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15 Oct - 16 Oct
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16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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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 grassy field with a bench and a mountain in the background.
A white door with a sign reading "BREAKFAST" above it, a thermometer, and a drawing of stacked cups with steam.

1. Cave Mountain Motel

Cave Mountain Motel
Windham
United States
Nancy
3.599.127 ₫
3.887.057 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Cave Mountain Motel
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 two-story building with a large front porch, a chimney, and a balcony.

2. Moore's Motel

Moore's Motel
Prattsville
United States
Marika
3.107.160 ₫
3.355.733 ₫ total
includes taxes & fees
16 Oct - 17 Oct
Moore's Motel
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.

3. Black Bear Lodge

Black Bear Lodge
Prattsville
United States
Adam
3.858.057 ₫
4.166.702 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Black Bear Lodge
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 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

Hotel Vienna
Windham
United States
Toni-Diane
3.006.177 ₫
3.693.895 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Hotel Vienna
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 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.

5. Eastwind Windham

Eastwind Windham
Windham
United States
Sharon
5.774.874 ₫
6.998.274 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Eastwind Windham
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 room with a wooden floor, a chair, a lamp, and a view through a window with a decorative frame.

6. Albergo Allegria Hotel

Albergo Allegria Hotel
Windham
United States
Roy
4.498.909 ₫
4.858.822 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Albergo Allegria Hotel
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.
A pool table with balls and a cue stick.
A glass of beer with a logo on it, placed on a straw surface.
A wooden room with a bed, a nightstand with a lamp, and a wall with tree decorations.

7. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
United States
Robin
3.460.600 ₫
3.737.448 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Jimmy OConnors Windham Mountain Inn
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.

8. The Winwood Condominiums

The Winwood Condominiums
Windham
United States
Abdul
4.375.917 ₫
4.725.990 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
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 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.

9. Wylder Hotel Windham

Wylder Hotel Windham
Windham
United States
Yousung
4.952.036 ₫
6.642.850 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Wylder Hotel Windham
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 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.

10. Antique Rose Inn Windham

Antique Rose Inn Windham
Windham
United States
David
3.495.555 ₫
3.775.199 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Antique Rose Inn Windham
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 wooden cabin with a door, surrounded by greenery and a stone pathway.
A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

11. The Haüs Windham

The Haüs Windham
Windham
United States
Erica
4.816.875 ₫
9.085.914 ₫ total
includes taxes & fees
3 Nov - 4 Nov
The Haüs Windham
Front of property
Private kitchen
Terrace/patio
Terrace/patio

12. Windham NY Escape

Windham NY Escape
Hensonville
United States
Miguel
11.108.097 ₫
14.042.292 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Windham NY Escape
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 large hotel with multiple floors, a parking lot, and a mountainous backdrop.

13. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
United Kingdom
Ryan
4.649.088 ₫
5.536.026 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A covered porch with outdoor seating, a staircase, and potted plants.
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".
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

14. The Colonial Motel

The Colonial Motel
Grand Gorge
United States
Eric
2.307.066 ₫
2.537.514 ₫ total
includes taxes & fees
18 Oct - 19 Oct
The Colonial Motel
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 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.

15. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
Hunter
United States
Marina
3.279.348 ₫
4.100.985 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hunter Lodge, a Bluebird by Lark
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 vintage car parked in front of a house surrounded by trees.
A dining table set with breakfast items, a red mug, and a glass of orange juice.

16. Mountain Treasure B&B

Mountain Treasure B&B
Maplecrest
United States
Daniel
4.298.238 ₫
4.642.097 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Mountain Treasure B&B
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 person walking towards a yellow door with stone walls and a bench to the left.

17. Starlite Motel

Starlite Motel
Big Indian
United States
Danielle
3.754.485 ₫
4.205.023 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Starlite Motel
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 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 deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

18. Hotel Mountain Brook

Hotel Mountain Brook
Tannersville
United States
Kristen
6.058.962 ₫
6.543.679 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Hotel Mountain Brook
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 stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.

19. Shandaken Inn

Shandaken Inn
Shandaken
United States
Gabriele
3.681.985 ₫
4.123.979 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Shandaken Inn
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 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.

20. The Perch Hotel

The Perch Hotel
East Windham
United States
Pushpavalli
5.020.604 ₫
5.422.252 ₫ total
includes taxes & fees
22 Oct - 23 Oct
The Perch Hotel
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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

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."
Debbie 3-night trip
Posted 13 hours ago
Hunter Lodge, a Bluebird by Lark
The Graham & Co.

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!"
Emir 1-night trip
Posted 15 hours ago
The Graham & Co.
The Colonial Motel

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"
Alexandria 2-night trip
Posted 15 hours ago
The Colonial Motel
Emerson Resort & Spa

Emerson Resort & Spa

10/10 Excellent
"Quiet walking trails, restaurant on property, shops & Kakeidescope on site. Bread alone in boiceville is 3 mins away."
Lisa 3-night trip
Posted 1 day ago
Emerson Resort & Spa
Shandaken Inn

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"
Lianne 2-night trip
Posted 2 days ago
Shandaken Inn
The Winwood Condominiums

The Winwood Condominiums

10/10 Excellent
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
Zihe 1-night trip
Posted 2 days ago
The Winwood Condominiums
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"Beautiful fall colors in a cozy and charming lodge!"
Vandhana 2-night trip
Posted 2 days ago
Kaatskill Mountain Club & Condos by Vail Resorts
SunView Motel

SunView Motel

8/10 Good
"Clean room and comfortable beds. For the price it’s a good deal"
Beth 4-night trip
Posted 3 days ago
SunView Motel
Deer Mountain Inn

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."
Elizabeth 1-night trip
Posted 8 days ago
Deer Mountain Inn

More cheap stays in Ashland

The Colonial Motel

The Colonial Motel

37283 NY-23 Grand Gorge NY
2.307.066 ₫
2.537.514 ₫ total
18 Oct - 19 Oct
includes taxes & fees
9.6/10 Exceptional! (498 reviews)
The Colonial Motel
SunView Motel

SunView Motel

5844 Main St Tannersville NY
3.419.171 ₫
3.692.601 ₫ total
18 Oct - 19 Oct
includes taxes & fees
8.6/10 Excellent! (633 reviews)
SunView Motel
Starlite Motel

Starlite Motel

8722 Route 28 Big Indian NY
3.754.485 ₫
4.205.023 ₫ total
19 Oct - 20 Oct
includes taxes & fees
9.2/10 Wonderful! (316 reviews)
Starlite Motel
Phoenicia Lodge

Phoenicia Lodge

5987 New York 28 Phoenicia NY
4.480.007 ₫
5.017.546 ₫ total
27 Oct - 28 Oct
includes taxes & fees
Phoenicia Lodge
The Perch Hotel

The Perch Hotel

7604 NY-23 East Windham NY
5.020.604 ₫
5.422.252 ₫ total
22 Oct - 23 Oct
includes taxes & fees
9.4/10 Exceptional! (45 reviews)
The Perch Hotel
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

61 LIFTSIDE DR Hunter NY
4.649.088 ₫
5.536.026 ₫ total
15 Nov - 16 Nov
includes taxes & fees
9.2/10 Wonderful! (437 reviews)
Kaatskill Mountain Club & Condos by Vail Resorts

Hotels in Ashland with star rating

Frequently asked questions

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.

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