Hotels in Ashland

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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 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.

Cave Mountain Motel

Windham

$139

$150 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

Hotel Vienna

Windham

$135

$163 total

includes taxes & fees

Sep 8 - Sep 9

A swimming pool with lounge chairs and potted plants.

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

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.

Moore's Motel

Prattsville

$120

$130 total

includes taxes & fees

Sep 7 - Sep 8

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.

Jimmy OConnors Windham Mountain Inn

Windham

$149

$160 total

includes taxes & fees

Sep 3 - Sep 4

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.

Black Bear Lodge

Prattsville

$149

$161 total

includes taxes & fees

Sep 7 - Sep 8

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 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".

The Colonial Motel

Grand Gorge

$99

$109 total

includes taxes & fees

Sep 3 - Sep 4

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

A garden with blooming pink flowers and green grass.

Antique Rose Inn Windham

Windham

$135

$146 total

includes taxes & fees

Sep 8 - Sep 9

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 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.

A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

The Winwood Condominiums

Windham

$169

$183 total

includes taxes & fees

Sep 3 - Sep 4

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

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

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.

Hunter Lodge, a Bluebird by Lark

Hunter

$127

$158 total

includes taxes & fees

Sep 13 - Sep 14

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

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.

A modern bedroom with a large bed, a view of greenery through floor-to-ceiling windows, and a wooden ceiling.

The Haüs Windham

Windham

$110

$350 total

includes taxes & fees

Sep 3 - Sep 4

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 building with a porch and outdoor seating area.

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

Albergo Allegria Hotel

Windham

$148

$160 total

includes taxes & fees

Sep 21 - Sep 22

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 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.

Mountain Treasure B&B

Maplecrest

$166

$179 total

includes taxes & fees

Sep 3 - Sep 4

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.

The Perch Hotel

East Windham

$187

$202 total

includes taxes & fees

Sep 3 - Sep 4

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

A large tree in a grassy area with a small white building in the background.

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

SunView Motel

Tannersville

$118

$128 total

includes taxes & fees

Sep 3 - Sep 4

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.

Eastwind Windham

Windham

$289

$344 total

includes taxes & fees

Sep 3 - Sep 4

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.

Hotel Mountain Brook

Tannersville

$175

$189 total

includes taxes & fees

Sep 7 - Sep 8

The Wheelhouse Inn

Pine Hill

$90

$101 total

includes taxes & fees

Sep 19 - Sep 20

Windham NY Escape

Hensonville

$429

$542 total

includes taxes & fees

Sep 10 - Sep 11

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

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

Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

$198

$235 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

Starlite Motel

Big Indian

$125

$140 total

includes taxes & fees

Sep 3 - Sep 4

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Go beyond your typical stay in Ashland

Pet friendly

Apartment

Pool

Hot tub

Family friendly

Cottage

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

The Colonial Motel

10/10 Excellent

"I love these older hotels where you feel like you’re in your own apartment rather than a sterile hotel room. This one has been very well maintained."

Phoenicia Lodge

8/10 Good

"Check in and out was very pleasant."

Hotel Vienna

10/10 Excellent

"We really enjoyed the experience."

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!"

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."

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.

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