Ashland Holiday Homes
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Holiday Homes in Ashland

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Our top choices for Ashland holiday homes

A living room with a green sofa, two lamps, a small table with a keyboard, and three paintings on the wall.

A kitchen with wooden cabinets, stainless steel appliances, a red lantern, and a fruit bowl on the counter.

A residential area with snow-covered houses and a Christmas tree with lights.

A snow-covered tree with bare branches, a building with a blue facade, and a clear blue sky.

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)

9.0/10

Wonderful

(64 reviews)

"Very nice hosts! Will come back again. Thanks very much!!"

juneid a.

The price is AU$339

AU$339

includes taxes & fees

19 Oct - 20 Oct

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)

9.2/10

Wonderful

(5 reviews)

"Great place to stay very accommodating more than expected "

Julia M.

The price is AU$787

AU$787

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.

A spacious living area with a wooden staircase, a kitchen in the background, and a large window providing a view of the outdoors.

A modern building with large windows, a covered outdoor area with seating, and a pool.

A modern living room with a stone fireplace, a large grey sectional sofa, a flat-screen TV, and a 'FAMILY' sign on the wall.

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)

9.6/10

Exceptional

(8 reviews)

"We loved ,.. place was very clean and organized "

Cristina L.

The price is AU$709

AU$709

includes taxes & fees

29 Oct - 30 Oct

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

A bedroom with a bed, wooden dresser, ceiling fan, framed pictures, and a view into the kitchen.

An outdoor deck with a hot tub, barbecue grill, and picnic tables.

A modern living room with a pool table, wooden flooring, and a dining area.

A spacious dining area with a high ceiling, exposed wooden beams, and hanging light fixtures.

4. Catskills Escape w/ Hot Tub & Fireplace

Catskills Escape w/ Hot Tub & Fireplace

Jewett

The price is AU$1,022

AU$1,022

includes taxes & fees

19 Oct - 20 Oct

Catskills Escape w/ Hot Tub & Fireplace

A wooden interior with a central fireplace, benches, and a window offering a forest view.

A wooden cabin interior with a central wood-burning stove, a bench with a bear pillow, and a window with a view of the outdoors.

A cozy room with a wooden ceiling, a beige sofa, a white armchair, a small table with a book, and a large window with a view of trees.

A wooden cabin with large windows, a porch with steps, and potted plants.

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)

10/10

Exceptional

(76 reviews)

"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "

Despina M.

The price is AU$963

AU$963

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.

A bedroom with a bed, a bedside table, a window with curtains, a shelf with a plant, and a sloped ceiling.

A hot tub with water, a house, and a tree with lights.

A living room with a green sofa, a yellow sofa, a coffee table with a bowl of fruit and a plant, a white chair, and a staircase in the background.

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)

10/10

Exceptional

(3 reviews)

"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "

Melissa R.

The price is AU$795

AU$795

includes taxes & fees

9 Nov - 10 Nov

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

A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

A two-story house with a stone chimney, wooden balconies, and a stone facade.

A spacious kitchen with wooden cabinets, a central island, and a dining area with chairs.

A cozy living room with a brown sectional sofa, plaid pillows, and a wooden coffee table.

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

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

Windham

The price is AU$1,525

AU$1,525

includes taxes & fees

21 Oct - 22 Oct

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

Two wooden Adirondack chairs on a covered patio with a wooden fence in the background.

A neatly made bed with white bedding and a single decorative pillow, a small bedside table, and a wall with a nature-themed mural.

A wooden cabinet with glass doors, a flat-screen TV mounted above it displaying various streaming services, and two vases with dried plants on either side.

A living room with a wooden sofa, green chairs, a coffee table, a floor lamp, and a painting on the wall.

8. 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)

10/10

Exceptional

(11 reviews)

"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "

Kimberly K.

The price is AU$519

AU$519

includes taxes & fees

19 Oct - 20 Oct

Brand New 2 Bdr. Townhome Minutes from Windham Mtn

A wooden deck with Adirondack chairs, a stone fireplace, and a scenic view.

A cozy cabin interior with a wooden ceiling, a dining area, a stone fireplace, and large windows offering a view of greenery.

A spacious living area with a wooden ceiling, a large brown leather sofa, a wooden coffee table, and a dining area with a wooden table and chairs.

A wooden cabin with a stone floor, a wooden desk, and a bench.

9. 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)

10/10

Exceptional

(17 reviews)

"Nice stay to hangout with family!"

rakesh r.

The price is AU$1,718

AU$1,718

includes taxes & fees

19 Oct - 20 Oct

Large Group Catskills Mountain Retreat near Hunter & Windham Mountains

A rustic wooden interior with a sofa, a dining table, and a TV mounted on the wall.

A small, single-story house with a porch, surrounded by trees and a grassy yard.

A rustic interior with exposed wooden beams, a loft bed, a red sofa, a white cabinet, and a foosball table.

A dining area with a long table and four white chairs with wooden legs. The room has exposed wooden beams and a white brick wall.

10. West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind

West Kill

10.0 out of 10, Exceptional, (18 reviews)

10/10

Exceptional

(18 reviews)

"Great stay"

Vijay S.

The price is AU$576

AU$576

includes taxes & fees

18 Oct - 19 Oct

West Kill Barnhouse: Ski, Work & Unwind

A house with a fire pit and outdoor seating.

A bedroom with a large window, a bed with white and blue bedding, two bedside tables with lamps, and a potted plant.

A modern living room with a sofa, coffee table, and a television.

A modern living room with a sofa, coffee table, and a fireplace. There is a dining area with a table and chairs. The room has a neutral color palette and features a brick accent wall.

11. 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)

10/10

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."

David H.

The price is AU$1,029

AU$1,029

includes taxes & fees

4 Nov - 5 Nov

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

12. 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)

10/10

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."

Alexandra I.

The price is AU$738

AU$738

includes taxes & fees

18 Oct - 19 Oct

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

A bathroom with a toilet, sink, and wooden cabinets.

A modern kitchen with wooden cabinets, stainless steel appliances, and a stone fireplace.

A spacious kitchen with wooden cabinets, a stone fireplace, and large windows.

A spacious living room with a large leather sofa, wooden coffee table, and a view of the outdoors through large windows.

13. Midnight Fox

Midnight Fox

Hunter

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"House was very clean and beds were super comfy after a day of skiing ! "

Caroline I.

The price is AU$621

AU$621

includes taxes & fees

19 Oct - 20 Oct

Midnight Fox

A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

A dining area with a table set for four, a vase with flowers, and a view of a forest through a large window with blinds.

A living room with a sectional sofa, a coffee table, and a wooden ceiling.

A spacious living area with a sofa, a coffee table, and a patterned rug.

14. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham

Windham

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"House is cozy and has everything you need. We enjoyed our stay."

William H.

The price is AU$728

AU$728

includes taxes & fees

1 Nov - 2 Nov

Pines Vignette • Modern 3BR Home in Windham

A covered outdoor area with a sofa, a table with a grill, and a tripod-mounted camera.

A bedroom with a bed, nightstands, a window, and an air conditioning unit.

A cozy living room with a stone fireplace, a blue sofa, and a television.

A modern kitchen with red cabinets, stainless steel appliances, and a dining area with a round table and yellow chairs.

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)

10/10

Exceptional

(9 reviews)

"Our stay was great: attentive host, comfortable lodgings, beautiful setting."

Carrie S.

The price is AU$586

AU$586

includes taxes & fees

29 Oct - 30 Oct

Gorgeous Mountains Views & Private Stream in Secluded Oasis

A wooden cabin with a porch, two chairs, and a table.

A dining area with a wooden table, six chairs, a central bowl, and a hanging light fixture.

A modern kitchen with a stainless steel refrigerator, a wooden bench, and a view of a green outdoor area through a glass door.

A modern kitchen with a wooden island, stainless steel appliances, and a view of greenery through large windows.

16. Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

Halcott Center

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Everything was perfect during my stay. The service was excellent, and everything went very smoothly. I’m really happy with the overall experience and would highly recommend it to anyone."

Hnin

The price is AU$606

AU$606

includes taxes & fees

8 Nov - 9 Nov

Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

A fire pit with two chairs in a backyard.

A two-story house with a porch, a garage, and a driveway.

A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a dining table with four chairs.

A bedroom with a wooden bed, a nightstand, a window with curtains, and a view of trees outside.

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 AU$969

AU$969

includes taxes & fees

28 Oct - 29 Oct

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

A cozy living room with a wooden ceiling, a sofa, a red chair, a fireplace, and a ceiling fan.

A kitchen with wooden cabinets, a gas stove, a microwave, and a dishwasher.

A hotel room with a television displaying a streaming service interface, a wooden cabinet with electronic devices, a bed with a patterned cover, and a framed painting on the wall.

A residential area with a well-maintained lawn, flowering plants, a large tree, and a house with a yellow exterior.

18. 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)

9.8/10

Exceptional

(18 reviews)

"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "

Jim D.

The price is AU$614

AU$614

includes taxes & fees

18 Oct - 19 Oct

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

A spacious living area with a large window, a ceiling fan, and a dining table set for four.

A dining area with a table set for two, a hanging pendant light, and a view of a green landscape through large windows.

A modern kitchen with wooden cabinets, a large island, a microwave, a toaster, and a dishwasher.

A spacious living area with a dining table, a fireplace, and a kitchen with wooden cabinets.

19. 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)

10/10

Exceptional

(16 reviews)

"The location was perfect, and the view of Hunter Mountain was beautiful. Our stay was enjoyable for travelers of all ages."

Allyson R.

The price is AU$1,029

AU$1,029

includes taxes & fees

21 Oct - 22 Oct

Catskill Mountain Hideaway with Amazing Hunter Mountain Views

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)

10/10

Exceptional

(5 reviews)

"Beautiful setting. Great light throughout the house. Convenient to the ski mountains"

Timothy M.

The price is AU$1,246

AU$1,246

includes taxes & fees

18 Oct - 19 Oct

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

Hotel Vienna

10/10 Excellent

"Clean room and helpful staff, good location."

Hongtao 1-night trip

Posted 6 hours ago

Hotel Vienna

The Graham & Co.

10/10 Excellent

"I had a pleasant stay! The place was nice and comfortable, and everything was good. Thank you for your hospitality. I would definitely recommend it!"

Emir 1-night trip

Posted 1 day ago

The Graham & Co.

The Colonial Motel

10/10 Excellent

"Cozy and nostalgic! I had a wonderful stay and it was a perfect escape from NYC :) Staff was incredibly helpful and kind, would definitely recommend"

Alexandria 2-night trip

Posted 1 day ago

The Colonial Motel

Emerson Resort & Spa

10/10 Excellent

"Quiet walking trails, restaurant on property, shops & Kakeidescope on site. Bread alone in boiceville is 3 mins away."

Lisa 3-night trip

Posted 2 days ago

Emerson Resort & Spa

Shandaken Inn

10/10 Excellent

"This property is exceptional from the food - bar - appointed room! I can't wait to visit again! The views -the service was impeccable! Thank you Katie and Jennifer(waitstaff) and owner Katie! You are all a WOW"

Lianne 2-night trip

Posted 2 days ago

Shandaken Inn

The Winwood Condominiums

10/10 Excellent

"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"

Zihe 1-night trip

Posted 2 days ago

The Winwood Condominiums

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent

"Beautiful fall colors in a cozy and charming lodge!"

Vandhana 2-night trip

Posted 2 days ago

Kaatskill Mountain Club & Condos by Vail Resorts

SunView Motel

8/10 Good

"Clean room and comfortable beds. For the price it’s a good deal"

Beth 4-night trip

Posted 3 days ago

SunView Motel

Deer Mountain Inn

10/10 Excellent

"Staff made you feel right at home, the server had immense knowledge in the food they were serving! You can also taste the chef’s effort that he put into each dish! I will definitely be back."

Elizabeth 1-night trip

Posted 8 days ago

Deer Mountain Inn

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews	245
Accommodation	540 Holiday Homes
Lowest Price	AU$339
Highest Price	AU$1,718

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Ashland on Expedia.com

Holiday Homes in Ashland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland holiday homes

1. 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!

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

4. Catskills Escape w/ Hot Tub & Fireplace

5. Mountain house with Scandinavian BBQ hut and Hot tub

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

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

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

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

10. West Kill Barnhouse: Ski, Work & Unwind

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

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

13. Midnight Fox

14. Pines Vignette • Modern 3BR Home in Windham

15. Gorgeous Mountains Views & Private Stream in Secluded Oasis

16. Large Cook's Kitchen; 1st Fl Bedroom w/ Ensuite; 10-Min to downtown Fleischmanns

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

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

19. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

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

Find holiday rentals that suit your style

Top Ashland Hotel Reviews

Hotel Vienna

Find out more about Ashland

Ashland Holiday Homes information

Explore a world of travel with Expedia