Hotels in Ashland

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This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Where to stay in Ashland?

Front of property

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (140 reviews)
Immerse in adventure at this welcoming mountain motel, just 5 minutes from Windham Mountain Resort. Hiking and biking trails await nearby, while complimentary breakfast, Wi-Fi, and parking enhance your Catskills getaway.
The price is $139
$150 total
includes taxes & fees
May 26 - May 27
Cave Mountain Motel
Outdoor pool

Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.8 out of 10, Excellent, (166 reviews)
Unwind in this tranquil motel offering quiet rooms and a refreshing outdoor pool. Free WiFi and parking make exploring nearby Pratt Museum and Zadock Pratt Museum convenient, while daily housekeeping ensures a comfortable countryside retreat.
The price is $120
$130 total
includes taxes & fees
May 26 - May 27
Moore's Motel
View from property

Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (136 reviews)
Discover a peaceful haven in Prattsville where tranquility meets convenience. This motel sits near Ashland Park and Bearpen Mountain State Forest, offering complimentary WiFi, parking, and daily housekeeping for a refreshing mountain getaway.
The price is $149
$161 total
includes taxes & fees
Jun 22 - Jun 23
Black Bear Lodge
Exterior

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
Windham
8.8 out of 10, Excellent, (353 reviews)
Feel the winter magic at this Windham hotel offering complimentary ski shuttle service just 5 minutes from Windham Mountain Resort. Enjoy sledding on-site, access to ski passes, and relax in the seasonal outdoor pool after a day on the slopes. Free WiFi and parking add value.
The price is $169
$183 total
includes taxes & fees
May 26 - May 27
Winwood Condominiums by Windham Mountain Club
View from room

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (801 reviews)
Nestled 5 minutes from Windham Mountain Resort, this charming hotel offers an indoor pool, complimentary breakfast, and free bike rentals. Explore nearby hiking trails or golfing options, then unwind on the peaceful terrace surrounded by mountain views.
The price is $158
$188 total
includes taxes & fees
May 26 - May 27
Hotel Vienna
Interior

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (28 reviews)
Feel the mountain magic at this Windham hotel, just 5 minutes from Windham Mountain Resort. After a day of skiing and snowboarding, return to comfort with free WiFi and parking. The Windham Country Club and Hudson Valley's natural beauty await your exploration nearby.
The price is $148
$241 total
includes taxes & fees
May 26 - May 27
The Haüs Windham
Front of property

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (130 reviews)
Escape to this charming Victorian B&B, just minutes from Windham Mountain Resort. Wake up to a complimentary full breakfast before heading out with ski passes. After a day on the slopes, unwind in the garden or terrace, with free WiFi and parking.
The price is $135
$146 total
includes taxes & fees
May 26 - May 27
Antique Rose Inn Windham
Exterior

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (98 reviews)
Mountain adventurers will love this hotel's prime location, just a 5-minute drive from Windham Mountain Resort. After exploring nearby attractions, cool off in the outdoor pool or grab a drink at the bar. With free WiFi, parking, and a café onsite, convenience meets comfort.
The price is $252
$322 total
includes taxes & fees
May 26 - May 27
Wylder Hotel Windham
Front of property

Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (279 reviews)
Explore Windham Mountain from this Victorian B&B offering free WiFi and parking. Discover nearby hiking trails and mountain biking, then unwind in the garden or terrace. Bike cleaning facilities and exceptional staff create a memorable Catskills escape.
The price is $163
$176 total
includes taxes & fees
May 26 - May 27
Albergo Allegria Hotel
Lushna Cabin | Free WiFi, bed sheets

Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (102 reviews)
Escape to the mountains near Windham Mountain Resort at this charming hotel. Enjoy convenient perks like free WiFi and parking while you explore nearby attractions. After a day outdoors, unwind with a refreshing drink at the inviting bar.
The price is $221
$268 total
includes taxes & fees
May 26 - May 27
Eastwind Windham
Classic Double Room, 1 King Bed with Sofa bed, Non Smoking | Iron/ironing board, free WiFi, bed sheets

The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club
2.5 star property
Windham
8.4 out of 10, Very Good, (5 reviews)
Discover this charming Windham ski hotel just 5 minutes from Windham Mountain Resort. Take advantage of the complimentary ski shuttle, WiFi, and parking while enjoying easy access to Windham Country Club. The outdoor pool offers refreshing relaxation after adventurous mountain excursions.
The price is $450
$486 total
includes taxes & fees
May 26 - May 27
The Outpost by Windham Mountain Club
Property entrance

The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (443 reviews)
Explore the Catskills from this welcoming motel near hiking trails and kayaking spots. The seasonal pool offers refreshing relaxation after outdoor adventures, while free WiFi and parking add convenience for nature enthusiasts.
The price is $89
$98 total
includes taxes & fees
Jun 1 - Jun 2
The Colonial Motel
Exterior

Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (294 reviews)
Mountain charm meets outdoor adventure at this cozy B&B. Located in Maplecrest, just a short drive from Windham Mountain Resort and Hunter Mountain. Enjoy free breakfast and WiFi, then explore hiking trails, kayaking, and mountain biking nearby.
The price is $169
$183 total
includes taxes & fees
May 26 - May 27
Mountain Treasure B&B
Panoramic Single Room, Valley View | Premium bedding, desk, cribs/infant beds, rollaway beds

The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.6 out of 10, Exceptional, (29 reviews)
Located in tranquil Cornwallville, this charming hotel offers premium bedding for restful nights after mountain adventures. Zoom Flume and Durham Center Museum are nearby attractions, with free WiFi and parking enhancing your Catskills getaway.
The price is $197
$213 total
includes taxes & fees
May 28 - May 29
The Perch Hotel
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, (948 reviews)
Just a short drive from Hunter Mountain and Kaaterskill Falls, this lodge offers free breakfast, WiFi, and parking. Guests rave about the clean rooms and helpful staff. Enjoy dinner at Hunter Tavern after a day of outdoor adventures.
The price is $118
$149 total
includes taxes & fees
Jun 2 - Jun 3
Hunter Lodge, a Bluebird by Lark
Exterior

Fairlawn Inn

Fairlawn Inn
3.0 star property
Hunter
8.8 out of 10, Excellent, (437 reviews)
Situated minutes from Hunter Mountain, this charming B&B offers free breakfast and parking. Adventure seekers will love the nearby skiing and mountain biking options, while Windham Mountain Resort provides additional outdoor fun just a short drive away.
The price is $259
$280 total
includes taxes & fees
Jun 13 - Jun 14
Fairlawn Inn
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, (361 reviews)
Feel the thrill of mountain adventure at this Hunter hotel with ski-in, ski-out access. After hitting the slopes, unwind in the outdoor pool, sauna, or steam room. Van Winkles restaurant serves American favorites, while free WiFi keeps you connected in this scenic mountain escape.
The price is $193
$229 total
includes taxes & fees
May 26 - May 27
Kaatskill Mountain Club & Condos by Vail Resorts
Exclusive House, Mountain View | Iron/ironing board, free WiFi

Red Feather Lodge

Red Feather Lodge
3.0 star property
Windham
The price is $1,999
$2,159 total
includes taxes & fees
May 26 - May 27
Red Feather Lodge
Garden

Amaya Bed&Breakfast

Amaya Bed&Breakfast
2.0 star property
Oak Hill
10.0 out of 10, Exceptional, (17 reviews)
The price is $405
$437 total
includes taxes & fees
May 26 - May 27
Amaya Bed&Breakfast
Mountain view

Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.2 out of 10, Very Good, (252 reviews)
Nestled in Shandaken among the Catskill Mountains, this inn offers free breakfast, WiFi, and parking. Enjoy outdoor tennis or cool off in the seasonal pool after exploring nearby attractions and natural beauty.
The price is $139
$156 total
includes taxes & fees
May 26 - May 27
Catskill Seasons Inn
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 landmarks in Ashland

Ashland Town Hall

Ashland Town Hall is worth a visit, located 1.5 mi (2.4 km) from central Ashland.
See properties

Check out reviews of Ashland hotels guests love

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Super spacious room/great common spaces. Tavern on site was perfect. Fire places and pit outdoors all fired up/much appreciated. coffee/treats throughout the day. Nice touch"
Lisa 2-night trip
Posted 16 hours ago
Hunter Lodge, a Bluebird by Lark

Frequently asked questions

What accommodations do travelers recommend in Ashland?
Guests like Eastwind Windham, Wylder Hotel Windham and Hotel Vienna.
Can I book a refundable accommodation in Ashland?
If you're looking for the flexibility to change your travel plans to Ashland, most hotels provide refundable* bookable rates. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Ashland if I want a vacation home instead of a traditional hotel?
If you want to find a good alternative to a hotel, browse our selection of 5 vacation homes.
What will the weather in Ashland be like during my visit?
The warmest months in Ashland are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 26°F. The rainiest months are July and August.
Why should I book my Ashland hotel through Hotels.com?
There are plenty of reasons to book your Ashland travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.