Choose from 112 vacation rentals located in Windham, New York. Top filters in Windham include Internet / Wifi, Kitchen / Kitchenette, and Parking. Prices range from $85 to $3,100 per night. Our most popular vacation rental types near Windham are Hotel and RV.

Top vacation rentals in Windham

Snow and ski sports
5.0
Outstanding(77 Reviews)
House
 in Windham
Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.
10 guests · 3 bedrooms · 3 baths
Ski in / Ski out · Pool · Pets allowed

Looking for the perfect place to call home during your trip to Windham? This House offers a comfort and style with top-notch amenities, including Dishwasher, Fireplace and Internet / Wifi, and more.

$$$$
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Bed and Breakfast
 in Windham
Beds on Clouds
Garden · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Windham? Look no further than our Bed and Breakfast, Beds on Clouds. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Smoking allowed, and more.

$$$$
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4.1
Excellent(128 Reviews)
Inn
 in Windham
Jimmy OConnor's Windham Mtn Inn
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking to create some memories in Windham? Look no further than our Inn, Jimmy OConnor's Windham Mtn Inn. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.

$$$$
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4.3
Excellent(7 Reviews)
Apartment
 in Windham
Townhouse W Private Deck & Mt View
Garden · Kitchen / Kitchenette · Air conditioner

This Apartment 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

Property view
4.7
Outstanding(11 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 $131 per night.

$$$$
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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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House
 in Windham
Hike and Golf Near Luxe Windham Getaway with Hot Tub
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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

$$$$
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5.0
Outstanding(1 Review)
House
 in Windham
The Mountain House Windham Retreat with Hot Tub!
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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

$$$$
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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 $85-$3,100. The average price for rentals in Windham is $425 per night.

What are the most popular vacation rental amenities in Windham?

  • Internet / Wifi
  • Kitchen / Kitchenette
  • Parking

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