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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Ashland holiday homes

A two-story building with large windows and a storefront.

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
8.8 out of 10, Excellent, (65 reviews)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
The price is £149
includes taxes & fees
2 Nov - 3 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Entryway area

2. Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Ashland
9.2 out of 10, Wonderful, (5 reviews)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is £416
includes taxes & fees
25 Oct - 26 Oct
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

3. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is £381
includes taxes & fees
21 Oct - 22 Oct
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A bedroom with a bed, a desk, a chair, a ceiling fan, and two windows.

4. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is £538
includes taxes & fees
20 Oct - 21 Oct
Catskills Escape w/ Hot Tub & Fireplace
A wooden interior with a central fireplace, benches, and a window offering a forest view.

5. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (76 reviews)
"Great stay highly recommend!"
United States
Shannon H.
The price is £516
includes taxes & fees
2 Nov - 3 Nov
Mountain house with Scandinavian BBQ hut and Hot tub
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

6. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is £420
includes taxes & fees
2 Nov - 3 Nov
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

7. Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (11 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
The price is £264
includes taxes & fees
20 Oct - 21 Oct
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

8. Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is £808
includes taxes & fees
26 Oct - 27 Oct
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

9. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is £307
includes taxes & fees
25 Oct - 26 Oct
West Kill Barnhouse: Ski, Work & Unwind
Interior

10. Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!

Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!
West Kill
10.0 out of 10, Exceptional, (2 reviews)
"If you've lived in an old house before, then you know what to expect. It was good for our needs during our short stay. The house is spacious and there is lots of light. The beds were comfortable and the water pressure was awesome. There is an a/c in every upstairs bedroom."
United States
Alexandra I.
Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

11. Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (15 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
The price is £339
includes taxes & fees
20 Oct - 21 Oct
Midnight Fox
A wooden deck with Adirondack chairs, a stone fireplace, and a scenic view.

12. Large Group Catskills Mountain Retreat near Hunter & Windham Mountains

Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
Prattsville
10.0 out of 10, Exceptional, (17 reviews)
"Nice stay to hangout with family!"
United States
rakesh r.
Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

13. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is £400
includes taxes & fees
1 Nov - 2 Nov
Pines Vignette • Modern 3BR Home in Windham
A bedroom with a bed, desk, chair, and a window with curtains.

14. Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes

Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
Windham
The price is £748
includes taxes & fees
20 Oct - 21 Oct
Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
A covered outdoor area with a sofa, a table with a grill, and a tripod-mounted camera.

15. Gorgeous Mountains Views & Private Stream in Secluded Oasis

Gorgeous Mountains Views & Private Stream in Secluded Oasis
Gilboa
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was great: attentive host, comfortable lodgings, beautiful setting."
United States
Carrie S.
The price is £302
includes taxes & fees
21 Oct - 22 Oct
Gorgeous Mountains Views & Private Stream in Secluded Oasis
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

16. Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!

Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is £333
includes taxes & fees
20 Oct - 21 Oct
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
A fire pit with two chairs in a backyard.

17. Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
The price is £472
includes taxes & fees
2 Nov - 3 Nov
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
A spacious living area with a large window, a ceiling fan, and a dining table set for four.

18. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (16 reviews)
"The location was perfect, and the view of Hunter Mountain was beautiful. Our stay was enjoyable for travelers of all ages."
United States
Allyson R.
The price is £528
includes taxes & fees
20 Oct - 21 Oct
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, and an oven. There is a wooden ceiling and a blue rug on the floor.

19. Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Hunter
9.6 out of 10, Exceptional, (13 reviews)
"Everything was great!"
United States
Samuel S.
The price is £625
includes taxes & fees
25 Oct - 26 Oct
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Interior

20. Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street

Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street
West Kill
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful setting. Great light throughout the house. Convenient to the ski mountains"
United States
Timothy M.
Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street
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 Ashland Hotel Reviews

SunView Motel

SunView Motel

10/10 Excellent
"There’s nothing about the hotel that I could complain about!"
Erick 2-night trip
Posted 1 hour ago
SunView Motel

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
245
Accommodation
551 Holiday Homes
Lowest Price
£149
Highest Price
£808