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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

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, (148 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
$139 nightly
The price is $150
Oct 1 - Oct 2
Total with taxes and fees
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, (862 reviews)
"Clean, comfortable, spacious rooms with good service. Nice place to stay while in the area."
United States
Jerrold
$151 nightly
The price is $163
Sep 8 - Sep 9
Total with taxes and fees
Hotel Vienna
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 accommodations for the price. The room was quiet and comfortable. Great value, and I'll definitely be staying here again."
United States
Cory
$120 nightly
The price is $130
Sep 7 - Sep 8
Total with taxes and fees
Moore's Motel
A covered porch with outdoor seating, a staircase, and potted plants.

4. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (487 reviews)
"Great place to stay!"
United States
Eric
$88 nightly
The price is $97
Sep 9 - Sep 10
Total with taxes and fees
The Colonial Motel
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, (153 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
Sep 7 - Sep 8
Total with taxes and fees
Black Bear Lodge
A log cabin with a wooden deck, benches, and a car parked outside.

6. Xenia Resort

Xenia Resort
2.5 star property
Jewett
9.2 out of 10, Wonderful, (68 reviews)
"Beautiful place and setting, lovely owners. "
United States
Andrew
$175 nightly
The price is $189
Sep 6 - Sep 7
Total with taxes and fees
Xenia Resort
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

7. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,012 reviews)
"great hotel"
United States
Yaacov
$147 nightly
The price is $158
Sep 15 - Sep 16
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
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
$260 nightly
The price is $281
Sep 30 - Oct 1
Total with taxes and fees
The Haüs Windham
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

9. 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 8 - Sep 9
Total with taxes and fees
Antique Rose Inn Windham
A large, two-story house with multiple porches and string lights.

10. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (286 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Sep 7 - Sep 8
Total with taxes and fees
Albergo Allegria Hotel
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

11. 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
Sep 7 - Sep 8
Total with taxes and fees
The Winwood Condominiums
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

12. 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
Oct 4 - Oct 5
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
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, (302 reviews)
"Service and breakfast were very good"
United States
Daniel
$169 nightly
The price is $183
Sep 10 - Sep 11
Total with taxes and fees
Mountain Treasure B&B

14. 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 11 - Sep 12
Total with taxes and fees
The Wheelhouse Inn
A two-story building with large windows and a storefront.

15. 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.
$135 nightly
The price is $146
Sep 14 - Sep 15
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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.

16. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (40 reviews)
"Really well kept friendly staff and was overall a joy to stay at The Perch! No complaints what so ever."
United States
Jason
$208 nightly
The price is $225
Sep 10 - Sep 11
Total with taxes and fees
The Perch Hotel
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

17. 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
$319 nightly
The price is $344
Sep 7 - Sep 8
Total with taxes and fees
Eastwind Windham
A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

18. SunView Motel

SunView Motel
2.5 star property
Tannersville
8.6 out of 10, Excellent, (607 reviews)
"Clean and cozy"
United States
Liliia
$118 nightly
The price is $128
Sep 6 - Sep 7
Total with taxes and fees
SunView Motel
A multi-story building with outdoor seating and a stone-paved patio.

19. 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, (418 reviews)
"great hotel and staff"
United States
jason
$208 nightly
The price is $225
Sep 21 - Sep 22
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A two-story building with large windows and a storefront.

20. 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
$237 nightly
The price is $256
Sep 7 - Sep 8
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"This is the second time we have come here and it was nice that we just happened to stay in the same room as last time. This is such a wholesome cozy place I would definitely recommend. The lodge is so comforting and so clean. The staff are so welcoming and very nice."
Ramona 2-night trip
Posted 3 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Ashland

Ashland Resorts information

Number of reviews
4,023
Accommodation
0 Resorts
Lowest Price
$97
Highest Price
$374

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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