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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13
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, (150 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
$139 nightly
The price is $150
Nov 1 - Nov 2
Total with taxes and fees
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, (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 16 - Oct 17
Total with taxes and fees
Moore's Motel
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, (156 reviews)
"We had a nice stay at the Black Bear. Great location and Kim was very accommodating."
United States
Adam
$149 nightly
The price is $161
Oct 18 - Oct 19
Total with taxes and fees
Black Bear Lodge
A log cabin with a deck, outdoor seating, and a view of a forest.

4. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (885 reviews)
"The location is excellent, easy to find and very attractive. The staff was friendly and courteous."
United States
Toni-Diane
$145 nightly
The price is $157
Oct 29 - Oct 30
Total with taxes and fees
Hotel Vienna
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

5. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (368 reviews)
"Great place for a couple."
United States
Abdul
$167 nightly
The price is $180
Oct 19 - Oct 20
Total with taxes and fees
The Winwood Condominiums
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)
"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
$124 nightly
The price is $134
Oct 18 - Oct 19
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
A large, two-story house with multiple porches and string lights.

7. 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
$174 nightly
The price is $188
Oct 18 - Oct 19
Total with taxes and fees
Albergo Allegria Hotel
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

8. 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
$135 nightly
The price is $146
Oct 19 - Oct 20
Total with taxes and fees
Antique Rose Inn Windham
A covered porch with outdoor seating, a staircase, and potted plants.

9. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (498 reviews)
"Great place to stay!"
United States
Eric
$77 nightly
The price is $85
Nov 3 - Nov 4
Total with taxes and fees
The Colonial Motel
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 large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

11. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (131 reviews)
"Wonderful stay"
United States
Yousung
$271 nightly
The price is $293
Oct 29 - Oct 30
Total with taxes and fees
Wylder Hotel Windham
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

12. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,007 reviews)
"Always a nice stay."
United States
Marina
$147 nightly
The price is $158
Nov 8 - Nov 9
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
A two-story building with large windows and a storefront.

13. 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)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
$216 nightly
The price is $233
Oct 18 - Oct 19
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A bedroom with a large window, a bed, and a view of a forest.

14. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (38 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
$352 nightly
The price is $380
Nov 2 - Nov 3
Total with taxes and fees
The Haüs Windham
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, (121 reviews)
"The cabin was adorable, everything at Dandies was delicious and Jamie was extremely helpful"
United States
Sharon
$295 nightly
The price is $318
Nov 15 - Nov 16
Total with taxes and fees
Eastwind Windham
A park with Adirondack chairs and a table, surrounded by trees.

16. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (304 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 wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

17. 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
$247 nightly
The price is $277
Oct 29 - Oct 30
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
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
$441 nightly
The price is $475
Oct 22 - Oct 23
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View
Property grounds

19. 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 multi-story building with outdoor seating and a stone-paved patio.

20. 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, (437 reviews)
"Great stay, beautiful place"
United Kingdom
Ryan
$194 nightly
The price is $210
Nov 15 - Nov 16
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
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
"The room was huge and very roomy!!! We had a beautiful view of the mountains! We loved our stay and would love to return."
Debbie 3-night trip
Posted 7 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Ashland

Ashland Resorts information

Number of reviews
4,651
Accommodation
0 Resorts
Lowest Price
$85
Highest Price
$380

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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