Book The Best Hotels in Ashland, NY for 2026 from CA $121 - Fully Refundable Options

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

Go beyond your typical stay in Ashland

Pet friendly

Apartment

Pool

Hot tub

Condo

Cottage

Family friendly

Cabin

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Ashland hotels

A log cabin with a deck, outdoor seating, and a view of a forest.

A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.

A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

A cozy cabin interior with a stone fireplace, wooden walls, a dining area with a red and black checkered tablecloth, and a television mounted above the fireplace.

1. Hotel Vienna

Windham

john

CA $164

CA $201 total

includes taxes & fees

Oct 1 - Oct 2

A swimming pool with lounge chairs and potted plants.

A two-story building with a large front porch, a chimney, and a balcony.

A two-story motel with a central staircase, balconies, and a grassy front yard.

A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.

2. Moore's Motel

Prattsville

Cory

CA $169

CA $183 total

includes taxes & fees

Sep 29 - Sep 30

A covered porch with outdoor seating, a staircase, and potted plants.

A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

A cozy room with a white sofa, a wooden table with a lamp, and a chair with a patterned cushion. There's a reception desk with a computer and a sign that says "Welcome".

A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

3. The Colonial Motel

Grand Gorge

Eric

CA $110

CA $121 total

includes taxes & fees

Oct 8 - Oct 9

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

A cozy lounge area with a sofa, armchairs, a coffee table, and a bookshelf.

A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.

A bedroom with a large window offering a view of a forested mountain.

4. Hunter Lodge, a Bluebird by Lark

Hunter

Shubhangi

CA $191

CA $237 total

includes taxes & fees

Oct 25 - Oct 26

A two-story building with a balcony, surrounded by well-maintained lawns and trees.

A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

A view from a room with a glass door onto an outdoor patio. The patio has a metal table and two chairs, a small pumpkin decoration, and a metal fence.

A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

5. The Winwood Condominiums

Windham

Abdul

CA $210

CA $227 total

includes taxes & fees

Sep 27 - Sep 28

A river flowing through a forested area with rocks and autumn-colored trees.

Two white Adirondack chairs in a forest with fallen leaves.

A dining area with a wooden table and a single green chair.

A front door with a WiFi sign, a Christmas wreath, and a bear statue.

6. Black Bear Lodge

Prattsville

Gerald

CA $210

CA $227 total

includes taxes & fees

Sep 29 - Sep 30

A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

A wooden staircase leading to a second floor, a red sofa with floral cushions, and a wooden floor.

A garden with blooming pink flowers and green grass.

A dining room with a wooden table, chairs, a chandelier, and a vase of flowers.

7. Antique Rose Inn Windham

Windham

David

CA $190

CA $206 total

includes taxes & fees

Sep 29 - Sep 30

A large, two-story house with multiple porches and string lights.

A room with a wooden floor, a chair, a lamp, and a view through a window with a decorative frame.

A room with a wooden wardrobe, a bed, a nightstand, a lamp, and a fireplace.

A building with a porch and outdoor seating area.

8. Albergo Allegria Hotel

Windham

Roy

CA $245

CA $265 total

includes taxes & fees

Sep 29 - Sep 30

A bedroom with a large window, a bed, and a view of a forest.

A wooden cabin with a door, surrounded by greenery and a stone pathway.

A modern bedroom with a large bed, a view of greenery through floor-to-ceiling windows, and a wooden ceiling.

A large, multi-story wooden house with a snow-covered roof and several lit windows, surrounded by bare trees and snow.

9. The Haüs Windham

Windham

Erica

CA $174

CA $400 total

includes taxes & fees

Oct 7 - Oct 8

A park with Adirondack chairs and a table, surrounded by trees.

A lamp post in a grassy area with autumn foliage in the background.

A dining table set with breakfast items, a red mug, and a glass of orange juice.

A vintage car parked in front of a house surrounded by trees.

10. Mountain Treasure B&B

Maplecrest

Daniel

CA $234

CA $253 total

includes taxes & fees

Oct 20 - Oct 21

A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

A bar with wooden chairs, a bar counter, and various bottles and glasses.

A wooden room with a bed, a nightstand with a lamp, and a wall with tree decorations.

11. Jimmy OConnors Windham Mountain Inn

Windham

James

CA $176

CA $191 total

includes taxes & fees

Oct 26 - Oct 27

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

A park with picnic tables and chairs, a tall cylindrical structure, and autumn-colored trees.

A hallway with a wooden door leading to a bathroom, a blue couch with a cushion, and a kitchen area with cabinets and a sink.

A large tree in a grassy area with a small white building in the background.

12. SunView Motel

Tannersville

Victoria

CA $147

CA $159 total

includes taxes & fees

Oct 1 - Oct 2

A multi-story building with outdoor seating and a stone-paved patio.

A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

13. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Nuria

CA $279

CA $332 total

includes taxes & fees

Sep 29 - Sep 30

14. The Wheelhouse Inn

Pine Hill

Allen

CA $240

CA $268 total

includes taxes & fees

Oct 16 - Oct 17

A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

A covered outdoor seating area with picnic tables and umbrellas, surrounded by a forest.

A reception desk with a mirror, potted plants, a welcome sign, and a bench with patterned cushions.

A modern kitchen with dark cabinets, a brick backsplash, and a central island.

15. Starlite Motel

Big Indian

Sarah

CA $176

CA $197 total

includes taxes & fees

Sep 29 - Sep 30

A wooden cabin with a triangular roof, a wooden door, and a bench outside.

A round wooden table with a hanging light fixture, surrounded by four stools, set against a backdrop of a large window with a view of trees and a wooden deck.

A wooden cabin with a balcony, surrounded by snow-covered trees.

A triangular wooden room with a bed and pillows, a window, and a view of a forested hill.

16. Eastwind Windham

Windham

Sharon

CA $343

CA $413 total

includes taxes & fees

Oct 6 - Oct 7

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

A room with two blue armchairs, a small round table, a lamp, and a large window with curtains.

A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.

17. Wylder Hotel Windham

Windham

Yousung

CA $388

CA $490 total

includes taxes & fees

Sep 27 - Sep 28

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

A wooden-paneled bedroom with a bed, bedside tables, and a hanging light fixture.

A bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.

A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

18. Hotel Mountain Brook

Tannersville

Kristen

CA $316

CA $341 total

includes taxes & fees

Sep 30 - Oct 1

A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

A modern bathroom with a glass sink, wooden vanity, and a large mirror.

A room with a curved wooden ceiling, large windows with wooden frames, two upholstered armchairs, a round table, and a potted plant.

A bathroom with a blue-tiled shower enclosure, a shelf with toiletries, and a handheld showerhead.

19. Shadowcrest

Fleischmanns

Margo

CA $186

CA $205 total

includes taxes & fees

Sep 27 - Sep 28

A pool table with balls and a cue stick, a wooden chair, and a table with chairs in the background.

A neatly made bed with a white headboard, two bedside lamps, and a dark blue throw blanket.

A two-story building with a balcony, surrounded by dense forest.

A two-story building with a dark exterior, surrounded by a grassy area with picnic tables.

20. Catskill Seasons Inn

Shandaken

Severn

CA $226

CA $253 total

includes taxes & fees

Sep 29 - Sep 30

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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

Urban Cowboy Lodge

10/10 Excellent

"A fabulous establishment, lots to do on site!"

The Colonial Motel

10/10 Excellent

"Absolutely wonderful place to stay"

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"I love how rustic the decor is, the dog friendly policy was my ultimate favorite. My puppy, boyfriend and I had a marvelous time and stay. The staff was wonderful helped me with trails, the restaurant food was delightful and so was the bar. Will be coming back!!"

Jimmy OConnors Windham Mountain Inn

10/10 Excellent

"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."

Emerson Resort & Spa

10/10 Excellent

"If you are looking for a very peaceful, serene getaway to completely reset, book this place immediately. The quiet, beautiful atmosphere makes it a true sanctuary.The hospitality here is next level. Jackie was incredibly nice and welcoming from start to finish. Jonathan went out of his way to take gorgeous birthday pictures for me the second I asked. The absolute hero of my trip was Kristine, who literally saved me when I found myself stranded in the middle of nowhere!This team protects your peace of mind, I am telling everyone about this gem, and I am definitely coming back to the Emerson!"

SunView Motel

8/10 Good

"Quiet and comfortable! We would definitely stay here again."

Shandaken Inn

8/10 Good

"The hotel staff is very friendly and provides excellent service . The room is clean and comfortable. The breakfast is not really good. The potatoes are too spicy. We asked the waitress if we could change. She rejected directly and didn’t give us any choices. However, when we had the breakfast in second day morning, we required to change too spicy potatoes. The waitress was very nice and helped change to fruit after she talked with supervisor. If the breakfast could give more choices, the hotel would be more attractive."

Starlite Motel

10/10 Excellent

"Great place to get away for the weekend. Spent our first wedding anniversary here and couldn’t have been happier."

The Graham & Co.

8/10 Good

"The owners and staff are very friendly. Relaxing atmosphere. We stayed in the deluxe double room. The oven and refrigerator in the room could use some attention and cleaning. Bathroom well stocked but shower was basic. Could use a little refurbishing."