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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Ashland holiday homes

Exterior

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
9.0 out of 10, Wonderful, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is €194
includes taxes & fees
12 Aug - 13 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Dining

2. 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 €539
includes taxes & fees
9 Aug - 10 Aug
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Property grounds

3. 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, (10 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 €313
includes taxes & fees
10 Aug - 11 Aug
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Interior

4. 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 €348
includes taxes & fees
12 Aug - 13 Aug
West Kill Barnhouse: Ski, Work & Unwind
Sauna

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, (73 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
The price is €570
includes taxes & fees
10 Aug - 11 Aug
Mountain house with Scandinavian BBQ hut and Hot tub
Interior

6. Escape the City. Discover the Heart of the Catskills.

Escape the City. Discover the Heart of the Catskills.
West Kill
10.0 out of 10, Exceptional, (1 review)
"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 €500
includes taxes & fees
6 Aug - 7 Aug
Escape the City. Discover the Heart of the Catskills.
Exterior

7. Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is €538
includes taxes & fees
11 Aug - 12 Aug
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Smart TV, books, stereo, computer monitors

8. Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
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 €378
includes taxes & fees
8 Aug - 9 Aug
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
TV, fireplace

9. Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Gilboa
The price is €171
includes taxes & fees
6 Aug - 7 Aug
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Interior

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 €370
includes taxes & fees
25 Aug - 26 Aug
Midnight Fox
TV, fireplace

11. 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 €627
includes taxes & fees
12 Aug - 13 Aug
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Exterior

12. 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 €471
includes taxes & fees
1 Sept - 2 Sept
Pines Vignette • Modern 3BR Home in Windham
Indoor pool, a heated pool

13. Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
10.0 out of 10, Exceptional, (1 review)
"Host had an amazing response time. Very easy to talk with via email. She had very clear and easy instructions on check in and check out. The place had lots of bedding, it was warm and inviting, had everything we needed. My daughter thought the “balcony” on the second floor which over looked the kitchen was cool! "
United States
Soonae S.
The price is €589
includes taxes & fees
6 Aug - 7 Aug
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Smart TV, fireplace

14. A world where time stands still, close to Belleayre Ski & Wedding venues.

A world where time stands still, close to Belleayre Ski & Wedding venues.
City Roxbury
9.4 out of 10, Exceptional, (50 reviews)
"Rooms were clean, kitchen fully equipped. Enjoyed it a lot with my family. Will definitely go back"
United States
Anonymous traveller
The price is €404
includes taxes & fees
6 Aug - 7 Aug
A world where time stands still, close to Belleayre Ski & Wedding venues.
Children’s area

15. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Haines Falls
10.0 out of 10, Exceptional, (1 review)
"House was clean and well kept, perfect for our family weekend trip!"
United States
Edward C.
The price is €318
includes taxes & fees
10 Aug - 11 Aug
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Interior

16. Cozy Waterfall Home | Close to All Mountains/Hikes

Cozy Waterfall Home | Close to All Mountains/Hikes
East Durham
10.0 out of 10, Exceptional, (3 reviews)
"The host is very responsive and the listing is accurate about what to expect with the property."
United States
John K.
The price is €264
includes taxes & fees
6 Aug - 7 Aug
Cozy Waterfall Home | Close to All Mountains/Hikes
Smart TV, fireplace, books

17. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Hunter
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and comfy place to stay. Communication with owner is quick and easy. Highly recommendations "
United States
ching yi t.
The price is €599
includes taxes & fees
12 Aug - 13 Aug
Catskill Mountain Hideaway with Amazing Hunter Mountain Views
Property grounds

18. 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, (12 reviews)
"Nice stay to hangout with family!"
United States
rakesh r.
The price is €1,077
includes taxes & fees
11 Aug - 12 Aug
Large Group Catskills Mountain Retreat near Hunter & Windham Mountains
TV, fireplace, stereo

19. West Elm Lodge near Skiing • Waterfront • Groups • Breweries

West Elm Lodge near Skiing • Waterfront • Groups • Breweries
West Kill
9.8 out of 10, Exceptional, (11 reviews)
"Great home, great host and we enjoyed our time there. Will plan to stay there again next year!"
United States
dominick s.
The price is €735
includes taxes & fees
18 Aug - 19 Aug
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
Interior

20. Spacious, stylish barn and Private Creek, Firepit

Spacious, stylish barn and Private Creek, Firepit
Denver
The price is €329
includes taxes & fees
2 Sept - 3 Sept
Spacious, stylish barn and Private Creek, Firepit
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

The Graham & Co.

The Graham & Co.

10/10 Excellent
"We had a wonderful stay at Graham & Co. The staff was incredibly friendly, welcoming, and helpful. They provided great recommendations for exploring the town, which made our trip even more enjoyable. The property was very clean, well maintained, and had a relaxing atmosphere. There were also plenty of activities to enjoy right on the property. We would definitely stay here again and highly recommend it!"
Melanie 2-night trip
Posted less than an hour ago
The Graham & Co.

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
261
Accommodation
552 Holiday Homes
Lowest Price
€171
Highest Price
€1,077