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Oct 30 - Nov 1
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Nov 6 - Nov 8

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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 ļæ„21,915
ļæ„23,668 total
includes taxes & fees
Nov 1 - Nov 2
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, (899 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is ļæ„17,737
ļæ„21,881 total
includes taxes & fees
Nov 2 - Nov 3
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 ļæ„18,919
ļæ„20,433 total
includes taxes & fees
Oct 31 - Nov 1
Moore's Motel
A river flowing through a forested area with rocks and autumn-colored trees.

4. 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 ļæ„23,491
ļæ„25,370 total
includes taxes & fees
Nov 3 - Nov 4
Black Bear Lodge
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

5. 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 ļæ„22,561
ļæ„32,248 total
includes taxes & fees
Oct 31 - Nov 1
Wylder Hotel Windham
A large, two-story house with multiple porches and string lights.

6. 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 ļæ„27,393
ļæ„29,584 total
includes taxes & fees
Nov 1 - Nov 2
Albergo Allegria Hotel
A rustic cabin with a stone foundation, a wooden roof, and a small porch.

7. 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 ļæ„22,112
ļæ„23,880 total
includes taxes & fees
Nov 15 - Nov 16
Jimmy OConnors Windham Mountain Inn
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

8. 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 ļæ„26,645
ļæ„28,777 total
includes taxes & fees
Nov 1 - Nov 2
The Winwood Condominiums
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

9. 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 ļæ„34,325
ļæ„41,677 total
includes taxes & fees
Nov 16 - Nov 17
Eastwind Windham
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 ļæ„21,284
ļæ„22,987 total
includes taxes & fees
Nov 5 - Nov 6
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 ļæ„24,902
ļæ„50,541 total
includes taxes & fees
Nov 2 - Nov 3
The HaĆ¼s Windham
A wooden table with a bottle of wine, two glasses, and a lit fire pit.

12. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,001 reviews)
"Always a nice stay."
United States
Marina
The price is ļæ„16,206
ļæ„20,907 total
includes taxes & fees
Nov 30 - Dec 1
Hunter Lodge, a Bluebird by Lark
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, (445 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is ļæ„26,818
ļæ„31,934 total
includes taxes & fees
Nov 22 - Nov 23
Kaatskill Mountain Club & Condos by Vail Resorts
A covered porch with outdoor seating, a staircase, and potted plants.

14. 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 ļæ„12,502
ļæ„13,752 total
includes taxes & fees
Nov 30 - Dec 1
The Colonial Motel
Terrace/patio

15. 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 ļæ„67,636
ļæ„85,501 total
includes taxes & fees
Oct 31 - Nov 1
Windham NY Escape
A blue house with a white door, a small porch, and a hammock in front.

16. 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 ļæ„26,172
ļæ„28,266 total
includes taxes & fees
Nov 1 - Nov 2
Mountain Treasure B&B
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

17. 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 ļæ„35,316
ļæ„38,141 total
includes taxes & fees
Nov 17 - Nov 18
Hotel Mountain Brook
A lodge with a registration area, a covered porch, and a pond with a bridge.

18. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.2 out of 10, Wonderful, (111 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 ļæ„26,246
ļæ„29,396 total
includes taxes & fees
Nov 2 - Nov 3
Emerson Resort & Spa
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

19. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (333 reviews)
"We really enjoyed our stay at the Inn. The room and bathroom were very clean and comfortable. After a long day of hiking it was great to have a restaurant and bar right on site. The menu had a lot of delicious looking options and our meal was very satisfying, The staff was very friendly and helpful. Excellent stay."
United States
Martha
The price is ļæ„22,419
ļæ„25,110 total
includes taxes & fees
Nov 15 - Nov 16
Shandaken Inn
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 šŸ‘Œ."
United States
Stephen
The price is ļæ„22,861
ļæ„25,604 total
includes taxes & fees
Nov 2 - Nov 3
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 loved our stay! The cabin was big, the lodge was beautiful, the staff was friendly. Perfect weekend getaway!"
Daniel 2-night trip
Posted less than an hour 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 ļæ„12,502 per night from Nov 30 to Dec 1
ļæ„12,502
ļæ„13,752 total
Nov 30 - Dec 1
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 traveler data. Two other options for your stay in the area are Emerson Resort & Spa and Hotel Vienna. See all available top hotels, or vacation rentals in Ashland.
What's the top vacation rental that Ashland has to offer?
Heart of Hunter Village; across MT!FALL Special3rd nt half OFF!"wknd stay: Visitors like this Ashland vacation home rental. It is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation. See all vacation rentals in Ashland.
If I need to cancel my hotel reservation in Ashland, will I receive a refund?
Yes! The majority of hotel room reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Ashland.
Where can I learn more about changing or cancelling my trip to Ashland?
For more information about rescheduling or cancelling your trip to Ashland, click here.
What are some accommodations 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 that feature an onsite pool. View all hotels with pools in Ashland.
What's the best accommodation near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Ashland like?
Travelers to Ashland will find plenty to explore and enjoy. In Ashland, there are 6 hotels and other accommodations to choose from. Find out more about Ashland.
What should I see while I'm in Ashland?
A favorite place to visit is Ashland Town Hall. You'll also find Windham Vineyards and Winery and Windham Mountain Resort in the area. Check out what more 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 temp of 65Ā°F, while the coldest months are January and February with an average of 26Ā°F. The snowiest months in Ashland are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

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