Windham Vacation Homes

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 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

Windham

"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."

David

HK$1,831 total

includes taxes & fees

18 Oct - 19 Oct

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.

HK$3,789 total

includes taxes & fees

3 Nov - 4 Nov

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.

HK$4,204 total

includes taxes & fees

3 Nov - 4 Nov

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.

HK$4,051 total

includes taxes & fees

1 Nov - 2 Nov

A fire pit with two chairs in a backyard.

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

Windham

HK$4,855 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Windham

HK$9,270 total

includes taxes & fees

14 Oct - 15 Oct

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

Ashland

Julia M.

HK$4,000 total

includes taxes & fees

12 Oct - 13 Oct

A house with a fire pit and outdoor seating.

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

Hensonville

David H.

HK$5,918 total

includes taxes & fees

4 Nov - 5 Nov

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

9. Catskills Escape w/ Hot Tub & Fireplace

Jewett

HK$5,571 total

includes taxes & fees

25 Oct - 26 Oct

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

Despina M.

HK$5,399 total

includes taxes & fees

2 Nov - 3 Nov

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

11. Midnight Fox

Hunter

Caroline I.

HK$3,476 total

includes taxes & fees

20 Oct - 21 Oct

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

12. Catskill Mountain Hideaway with Amazing Hunter Mountain Views

Hunter

ching yi t.

HK$5,403 total

includes taxes & fees

20 Oct - 21 Oct

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

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

Hunter

Jim D.

HK$3,424 total

includes taxes & fees

15 Oct - 16 Oct

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

14. West Kill Barnhouse: Ski, Work & Unwind

West Kill

Vijay S.

HK$3,238 total

includes taxes & fees

25 Oct - 26 Oct

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

East Durham

Jen C.

HK$2,727 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Halcott Center

Hnin

HK$3,380 total

includes taxes & fees

8 Nov - 9 Nov

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

17. The Homestead at Carter Bridge Estate

Freehold

ELIZABETH

HK$8,919 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Tannersville

NANCY

HK$5,543 total

includes taxes & fees

2 Nov - 3 Nov

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

West Kill

Alexandra I.

HK$4,106 total

includes taxes & fees

12 Oct - 13 Oct

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

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

East Jewett

Beth C.

HK$6,043 total

includes taxes & fees

27 Oct - 28 Oct

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Top Windham Hotel Reviews

AutoCamp Catskills

8/10 Good

"Our stay was great , we really enjoyed the clubhouse the boardgames, a small hike on the property and the airstream was nicely equipped with outside grill, smart tv, and very nice outdoor space. Cleaning wise it was okay, we found hair in the shower drain, futon cover felt unwashed and I wish they had coffee in the clubhouse throughout the day. Would definitely recommend it!"

Urban Cowboy Lodge

8/10 Good

"Awesome to visit , relax, and enjoy the surroundings. The vibes were sooooo chill, the staff were so cool. But they had 1 big flaw, watch out for the hidden fees, check your bill and invoices before check. They add additional fees if you charge anything to your room for purchases which is crazy. Any charge to your room will be given a servicing fee. If you order breakfast, and pick it up yourself but charge it to your room, you get a fee. If you have dinner or drinks or lunch, and charge it to your room, there’s an extra fee.!!!! So bring cash or pay your bill up front… they use a system called Toast for their credit transactions, and they charge you the convenience / service fee for this system which can be as much as $40 per transaction."

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