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Ashland

Venture to sights like Ashland Town Hall as you discover the local area in Ashland.

See all hotels in Ashland

Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Spacious room, comfortable. nice staff. Facilities well equipped equipped "
Rivka 2-night trip
Posted 2 days ago
Hotel Vienna

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 at Hunter Mountain. See all available top hotels, or vacation rentals in Ashland.

What are some of the best holiday rentals that Ashland has to offer?

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores: This holiday home rental outside of Ashland is located in the city centre, and offers a balcony, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. 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 at Hunter Mountain and The Colonial Motel 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.