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Holiday Homes in Ashland

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Our top choices for Ashland holiday homes

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, (66 reviews)
"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."
United States
April
The price is €172
includes taxes & fees
10 Nov - 11 Nov
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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 €432
includes taxes & fees
10 Nov - 11 Nov
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is €420
includes taxes & fees
10 Nov - 11 Nov
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

4. Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
Windham
10.0 out of 10, Exceptional, (1 review)
"My stay was very short but we maximized our time by enjoying the properties endless offerings. Lots of things to do and board games were available. Plenty of room and beds every one. View from jacuzzi was phenomenal to see the stars at night. I’d recommend definitely and will revisit during winter"
United States
Lobid C.
The price is €661
includes taxes & fees
10 Nov - 11 Nov
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

5. 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 €460
includes taxes & fees
11 Nov - 12 Nov
2 Min Walk to Windham Town | Hot Tub | Fire Pit

6. Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain

Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain
Windham
Luxury Windham Escape w/ Hot Tub, Ski on/off one block from Mountain

7. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
Catskills Escape w/ Hot Tub & Fireplace

8. The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
Hensonville
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic property. Especially good for families or groups. So much to do right on property, almost no need to leave. Place was exactly as described."
United States
David H.
The price is €662
includes taxes & fees
16 Nov - 17 Nov
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!

9. 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 €460
includes taxes & fees
10 Nov - 11 Nov
Pines Vignette • Modern 3BR Home in Windham

10. 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 €386
includes taxes & fees
23 Nov - 24 Nov
Midnight Fox

11. 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, (18 reviews)
"Nice stay to hangout with family!"
United States
rakesh r.
The price is €1,209
includes taxes & fees
29 Nov - 30 Nov
Large Group Catskills Mountain Retreat near Hunter & Windham Mountains

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

Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes
Windham
The price is €803
includes taxes & fees
10 Nov - 11 Nov
Luxury Windham Retreat w/ Hot Tub & Fireplace, Mins to Slopes

13. 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 €379
includes taxes & fees
13 Nov - 14 Nov
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!

14. 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.
The price is €478
includes taxes & fees
1 Dec - 2 Dec
Escape the City for Catskills, Minutes to Skiing. Entire house, sleeps 10!

15. 5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn
Windham
The price is €551
includes taxes & fees
30 Nov - 1 Dec
5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

16. 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 €606
includes taxes & fees
10 Nov - 11 Nov
Catskill Mountain Hideaway with Amazing Hunter Mountain Views

17. 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 €350
includes taxes & fees
10 Nov - 11 Nov
Gorgeous Mountains Views & Private Stream in Secluded Oasis

18. Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15

Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15
West Kill
10.0 out of 10, Exceptional, (1 review)
"It was a great spot for all three generations to be together for the holiday. House was clean and close to lots of hikes. Hosts were available."
United States
Kate R.
The price is €911
includes taxes & fees
1 Dec - 2 Dec
Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15

19. 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.
The price is €770
includes taxes & fees
23 Nov - 24 Nov
Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street

20. 2BR Mountain View Home with Pool & 3 mins to Ski Slopes

2BR Mountain View Home with Pool & 3 mins to Ski Slopes
Tannersville
9.8 out of 10, Exceptional, (98 reviews)
"Great location, house is a bit run down. If you’re there just for skiing, this would be a great home."
United States
Murodjon R.
The price is €324
includes taxes & fees
10 Nov - 11 Nov
2BR Mountain View Home with Pool & 3 mins to Ski Slopes
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

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
147
Accommodation
535 Holiday Homes
Lowest Price
€172
Highest Price
€1,209