Default HTG hotel image

Search Resort Hotels in Ashland from CA $122

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

1. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (152 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is CA $195
CA $210 total
includes taxes & fees
Nov 9 - Nov 10
Cave Mountain Motel

2. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (184 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
The price is CA $168
CA $182 total
includes taxes & fees
Nov 8 - Nov 9
Moore's Motel

3. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (160 reviews)
"We had a nice stay at the Black Bear. Great location and Kim was very accommodating."
United States
Adam
The price is CA $209
CA $226 total
includes taxes & fees
Nov 8 - Nov 9
Black Bear Lodge

4. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (906 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is CA $158
CA $195 total
includes taxes & fees
Nov 15 - Nov 16
Hotel Vienna

5. 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, (46 reviews)
"Great, highly recommend"
United States
Rebecca
The price is CA $95
CA $166 total
includes taxes & fees
Nov 8 - Nov 9
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

6. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (376 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is CA $237
CA $256 total
includes taxes & fees
Nov 8 - Nov 9
The Winwood Condominiums

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
The price is CA $208
CA $225 total
includes taxes & fees
Nov 12 - Nov 13
Jimmy OConnors Windham Mountain Inn

8. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (504 reviews)
"Great place to stay!"
United States
Eric
The price is CA $111
CA $122 total
includes taxes & fees
Nov 10 - Nov 11
The Colonial Motel

9. 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
The price is CA $244
CA $263 total
includes taxes & fees
Nov 8 - Nov 9
Albergo Allegria Hotel

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
The price is CA $189
CA $204 total
includes taxes & fees
Nov 12 - Nov 13
Antique Rose Inn Windham

11. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 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
The price is CA $204
CA $431 total
includes taxes & fees
Nov 9 - Nov 10
The Haüs Windham

12. 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, (66 reviews)
"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."
United States
April
The price is CA $154
CA $260 total
includes taxes & fees
Nov 9 - Nov 10
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

13. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (136 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is CA $305
CA $399 total
includes taxes & fees
Nov 29 - Nov 30
Wylder Hotel Windham

14. 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
The price is CA $324
CA $391 total
includes taxes & fees
Nov 15 - Nov 16
Eastwind Windham

15. Romantic Catskill Getaway | HotTub w/Mountain View

Romantic Catskill Getaway | HotTub w/Mountain View
Prattsville
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful stay! The cabin was clean, cozy, and peaceful, surrounded by beautiful nature. It was the perfect place to relax and enjoy the tranquility. Thank you for your warm hospitality! We would love to come back again."
United States
Alena
The price is CA $314
CA $627 total
includes taxes & fees
Nov 10 - Nov 11
Romantic Catskill Getaway | HotTub w/Mountain View

16. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,010 reviews)
"Always a nice stay."
United States
Marina
The price is CA $178
CA $223 total
includes taxes & fees
Dec 7 - Dec 8
Hunter Lodge, a Bluebird by Lark

17. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (307 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is CA $233
CA $251 total
includes taxes & fees
Nov 8 - Nov 9
Mountain Treasure B&B

18. Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.8 out of 10, Exceptional, (11 reviews)
"Secluded yet convenient. Homey. Quaint. Loved it! Will stay again!"
United States
Amber C.
The price is CA $168
CA $385 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Cabin-Catskills secluded Mountain retreat

19. The Wheelhouse Inn

The Wheelhouse Inn
2.5 star property
Pine Hill
8.4 out of 10, Very good, (135 reviews)
"I have nothing negative to say about my stay! The inn was clean and safe and Cinthia was very responsive and accommodating. It is a perfect location to access various hikes and other interests in the Catskills area."
United States
Victoria
The price is CA $140
CA $157 total
includes taxes & fees
Dec 4 - Dec 5
The Wheelhouse Inn

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, (449 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is CA $238
CA $284 total
includes taxes & fees
Nov 22 - Nov 23
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Find out more about Ashland

Ashland Resorts information

Number of reviews
4,026
Accommodation
0 Resorts
Lowest Price
CA $122
Highest Price
CA $627

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.

Explore a world of travel with Expedia