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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

A swimming pool with lounge chairs and potted plants.

1. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (181 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
$120 nightly
The price is $130
Oct 6 - Oct 7
Total with taxes and fees
Moore's 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, (879 reviews)
"Very nice property with very nice rooms and great staff. Would definitely recommend!"
United States
Paul
$151 nightly
The price is $163
Oct 5 - Oct 6
Total with taxes and fees
Hotel Vienna
A river flowing through a forested area with rocks and autumn-colored trees.

3. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (155 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
Oct 4 - Oct 5
Total with taxes and fees
Black Bear Lodge
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

4. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (365 reviews)
"Great place for a couple."
United States
Abdul
$144 nightly
The price is $155
Nov 1 - Nov 2
Total with taxes and fees
The Winwood Condominiums
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

5. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (137 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Oct 5 - Oct 6
Total with taxes and fees
Antique Rose Inn Windham
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

6. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.2 out of 10, Wonderful, (10 reviews)
"The staff was super friendly and helpful. Mel took great care of us at the bar and got us checked in smoothly. She was happy to help us with local shopping and events. We will definitely come back next year!!! :-)"
United States
James
$135 nightly
The price is $146
Oct 5 - Oct 6
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
A covered porch with outdoor seating, a staircase, and potted plants.

7. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (496 reviews)
"Great place to stay!"
United States
Eric
$80 nightly
The price is $88
Oct 19 - Oct 20
Total with taxes and fees
The Colonial Motel
A large, two-story house with multiple porches and string lights.

8. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (288 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Oct 4 - Oct 5
Total with taxes and fees
Albergo Allegria Hotel
A bedroom with a large window, a bed, and a view of a forest.

9. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (36 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
$282 nightly
The price is $305
Oct 7 - Oct 8
Total with taxes and fees
The Haüs Windham
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.
$125 nightly
The price is $135
Nov 1 - Nov 2
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

11. 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)
"I have been there twice and have really enjoyed my stay both times"
United States
Shubhangi
$155 nightly
The price is $168
Nov 1 - Nov 2
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
A park with Adirondack chairs and a table, surrounded by trees.

12. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (303 reviews)
"Service and breakfast were very good"
United States
Daniel
$166 nightly
The price is $179
Oct 20 - Oct 21
Total with taxes and fees
Mountain Treasure B&B
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

13. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (128 reviews)
"Wonderful stay"
United States
Yousung
$361 nightly
The price is $390
Oct 29 - Oct 30
Total with taxes and fees
Wylder Hotel Windham
A two-story building with large windows and a storefront.

14. 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, (64 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
$238 nightly
The price is $257
Oct 5 - Oct 6
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

15. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (120 reviews)
"The cabin was adorable, everything at Dandies was delicious and Jamie was extremely helpful"
United States
Sharon
$319 nightly
The price is $344
Oct 4 - Oct 5
Total with taxes and fees
Eastwind Windham
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
$254 nightly
The price is $284
Oct 4 - Oct 5
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
Property grounds

17. The Wheelhouse Inn

The Wheelhouse Inn
2.5 star property
Pine Hill
8.6 out of 10, Excellent, (132 reviews)
"The location is convenient for Belleyare skiers."
United States
Allen
$90 nightly
The price is $101
Oct 30 - Oct 31
Total with taxes and fees
The Wheelhouse Inn
A deck with a fire pit, outdoor seating, and a view of the landscape.

18. Romantic Catskill Getaway | HotTub w/Mountain View

Romantic Catskill Getaway | HotTub w/Mountain View
Prattsville
10.0 out of 10, Exceptional, (3 reviews)
"Really beautiful place"
United States
Ramsey
$546 nightly
The price is $588
Oct 4 - Oct 5
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View
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, (432 reviews)
"Great stay, beautiful place"
United Kingdom
Ryan
$197 nightly
The price is $212
Nov 1 - Nov 2
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A wooden interior with a central fireplace, benches, and a window offering a forest view.

20. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
$637 nightly
The price is $688
Nov 2 - Nov 3
Total with taxes and fees
Mountain house with Scandinavian BBQ hut and Hot tub
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

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

8/10 Good
"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."
Robin 1-night trip
Posted 5 hours ago
Jimmy OConnors Windham Mountain Inn

Find out more about Ashland

Ashland Resorts information

Number of reviews
2,866
Accommodation
0 Resorts
Lowest Price
$88
Highest Price
$542

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 Vineyards and Winery, and Windham Mountain Resort are a few interesting places to visit nearby. Other attractions in the area include Windham Country Club and Hunter Mountain.
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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