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13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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Our top choices for Ashland hotels

A motel with a covered porch, neatly arranged lounge chairs, and a well-maintained garden with yellow flowers.

1. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (152 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is Rp2.514.371
Rp2.715.521 total
includes taxes & fees
10 Nov - 11 Nov
Cave Mountain Motel
A swimming pool with lounge chairs and potted plants.

2. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (184 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
The price is Rp2.170.680
Rp2.344.334 total
includes taxes & fees
10 Nov - 11 Nov
Moore's Motel
A wooden sign for Black Bear Lodge with a phone number.

3. 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 Rp2.695.261
Rp2.910.882 total
includes taxes & fees
10 Nov - 11 Nov
Black Bear Lodge
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 Rp3.142.964
Rp3.394.401 total
includes taxes & fees
10 Nov - 11 Nov
Albergo Allegria Hotel
A log cabin with a deck, outdoor seating, and a view of a forest.

5. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (910 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is Rp2.035.012
Rp2.510.390 total
includes taxes & fees
15 Nov - 16 Nov
Hotel Vienna
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

6. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (377 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is Rp3.057.041
Rp3.301.604 total
includes taxes & fees
10 Nov - 11 Nov
The Winwood Condominiums
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

7. 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 Rp3.938.304
Rp4.781.931 total
includes taxes & fees
16 Nov - 17 Nov
Eastwind Windham
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

8. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is Rp4.137.588
Rp5.373.046 total
includes taxes & fees
29 Nov - 30 Nov
Wylder Hotel Windham
A rustic cabin with a stone foundation, a wooden roof, and a small porch.

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. There’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 Rp2.686.217
Rp2.901.115 total
includes taxes & fees
12 Nov - 13 Nov
Jimmy OConnors Windham Mountain Inn
Front of property

10. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (3 reviews)
"The best "
United States
Miguel
The price is Rp7.760.181
Rp9.810.026 total
includes taxes & fees
10 Nov - 11 Nov
Windham NY Escape
A two-story house with a wrap-around porch, a steeply pitched roof, and a small tower-like structure on the roof.

11. 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 Rp2.442.015
Rp2.637.376 total
includes taxes & fees
11 Nov - 12 Nov
Antique Rose Inn Windham
A bedroom with a large window, a bed, and a view of a forest.

12. The Haüs Windham

The Haüs 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 Rp2.813.201
Rp5.751.426 total
includes taxes & fees
17 Nov - 18 Nov
The Haüs Windham
A multi-story building with outdoor seating and a stone-paved patio.

13. 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, (451 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is Rp3.076.939
Rp3.663.927 total
includes taxes & fees
22 Nov - 23 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A wooden table with a bottle of wine, two glasses, and a lit fire pit.

14. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,011 reviews)
"Always a nice stay."
United States
Marina
The price is Rp2.444.728
Rp3.031.028 total
includes taxes & fees
18 Nov - 19 Nov
Hunter Lodge, a Bluebird by Lark
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, (504 reviews)
"Great place to stay!"
United States
Eric
The price is Rp1.611.730
Rp1.772.722 total
includes taxes & fees
10 Nov - 11 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, (614 reviews)
"Overall amazing stay! Location, staff, food, aesthetic and coziness all 10/10!"
United States
Kim
The price is Rp4.051.936
Rp4.376.091 total
includes taxes & fees
17 Nov - 18 Nov
Hotel Mountain Brook
A lodge with a registration area, a covered porch, and a pond with a bridge.

17. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.0 out of 10, Wonderful, (117 reviews)
"Lovely setting, room was clean and comfortable. We ate dinner and breakfast at the hotel restaurant and enjoyed both meals."
United States
Kathleen
The price is Rp3.237.931
Rp3.626.482 total
includes taxes & fees
11 Nov - 12 Nov
Emerson Resort & Spa
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

18. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (334 reviews)
"Beautiful Inn. Every detail was so well thought out!"
United States
Nancy Joan
The price is Rp2.572.256
Rp2.881.035 total
includes taxes & fees
11 Nov - 12 Nov
Shandaken Inn
A park with Adirondack chairs and a table, surrounded by trees.

19. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (307 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is Rp3.002.774
Rp3.242.996 total
includes taxes & fees
15 Nov - 16 Nov
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.

20. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (321 reviews)
"The special game room in the back yard that is screened is excellent 👌."
United States
Stephen
The price is Rp2.622.905
Rp2.937.654 total
includes taxes & fees
10 Nov - 11 Nov
Starlite Motel
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

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent
"We had a great time. The pool, hot tubs and saunas were amazing. The bar and restaurant was very good. No need to drive out of the hotel for a drink or dinner. Just wished the bar was open until later. Bedroom was very nice. We stayed in a deluxe studio and it was nicely stocked with everything we needed. We will definitely be coming back. Planning to come with the family for snow fun."
Alyson 2-night trip
Posted 14 hours ago
Kaatskill Mountain Club & Condos by Vail Resorts

More cheap stays in Ashland

The Colonial Motel

The Colonial Motel

37283 NY-23 Grand Gorge NY
The price is Rp1.611.730 per night from 10 Nov to 11 Nov
Rp1.611.730
Rp1.772.722 total
10 Nov - 11 Nov
includes taxes & fees
9.6/10 Exceptional! (504 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 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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