Windham, NY Vacation Homes from ￥30,890

A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

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Our top choices for Windham vacation 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

Windham

juneid a.

￥30,890 total

includes taxes & fees

Nov 2 - Nov 3

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

Cristina L.

￥81,065 total

includes taxes & fees

Oct 20 - Oct 21

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

Windham

Melissa R.

￥88,744 total

includes taxes & fees

Nov 9 - Nov 10

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

4. Pines Vignette • Modern 3BR Home in Windham

Windham

William H.

￥82,259 total

includes taxes & fees

Oct 19 - Oct 20

A fire pit with two chairs in a backyard.

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

Windham

￥98,271 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a bed, desk, chair, and a window with curtains.

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

Windham

￥156,412 total

includes taxes & fees

Oct 31 - Nov 1

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

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

Windham

￥168,203 total

includes taxes & fees

Oct 20 - Oct 21

8. Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ashland

Julia M.

￥87,208 total

includes taxes & fees

Oct 25 - Oct 26

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

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

Hensonville

Kimberly K.

￥58,196 total

includes taxes & fees

Oct 19 - Oct 20

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

10. Mountain house with Scandinavian BBQ hut and Hot tub

Jewett

Shannon H.

￥108,711 total

includes taxes & fees

Nov 2 - Nov 3

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

11. Midnight Fox

Hunter

Caroline I.

￥70,003 total

includes taxes & fees

Oct 20 - Oct 21

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

12. Catskills Escape w/ Hot Tub & Fireplace

Jewett

￥111,278 total

includes taxes & fees

Oct 19 - Oct 20

A living room with a fireplace, a television, a sofa, and a dining area with chairs.

13. Town Home near Hunter Mntn

Tannersville

Guadalupe G.

￥74,410 total

includes taxes & fees

Nov 1 - Nov 2

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

14. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Hunter

Allyson R.

￥112,040 total

includes taxes & fees

Oct 20 - Oct 21

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

15. West Kill Barnhouse: Ski, Work & Unwind

West Kill

Vijay S.

￥65,193 total

includes taxes & fees

Nov 1 - Nov 2

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.

16. Cozy Waterfall Oasis + Firepit

East Durham

Holly C.

￥52,262 total

includes taxes & fees

Oct 19 - Oct 20

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

West Kill

Alexandra I.

A dining area with a wooden table, a woven pendant light, candles, a bottle of wine, and a vase with flowers.

18. Hot Tub • Game Room • Fire Pit • 15 Private Acres

East Jewett

Beth C.

￥130,044 total

includes taxes & fees

Nov 3 - Nov 4

A two-story house with a patio area, outdoor seating, and a small tree.

19. The Homestead at Carter Bridge Estate

Freehold

ELIZABETH

￥181,976 total

includes taxes & fees

Oct 19 - Oct 20

A round table with a candle, a book, and a vase with dried flowers.

20. Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Tannersville

NANCY

￥109,224 total

includes taxes & fees

Nov 2 - Nov 3

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Top Windham Hotel Reviews

Urban Cowboy Lodge

10/10 Excellent

"Amazing"

Hunter Lodge, a Bluebird by Lark

10/10 Excellent

"My husband and I have stayed at this hotel previously we are returned visitors. Our room was immaculate. We had a balcony that overlooked the beautiful mountains and gorgeous trees in the fall. The room itself was impeccable the bathroom Stella. I would definitely recommend this hotel to anyone. There were many families there and enjoyed the breakfast bagels, cereal, coffee, oatmeal, and or yogurt where we ate for breakfast was very clean. I must mention that there’s a beautiful sitting room in the lobby for comfort reading this games very quaint. It is dog, friendly only certain rooms. The outside has a beautiful balcony. The landscaping was very inviting. There are tables and chairs outside that you can sit and you can even have a fire in the evening. It’s a very welcoming place. Definitely recommend."

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10/10 Excellent

"Dancing Horse Farm is a beautiful place surrounded by gorgeous mountains and breathtaking scenery The pictures just give you a hint of the amazing beauty of this property The interior of the home is clean , spacious, equipped with every modern convenience The rooms are comfortable Each with its own unique design and quality The bathrooms are sanitary and bright Every where you look you can see the owner Greg has put his heart into the care of this house He has thought of every detail Your every need is met staying at this property The grounds offer opportunities for hiking , serene walks and deep relaxation The added touch is the barn with its three adorable goats A big attraction for younger children The area Windham offers restaurants, breweries, shops, markets a great fun location The house , the location, the owner Greg all are outstanding I can go on and onOur family fell in love with it all and will make Dancing Horse Farm our annual tradition"

Find out more about Windham

Windham Vacation Homes information

Number of reviews	200
Accommodation	726 Vacation Homes
Lowest Price	￥30,890
Highest Price	￥181,976

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windham vacation homes

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

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

3. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

4. Pines Vignette • Modern 3BR Home in Windham

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

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

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

8. Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

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