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Ashland Hotels

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Tonight
31 Aug - 1 Sept
Tomorrow
1 Sept - 2 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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Our top choices for Ashland hotels

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.

1. Hotel Vienna

Hotel Vienna
Windham
United States
Jerrold
€122
includes taxes & fees
14 Sept - 15 Sept
Hotel Vienna
A swimming pool with lounge chairs and potted plants.
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.
A two-story building with a large front porch, a chimney, and a balcony.

2. Moore's Motel

Moore's Motel
Prattsville
United States
Dylan
€112
includes taxes & fees
1 Sept - 2 Sept
Moore's Motel
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 sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
A swimming pool with a fenced deck, lounge chairs, and umbrellas.

3. The Colonial Motel

The Colonial Motel
Grand Gorge
United States
Eric
€85
includes taxes & fees
1 Sept - 2 Sept
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 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.

4. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
Hunter
United States
Yaacov
€137
includes taxes & fees
10 Sept - 11 Sept
Hunter Lodge, a Bluebird by Lark
A bedroom with a large window, a bed, and a view of a forest.
A wooden cabin with a door, surrounded by greenery and a stone pathway.
A large, multi-story wooden house with a snow-covered roof and several lit windows, surrounded by bare trees and snow.
A modern bedroom with a large bed, a view of greenery through floor-to-ceiling windows, and a wooden ceiling.

5. The Haüs Windham

The Haüs Windham
Windham
United States
Raven Jane
€286
includes taxes & fees
1 Sept - 2 Sept
The Haüs Windham
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 front door with a WiFi sign, a Christmas wreath, and a bear statue.
A dining area with a wooden table and a single green chair.

6. Black Bear Lodge

Black Bear Lodge
Prattsville
United States
Gerald
€139
includes taxes & fees
1 Sept - 2 Sept
Black Bear Lodge
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.

7. Antique Rose Inn Windham

Antique Rose Inn Windham
Windham
United States
David
€126
includes taxes & fees
1 Sept - 2 Sept
Antique Rose Inn Windham
A park with Adirondack chairs and a table, surrounded by trees.
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.
A well-lit hallway with a wooden staircase, a decorative vase, and a dining area with a table and chairs.

8. Mountain Treasure B&B

Mountain Treasure B&B
Maplecrest
United States
Daniel
€136
includes taxes & fees
1 Sept - 2 Sept
Mountain Treasure B&B
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 grassy field with a wooden structure overhead, possibly a gazebo or pavilion.

9. Albergo Allegria Hotel

Albergo Allegria Hotel
Windham
United States
Roy
€162
includes taxes & fees
1 Sept - 2 Sept
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 bar with wooden chairs, a bar counter, and various bottles and glasses.
A glass of beer with a logo on it, placed on a straw surface.

10. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
United States
Amy
€138
includes taxes & fees
1 Sept - 2 Sept
Jimmy OConnors Windham Mountain Inn
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 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.

11. The Winwood Condominiums

The Winwood Condominiums
Windham
United States
Abdul
€167
includes taxes & fees
1 Sept - 2 Sept
The Winwood Condominiums

12. The Wheelhouse Inn

The Wheelhouse Inn
Pine Hill
United States
Allen
€87
includes taxes & fees
19 Sept - 20 Sept
The Wheelhouse 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 spacious indoor area with a long wooden floor, a central seating area with a sofa and chairs, and a pool table.
A staircase leading to a room with a stone floor, a potted plant, and a wooden chair.
A spacious living area with a wooden floor, leather sofas, and a dining table.

13. The Perch Hotel

The Perch Hotel
East Windham
United States
Jason
€151
includes taxes & fees
3 Sept - 4 Sept
The Perch Hotel
A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.
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.
A modern bathroom with a glass sink, wooden vanity, and a large mirror.

14. Shadowcrest

Shadowcrest
Fleischmanns
United States
Margo
€125
includes taxes & fees
1 Sept - 2 Sept
Shadowcrest
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.
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.
A bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.

15. Hotel Mountain Brook

Hotel Mountain Brook
Tannersville
United States
Qiang
€163
includes taxes & fees
7 Sept - 8 Sept
Hotel Mountain Brook
A wooden cabin with a triangular roof, a wooden door, and a bench outside.
A triangular wooden room with a bed and pillows, a window, and a view of a forested hill.
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.

16. Eastwind Windham

Eastwind Windham
Windham
United States
Claire
€258
includes taxes & fees
1 Sept - 2 Sept
Eastwind Windham
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.
A bar area with wooden paneling, a central arch, and multiple liquor bottles.
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.

17. Shandaken Inn

Shandaken Inn
Shandaken
United States
Briana
€196
includes taxes & fees
1 Oct - 2 Oct
Shandaken Inn
A room with two beds, wooden headboards, a red accent wall, and wooden flooring.
A park with picnic tables and chairs, a tall cylindrical structure, and autumn-colored trees.
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.

18. SunView Motel

SunView Motel
Tannersville
United States
Arnold
€123
includes taxes & fees
3 Sept - 4 Sept
SunView Motel
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 cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

19. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
United States
jason
€193
includes taxes & fees
30 Sept - 1 Oct
Kaatskill Mountain Club & Condos by Vail Resorts
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.

20. Starlite Motel

Starlite Motel
Big Indian
United States
Sarah
€121
includes taxes & fees
1 Sept - 2 Sept
Starlite Motel
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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

Hotel Vienna

Hotel Vienna

10/10 Excellent
"We really enjoyed the experience."
David 2-night trip
Posted 5 hours ago
Hotel Vienna
The Colonial Motel

The Colonial Motel

10/10 Excellent
"Great place to stay!"
Eric 2-night trip
Posted 14 hours ago
The Colonial Motel
Phoenicia Lodge

Phoenicia Lodge

8/10 Good
"Friendly staff"
Jacque 1-night trip
Posted 1 day ago
Phoenicia Lodge
Meadowood Inn

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."
Jonathan 1-night trip
Posted 2 days ago
Meadowood Inn
Hotel Mountain Brook

Hotel Mountain Brook

10/10 Excellent
"Very cute place. Mountains air. Yummy breakfast"
Ann 2-night trip
Posted 3 days ago
Hotel Mountain Brook
The Graham & Co.

The Graham & Co.

10/10 Excellent
"Wonderful Stay"
Daniel 2-night trip
Posted 5 days ago
The Graham & Co.
Eastwind Windham

Eastwind Windham

10/10 Excellent
"The staff was friendly and the room was clean and comfortable. Would love to come back again!"
Claire 1-night trip
Posted 13 days ago
Eastwind Windham
Emerson Resort & Spa

Emerson Resort & Spa

8/10 Good
"The Emerson is a great resort/spa. Our room was just beautiful, clean , and comfortable. However, you will need to plan your stay well before you arrive since spa treatments book up quickly. My stay was spur of the moment so there was no availability, not even for a pedicure. Also be advised that there is no cell service (didn’t matter to me) but there is WiFi. I was aware that the restaurant was closed on the days of my stay so I can’t comment on the food. Even though this is a nice place, I don’t think I’ll be staying here again."
Justine 1-night trip
Posted 2 weeks ago
Emerson Resort & Spa
Jimmy OConnors Windham Mountain Inn

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."
Ian 1-night trip
Posted 3 weeks ago
Jimmy OConnors Windham Mountain Inn

More cheap stays in Ashland

The Colonial Motel

The Colonial Motel

37283 NY-23 Grand Gorge NY
€85
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (484 reviews)
The Colonial Motel
Moore's Motel

Moore's Motel

14672 Main Street Prattsville NY
€112
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (176 reviews)
Moore's Motel
Starlite Motel

Starlite Motel

8722 Route 28 Big Indian NY
€121
1 Sept - 2 Sept
includes taxes & fees
Starlite Motel
Catskill Seasons Inn

Catskill Seasons Inn

178 Route 42 Shandaken NY
€155
1 Sept - 2 Sept
includes taxes & fees
Catskill Seasons Inn
Phoenicia Lodge

Phoenicia Lodge

5987 New York 28 Phoenicia NY
€167
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (65 reviews)
Phoenicia Lodge
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

61 LIFTSIDE DR Hunter NY
€193
30 Sept - 1 Oct
includes taxes & fees
9.2/10 Wonderful! (417 reviews)
Kaatskill Mountain Club & Condos by Vail Resorts

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 Wylder Hotel Windham and Emerson Resort & Spa. See all available top hotels, or vacation rentals in Ashland.
What are some of the best holiday rentals that Ashland has to offer?
Catskill Mountain Retreat -- private, beautiful views, hot tub, game rm, firepit: This holiday home rental outside of Ashland is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a library and 1 hot tub so that you can immerse yourself in your holiday. See all 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?
Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool and complimentary bicycles. Emerson Resort & Spa 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 7 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 Mountain Resort and Windham Country Club 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.

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