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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6
In one month
Sep 18 - Sep 20
In two months
Oct 16 - Oct 18
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

View from room

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (845 reviews)
"The only thing I didn't like was the pool was small and the granola they had out was stale for breakfast. Place is very nice and clean."
United States
John
$128 nightly
The price is $138
Aug 19 - Aug 20
Total with taxes and fees
Hotel Vienna
Front of property

2. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (146 reviews)
"Staff was friendly and helpful. While the property was dated, it was clean and comfortable. Would definitely stay again at this place should I return to Windham"
United States
Sarah
$139 nightly
The price is $150
Aug 19 - Aug 20
Total with taxes and fees
Cave Mountain Motel
Outdoor pool

3. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.8 out of 10, Excellent, (176 reviews)
"Great place. Right on BDR. Bring coffee or breakfast. Town does not have any place to get it."
United States
Dylan
$120 nightly
The price is $130
Aug 19 - Aug 20
Total with taxes and fees
Moore's Motel
Property entrance

4. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (474 reviews)
"Had a great stay!"
United States
Juerg
$86 nightly
The price is $95
Sep 3 - Sep 4
Total with taxes and fees
The Colonial Motel
View from property

5. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (151 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
Aug 19 - Aug 20
Total with taxes and fees
Black Bear Lodge
Free self parking

6. Xenia Resort

Xenia Resort
2.5 star property
Jewett
9.2 out of 10, Wonderful, (68 reviews)
"Beautiful place and setting, lovely owners. "
United States
Andrew
$150 nightly
The price is $162
Aug 19 - Aug 20
Total with taxes and fees
Xenia Resort
Double Room, Mountain View | Exterior

7. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
8.6 out of 10, Excellent, (4 reviews)
"What a gem of a property! The brother and sister that own and operate this place are so sweet and hospitable, and the bar and motel are quaint and charming in a cozy, woodsy way. If I’m ever in the area I would absolutely stay here again."
United States
Amy
$135 nightly
The price is $146
Aug 19 - Aug 20
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
Dinner served

8. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,005 reviews)
"It was great and cozy"
United States
Yessenia
$147 nightly
The price is $158
Aug 31 - Sep 1
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Exterior

9. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (359 reviews)
"It was so comfortable to stay there, we skied and was the perfect place to stay for a couple nights. "
United States
Nicoletta
$167 nightly
The price is $180
Aug 19 - Aug 20
Total with taxes and fees
The Winwood Condominiums
Front of property

10. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (136 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Aug 19 - Aug 20
Total with taxes and fees
Antique Rose Inn Windham
Property amenity

11. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (300 reviews)
"Service and breakfast were very good"
United States
Daniel
$146 nightly
The price is $158
Aug 24 - Aug 25
Total with taxes and fees
Mountain Treasure B&B
Exterior

12. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (284 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Aug 19 - Aug 20
Total with taxes and fees
Albergo Allegria Hotel
Lushna Cabin | WiFi (free), bed sheets

13. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (115 reviews)
"The staff was friendly and the room was clean and comfortable. Would love to come back again!"
United States
Claire
$228 nightly
The price is $246
Aug 19 - Aug 20
Total with taxes and fees
Eastwind Windham
Interior

14. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (34 reviews)
"Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up...
United States
Raven Jane
$209 nightly
The price is $225
Aug 19 - Aug 20
Total with taxes and fees
The Haüs Windham
Exterior

15. 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.
$145 nightly
The price is $157
Aug 23 - Aug 24
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Panoramic Single Room, Valley View | Premium bedding, desk, cribs (surcharge), rollaway beds (surcharge)

16. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (36 reviews)
"Really well kept friendly staff and was overall a joy to stay at The Perch! No complaints what so ever."
United States
Jason
$180 nightly
The price is $195
Aug 20 - Aug 21
Total with taxes and fees
The Perch Hotel
Exterior

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, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
$206 nightly
The price is $222
Aug 19 - Aug 20
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

18. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (117 reviews)
"It’s our favorite place, third summer we have been here. It’s heavenly!!"
United States
Linda
$303 nightly
The price is $327
Aug 23 - Aug 24
Total with taxes and fees
Wylder Hotel Windham
Exterior

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, (412 reviews)
"We visited during the summer and very much enjoyed the outdoor pool."
United States
Juliette
$215 nightly
The price is $235
Sep 16 - Sep 17
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
Front of property

20. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (281 reviews)
"Smooth checking, friendly host, cozy and pretty rooms."
United States
Maria
$120 nightly
The price is $133
Aug 20 - Aug 21
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

The Hidden Inn

The Hidden Inn

8/10 Good
"Very nice!"
Marilyn 1-night trip
Posted 1 hour ago
The Hidden Inn

Find out more about Ashland

Ashland Resorts information

Number of reviews
2,712
Accommodation
0 Resorts
Lowest Price
$95
Highest Price
$327

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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