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Compare 129 Cottages in Ashland with updated reviews, rates, and availability.

Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!

10.0 out of 10, Exceptional, (14)
"Short vacation for us to escape the city. This place is very nice and quite, we love it! Thank you!"
Romantic cottage w/hot tub . Close to skiing and breweries . Pet friendly!

The Cabin at Chichester in the Catskills Mountains

9.8 out of 10, Exceptional, (182)
"Really clean property and amazing manager"
The Cabin at Chichester in the Catskills Mountains

Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

9.6 out of 10, Exceptional, (16)
"We loved the stay at this cabin."
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn

Stream Come True! Ski, hike, spa, flow, relax...

10.0 out of 10, Exceptional, (5)
"Tranquil sounds of flowing water all day was very relaxing. Property was just as described. Thank you!"
Stream Come True! Ski, hike, spa, flow, relax...

Charming Retreat 5 Minute Walk to Main Street & 7 Minutes to Hunter Mountain

10.0 out of 10, Exceptional, (3)
"Matched the pictures and responsive host. Really good location for skiing and town."
Charming Retreat 5 Minute Walk to Main Street & 7 Minutes to Hunter Mountain

Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls

10.0 out of 10, Exceptional, (2)
"The place was clean, the area was adorable and close to everything, and the communication with the owner was quick and painless. Would stay again. "
The price is SAR 894
SAR 2,400 total
includes taxes & fees
26 May - 27 May
Cozy Mountain Getaway | Hot Tub | Grill | Fire Pit | 5 Min to Kaaterskills Falls

Spacious Cozy Getaway in the Catskills: King bed/ Game Room

9.2 out of 10, Wonderful, (15)
"The house was beautiful and comfy."
Spacious Cozy Getaway in the Catskills: King bed/ Game Room

Cozy Cottage with Stunning Mountain Views

10.0 out of 10, Exceptional, (95)
"Great location only 15 minutes from Belleayre. Paul was a great host and checked in with us to make sure everything was ok. Beautiful mountain views. "
Cozy Cottage with Stunning Mountain Views

Mountain Views & Brook Access: Home in Arkville!

3.0 star property
Mountain Views & Brook Access: Home in Arkville!

Modern Country Cottage

10.0 out of 10, Exceptional, (2)
Modern Country Cottage

Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

10.0 out of 10, Exceptional, (3)
"Very kind and can tell they put a lot of effort in hosting"
Charming 2-bedroom cottage with WiFi and AC in fabulous Phoenicia

Modern Cottage 1 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

9.2 out of 10, Wonderful, (9)
"Definitely enjoyed my stay at the Lorca. It was clean, neat and tidy and was close to Belleayre. Peakamoose restaurant served an amazing dinner apres ski. Available grill and firepit provided a perfect getaway long weekend for us."
Modern Cottage 1 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

10.0 out of 10, Exceptional, (20)
"We had a wonderful stay at the cottage. Place was perfect and met all our needs. The cottage was lovely and cozy, truly home away from home. The host, Agnes, was kind and very helpful. Will definitely be back."
The price is SAR 1,347
SAR 2,050 total
includes taxes & fees
11 May - 12 May
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Charming Cottage In The Catskills. Ski, Golf, Hike, Bike And More.

9.6 out of 10, Exceptional, (64)
"We had a wonderful, relaxing stay."
Charming Cottage In The Catskills. Ski, Golf, Hike, Bike And More.

Jewett Cabin w/ Viewing Deck - 10 Mins to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location and very clean and comfortable stay!"
Jewett Cabin w/ Viewing Deck - 10 Mins to Skiing!

Tiny House on Walnut Grove

2.0 star property
4.0 out of 10, (1)
The price is SAR 563
SAR 1,041 total
includes taxes & fees
11 May - 12 May
Tiny House on Walnut Grove

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

The price is SAR 405
SAR 748 total
includes taxes & fees
11 May - 12 May
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Cozy Catskills Cabin - 12 Mi to Windham Mountain!

3.0 star property
Cozy Catskills Cabin - 12 Mi to Windham Mountain!

Cozy Ski House Retreat minutes to Belleayre Mountain Resort

10.0 out of 10, Exceptional, (4)
"Cozy house, loved how close it was to mountain. Perfect for my family!"
Cozy Ski House Retreat minutes to Belleayre Mountain Resort

Catskills Mountain Cabin in Bloomville!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful and cozy home Peaceful scenery PERFECT fit for our large families "
Catskills Mountain Cabin in Bloomville!
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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Other property types in Ashland

Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain

8.6 out of 10, Excellent, (14)
"It was a nice getaway in a quaint area!"
Catskills Cabin with Hot Tub near Hiking located Minutes to Belleayre Mountain

Starlite Motel

2.5 star property
9.2 out of 10, Wonderful, (252)
"Great Upstate location! Very welcoming."
The price is SAR 431
SAR 498 total
includes taxes & fees
21 May - 22 May
Starlite Motel

Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year

10.0 out of 10, Exceptional, (20)
"Beautiful house and excellent location between Hunter and Windham mountains "
Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year
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.