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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
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 12 - Oct 13
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, (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 12 - Oct 13
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, (882 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 log cabin with a wooden deck, benches, and a car parked outside.

5. Xenia Resort

Xenia Resort
2.5 star property
Jewett
9.2 out of 10, Wonderful, (71 reviews)
"The owners are very nice. We got a personal tour of the property and enjoyed our conversation. Unfortunately, I was in town to visit family and couldn’t take advantage of the amenities, but the setting is absolutely gorgeous."
United States
Wendy
$170 nightly
The price is $184
Oct 11 - Oct 12
Total with taxes and fees
Xenia Resort
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

6. 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
$169 nightly
The price is $183
Nov 1 - Nov 2
Total with taxes and fees
The Winwood Condominiums
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
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
$135 nightly
The price is $146
Oct 14 - Oct 15
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
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 12 - Oct 13
Total with taxes and fees
Albergo Allegria Hotel
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, (497 reviews)
"Great place to stay!"
United States
Eric
$77 nightly
The price is $85
Oct 15 - Oct 16
Total with taxes and fees
The Colonial Motel
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, (137 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Oct 12 - Oct 13
Total with taxes and fees
Antique Rose Inn Windham
A two-story building with large windows and a storefront.

11. 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.

12. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,006 reviews)
"I have been there twice and have really enjoyed my stay both times"
United States
Shubhangi
$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)
"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
$215 nightly
The price is $232
Oct 11 - Oct 12
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, (37 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
$320 nightly
The price is $345
Nov 3 - Nov 4
Total with taxes and fees
The Haüs Windham
A park with Adirondack chairs and a table, surrounded by trees.

15. 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.

16. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (128 reviews)
"Wonderful stay"
United States
Yousung
$342 nightly
The price is $370
Oct 11 - Oct 12
Total with taxes and fees
Wylder Hotel Windham
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, (121 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 12 - Oct 13
Total with taxes and fees
Eastwind Windham
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
$482 nightly
The price is $520
Oct 12 - Oct 13
Total with taxes and fees
Romantic Catskill Getaway | HotTub w/Mountain View
A wooden picnic table with benches, a hammock, and a potted plant in a room with large windows and wooden floors.

19. 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
Oct 12 - Oct 13
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

20. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (322 reviews)
"Been to many hotels up in the catskillls and this place is one of the best! Great amenities, clean spaces, and a really great bar/hotel on site. EV charging stations were a huge plus!"
United States
Karina
$158 nightly
The price is $177
Oct 27 - Oct 28
Total with taxes and fees
Shandaken Inn
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
"Hunter Lodge was lovely in every way. We would definitely return."
Annajane 1-night trip
Posted 7 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Ashland

Ashland Resorts information

Number of reviews
3,548
Accommodation
0 Resorts
Lowest Price
$85
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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