Hotels in Ashland

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Where to stay in Ashland?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Ashland on Hotels.com. These Ashland hotels consistently deliver on comfort, location and traveler experience. Last updated on August 27, 2026.

1. Moore's Motel

Prattsville

CNY807

CNY871 total

includes taxes & fees

Sep 1 - Sep 2

2. Hotel Vienna

Windham

CNY775

CNY953 total

includes taxes & fees

Sep 14 - Sep 15

Blackout drapes, WiFi (free), bed sheets

3. The Winwood Condominiums

Windham

CNY1,204

CNY1,300 total

includes taxes & fees

Sep 1 - Sep 2

Seasonal outdoor pool, pool umbrellas, sun loungers

4. The Colonial Motel

Grand Gorge

CNY599

CNY659 total

includes taxes & fees

Sep 1 - Sep 2

Double Room, Mountain View | Food and drink

Double Room, Mountain View | Bar (on property)

Double Room, Mountain View | WiFi (free)

5. Jimmy OConnors Windham Mountain Inn

Windham

CNY998

CNY1,078 total

includes taxes & fees

Aug 30 - Aug 31

6. Black Bear Lodge

Prattsville

CNY1,001

CNY1,082 total

includes taxes & fees

Sep 1 - Sep 2

7. Windham NY Escape

Hensonville

CNY2,884

CNY3,646 total

includes taxes & fees

Aug 28 - Aug 29

Room 3 | Premium bedding, down comforters, desk, laptop workspace

8. Albergo Allegria Hotel

Windham

CNY1,168

CNY1,261 total

includes taxes & fees

Aug 30 - Aug 31

In-room safe, iron/ironing board, cribs (free)

9. Wylder Hotel Windham

Windham

CNY1,480

CNY1,935 total

includes taxes & fees

Aug 30 - Aug 31

10. Hunter Lodge, a Bluebird by Lark

Hunter

CNY851

CNY1,065 total

includes taxes & fees

Sep 7 - Sep 8

11. Antique Rose Inn Windham

Windham

CNY907

CNY980 total

includes taxes & fees

Sep 21 - Sep 22

Cottage, 2 Bedrooms (Guest House) | Down comforters, memory foam beds, soundproofing, WiFi (free)

12. Mountain Treasure B&B

Maplecrest

CNY982

CNY1,061 total

includes taxes & fees

Aug 31 - Sep 1

13. Eastwind Windham

Windham

CNY1,267

CNY1,558 total

includes taxes & fees

Aug 30 - Aug 31

Panoramic Single Room, Valley View | Premium bedding, desk, cribs (surcharge), rollaway beds (surcharge)

Panoramic Double Room, Mountain View | Balcony

14. The Perch Hotel

East Windham

CNY1,091

CNY1,179 total

includes taxes & fees

Sep 3 - Sep 4

The Faerie Forest | Living area | 45-inch flat-screen TV with cable channels, Netflix, DVD player

Crown of the Pendragons | Bathroom | Hair dryer, bathrobes, slippers, towels

15. The Roxbury

Roxbury

CNY1,990

CNY2,324 total

includes taxes & fees

Aug 30 - Aug 31

16. Fairlawn Inn

Hunter

CNY1,741

CNY1,880 total

includes taxes & fees

Sep 20 - Sep 21

17. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

CNY1,328

CNY1,582 total

includes taxes & fees

Sep 24 - Sep 25

Cabin, Ensuite (Private Cabin w/ Pullout) - This unit is not pet friendly | Premium bedding, bed sheets

Room, Ensuite (Deluxe East Lodge Room) | Premium bedding, bed sheets

18. Hotel Mountain Brook

Tannersville

CNY1,203

CNY1,299 total

includes taxes & fees

Sep 8 - Sep 9

Premium bedding, down comforters, memory foam beds, WiFi (free)

Luxury Duplex, Housekeeping, Mountainside | Living area | Smart TV, streaming services

19. The Haüs Windham

Windham

CNY1,009

CNY2,098 total

includes taxes & fees

Sep 1 - Sep 2

Deluxe Double Room | Premium bedding, down comforters, iron/ironing board (on request)

Deluxe Double Room | Bathroom | Free toiletries, hair dryer, towels, soap

Premium Double Room | Premium bedding, down comforters, iron/ironing board (on request)

20. Catskill Seasons Inn

Shandaken

CNY1,075

CNY1,204 total

includes taxes & fees

Aug 30 - Aug 31

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Go beyond your typical stay in Ashland

Pet friendly

Apartment

Pool

Hot tub

Cottage

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

The Graham & Co.

10/10 Excellent

"Wonderful Stay"

The Hidden Inn

10/10 Excellent

"Property was nice and clean. Parking lot right besides the house. Restaurant downstairs to dine, which unfortunately, we didn’t get a chance to make it to. I was bummed, a lot of locals said the food was delicious! We stayed there for a wedding. Rooms are small basically just a room and bathroom. Not much walking room but we just stayed there to sleep and shower so it was fine for us. And all I cared was that it was clean, which it was ! Only recommendation is to put a full length mirror for us ladies who are going to a wedding or someplace nice. We would love to see how we look before we leave. We would definitely stay here again and recommend this hotel! Oh and just for the older folk there is no elevator so pack light bc you will be walking up stairs to the rooms."

The Colonial Motel

10/10 Excellent

"Very nice"

Catskill Seasons Inn

10/10 Excellent

"Easy self check-in, clean room, nice pool, nice fire pit, plenty of parking."

Eastwind Windham

10/10 Excellent

"The staff was friendly and the room was clean and comfortable. Would love to come back again!"

Emerson Resort & Spa

8/10 Good

"The Emerson is a great resort/spa. Our room was just beautiful, clean , and comfortable. However, you will need to plan your stay well before you arrive since spa treatments book up quickly. My stay was spur of the moment so there was no availability, not even for a pedicure. Also be advised that there is no cell service (didn’t matter to me) but there is WiFi. I was aware that the restaurant was closed on the days of my stay so I can’t comment on the food. Even though this is a nice place, I don’t think I’ll be staying here again."

Urban Cowboy Lodge

8/10 Good

"Room has unique personality, however the room is too small for what I paid for. And we've been told the room will be cleaned daily, never happened. The overall experience is tranquil weekend getaway."

Jimmy OConnors Windham Mountain Inn

8/10 Good

"This place is definitely dated but it was clean and the beds were comfortable. Chose to stay here when riding into tue area on the bike becasue of it had a detached restaurant/bar which makes dinner easier. Food was ok and bar was cool."

Frequently asked questions

How much does a hotel room cost in Ashland?

You can discover great hotels in Ashland from CNY659 with properties to suit all budgets and needs. To find an affordable hotel in Ashland that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".

How can I find deals and earn rewards at Ashland hotels?

Discover great deals on Ashland hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Ashland hotels.

Can I book Ashland hotels with free cancellation?

In order to book a refundable Ashland hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are some popular hotels in central Ashland?

For hotels in central Ashland, check out Hotel Vienna and Albergo Allegria Hotel. Travelers love Hotel Vienna for its location, as well as the indoor pool, free continental breakfast and private picnics this hotel offers. Albergo Allegria Hotel is another popular central bed & breakfast with free parking, a terrace and concierge services. When you stay at one of these central hotels, you'll be in easy reach of top sights including Windham Mountain Resort.

What accommodations do travelers recommend in Ashland?

Guests like Wylder Hotel Windham, Hotel Vienna 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.

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