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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (857 reviews)
"lots of place to walk around"
United States
mordechai
$140 nightly
The price is $151
Sep 1 - Sep 2
Total with taxes and fees
Hotel Vienna
A covered porch with outdoor seating, a staircase, and potted plants.

2. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (483 reviews)
"Had a great stay!"
United States
Juerg
$77 nightly
The price is $85
Sep 28 - Sep 29
Total with taxes and fees
The Colonial Motel
A swimming pool with lounge chairs and potted plants.

3. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.8 out of 10, Excellent, (176 reviews)
"Great place. Right on BDR. Bring coffee or breakfast. Town does not have any place to get it."
United States
Dylan
$120 nightly
The price is $130
Sep 1 - Sep 2
Total with taxes and fees
Moore's Motel
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

4. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,002 reviews)
$144 nightly
The price is $156
Sep 10 - Sep 11
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
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, (152 reviews)
"Perfect quiet little motel close to great hikes. Staff was courteous and had tons of information on things to do in the area."
United States
Gerald
$149 nightly
The price is $161
Aug 30 - Aug 31
Total with taxes and fees
Black Bear Lodge
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

6. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (136 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Sep 1 - Sep 2
Total with taxes and fees
Antique Rose Inn Windham
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

7. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
8.6 out of 10, Excellent, (4 reviews)
"What a gem of a property! The brother and sister that own and operate this place are so sweet and hospitable, and the bar and motel are quaint and charming in a cozy, woodsy way. If I’m ever in the area I would absolutely stay here again."
United States
Amy
$135 nightly
The price is $146
Sep 29 - Sep 30
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
A bedroom with a large window, a bed, and a view of a forest.

8. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (34 reviews)
"Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up...
United States
Raven Jane
$328 nightly
The price is $354
Sep 3 - Sep 4
Total with taxes and fees
The Haüs Windham
A park with Adirondack chairs and a table, surrounded by trees.

9. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (302 reviews)
"Service and breakfast were very good"
United States
Daniel
$146 nightly
The price is $158
Aug 31 - Sep 1
Total with taxes and fees
Mountain Treasure B&B
A two-story building with large windows and a storefront.

10. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
$122 nightly
The price is $132
Aug 30 - Aug 31
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

11. The Wheelhouse Inn

The Wheelhouse Inn
2.5 star property
Pine Hill
8.6 out of 10, Excellent, (131 reviews)
"The location is convenient for Belleyare skiers."
United States
Allen
$90 nightly
The price is $101
Sep 19 - Sep 20
Total with taxes and fees
The Wheelhouse Inn
A large, two-story house with multiple porches and string lights.

12. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (285 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Aug 30 - Aug 31
Total with taxes and fees
Albergo Allegria Hotel
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

13. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (116 reviews)
"The staff was friendly and the room was clean and comfortable. Would love to come back again!"
United States
Claire
$247 nightly
The price is $266
Aug 30 - Aug 31
Total with taxes and fees
Eastwind Windham
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

14. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (363 reviews)
"Great place for a couple."
United States
Abdul
$167 nightly
The price is $180
Aug 30 - Aug 31
Total with taxes and fees
The Winwood Condominiums
A two-story building with large windows and a storefront.

15. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (63 reviews)
"Overall great experience. Very central location. Host lives in building, so is always available. They grow tomato's and cucumbers on the balcony that they invited us to "take as much as you want" My only discomfort with this place was the dust and dirty dishes. The people before us half-washed the things they used and the place seemed like it needed a pass with a vacuum cleaner. The floors were not very clean. In general, I greatly enjoyed my stay here."
United States
David
$205 nightly
The price is $221
Aug 30 - Aug 31
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

16. Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.8 out of 10, Exceptional, (11 reviews)
"Great place to get away. "
United States
Joshua
$256 nightly
The price is $287
Aug 30 - Aug 31
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
A multi-story building with outdoor seating and a stone-paved patio.

17. 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, (417 reviews)
"great hotel and staff"
United States
jason
$204 nightly
The price is $224
Sep 29 - Sep 30
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

18. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (283 reviews)
"Host was very nice and bed was clean and comfortable. The bathroom in our room was newly renovated and the big shower had great water pressure!"
United States
Margo
$130 nightly
The price is $143
Sep 1 - Sep 2
Total with taxes and fees
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.

19. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (38 reviews)
"Really well kept friendly staff and was overall a joy to stay at The Perch! No complaints what so ever."
United States
Jason
$200 nightly
The price is $216
Sep 10 - Sep 11
Total with taxes and fees
The Perch Hotel
A wooden cabin interior with a kitchen area, wooden cabinets, a black stove, and a black refrigerator.

20. Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Roxbury
10.0 out of 10, Exceptional, (19 reviews)
"Perfect little cabin for our Thanksgiving getaway! "
United States
Gabrielle G.
$195 nightly
The price is $215
Sep 13 - Sep 14
Total with taxes and fees
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
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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Top Ashland Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Was just amazing! Everyone one so friendly and the place and area is very picturesque!"
Ruben 3-night trip
Posted 2 hours ago
Hotel Vienna

Find out more about Ashland

Ashland Resorts information

Number of reviews
4,596
Accommodation
0 Resorts
Lowest Price
$85
Highest Price
$354

Frequently asked questions

What is Ashland like for a resort vacation?
You deserve a break, and a resort is the perfect place to pamper yourself with the services and amenities you need for a relaxing time in Ashland. One of the comfortable resorts in the area might be just what you're searching for, whether you want an amazing pool, a state-of-the-art fitness center, or nightly entertainment options.
What can I do in Ashland?
Ashland Town Hall, Windham Mountain Resort, and Windham Country Club are a few interesting places to visit nearby. Other attractions in the area include Hunter Mountain and Kaatskill Flyer Ski Lift.
What's the seasonal weather like in Ashland?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°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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