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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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
9.0 out of 10, Wonderful, (64 reviews)
"Overall great experience. Very central location. Host lives in building, so is always available. They grow tomato's and cucumbers on the balcony that they invited us to "take as much as you want" My only discomfort with this place was the dust and dirty dishes. The people before us half-washed the things they used and the place seemed like it needed a pass with a vacuum cleaner. The floors were not very clean. In general, I greatly enjoyed my stay here."
United States
David
The price is €227
includes taxes & fees
24 Sept - 25 Sept
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

2. 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 €432
includes taxes & fees
23 Sept - 24 Sept
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

3. 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.
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A large, two-story house with a stone facade, a wooden deck, and a clear sky.

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
The price is €487
includes taxes & fees
23 Sept - 24 Sept
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

5. 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 €358
includes taxes & fees
4 Oct - 5 Oct
West Kill Barnhouse: Ski, Work & Unwind
Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

6. 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 €317
includes taxes & fees
23 Sept - 24 Sept
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
A bedroom with a bed, a desk, a chair, a ceiling fan, and two windows.

7. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace
Jewett
The price is €570
includes taxes & fees
6 Oct - 7 Oct
Catskills Escape w/ Hot Tub & Fireplace
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

8. 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 €464
includes taxes & fees
23 Sept - 24 Sept
Pines Vignette • Modern 3BR Home in Windham
A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

9. 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 €381
includes taxes & fees
24 Sept - 25 Sept
Check our Reviews! Spectacular Views! King bed! Upgraded Baths n Kitchen!
A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

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 €379
includes taxes & fees
19 Oct - 20 Oct
Midnight Fox
A covered outdoor area with a sofa, a table with a grill, and a tripod-mounted camera.

11. Gorgeous Mountains Views & Private Stream in Secluded Oasis

Gorgeous Mountains Views & Private Stream in Secluded Oasis
Gilboa
10.0 out of 10, Exceptional, (8 reviews)
"Our stay was great: attentive host, comfortable lodgings, beautiful setting."
United States
Carrie S.
The price is €362
includes taxes & fees
5 Oct - 6 Oct
Gorgeous Mountains Views & Private Stream in Secluded Oasis

12. Escape the City. Discover the Heart of the Catskills. Entire house, sleeps 10!

Escape the City. Discover the Heart of the Catskills. 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. Discover the Heart of the Catskills. Entire house, sleeps 10!
A wooden interior with a central fireplace, benches, and a window offering a forest view.

13. 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, (74 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 €607
includes taxes & fees
6 Oct - 7 Oct
Mountain house with Scandinavian BBQ hut and Hot tub
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.

14. 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 €571
includes taxes & fees
23 Sept - 24 Sept
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A modern kitchen with a stainless steel refrigerator, a dining area with a table and chairs, and a living room with a sofa and a lamp.

15. Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.6 out of 10, Exceptional, (18 reviews)
"Everything was perfect!"
United States
Jen C.
Cozy Waterfall Oasis + Firepit
A two-story house with a stone chimney, wooden deck, and a stone staircase leading to the entrance.

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

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is €953
includes taxes & fees
29 Sept - 30 Sept
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
A wooden dining table with a lamp, a mirror, and a vase with branches.

17. Spacious & Stylish Barn Retreat: Fall Leaves, Firepit & Creek Views

Spacious & Stylish Barn Retreat: Fall Leaves, Firepit & Creek Views
Denver
The price is €320
includes taxes & fees
29 Sept - 30 Sept
Spacious & Stylish Barn Retreat: Fall Leaves, Firepit & Creek Views
A fire pit with two chairs in a backyard.

18. NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM

NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
Windham
The price is €534
includes taxes & fees
23 Sept - 24 Sept
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
A living room with a leather rug, wooden chairs, a sofa, and a decorative wall hanging.

19. 2BR Barnhouse Horse Farm Views near hiking, Phoenica, Hunter

2BR Barnhouse Horse Farm Views near hiking, Phoenica, Hunter
Hunter
9.8 out of 10, Exceptional, (9 reviews)
"Great host. Very quiet place to relax."
United States
Evan H.
The price is €293
includes taxes & fees
5 Oct - 6 Oct
2BR Barnhouse Horse Farm Views near hiking, Phoenica, Hunter
A house with a fire pit and outdoor seating.

20. 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)
"House had everything, very clean, host very responsive, located close to everything. Great family vacation!"
United States
Jaylyn B.
The price is €687
includes taxes & fees
20 Oct - 21 Oct
The Hensonville Honeypot - Hottub, Movie Theatre & Mountain Bikes!
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

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

10/10 Excellent
"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."
Christopher 2-night trip
Posted 13 hours ago
Jimmy OConnors Windham Mountain Inn

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
244
Accommodation
552 Holiday Homes
Lowest Price
€227
Highest Price
€687