𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Ashland (2026)

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Our top choices for Ashland hotels

A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

A hotel room with two beds, wooden paneling on the walls, and two framed pictures.

A grassy field with a bench and a mountain in the background.

A kitchen with wooden cabinets, a refrigerator, and a window overlooking greenery.

1. Cave Mountain Motel

Windham

Nancy

S$193

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with lounge chairs and potted plants.

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

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

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

2. Moore's Motel

Prattsville

Marika

S$166

includes taxes & fees

19 Oct - 20 Oct

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

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

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

Two white Adirondack chairs in a forest with fallen leaves.

3. Black Bear Lodge

Prattsville

Adam

S$206

includes taxes & fees

21 Oct - 22 Oct

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

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

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

4. Hotel Vienna

Windham

Toni-Diane

S$183

includes taxes & fees

8 Nov - 9 Nov

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.

5. The Winwood Condominiums

Windham

Abdul

S$234

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A building with a porch and outdoor seating area.

6. Albergo Allegria Hotel

Windham

Roy

S$240

includes taxes & fees

18 Oct - 19 Oct

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 pool table with balls and a cue stick.

7. Jimmy OConnors Windham Mountain Inn

Windham

Robin

S$185

includes taxes & fees

21 Oct - 22 Oct

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

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.

A garden with blooming pink flowers and green grass.

8. Antique Rose Inn Windham

Windham

David

S$187

includes taxes & fees

20 Oct - 21 Oct

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.

9. The Colonial Motel

Grand Gorge

Eric

S$106

includes taxes & fees

15 Nov - 16 Nov

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

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.

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

10. Wylder Hotel Windham

Windham

Yousung

S$330

includes taxes & fees

29 Oct - 30 Oct

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

11. Hunter Lodge, a Bluebird by Lark

Hunter

Marina

S$203

includes taxes & fees

8 Nov - 9 Nov

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

12. Eastwind Windham

Windham

Sharon

S$347

includes taxes & fees

15 Nov - 16 Nov

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

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

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.

13. The Haüs Windham

Windham

Erica

S$451

includes taxes & fees

3 Nov - 4 Nov

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

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

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

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

14. Mountain Treasure B&B

Maplecrest

Daniel

S$229

includes taxes & fees

20 Oct - 21 Oct

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

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.

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

15. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Ryan

S$269

includes taxes & fees

15 Nov - 16 Nov

16. The Wheelhouse Inn

Pine Hill

Allen

S$129

includes taxes & fees

14 Nov - 15 Nov

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

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

17. Shadowcrest

Fleischmanns

David

S$186

includes taxes & fees

12 Nov - 13 Nov

A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.

A bar area with wooden paneling, a central arch, and multiple liquor bottles.

18. Shandaken Inn

Shandaken

Gabriele

S$204

includes taxes & fees

8 Nov - 9 Nov

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

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.

19. The Perch Hotel

East Windham

Pushpavalli

S$249

includes taxes & fees

22 Oct - 23 Oct

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

A person walking towards a yellow door with stone walls and a bench to the left.

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.

20. Starlite Motel

Big Indian

Danielle

S$208

includes taxes & fees

21 Oct - 22 Oct

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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

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"The room was huge and very roomy!!! We had a beautiful view of the mountains! We loved our stay and would love to return."

The Graham & Co.

10/10 Excellent

"I had a pleasant stay! The place was nice and comfortable, and everything was good. Thank you for your hospitality. I would definitely recommend it!"

The Colonial Motel

10/10 Excellent

"Cozy and nostalgic! I had a wonderful stay and it was a perfect escape from NYC :) Staff was incredibly helpful and kind, would definitely recommend"

Emerson Resort & Spa

10/10 Excellent

"Quiet walking trails, restaurant on property, shops & Kakeidescope on site. Bread alone in boiceville is 3 mins away."

Shandaken Inn

10/10 Excellent

"This property is exceptional from the food - bar - appointed room! I can't wait to visit again! The views -the service was impeccable! Thank you Katie and Jennifer(waitstaff) and owner Katie! You are all a WOW"

The Winwood Condominiums

10/10 Excellent

"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent

"Beautiful fall colors in a cozy and charming lodge!"

SunView Motel

8/10 Good

"Clean room and comfortable beds. For the price it’s a good deal"

Deer Mountain Inn

10/10 Excellent

"Staff made you feel right at home, the server had immense knowledge in the food they were serving! You can also taste the chef’s effort that he put into each dish! I will definitely be back."

More cheap stays in Ashland

The Colonial Motel

37283 NY-23 Grand Gorge NY

S$106

15 Nov - 16 Nov

includes taxes & fees

9.6/10 Exceptional! (498 reviews)

SunView Motel

5844 Main St Tannersville NY

S$183

25 Oct - 26 Oct

includes taxes & fees

8.6/10 Excellent! (633 reviews)

Starlite Motel

8722 Route 28 Big Indian NY

S$208

21 Oct - 22 Oct

includes taxes & fees

9.2/10 Wonderful! (316 reviews)

Phoenicia Lodge

5987 New York 28 Phoenicia NY

S$248

19 Oct - 20 Oct

includes taxes & fees

The Perch Hotel

7604 NY-23 East Windham NY

S$249

22 Oct - 23 Oct

includes taxes & fees

9.4/10 Exceptional! (45 reviews)

Kaatskill Mountain Club & Condos by Vail Resorts

61 LIFTSIDE DR Hunter NY

S$269

15 Nov - 16 Nov

includes taxes & fees

9.2/10 Wonderful! (437 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 Emerson Resort & Spa and Hotel Vienna. 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?

Emerson Resort & Spa: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli. Hotel Vienna 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 6 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 Vineyards and Winery and Windham Mountain Resort 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$106

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. Cave Mountain Motel

2. Moore's Motel

3. Black Bear Lodge

4. Hotel Vienna

5. The Winwood Condominiums

6. Albergo Allegria Hotel

7. Jimmy OConnors Windham Mountain Inn

8. Antique Rose Inn Windham

9. The Colonial Motel

10. Wylder Hotel Windham

11. Hunter Lodge, a Bluebird by Lark

12. Eastwind Windham

13. The Haüs Windham

14. Mountain Treasure B&B

15. Kaatskill Mountain Club & Condos by Vail Resorts

16. The Wheelhouse Inn

17. Shadowcrest

18. Shandaken Inn

19. The Perch Hotel

20. Starlite Motel

Stay near popular Ashland attractions

Ashland Town Hall

Top Ashland Hotel Reviews

Hunter Lodge, a Bluebird by Lark

The Graham & Co.

The Colonial Motel

Emerson Resort & Spa

Shandaken Inn

The Winwood Condominiums

Kaatskill Mountain Club & Condos by Vail Resorts

SunView Motel

Deer Mountain Inn

More cheap stays in Ashland

The Colonial Motel

SunView Motel

Starlite Motel

Phoenicia Lodge

The Perch Hotel

Kaatskill Mountain Club & Condos by Vail Resorts

Frequently asked questions

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