Ashland hotels from RM 361

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Go beyond your typical stay in Ashland

pet-friendly image
Pet friendly
Pet friendly
Pool image
Pool
Pool

Check prices for these dates

Tonight
12 Nov - 13 Nov
Tomorrow
13 Nov - 14 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Ashland hotels

A sign for Cave Mountain Motel with a rustic stone wall and greenery.

1. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (152 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is RM564
RM609 total
includes taxes & fees
15 Nov - 16 Nov
Cave Mountain Motel
A log cabin with a deck, outdoor seating, and a view of a forest.

2. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (910 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is RM456
RM563 total
includes taxes & fees
19 Nov - 20 Nov
Hotel Vienna
A swimming pool with lounge chairs and potted plants.

3. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (184 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
The price is RM487
RM526 total
includes taxes & fees
15 Nov - 16 Nov
Moore's Motel
Two white Adirondack chairs in a forest with fallen leaves.

4. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (160 reviews)
"We had a nice stay at the Black Bear. Great location and Kim was very accommodating."
United States
Adam
The price is RM604
RM653 total
includes taxes & fees
16 Nov - 17 Nov
Black Bear Lodge
A large, two-story house with multiple porches and string lights.

5. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (289 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is RM705
RM761 total
includes taxes & fees
15 Nov - 16 Nov
Albergo Allegria Hotel
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, (377 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is RM686
RM740 total
includes taxes & fees
15 Nov - 16 Nov
The Winwood Condominiums
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

7. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (139 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is RM804
RM1,071 total
includes taxes & fees
23 Nov - 24 Nov
Wylder Hotel Windham
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

8. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (122 reviews)
"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."
United States
Danica
The price is RM905
RM1,096 total
includes taxes & fees
13 Dec - 14 Dec
Eastwind 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
9.2 out of 10, Wonderful, (10 reviews)
"We had a wedding in the area and this place was perfect for our needs. There’s a bar to the front of the property, which was fun to hang out and play pool. The beds were comfortable and the rooms were clean."
United States
Robin
The price is RM602
RM651 total
includes taxes & fees
24 Nov - 25 Nov
Jimmy OConnors Windham Mountain Inn
A bedroom with a large window, a bed, and a view of a forest.

10. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 reviews)
"Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. "
United States
Erica
The price is RM631
RM1,290 total
includes taxes & fees
16 Nov - 17 Nov
The Haüs Windham
A two-story house with a wrap-around porch, a steeply pitched roof, and a small tower-like structure on the roof.

11. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"A fantastic stay!"
United States
David
The price is RM548
RM591 total
includes taxes & fees
17 Nov - 18 Nov
Antique Rose Inn Windham
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

12. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,015 reviews)
"Always a nice stay."
United States
Marina
The price is RM517
RM646 total
includes taxes & fees
22 Nov - 23 Nov
Hunter Lodge, a Bluebird by Lark
A park with Adirondack chairs and a table, surrounded by trees.

13. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (307 reviews)
"Service and breakfast were very good"
United States
Daniel
The price is RM673
RM727 total
includes taxes & fees
15 Nov - 16 Nov
Mountain Treasure B&B
A covered porch with outdoor seating, a staircase, and potted plants.

14. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (504 reviews)
"Great place to stay!"
United States
Eric
The price is RM361
RM398 total
includes taxes & fees
16 Nov - 17 Nov
The Colonial Motel
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

15. Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
Tannersville
9.8 out of 10, Exceptional, (615 reviews)
"Overall amazing stay! Location, staff, food, aesthetic and coziness all 10/10!"
United States
Kim
The price is RM909
RM981 total
includes taxes & fees
18 Nov - 19 Nov
Hotel Mountain Brook
A multi-story building with outdoor seating and a stone-paved patio.

16. 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, (452 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is RM690
RM822 total
includes taxes & fees
22 Nov - 23 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

17. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (335 reviews)
"Beautiful Inn. Every detail was so well thought out!"
United States
Nancy Joan
The price is RM577
RM646 total
includes taxes & fees
15 Nov - 16 Nov
Shandaken Inn
Front of property

18. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (4 reviews)
"The best "
United States
Miguel
The price is RM1,740
RM2,200 total
includes taxes & fees
16 Nov - 17 Nov
Windham NY Escape
A large, white, two-story house with a turret and a wrap-around porch, surrounded by lush greenery.

19. Shadowcrest

Shadowcrest
3.5 star property
Fleischmanns
9.8 out of 10, Exceptional, (297 reviews)
"I had a wonderful stay at Shadowcrest! The aesthetic was incredibly nice and cozy, making it the perfect place to relax. The host was also super kind and helpful throughout my visit. I highly recommend staying here!"
United States
Andres
The price is RM535
RM589 total
includes taxes & fees
15 Nov - 16 Nov
Shadowcrest
A snow-covered lodge with a stone chimney, lit windows, and snow-laden trees in front.

20. Deer Mountain Inn

Deer Mountain Inn
2.0 star property
Haines Falls
9.8 out of 10, Exceptional, (14 reviews)
"Best hotel I’ve ever stayed at! Staff is so friendly and there are so many thoughtful touches, like the beautiful delicious breakfast each morning and the guest attic to hang out in upstairs. Cannot wait to come back!!"
United States
Julia
The price is RM1,606
RM1,844 total
includes taxes & fees
7 Dec - 8 Dec
Deer Mountain 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.
View all properties

Stay near popular Ashland attractions

Ashland Town Hall

Ashland Town Hall is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels?
See properties

Frequently Asked Questions

If I need to cancel my hotel reservation in Ashland, will I receive a refund?

Yes, most hotel room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your scheduled arrival. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Ashland.

What are some accommodation options with pools in Ashland?

Emerson Resort & Spa: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli. Hotel Vienna and Kaatskill Mountain Club & Condos by Vail Resorts are two additional hotels with an on-site pool. View all hotels with pools in Ashland.

What is staying in Ashland like?

Travellers to Ashland will find plenty to explore and enjoy. In Ashland, there are 6 hotels and other accommodation options to choose from. Find out more about Ashland.

What should I do while I'm visiting Ashland?

A favourite place to visit is Ashland Town Hall. You'll also find Windham Vineyards and Winery and Windham Mountain Resort in the area. Take a look at what more there is to see and do in Expedia's Ashland guide.

What's the weather like in Ashland?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Ashland are January, March, December and November, with each month seeing an average of 18 cm of snowfall.

What's the best place for a stay in Ashland?

Hunter Lodge, a Bluebird by Lark, located 11.5 mi (18.4 km) from the heart of Ashland, is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Emerson Resort & Spa and Hotel Vienna. See all available top hotels, or vacation rentals in Ashland.