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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (878 reviews)
"Very nice property with very nice rooms and great staff. Would definitely recommend!"
United States
Paul
$145 nightly
The price is $157
Oct 1 - Oct 2
Total with taxes and fees
Hotel Vienna
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, (180 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
Sep 28 - Sep 29
Total with taxes and fees
Moore's Motel
A covered porch with outdoor seating, a staircase, and potted plants.

3. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (495 reviews)
"Great place to stay!"
United States
Eric
$81 nightly
The price is $89
Sep 29 - Sep 30
Total with taxes and fees
The Colonial 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, (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
Sep 28 - Sep 29
Total with taxes and fees
Black Bear Lodge
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, (364 reviews)
"Great place for a couple."
United States
Abdul
$169 nightly
The price is $183
Sep 28 - Sep 29
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.

6. 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
Sep 28 - Sep 29
Total with taxes and fees
Antique Rose Inn Windham
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, (1,018 reviews)
"I have been there twice and have really enjoyed my stay both times"
United States
Shubhangi
$166 nightly
The price is $180
Oct 26 - Oct 27
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, (35 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
$324 nightly
The price is $350
Sep 28 - Sep 29
Total with taxes and fees
The Haüs Windham
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

9. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.4 out of 10, Exceptional, (9 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
Sep 29 - Sep 30
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
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 28 - Sep 29
Total with taxes and fees
Albergo Allegria Hotel
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.
$127 nightly
The price is $137
Sep 28 - Sep 29
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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 room with a view of a landscape through a window, a chair, a table with a laptop, and a bed with books on it.

13. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (41 reviews)
"Really well kept friendly staff and was overall a joy to stay at The Perch! No complaints what so ever."
United States
Jason
$350 nightly
The price is $378
Oct 22 - Oct 23
Total with taxes and fees
The Perch Hotel
A multi-story building with outdoor seating and a stone-paved patio.

14. 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, (429 reviews)
"Great location to amazing trails and great accommodations"
United States
Nuria
$217 nightly
The price is $235
Oct 27 - Oct 28
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

15. SunView Motel

SunView Motel
2.5 star property
Tannersville
8.6 out of 10, Excellent, (619 reviews)
"Great hotel!"
United States
Victoria
$118 nightly
The price is $128
Oct 1 - Oct 2
Total with taxes and fees
SunView Motel
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

16. 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
Sep 28 - Sep 29
Total with taxes and fees
Eastwind Windham
A two-story building with large windows and a storefront.

17. 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
$230 nightly
The price is $248
Sep 28 - Sep 29
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

18. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (128 reviews)
"Wonderful stay"
United States
Yousung
$405 nightly
The price is $438
Oct 11 - Oct 12
Total with taxes and fees
Wylder Hotel Windham
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

19. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (314 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Sep 28 - Sep 29
Total with taxes and fees
Starlite Motel
A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

20. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (290 reviews)
"The house is beautiful and our room lovely . Will stay again"
Canada
David
$165 nightly
The price is $182
Oct 5 - Oct 6
Total with taxes and fees
Shadowcrest
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

SunView Motel

SunView Motel

10/10 Excellent
"Exceptionally clean and with terrific refridg, freezer and microwave. Very recently re modelled and hardwood floors!! Bathroom lovely tiles floor and large shower. Good water pressure and soft mountain water. Great room size. Very quiet, busy road only. Highly organized staff to keep things moving well for visitors( regarding keys and internet.) Will stay again and what hillside views!!! Not fancy but so well done. Loved the drive up the 4 mile switch backs to get there. Diner nearby"
Eileen 4-night trip
Posted 2 days ago
SunView Motel

Find out more about Ashland

Ashland Resorts information

Number of reviews
3,536
Accommodation
0 Resorts
Lowest Price
$89
Highest Price
$438

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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