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Best Resorts in Ashland

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20
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, (151 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
$139 nightly
The price is $150
Oct 25 - Oct 26
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, (894 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
$141 nightly
The price is $152
Nov 2 - Nov 3
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
8.6 out of 10, Excellent, (182 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 25 - Oct 26
Total with taxes and fees
Moore's Motel
A river flowing through a forested area with rocks and autumn-colored trees.

4. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (158 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 25 - Oct 26
Total with taxes and fees
Black Bear Lodge
A large, two-story house with multiple porches and string lights.

5. 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 25 - Oct 26
Total with taxes and fees
Albergo Allegria Hotel
A rustic cabin with a stone foundation, a wooden roof, and a small porch.

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
$144 nightly
The price is $155
Oct 25 - Oct 26
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

7. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (133 reviews)
"Loved our stay, will go anytime for a little weekend getaway from nyc!"
United States
Yassaman Modarres
$218 nightly
The price is $236
Oct 31 - Nov 1
Total with taxes and fees
Wylder Hotel Windham
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

8. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (371 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
$167 nightly
The price is $180
Oct 25 - Oct 26
Total with taxes and fees
The Winwood Condominiums
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

9. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (122 reviews)
"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."
United States
Danica
$251 nightly
The price is $270
Nov 24 - Nov 25
Total with taxes and fees
Eastwind Windham
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, (138 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Oct 26 - Oct 27
Total with taxes and fees
Antique Rose Inn Windham
A wooden cabin interior with a central wood-burning stove, a bench with a bear pillow, and a window with a view of the outdoors.

11. 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, (77 reviews)
"Great stay highly recommend!"
United States
Shannon H.
$596 nightly
The price is $644
Nov 1 - Nov 2
Total with taxes and fees
Mountain house with Scandinavian BBQ hut and Hot tub
A two-story building with large windows and a storefront.

12. 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 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
8.8 out of 10, Excellent, (65 reviews)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
$181 nightly
The price is $195
Nov 2 - Nov 3
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, (39 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 18 - Nov 19
Total with taxes and fees
The Haüs Windham
A restaurant with wooden floors, stone walls, and a fireplace. Tables and chairs are arranged for dining.

15. 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)
"Always a nice stay."
United States
Marina
$133 nightly
The price is $144
Nov 23 - Nov 24
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
A multi-story building with outdoor seating and a stone-paved patio.

16. 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, (440 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
$180 nightly
The price is $194
Nov 24 - Nov 25
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A covered porch with outdoor seating, a staircase, and potted plants.

17. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (501 reviews)
"Great place to stay!"
United States
Eric
$81 nightly
The price is $89
Oct 25 - Oct 26
Total with taxes and fees
The Colonial Motel
A park with Adirondack chairs and a table, surrounded by trees.

18. 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 26 - Oct 27
Total with taxes and fees
Mountain Treasure B&B
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

19. Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
Tannersville
9.8 out of 10, Exceptional, (611 reviews)
"Overall amazing stay! Location, staff, food, aesthetic and coziness all 10/10!"
United States
Kim
$244 nightly
The price is $264
Nov 3 - Nov 4
Total with taxes and fees
Hotel Mountain Brook
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

20. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (329 reviews)
"Had the most amazing time and the property & staff were absolutely the best I’ve come across on any trip I’ve ever taken!! So genuinely kind & caring about guests and you can tell they really put their heart into maintaining the property! Amazing, magical place and will definitely be coming back!"
United States
Ada
$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

The Colonial Motel

The Colonial Motel

8/10 Good
"Very nice and clean place the bed was good the staff was great the price is worth I would go back there"
Sheila 1-night trip
Posted 11 hours ago
The Colonial Motel

Find out more about Ashland

Ashland Resorts information

Number of reviews
4,159
Accommodation
0 Resorts
Lowest Price
$89
Highest Price
$644

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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