Hotels in Ashland

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Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Ashland?

A swimming pool with lounge chairs and potted plants.

1. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (183 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
Oct 30 - Oct 31
Moore's Motel
A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

2. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (151 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
Nov 1 - Nov 2
Cave Mountain Motel
A river flowing through a forested area with rocks and autumn-colored trees.

3. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (160 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
Nov 3 - Nov 4
Black Bear Lodge
A log cabin with a deck, outdoor seating, and a view of a forest.

4. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (898 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 $125
$152 total
includes taxes & fees
Nov 2 - Nov 3
Hotel Vienna
A rustic cabin with a stone foundation, a wooden roof, and a small porch.

5. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.2 out of 10, Wonderful, (10 reviews)
The price is $149
$160 total
includes taxes & fees
Nov 12 - Nov 13
Jimmy OConnors Windham Mountain Inn
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

6. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (372 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
Nov 1 - Nov 2
The Winwood Condominiums
A covered porch with outdoor seating, a staircase, and potted plants.

7. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (501 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
Nov 1 - Nov 2
The Colonial Motel
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

8. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (134 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 $179
$243 total
includes taxes & fees
Oct 30 - Oct 31
Wylder Hotel Windham
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

9. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (138 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
Nov 4 - Nov 5
Antique Rose Inn Windham
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, (289 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 $174
$188 total
includes taxes & fees
Nov 2 - Nov 3
Albergo Allegria Hotel
A bedroom with a large window, a bed, and a view of a forest.

11. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 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 $176
$340 total
includes taxes & fees
Nov 2 - Nov 3
The Haüs Windham
A wooden table with a bottle of wine, two glasses, and a lit fire pit.

12. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,012 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
Nov 8 - Nov 9
Hunter Lodge, a Bluebird by Lark
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

13. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (122 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 $239
$288 total
includes taxes & fees
Nov 15 - Nov 16
Eastwind Windham
A park with Adirondack chairs and a table, surrounded by trees.

14. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (306 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 $166
$179 total
includes taxes & fees
Nov 1 - Nov 2
Mountain Treasure B&B
A multi-story building with outdoor seating and a stone-paved patio.

15. 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, (443 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 $170
$203 total
includes taxes & fees
Nov 22 - Nov 23
Kaatskill Mountain Club & Condos by Vail Resorts
Property grounds

16. The Wheelhouse Inn

The Wheelhouse Inn
2.5 star property
Pine Hill
8.4 out of 10, Very good, (135 reviews)
This charming Pine Hill hotel offers convenient access to popular attractions. You'll find complimentary WiFi and parking for hassle-free exploration of the nearby Catskill Mountains and Pine Hill Community Center.
The price is $90
$101 total
includes taxes & fees
Nov 6 - Nov 7
The Wheelhouse Inn
A large two-story house with a snow-covered roof and a front porch.

17. Meadowood Inn

Meadowood Inn
3.0 star property
Arkville
9.6 out of 10, Exceptional, (304 reviews)
Nestled in Arkville, this charming inn offers easy access to Belleayre Mountain Ski Center. Hikers and mountain bikers love the nearby trails, while skiers appreciate the proximity to slopes. Fellow travelers rave about the helpful staff and delicious free breakfast.
The price is $122
$159 total
includes taxes & fees
Nov 22 - Nov 23
Meadowood Inn
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

18. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (331 reviews)
Seasonal outdoor pool and 24-hour fitness center complement the free WiFi, breakfast, and parking at this mountain retreat. Just a 10-minute drive to Belleayre Mountain Ski Center with attentive staff to enhance your Catskill adventure.
The price is $158
$177 total
includes taxes & fees
Nov 2 - Nov 3
Shandaken Inn
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, (321 reviews)
Embrace the Catskill charm at this cozy mountain aparthotel, just a quick drive from Belleayre Mountain Ski Center. Rooms feature handy refrigerators and microwaves, while the garden and terrace offer peaceful outdoor spaces to unwind after skiing adventures.
The price is $145
$162 total
includes taxes & fees
Nov 2 - Nov 3
Starlite Motel
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.

20. The Perch Hotel

The Perch Hotel
2.0 star property
East Windham
9.4 out of 10, Exceptional, (46 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 $219
$236 total
includes taxes & fees
Nov 5 - Nov 6
The Perch Hotel
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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Go beyond your typical stay in Ashland

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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

A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.
Cave Mountain Motel

Cave Mountain Motel

Cave Mountain Motel
Windham

10/10 Exceptional

Cozy,clean and cute place, great host!
United States
Petra
Reviewed January 26, 2022
Cave Mountain Motel

Frequently Asked Questions

What accommodations do travelers recommend in Ashland?

Guests like Hotel Vienna, Wylder Hotel Windham and Eastwind Windham.

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.