Default HTG hotel image

Best Resorts in Ashland

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, (877 reviews)
"Clean quiet breakfast was amazing"
United States
john
$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, (178 reviews)
"Great accommodations for the price. The room was quiet and comfortable. Great value, and I'll definitely be staying here again."
United States
Cory
$120 nightly
The price is $130
Sep 25 - Sep 26
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, (494 reviews)
"Great place to stay!"
United States
Eric
$89 nightly
The price is $98
Oct 15 - Oct 16
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 27 - Sep 28
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
$167 nightly
The price is $180
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, (1,015 reviews)
"I have been there twice and have really enjoyed my stay both times"
United States
Shubhangi
$155 nightly
The price is $168
Oct 25 - Oct 26
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)
$282 nightly
The price is $305
Oct 7 - Oct 8
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
$149 nightly
The price is $160
Oct 6 - Oct 7
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 27 - Sep 28
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.
$135 nightly
The price is $146
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 18 - Oct 19
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
$362 nightly
The price is $391
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, (428 reviews)
"Great location to amazing trails and great accommodations"
United States
Nuria
$207 nightly
The price is $224
Sep 30 - Oct 1
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, (617 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, (118 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 27 - Sep 28
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
$237 nightly
The price is $256
Sep 27 - Sep 28
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
$349 nightly
The price is $377
Sep 27 - Sep 28
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, (288 reviews)
"Host was very nice and bed was clean and comfortable. The bathroom in our room was newly renovated and the big shower had great water pressure!"
United States
Margo
$130 nightly
The price is $143
Oct 6 - Oct 7
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"I love how rustic the decor is, the dog friendly policy was my ultimate favorite. My puppy, boyfriend and I had a marvelous time and stay. The staff was wonderful helped me with trails, the restaurant food was delightful and so was the bar. Will be coming back!!"
Amy 2-night trip
Posted 11 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Ashland

Ashland Resorts information

Number of reviews
4,274
Accommodation
0 Resorts
Lowest Price
$98
Highest Price
$391

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.

Explore a world of travel with Expedia