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Ashland Hotels

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Check prices for these dates

Tonight
15 Oct - 16 Oct
Tomorrow
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 hotel room with two beds, wooden paneling on the walls, and two framed pictures.
A kitchen with wooden cabinets, a refrigerator, and a window overlooking greenery.
A grassy field with a bench and a mountain in the background.

1. Cave Mountain Motel

Cave Mountain Motel
Windham
United States
Nancy
€134
includes taxes & fees
4 Nov - 5 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
€116
includes taxes & fees
18 Oct - 19 Oct
Moore's Motel
A river flowing through a forested area with rocks and autumn-colored trees.
Two white Adirondack chairs in a forest with fallen leaves.
A front door with a WiFi sign, a Christmas wreath, and a bear statue.
A wooden sign for Black Bear Lodge with a phone number.

3. Black Bear Lodge

Black Bear Lodge
Prattsville
United States
Adam
€144
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 woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.
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 modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

4. Hotel Vienna

Hotel Vienna
Windham
United States
Toni-Diane
€127
includes taxes & fees
10 Nov - 11 Nov
Hotel Vienna
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 wooden room with a bed, a nightstand with a lamp, and a wall with tree decorations.
A pool table with balls and a cue stick.

5. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
United States
Robin
€129
includes taxes & fees
18 Oct - 19 Oct
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 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 compact living space with a kitchen, dining area, and seating.

6. The Winwood Condominiums

The Winwood Condominiums
Windham
United States
Abdul
€163
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
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 wooden staircase leading to a second floor, a red sofa with floral cushions, and a wooden floor.
A covered outdoor seating area with wicker chairs and a table, surrounded by white railings and hanging planters.

7. Antique Rose Inn Windham

Antique Rose Inn Windham
Windham
United States
David
€130
includes taxes & fees
20 Oct - 21 Oct
Antique Rose Inn Windham
A covered porch with outdoor seating, a staircase, and potted plants.
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
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.

8. The Colonial Motel

The Colonial Motel
Grand Gorge
United States
Eric
€88
includes taxes & fees
20 Oct - 21 Oct
The Colonial Motel
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.

9. Albergo Allegria Hotel

Albergo Allegria Hotel
Windham
United States
Roy
€168
includes taxes & fees
18 Oct - 19 Oct
Albergo Allegria Hotel
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 circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.

10. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
Hunter
United States
Marina
€141
includes taxes & fees
8 Nov - 9 Nov
Hunter Lodge, a Bluebird by Lark
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.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

11. Wylder Hotel Windham

Wylder Hotel Windham
Windham
United States
Yousung
€230
includes taxes & fees
29 Oct - 30 Oct
Wylder Hotel Windham
A bedroom with a large bed, a ceiling fan, a painting, a lamp, and a small table with a statue.
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.

12. Mountain Treasure B&B

Mountain Treasure B&B
Maplecrest
United States
Daniel
€160
includes taxes & fees
26 Oct - 27 Oct
Mountain Treasure B&B
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 large, multi-story wooden house with a snow-covered roof and several lit windows, surrounded by bare trees and snow.

13. The Haüs Windham

The Haüs Windham
Windham
United States
Erica
€314
includes taxes & fees
3 Nov - 4 Nov
The Haüs Windham
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 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.

14. Eastwind Windham

Eastwind Windham
Windham
United States
Sharon
€247
includes taxes & fees
15 Nov - 16 Nov
Eastwind Windham
Property grounds
Interior
Room
Interior

15. The Wheelhouse Inn

The Wheelhouse Inn
Pine Hill
United States
Allen
€90
includes taxes & fees
30 Oct - 31 Oct
The Wheelhouse Inn
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 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.

16. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
United Kingdom
Ryan
€191
includes taxes & fees
15 Nov - 16 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
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.

17. Shandaken Inn

Shandaken Inn
Shandaken
United States
Gabriele
€142
includes taxes & fees
27 Oct - 28 Oct
Shandaken Inn
A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.
A hotel room with a bed, white curtains, and wall-mounted light fixtures.
A bathroom with a blue-tiled shower enclosure, a shelf with toiletries, and a handheld showerhead.
A room with a curved wooden ceiling, large windows with wooden frames, two upholstered armchairs, a round table, and a potted plant.

18. Shadowcrest

Shadowcrest
Fleischmanns
Canada
David
€130
includes taxes & fees
27 Oct - 28 Oct
Shadowcrest
A large two-story house with a snow-covered roof and a front porch.
A neatly made bed with a headboard, two bedside tables with lamps, and a window with sheer curtains.
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 patterned pillows, a painting above it, and two bedside lamps.

19. Meadowood Inn

Meadowood Inn
Arkville
United States
Catherine
€142
includes taxes & fees
26 Oct - 27 Oct
Meadowood Inn
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
Danielle
€145
includes taxes & fees
19 Oct - 20 Oct
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

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 15 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 17 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 17 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 2 days 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
€88
20 Oct - 21 Oct
includes taxes & fees
9.6/10 Exceptional! (498 reviews)
The Colonial Motel
SunView Motel

SunView Motel

5844 Main St Tannersville NY
€128
25 Oct - 26 Oct
includes taxes & fees
8.6/10 Excellent! (633 reviews)
SunView Motel
Starlite Motel

Starlite Motel

8722 Route 28 Big Indian NY
€145
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
€173
19 Oct - 20 Oct
includes taxes & fees
Phoenicia Lodge
The Perch Hotel

The Perch Hotel

7604 NY-23 East Windham NY
€187
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
€191
15 Nov - 16 Nov
includes taxes & fees
9.2/10 Wonderful! (437 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 Emerson Resort & Spa and Hotel Vienna. See all available top hotels, or vacation rentals in Ashland.
What are some of the best holiday rentals that Ashland has to offer?
Heart of Hunter Village; across MT!Spring Special3rd night half OFF!" W/weekend: This holiday home rental outside of Ashland is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 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, an arcade/games room 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?
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 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 6 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 Vineyards and Winery and Windham Mountain Resort 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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