𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Ashland (2026)

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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 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.

1. Hotel Vienna

Windham

Jerrold

S$181

includes taxes & fees

14 Sept - 15 Sept

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 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.

2. Moore's Motel

Prattsville

Dylan

S$165

includes taxes & fees

1 Sept - 2 Sept

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.

3. Hunter Lodge, a Bluebird by Lark

Hunter

Yaacov

S$202

includes taxes & fees

10 Sept - 11 Sept

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.

Two white Adirondack chairs in a forest with fallen leaves.

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

4. Black Bear Lodge

Prattsville

Gerald

S$205

includes taxes & fees

1 Sept - 2 Sept

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

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 swimming pool with a fenced deck, lounge chairs, and umbrellas.

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

5. The Colonial Motel

Grand Gorge

Eric

S$121

includes taxes & fees

7 Sept - 8 Sept

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.

6. 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

S$423

includes taxes & fees

1 Sept - 2 Sept

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

A garden with blooming pink flowers and green grass.

A covered outdoor seating area with wicker chairs and a table, surrounded by white railings and hanging planters.

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

7. Antique Rose Inn Windham

Windham

David

S$186

includes taxes & fees

1 Sept - 2 Sept

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.

8. Mountain Treasure B&B

Maplecrest

Daniel

S$201

includes taxes & fees

1 Sept - 2 Sept

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.

9. Jimmy OConnors Windham Mountain Inn

Windham

Amy

S$196

includes taxes & fees

1 Oct - 2 Oct

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 building with a porch and outdoor seating area.

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

10. Albergo Allegria Hotel

Windham

Roy

S$239

includes taxes & fees

1 Sept - 2 Sept

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

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

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.

11. The Winwood Condominiums

Windham

Abdul

S$246

includes taxes & fees

1 Sept - 2 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 staircase leading to a room with a stone floor, a potted plant, and a wooden chair.

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

A spacious indoor area with a long wooden floor, a central seating area with a sofa and chairs, and a pool table.

12. The Perch Hotel

East Windham

Jason

S$223

includes taxes & fees

3 Sept - 4 Sept

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

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

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.

13. Wylder Hotel Windham

Windham

Shardei

S$416

includes taxes & fees

2 Sept - 3 Sept

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

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

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.

14. Eastwind Windham

Windham

Claire

S$376

includes taxes & fees

1 Oct - 2 Oct

15. The Wheelhouse Inn

Pine Hill

Allen

S$128

includes taxes & fees

19 Sept - 20 Sept

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

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

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

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

16. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

jason

S$285

includes taxes & fees

30 Sept - 1 Oct

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.

17. Hotel Mountain Brook

Tannersville

Qiang

S$241

includes taxes & fees

7 Sept - 8 Sept

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

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

A hotel room with a bed, white curtains, and wall-mounted light fixtures.

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

18. Shadowcrest

Fleischmanns

Margo

S$168

includes taxes & fees

2 Sept - 3 Sept

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

A bathroom with three sinks, a trash can, and a chair.

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.

19. SunView Motel

Tannersville

Arnold

S$182

includes taxes & fees

1 Sept - 2 Sept

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

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

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

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

20. Starlite Motel

Big Indian

Sarah

S$178

includes taxes & fees

1 Sept - 2 Sept

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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

Hotel Vienna

10/10 Excellent

"We really enjoyed the experience."

The Colonial Motel

10/10 Excellent

"Great place to stay!"

Phoenicia Lodge

8/10 Good

"Friendly staff"

Meadowood Inn

10/10 Excellent

"Lovely. Accommodating. Owner/host was delightful. Breakfast was out of this world. I’d stay here every time I’m in town if available."

Hotel Mountain Brook

10/10 Excellent

"Very cute place. Mountains air. Yummy breakfast"

The Graham & Co.

10/10 Excellent

"Wonderful 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."

Jimmy OConnors Windham Mountain Inn

8/10 Good

"This place is definitely dated but it was clean and the beds were comfortable. Chose to stay here when riding into tue area on the bike becasue of it had a detached restaurant/bar which makes dinner easier. Food was ok and bar was cool."

More cheap stays in Ashland

The Colonial Motel

37283 NY-23 Grand Gorge NY

S$121

7 Sept - 8 Sept

includes taxes & fees

9.6/10 Exceptional! (484 reviews)

Moore's Motel

14672 Main Street Prattsville NY

S$165

1 Sept - 2 Sept

includes taxes & fees

8.8/10 Excellent! (176 reviews)

Starlite Motel

8722 Route 28 Big Indian NY

S$178

1 Sept - 2 Sept

includes taxes & fees

Catskill Seasons Inn

178 Route 42 Shandaken NY

S$228

1 Sept - 2 Sept

includes taxes & fees

Phoenicia Lodge

5987 New York 28 Phoenicia NY

S$247

7 Sept - 8 Sept

includes taxes & fees

9/10 Wonderful! (65 reviews)

Kaatskill Mountain Club & Condos by Vail Resorts

61 LIFTSIDE DR Hunter NY

S$285

30 Sept - 1 Oct

includes taxes & fees

9.2/10 Wonderful! (417 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 Wylder Hotel Windham and Emerson Resort & Spa. See all available top hotels, or 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?

Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool and complimentary bicycles. Emerson Resort & Spa and Kaatskill Mountain Club & Condos by Vail Resorts are two additional hotels with an on-site pool. View all hotels with pools in Ashland.

What is staying in Ashland like?

Travellers to Ashland will find plenty to explore and enjoy. In Ashland, there are 7 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. You'll also find Windham Mountain Resort and Windham Country Club 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

Cobleskill Holiday Rentals

Ashland Hotels from S$121

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Ashland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Ashland hotels

1. Hotel Vienna

2. Moore's Motel

3. Hunter Lodge, a Bluebird by Lark

4. Black Bear Lodge

5. The Colonial Motel

6. The Haüs Windham

7. Antique Rose Inn Windham

8. Mountain Treasure B&B

9. Jimmy OConnors Windham Mountain Inn

10. Albergo Allegria Hotel

11. The Winwood Condominiums

12. The Perch Hotel

13. Wylder Hotel Windham

14. Eastwind Windham

15. The Wheelhouse Inn

16. Kaatskill Mountain Club & Condos by Vail Resorts

17. Hotel Mountain Brook

18. Shadowcrest

19. SunView Motel

20. Starlite Motel

Stay near popular Ashland attractions

Ashland Town Hall

Top Ashland Hotel Reviews

Hotel Vienna

The Colonial Motel

Phoenicia Lodge

Meadowood Inn

Hotel Mountain Brook

The Graham & Co.

Eastwind Windham

Emerson Resort & Spa

Jimmy OConnors Windham Mountain Inn

More cheap stays in Ashland

The Colonial Motel

Moore's Motel

Starlite Motel

Catskill Seasons Inn

Phoenicia Lodge

Kaatskill Mountain Club & Condos by Vail Resorts

Frequently asked questions

Explore a world of travel with Expedia

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