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Ashland Hotels from ā‚¹8,390

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30 Oct - 1 Nov
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6 Nov - 8 Nov

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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.

1. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (151 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is ā‚¹13,222
ā‚¹14,279 total
includes taxes & fees
29 Oct - 30 Oct
Cave Mountain Motel
A log cabin with a deck, outdoor seating, and a view of a forest.

2. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (898 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is ā‚¹10,701
ā‚¹13,201 total
includes taxes & fees
2 Nov - 3 Nov
Hotel Vienna
A swimming pool with lounge chairs and potted plants.

3. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (183 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
The price is ā‚¹11,414
ā‚¹12,327 total
includes taxes & fees
30 Oct - 31 Oct
Moore's Motel
A large, two-story house with multiple porches and string lights.

4. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (289 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is ā‚¹16,527
ā‚¹17,849 total
includes taxes & fees
29 Oct - 30 Oct
Albergo Allegria Hotel
A river flowing through a forested area with rocks and autumn-colored trees.

5. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (160 reviews)
"We had a nice stay at the Black Bear. Great location and Kim was very accommodating."
United States
Adam
The price is ā‚¹14,173
ā‚¹15,307 total
includes taxes & fees
29 Oct - 30 Oct
Black Bear Lodge
A bedroom with a large bed, a sofa, a small table, and a window with curtains.

6. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (134 reviews)
"Loved our stay, will go anytime for a little weekend getaway from nyc!"
United States
Yassaman Modarres
The price is ā‚¹13,612
ā‚¹19,456 total
includes taxes & fees
31 Oct - 1 Nov
Wylder Hotel Windham
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

7. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (372 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is ā‚¹16,075
ā‚¹17,361 total
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

8. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (122 reviews)
"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."
United States
Danica
The price is ā‚¹21,971
ā‚¹26,552 total
includes taxes & fees
15 Nov - 16 Nov
Eastwind Windham
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

9. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.2 out of 10, Wonderful, (10 reviews)
"We had a wedding in the area and this place was perfect for our needs. Thereā€™s a bar to the front of the property, which was fun to hang out and play pool. The beds were comfortable and the rooms were clean."
United States
Robin
The price is ā‚¹14,125
ā‚¹15,255 total
includes taxes & fees
12 Nov - 13 Nov
Jimmy OConnors Windham Mountain Inn
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

10. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"A fantastic stay!"
United States
David
The price is ā‚¹12,841
ā‚¹13,868 total
includes taxes & fees
29 Oct - 30 Oct
Antique Rose Inn Windham
A bedroom with a large window, a bed, and a view of a forest.

11. The HaĆ¼s Windham

The HaĆ¼s Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 reviews)
"Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. "
United States
Erica
The price is ā‚¹15,024
ā‚¹30,493 total
includes taxes & fees
2 Nov - 3 Nov
The HaĆ¼s Windham
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

12. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,010 reviews)
"Always a nice stay."
United States
Marina
The price is ā‚¹11,238
ā‚¹14,192 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.

13. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (306 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is ā‚¹15,790
ā‚¹17,053 total
includes taxes & fees
29 Oct - 30 Oct
Mountain Treasure B&B
A multi-story building with outdoor seating and a stone-paved patio.

14. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (443 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is ā‚¹16,180
ā‚¹19,267 total
includes taxes & fees
22 Nov - 23 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A covered porch with outdoor seating, a staircase, and potted plants.

15. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (501 reviews)
"Great place to stay!"
United States
Eric
The price is ā‚¹7,628
ā‚¹8,390 total
includes taxes & fees
3 Nov - 4 Nov
The Colonial Motel
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

16. Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
Tannersville
9.8 out of 10, Exceptional, (612 reviews)
"Overall amazing stay! Location, staff, food, aesthetic and coziness all 10/10!"
United States
Kim
The price is ā‚¹23,227
ā‚¹25,085 total
includes taxes & fees
3 Nov - 4 Nov
Hotel Mountain Brook
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

17. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.2 out of 10, Wonderful, (110 reviews)
"The Emmerson Resort & Spa is great! The room was super clean and the bed was very comfortable. The resort is great and has everything you need. We loved staying here!"
United States
Jeremy
The price is ā‚¹15,040
ā‚¹16,845 total
includes taxes & fees
29 Oct - 30 Oct
Emerson Resort & Spa
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

18. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (331 reviews)
"Amazing stay! Will definitely be back and bonus: restaurant on site is also incredible!"
United States
Lauren
The price is ā‚¹13,536
ā‚¹15,161 total
includes taxes & fees
2 Nov - 3 Nov
Shandaken Inn
A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

19. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (293 reviews)
"We were so excited to go stay at the Shadowcrest and it completely exceeded our expectations! The host was so wonderful and the room was beautiful and so comfortable. We canā€™t wait to come back!"
United States
Amanda
The price is ā‚¹12,556
ā‚¹13,811 total
includes taxes & fees
29 Oct - 30 Oct
Shadowcrest
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.

20. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.4 out of 10, Exceptional, (46 reviews)
"Mountain View and cozy vibes are on point."
United States
Pushpavalli
The price is ā‚¹18,015
ā‚¹19,456 total
includes taxes & fees
5 Nov - 6 Nov
The Perch Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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 Mountain Brook

Hotel Mountain Brook

8/10 Good
"This is a sweet little spot that feels like an iconic mountian getaway. Our only issue would be to warn people who have a sensitive nose. The owners have very strong incense sticks"
Ed 2-night trip
Posted 2 hours ago
Hotel Mountain Brook

More cheap stays in Ashland

The Colonial Motel

The Colonial Motel

37283 NY-23 Grand Gorge NY
The price is ā‚¹7,628 per night from 3 Nov to 4 Nov
ā‚¹7,628
ā‚¹8,390 total
3 Nov - 4 Nov
includes taxes & fees
9.6/10 Exceptional! (501 reviews)

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.
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 18Ā°C, while the coldest months are January and February, with an average of -3Ā°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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