Best Ashland Hotels in 2026 from HK$768 - Fully Refundable Options

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Our top choices for Ashland hotels

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

A wooden covered bridge in a forested area with a paved path leading to it.

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.

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

1. Hotel Vienna

Windham

mordechai

HK$910

HK$1,119 total

includes taxes & fees

24 Aug - 25 Aug

A swimming pool with lounge chairs and potted plants.

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

A hotel room with two beds, a desk, a chair, and a TV on a stand.

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

2. Moore's Motel

Prattsville

Dylan

HK$941

HK$1,016 total

includes taxes & fees

24 Aug - 25 Aug

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

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".

3. The Colonial Motel

Grand Gorge

Juerg

HK$699

HK$768 total

includes taxes & fees

24 Aug - 25 Aug

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 compact living space with a kitchen, dining area, and seating.

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.

4. The Winwood Condominiums

Windham

Abdul

HK$1,306

HK$1,410 total

includes taxes & fees

25 Aug - 26 Aug

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

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.

A wooden sign for Black Bear Lodge with a phone number.

5. Black Bear Lodge

Prattsville

Gerald

HK$1,168

HK$1,262 total

includes taxes & fees

24 Aug - 25 Aug

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

A modern living room with a large window, a blue sofa, a wooden coffee table, and a rustic wooden wall.

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

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

6. Hunter Lodge, a Bluebird by Lark

Hunter

sarah

HK$993

HK$1,242 total

includes taxes & fees

7 Sept - 8 Sept

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

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

A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

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

7. Wylder Hotel Windham

Windham

Shardei

HK$1,711

HK$2,240 total

includes taxes & fees

26 Aug - 27 Aug

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 cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.

8. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

jason

HK$1,394

HK$1,660 total

includes taxes & fees

31 Aug - 1 Sept

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 bar area with wooden beams, a bar counter, and four bar stools.

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

9. Eastwind Windham

Windham

Claire

HK$1,417

HK$1,750 total

includes taxes & fees

25 Aug - 26 Aug

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

A building with a porch and outdoor seating area.

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

A grassy field with a wooden structure overhead, possibly a gazebo or pavilion.

10. Albergo Allegria Hotel

Windham

Roy

HK$1,362

HK$1,471 total

includes taxes & fees

24 Aug - 25 Aug

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

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

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

11. Jimmy OConnors Windham Mountain Inn

Windham

Amy

HK$1,164

HK$1,257 total

includes taxes & fees

24 Aug - 25 Aug

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 well-lit hallway with a wooden staircase, a decorative vase, and a dining area with a table and chairs.

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

12. Mountain Treasure B&B

Maplecrest

Daniel

HK$1,145

HK$1,237 total

includes taxes & fees

24 Aug - 25 Aug

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.

13. Antique Rose Inn Windham

Windham

David

HK$1,058

HK$1,143 total

includes taxes & fees

31 Aug - 1 Sept

A room with a view of a landscape through a window, a chair, a table with a laptop, and a bed with books on it.

A chair with a blanket, a potted plant, and a view of a snowy landscape through a glass door.

A staircase leading to a room with a stone floor, a potted plant, and a wooden chair.

A spacious living area with a wooden floor, leather sofas, and a dining table.

14. The Perch Hotel

East Windham

Jason

HK$1,273

HK$1,375 total

includes taxes & fees

27 Aug - 28 Aug

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

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.

A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

15. The Haüs Windham

Windham

"Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up...

Raven Jane

HK$653

HK$1,881 total

includes taxes & fees

21 Sept - 22 Sept

A wooden staircase with a natural, tree-like design leading to a room with a stone wall and a door.

A rustic wooden structure with a natural, forest-like setting.

A wooden staircase with a natural, forest-like design, leading to a room with a rustic door.

A forest-themed interior with a wooden bridge, a statue, and a wall with a circular window.

16. The Roxbury

Roxbury

Jennifer

HK$2,321

HK$2,710 total

includes taxes & fees

24 Aug - 25 Aug

17. Windham NY Escape

Hensonville

Miguel

HK$3,363

HK$4,252 total

includes taxes & fees

24 Aug - 25 Aug

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

A modern hotel lobby with a wooden floor, a reception desk, two patterned armchairs, a chandelier, and a view of the outdoors through a glass door.

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

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

Qiang

HK$1,403

HK$1,516 total

includes taxes & fees

14 Sept - 15 Sept

A large, white, two-story building with a symmetrical facade, central entrance, and columns.

A grand hallway with ornate stained glass windows, a central column, and a chandelier.

A fireplace with a mantel displaying framed photos, a clock, and a tiled backsplash.

A bedroom with a large bed, a chandelier, a mirror, and a door.

19. The Queen of the Catskills B&B

Stamford

john

HK$1,305

HK$1,436 total

includes taxes & fees

28 Aug - 29 Aug

A large, multi-story house with a prominent tower, surrounded by a well-maintained lawn and trees.

A richly decorated living room with a sofa, a coffee table, and a colorful stained glass lamp.

A pathway lined with trees and illuminated string lights, leading to a building with a visible entrance.

A covered porch with a red floor, potted plants, and red umbrellas.

20. Fairlawn Inn

Hunter

Rachel

HK$2,031

HK$2,193 total

includes taxes & fees

20 Sept - 21 Sept

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Top Ashland Hotel Reviews

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"Nice and cozy room Room was so clean 😍"

The Colonial Motel

10/10 Excellent

"This place is much more than a motel. Surprised by newly renovated room with fridge and microwave as well as keurig coffee maker with adequate supplies, closet space, etc. Very friendly staff and a quiet town. Parking right outside the room is a great plus. There is also space outside the room with a chair to sit down and enjoy the summer. Great place and I will stay again."

The Graham & Co.

10/10 Excellent

"This recently renovated hotel is delightfully retro chic. Comfortable, clean, and well run. Three fire pits make for fun evenings with children eating s'mores. Coffee ready every morning (with real milk and cream) in the reception area and continental breakfasts delivered to your door on weekends. Lovely pool area. Short walk to downtown Phoenicia shops and restaurants. We enjoyed our stay!"

Hotel Mountain Brook

10/10 Excellent

"such a fun getaway! Staff were very helpful and showed a lot of care. Would recommend!!"

The Hidden Inn

10/10 Excellent

"Very clean. We chose a smaller room and it had everything we needed without losing character or feeling cramped. Restaurant was very good, albeit expensive. The continental breakfast was nice. Inn has been beautifully restored- a lot of care and time went into the choices. We really enjoyed the breakfast area view and sunshine. Nice trail behind the Inn- goes 14 miles if you have the time and energy!!"

Catskill Seasons Inn

8/10 Good

"My experience was very good as I stayed there for two nights as I was attending a wedding in that area. I didn't use lots of amenities they provided such as pool , bar, etc. The staff was very helpful over the phone and the rooms are very clean."

Phoenicia Lodge

10/10 Excellent

"Amazing spot!!!! Beautiful location in the mountains. You deffinetly feel like you're getting away from everything when you stay the night here. Peaceful. The lady Sandra at the front was so sweet and gave such great hospitality!!! 10/10!!! Their shower is hot and the bathrooms are clean. Bed had excellent amount of pillows.... Definitely making this a yearly stay!!!!"

Eastwind Windham

10/10 Excellent

"The staff was friendly and the room was clean and comfortable. Would love to come back again!"

Emerson Resort & Spa

8/10 Good

"The Emerson is a great resort/spa. Our room was just beautiful, clean , and comfortable. However, you will need to plan your stay well before you arrive since spa treatments book up quickly. My stay was spur of the moment so there was no availability, not even for a pedicure. Also be advised that there is no cell service (didn’t matter to me) but there is WiFi. I was aware that the restaurant was closed on the days of my stay so I can’t comment on the food. Even though this is a nice place, I don’t think I’ll be staying here again."