
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 storesWindham
8.8 out of 10, Excellent, (66 reviews)
The price is €172
includes taxes & fees
10 Nov - 11 Nov

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)
The price is €432
includes taxes & fees
10 Nov - 11 Nov

3. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets WelcomeWindham
9.0 out of 10, Wonderful, (9 reviews)
The price is €420
includes taxes & fees
10 Nov - 11 Nov

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 & WMCWindham
10.0 out of 10, Exceptional, (1 review)
The price is €661
includes taxes & fees
10 Nov - 11 Nov

5. 2 Min Walk to Windham Town | Hot Tub | Fire Pit
2 Min Walk to Windham Town | Hot Tub | Fire PitWindham
10.0 out of 10, Exceptional, (3 reviews)
The price is €460
includes taxes & fees
11 Nov - 12 Nov

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 MountainWindham

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)
The price is €662
includes taxes & fees
16 Nov - 17 Nov

9. Pines Vignette • Modern 3BR Home in Windham
Pines Vignette • Modern 3BR Home in WindhamWindham
10.0 out of 10, Exceptional, (2 reviews)
The price is €460
includes taxes & fees
10 Nov - 11 Nov

10. Midnight Fox
Midnight FoxHunter
10.0 out of 10, Exceptional, (15 reviews)
The price is €386
includes taxes & fees
23 Nov - 24 Nov

11. Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
Large Group Catskills Mountain Retreat near Hunter & Windham MountainsPrattsville
10.0 out of 10, Exceptional, (18 reviews)
The price is €1,209
includes taxes & fees
29 Nov - 30 Nov

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

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)
The price is €379
includes taxes & fees
13 Nov - 14 Nov

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)
The price is €478
includes taxes & fees
1 Dec - 2 Dec

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 MtnWindham
The price is €551
includes taxes & fees
30 Nov - 1 Dec

16. Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Catskill Mountain Hideaway with Amazing Hunter Mountain ViewsHunter
10.0 out of 10, Exceptional, (16 reviews)
The price is €606
includes taxes & fees
10 Nov - 11 Nov

17. Gorgeous Mountains Views & Private Stream in Secluded Oasis
Gorgeous Mountains Views & Private Stream in Secluded OasisGilboa
10.0 out of 10, Exceptional, (9 reviews)
The price is €350
includes taxes & fees
10 Nov - 11 Nov

18. Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15
Victorian Charm meets Modern Luxury: Combined Houses with 7 Bedrooms, Sleeps 15West Kill
10.0 out of 10, Exceptional, (1 review)
The price is €911
includes taxes & fees
1 Dec - 2 Dec

19. Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the Street
Entire Renovated Country House, Sleeps 7, Pets, EV, Creek Across the StreetWest Kill
10.0 out of 10, Exceptional, (5 reviews)
The price is €770
includes taxes & fees
23 Nov - 24 Nov

20. 2BR Mountain View Home with Pool & 3 mins to Ski Slopes
2BR Mountain View Home with Pool & 3 mins to Ski SlopesTannersville
9.8 out of 10, Exceptional, (98 reviews)
The price is €324
includes taxes & fees
10 Nov - 11 Nov
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

Kaatskill Mountain Club & Condos by Vail Resorts
10/10 Excellent
Find out more about Ashland
Ashland Holiday Homes information
Number of reviews | 147 |
|---|---|
Accommodation | 535 Holiday Homes |
Lowest Price | €172 |
Highest Price | €1,209 |




































































