Choose from 109 vacation rentals located in Windham, New York. Top filters in Windham include Internet / Wifi, Kitchen / Kitchenette, and Parking. Prices range from $88 to $3,516 per night. Our most popular vacation rental types near Windham are Hotel and RV.

Top vacation rentals in Windham

Exterior
5.0
Outstanding(76 Reviews)
House
 in Windham
Mountain Escape 5 Minutes to Ski Resort
12 guests · 3 bedrooms · 2 baths
Pets allowed · Kitchen / Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our House in Windham has everything you need for a rejuvenating stay. Treat yourself to Mountain Escape 5 Minutes to Ski Resort's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
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Outside
4.8
Outstanding(89 Reviews)
House
 in Windham
Windham House Ski Hunter or Belleayer Mt too. Fireplace, High Speed WiFi & More
8 guests · 4 bedrooms · 2 baths
Garden · Pool · Pets allowed

Business stays, family stays, couples stay, getaway vacation, and rental in Windham at Windham House Ski Hunter or Belleayer Mt too. Fireplace, High Speed WiFi & More for $310 for your next trip.

$$$$
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Property view
3.7
Good(21 Reviews)
Hotel
 in Windham
3star
Winwood Inn & Condominiums
Garden · Kitchen / Kitchenette · Air conditioner

This attractive Hotel in Windham, $152 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.6
Outstanding(7 Reviews)
Condo
 in Windham
Townhouse W Private Deck & Mt View
Garden · Kitchen / Kitchenette · Air conditioner

This Condo in Windham, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Vacation rentals with internet & wifi in Windham

Cutest cabin living with a barn door that slides open & close to the bathroom
5.0
Outstanding(59 Reviews)
Cabin
 in Windham
Cutest Cabin in Windham Spring wedding & Spring break stays
2 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Looking for the perfect place to call home during your trip to Windham? This Cabin offers a comfort and style with top-notch amenities, including Internet / Wifi, Balcony / Patio and Kitchen / Kitchenette, and more.

$$$$
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Property view
4.7
Outstanding(9 Reviews)
Bed and Breakfast
 in Windham
Georgian Garden
Garden · Kitchen / Kitchenette · Air conditioner

When traveling to Windham, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $135 per night.

$$$$
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Cozy Living Room with Exposed Post & Beam Construction
4.9
Outstanding(46 Reviews)
House
 in Windham
ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!
13 guests · 4 bedrooms · 4 baths
Ski in / Ski out · Garden · Pool

Nestled in Windham, this House is perfect for your next vacation. Enjoy ON MOUNTAIN - 4 BED, 4 BATH RETREAT - WALK TO SLOPES!'s top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Living room with deck access
5.0
Outstanding(40 Reviews)
House
 in Windham
Windham Family Getaway
9 guests · 3 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Looking for a House in Windham, this House for $249 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Windham

Windham travel guide

Let us help you plan your perfect Windham vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Windham, and more.

Frequently asked questions

What is the price range for rentals in Windham?

Vacation rentals in Windham have a price range between $88-$3,516. The average price for rentals in Windham is $450 per night.

What are the most popular vacation rental amenities in Windham?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Parking

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