Top 10 Hotels in Ashland, NY from ₩131,418 - Competitive Prices

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

A white door with a sign reading "BREAKFAST" above it, a thermometer, and a drawing of stacked cups with steam.

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

1. Cave Mountain Motel

Windham

Nancy

₩186,399

₩201,311 total

includes taxes & fees

Nov 5 - Nov 6

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 motel with a central staircase, balconies, and a grassy front yard.

2. Moore's Motel

Prattsville

Marika

₩160,920

₩173,794 total

includes taxes & fees

Oct 18 - Oct 19

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

3. Hotel Vienna

Windham

Hongtao

₩155,690

₩191,306 total

includes taxes & fees

Nov 12 - Nov 13

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.

Two white Adirondack chairs in a forest with fallen leaves.

4. Black Bear Lodge

Prattsville

Adam

₩199,809

₩215,794 total

includes taxes & fees

Oct 22 - Oct 23

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

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

A building with a porch and outdoor seating area.

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

5. Albergo Allegria Hotel

Windham

Roy

₩232,999

₩251,639 total

includes taxes & fees

Oct 18 - Oct 19

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.

6. Eastwind Windham

Windham

Sharon

₩313,323

₩378,321 total

includes taxes & fees

Nov 15 - Nov 16

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 pool table with balls and a cue stick.

7. Jimmy OConnors Windham Mountain Inn

Windham

Robin

₩179,225

₩193,563 total

includes taxes & fees

Oct 18 - Oct 19

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.

8. Wylder Hotel Windham

Windham

Yassaman Modarres

₩204,147

₩287,529 total

includes taxes & fees

Oct 30 - Oct 31

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

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

9. The Winwood Condominiums

Windham

Zihe

₩226,629

₩244,759 total

includes taxes & fees

Nov 1 - Nov 2

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.

10. Antique Rose Inn Windham

Windham

David

₩181,035

₩195,518 total

includes taxes & fees

Oct 22 - Oct 23

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.

11. The Haüs Windham

Windham

Erica

₩249,467

₩470,560 total

includes taxes & fees

Nov 3 - Nov 4

12. Windham NY Escape

Hensonville

Miguel

₩575,289

₩727,250 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

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

13. The Colonial Motel

Grand Gorge

Eric

₩119,483

₩131,418 total

includes taxes & fees

Oct 19 - Oct 20

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

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.

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

14. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Ryan

₩240,777

₩286,711 total

includes taxes & fees

Nov 15 - Nov 16

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.

15. Hunter Lodge, a Bluebird by Lark

Hunter

Marina

₩169,838

₩212,392 total

includes taxes & fees

Nov 15 - Nov 16

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

16. Mountain Treasure B&B

Maplecrest

Daniel

₩222,606

₩240,414 total

includes taxes & fees

Oct 22 - Oct 23

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

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.

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

17. Starlite Motel

Big Indian

Danielle

₩194,445

₩217,778 total

includes taxes & fees

Oct 19 - Oct 20

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

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.

18. Hotel Mountain Brook

Tannersville

Kristen

₩313,794

₩338,898 total

includes taxes & fees

Nov 8 - Nov 9

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 stone building with a chimney, a pool, and a sign for Shandaken Inn.

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

19. Shandaken Inn

Shandaken

Lianne

₩190,690

₩213,581 total

includes taxes & fees

Nov 10 - Nov 11

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

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

20. The Perch Hotel

East Windham

Pushpavalli

₩241,211

₩260,509 total

includes taxes & fees

Oct 22 - Oct 23

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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

SunView Motel

10/10 Excellent

"We had a pleasant stay at Sunview Motel. The staff were helpful and responsive when we reached out for assistance. The room served our needs, and we appreciated the support during our visit. Overall, we had a good experience and thank the staff for their help."

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"My husband and I have stayed at this hotel previously we are returned visitors. Our room was immaculate. We had a balcony that overlooked the beautiful mountains and gorgeous trees in the fall. The room itself was impeccable the bathroom Stella. I would definitely recommend this hotel to anyone. There were many families there and enjoyed the breakfast bagels, cereal, coffee, oatmeal, and or yogurt where we ate for breakfast was very clean. I must mention that there’s a beautiful sitting room in the lobby for comfort reading this games very quaint. It is dog, friendly only certain rooms. The outside has a beautiful balcony. The landscaping was very inviting. There are tables and chairs outside that you can sit and you can even have a fire in the evening. It’s a very welcoming place. Definitely recommend."

Hotel Vienna

10/10 Excellent

"Clean room and helpful staff, good location."

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!"

More cheap stays in Ashland

The Colonial Motel

37283 NY-23 Grand Gorge NY

₩119,483

₩131,418 total

Oct 19 - Oct 20

includes taxes & fees

9.6/10 Exceptional! (498 reviews)

SunView Motel

5844 Main St Tannersville NY

₩177,079

₩191,240 total

Oct 18 - Oct 19

includes taxes & fees

8.6/10 Excellent! (634 reviews)

Starlite Motel

8722 Route 28 Big Indian NY

₩194,445

₩217,778 total

Oct 19 - Oct 20

includes taxes & fees

Phoenicia Lodge

5987 New York 28 Phoenicia NY

₩232,020

₩259,859 total

Oct 28 - Oct 29

includes taxes & fees

The Perch Hotel

7604 NY-23 East Windham NY

₩241,211

₩260,509 total

Oct 22 - Oct 23

includes taxes & fees

9.4/10 Exceptional! (45 reviews)

Kaatskill Mountain Club & Condos by Vail Resorts

61 LIFTSIDE DR Hunter NY

₩240,777

₩286,711 total

Nov 15 - Nov 16

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 traveler data. Two other options for your stay in 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! The majority of hotel room reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Ashland.

Where can I learn more about changing or cancelling my trip to Ashland?

For more information about rescheduling or cancelling your trip to Ashland, click here.

What are some accommodations 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 that feature an onsite pool. View all hotels with pools in Ashland.

What's the best accommodation near Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What is staying in Ashland like?

Travelers to Ashland will find plenty to explore and enjoy. In Ashland, there are 6 hotels and other accommodations to choose from. Find out more about Ashland.

What should I see while I'm in Ashland?

A favorite place to visit is Ashland Town Hall. You'll also find Windham Vineyards and Winery and Windham Mountain Resort in the area. Check out what more 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 temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Ashland are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia

Book Hotels in Ashland on Expedia.com

Find hotels in Ashland, NY from ₩131,418

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. Hotel Vienna

4. Black Bear Lodge

5. Albergo Allegria Hotel

6. Eastwind Windham

7. Jimmy OConnors Windham Mountain Inn

8. Wylder Hotel Windham

9. The Winwood Condominiums

10. Antique Rose Inn Windham

11. The Haüs Windham

12. Windham NY Escape

13. The Colonial Motel

14. Kaatskill Mountain Club & Condos by Vail Resorts

15. Hunter Lodge, a Bluebird by Lark

16. Mountain Treasure B&B

17. Starlite Motel

18. Hotel Mountain Brook

19. Shandaken Inn

20. The Perch Hotel

Stay near popular Ashland attractions

Ashland Town Hall

Top Ashland Hotel Reviews

SunView Motel

Hunter Lodge, a Bluebird by Lark

Hotel Vienna

The Graham & Co.

The Colonial Motel

Emerson Resort & Spa

Shandaken Inn

The Winwood Condominiums

Kaatskill Mountain Club & Condos by Vail Resorts

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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