Default HTG hotel image

Best Resorts in Ashland

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Aug 7 - Aug 9
In two weeks
Aug 14 - Aug 16
In one month
Aug 28 - Aug 30
In two months
Sep 25 - Sep 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

Front of property

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 2 - Aug 3
Total with taxes and fees
Cave Mountain Motel
Outdoor pool

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (174 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
Aug 2 - Aug 3
Total with taxes and fees
Moore's Motel
View from room

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (835 reviews)
"The property was super clean , friendly staff and great amenities! Can wait to get back there ."
United States
Laszlo
$151 nightly
The price is $163
Aug 5 - Aug 6
Total with taxes and fees
Hotel Vienna
Property entrance

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (465 reviews)
"Absolutely wonderful place to stay. We will be contacting them for next years trip."
United States
Karen
$88 nightly
The price is $97
Aug 2 - Aug 3
Total with taxes and fees
The Colonial Motel
View from property

Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (146 reviews)
"Clean and owners very friendly also pet friendly and we definitely will be back"
United States
Arlene
$149 nightly
The price is $161
Aug 2 - Aug 3
Total with taxes and fees
Black Bear Lodge
Dinner served

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,014 reviews)
"It was great and cozy"
United States
Yessenia
$129 nightly
The price is $140
Aug 11 - Aug 12
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Front of property

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (133 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Aug 3 - Aug 4
Total with taxes and fees
Antique Rose Inn Windham
Exterior

The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (358 reviews)
"It was so comfortable to stay there, we skied and was the perfect place to stay for a couple nights. "
United States
Nicoletta
$161 nightly
The price is $174
Aug 3 - Aug 4
Total with taxes and fees
The Winwood Condominiums
Property amenity

Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (296 reviews)
"The room was clean and comfortable, the breakfast was great. We had a good stay. "
United States
cynthia
$146 nightly
The price is $158
Aug 10 - Aug 11
Total with taxes and fees
Mountain Treasure B&B
Lushna Cabin | WiFi (free), bed sheets

Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (112 reviews)
"The place is perfect for couples, very quiet and relaxing. The cabin was clean and well mantained, the property has bikes that you can use. They welcome you with a smores kit. I recommend this place a lot!"
United States
Marta
$204 nightly
The price is $220
Aug 5 - Aug 6
Total with taxes and fees
Eastwind Windham
Double Room, Mountain View | Exterior

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
8.8 out of 10, Excellent, (3 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
$147 nightly
The price is $159
Aug 12 - Aug 13
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
Exterior

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 2 - Aug 3
Total with taxes and fees
Albergo Allegria Hotel
Interior

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (33 reviews)
"Can’t complain one bit"
United States
Christopher
$209 nightly
The price is $225
Aug 3 - Aug 4
Total with taxes and fees
The Haüs Windham
Exterior

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 2 - Aug 3
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (108 reviews)
"It’s our favorite place, third summer we have been here. It’s heavenly!!"
United States
Linda
$296 nightly
The price is $320
Aug 16 - Aug 17
Total with taxes and fees
Wylder Hotel Windham
Panoramic Single Room, Valley View | Premium bedding, desk, cribs (surcharge), rollaway beds (surcharge)

The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (33 reviews)
"This is a really charming hotel with amazing views and very friendly and helpful staff. We wish we could've stayed longer!"
United States
Reid
$169 nightly
The price is $183
Aug 6 - Aug 7
Total with taxes and fees
The Perch Hotel
Exterior

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.
$204 nightly
The price is $220
Aug 3 - Aug 4
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

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, (401 reviews)
"I like the place, the staff are very nice"
United States
Reina
$222 nightly
The price is $240
Aug 3 - Aug 4
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
Dining

Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
Gilboa
9.6 out of 10, Exceptional, (9 reviews)
"Great place to get away. "
United States
Joshua
$254 nightly
The price is $284
Aug 2 - Aug 3
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat
Premium House, Kitchen, Mountain View | Private kitchen | Coffee/tea maker, full-size fridge, microwave

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (308 reviews)
"Very nice for the price. The full kitchen was great stocked with plates, glasses, pans etc. The beds seemed new and very comfortable and the bathroom was brand new and exceptionally nice. They have definitely been putting effort into updating the rooms and it shows. I would definitely stay there again."
United States
Sean
$125 nightly
The price is $140
Aug 3 - Aug 4
Total with taxes and fees
Starlite Motel
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

Hotel Mountain Brook

Hotel Mountain Brook

10/10 Excellent
"Great staff, breakfast, beautiful and clean"
Eban 1-night trip
Posted 7 hours ago
Hotel Mountain Brook

Find out more about Ashland

Ashland Resorts information

Number of reviews
2,542
Accommodation
0 Resorts
Lowest Price
$97
Highest Price
$320

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 Zoom Flume.
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