Top 10 Hotels in Ashland, NY in 2026 (from $89)

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Where to stay in Ashland?

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

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.

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

1. Cave Mountain Motel

Windham

$139

$150 total

includes taxes & fees

Nov 1 - Nov 2

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.

2. Jimmy OConnors Windham Mountain Inn

Windham

$134

$144 total

includes taxes & fees

Oct 14 - Oct 15

A swimming pool with lounge chairs and potted plants.

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

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.

3. Moore's Motel

Prattsville

$120

$130 total

includes taxes & fees

Oct 14 - Oct 15

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.

4. Hotel Vienna

Windham

$129

$157 total

includes taxes & fees

Oct 29 - Oct 30

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

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

Two white Adirondack chairs in a forest with fallen leaves.

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

5. Black Bear Lodge

Prattsville

$149

$161 total

includes taxes & fees

Oct 14 - Oct 15

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.

6. The Winwood Condominiums

Windham

$167

$180 total

includes taxes & fees

Oct 14 - Oct 15

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

7. The Colonial Motel

Grand Gorge

$89

$98 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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

A garden with blooming pink flowers and green grass.

8. Antique Rose Inn Windham

Windham

$135

$146 total

includes taxes & fees

Oct 14 - Oct 15

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.

9. Albergo Allegria Hotel

Windham

$174

$188 total

includes taxes & fees

Oct 14 - Oct 15

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

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

10. The Haüs Windham

Windham

$207

$373 total

includes taxes & fees

Nov 3 - Nov 4

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

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.

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

11. Mountain Treasure B&B

Maplecrest

$166

$179 total

includes taxes & fees

Oct 20 - Oct 21

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

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

12. Hunter Lodge, a Bluebird by Lark

Hunter

$127

$158 total

includes taxes & fees

Nov 8 - Nov 9

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

13. Eastwind Windham

Windham

$289

$344 total

includes taxes & fees

Oct 14 - Oct 15

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

14. Wylder Hotel Windham

Windham

$275

$347 total

includes taxes & fees

Nov 12 - Nov 13

15. The Wheelhouse Inn

Pine Hill

$90

$101 total

includes taxes & fees

Oct 16 - Oct 17

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

$178

$212 total

includes taxes & fees

Nov 11 - Nov 12

17. Windham NY Escape

Hensonville

$429

$542 total

includes taxes & fees

Oct 14 - Oct 15

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

A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.

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

$158

$177 total

includes taxes & fees

Oct 27 - Oct 28

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

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

19. Starlite Motel

Big Indian

$145

$162 total

includes taxes & fees

Oct 14 - Oct 15

A large two-story house with a snow-covered roof and a front porch.

A neatly made bed with patterned pillows, a painting above it, and two bedside lamps.

A two-story house with a gabled roof, a front porch with a railing, and a small front yard with yellow flowers.

A neatly made bed with a headboard, two bedside tables with lamps, and a window with sheer curtains.

20. Meadowood Inn

Arkville

$122

$159 total

includes taxes & fees

Oct 15 - Oct 16

View all properties

Go beyond your typical stay in Ashland

Top landmarks in Ashland

Ashland Town Hall

Ashland Town Hall is worth a visit, located 1.5 mi (2.4 km) from central Ashland.

See properties

Check out reviews of Ashland hotels guests love

Cave Mountain Motel

Windham

10/10 Exceptional

Petra

Hotel Vienna

Windham

10/10 Exceptional

michael

Jimmy OConnors Windham Mountain Inn

Windham

10/10 Exceptional

Christopher

The Colonial Motel

Grand Gorge

10/10 Exceptional

Step back in time when a place to stay was charming, clean and had an owner who was actually on property and cared about your stay and well being. If you’re looking for the above and a little mystic, look no further. This place has history that comes along with the beautiful well appointed room. Just an all out classy mix of antique furnishings as well as modern touches like an internet connection that works, in room Keurig coffee maker , comfortable bed and clean bathroom. Our only regret was...

Paula

Moore's Motel

Prattsville

10/10 Exceptional

Michael

Albergo Allegria Hotel

Windham

10/10 Exceptional

NH couple

Antique Rose Inn Windham

Windham

10/10 Exceptional

Anonymous traveler

Mountain Treasure B&B

Maplecrest

10/10 Exceptional

Alina

Hunter Lodge, a Bluebird by Lark

Hunter

10/10 Exceptional

Craig

Eastwind Windham

Windham

10/10 Exceptional

Mercy

Shandaken Inn

Shandaken

10/10 Exceptional

Anonymous traveler

Wylder Hotel Windham

Windham

10/10 Exceptional

Charles

The Haüs Windham

Windham

10/10 Exceptional

thespena

Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

10/10 Exceptional

Joseph

A snow-covered lodge with a stone chimney, lit windows, and snow-laden trees in front.

A wooden deck with a fire pit surrounded by Adirondack chairs.

A bar area with wooden bar stools, a fireplace, and a variety of bottles and glasses on shelves.

A wooden room with a bed, a window with curtains, a nightstand with a lamp, and a vase with flowers.

Deer Mountain Inn

Haines Falls

10/10 Exceptional

Mark

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

Shadowcrest

Fleischmanns

10/10 Exceptional

Elena

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

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

The Perch Hotel

East Windham

10/10 Exceptional

A Hidden Gem with Million-Dollar Views! We had such a magical stay at The Perch Hotel in East Windham! The view alone is worth the trip — on a clear day, you can see FIVE states from the property. Yes, five! It’s absolutely breathtaking and made for the perfect backdrop to relax and soak in the Catskills air. The vibe of the hotel is something special — a perfect blend of modern comfort and mid-century charm that instantly transported me back to the golden era of Catskill tourism. It’s stylish...

Emmi

Meadowood Inn

Arkville

10/10 Exceptional

John

Frequently Asked Questions

What accommodations do travelers recommend in Ashland?

Guests like Hotel Vienna, Wylder Hotel Windham and Eastwind Windham.

Can I book a refundable accommodation in Ashland?

If you're looking for the flexibility to change your travel plans to Ashland, most hotels provide refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Ashland if I want a vacation home instead of a traditional hotel?

If you want to find a good alternative to a hotel, browse our selection of 5 vacation homes.

What will the weather in Ashland be like during my visit?

The warmest months in Ashland are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 26°F. The rainiest months are July and August.

Why should I book my Ashland hotel through Hotels.com?

There are plenty of reasons to book your Ashland travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.