Windham vacation rentals

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Recommended by KAYAK

Best Windham vacation rentals

Studio 3 Beds-Slp 3. Downtown Windham. Next To The Ski Resort. Close To Hunter - Windham - Property amenity
Studio 3 Beds-Slp 3. Downtown Windham. Next To The Ski Resort. Close To Hunter
Windham, NY
9.2Wonderful(18)
Apartment
$156+
Check availability
Townhouse-Slp 8 Mt View/6 Beds. Downtown Windham. Walk To Restaurants And Stores - Windham - Balcony
Townhouse-Slp 8 Mt View/6 Beds. Downtown Windham. Walk To Restaurants And Stores
Windham, NY
8.3Very good(23)
House
Free Wi-Fi
$294+
Check availability
Cozy Caboose in the city - Windham - Kitchen
Cozy Caboose in the city
Windham, NY
9.9Wonderful(59)
Apartment
$257+
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Redwood Retreat in Windham - minutes to Mtn! - Windham - Living room
Redwood Retreat in Windham - minutes to Mtn!
Windham, NY
9.6Wonderful(30)
House
Parking
Free Wi-Fi
Pool
$396+
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4 Mi to Windham Mountain Ski Getaway! - Windham - Living room
4 Mi to Windham Mountain Ski Getaway!
Windham, NY
9.8Wonderful(13)
House
Free Wi-Fi
$398+
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Windham Home Near Mountain Biking and Hiking Trails! - Windham - Bedroom
Windham Home Near Mountain Biking and Hiking Trails!
Windham, NY
6.0Okay(1)
House
Free Wi-Fi
$312+
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Vacation Rental Home about 2 Mi to Windham Mountain! - Windham - Living room
Vacation Rental Home about 2 Mi to Windham Mountain!
Windham, NY
9.3Wonderful(3)
House
Free Wi-Fi
Pet friendly
$387+
Check availability
Windham Chalet+Gorgeous View - Windham - Property amenity
Windham Chalet+Gorgeous View
Windham, NY
9.7Wonderful(7)
House
Free Wi-Fi
$441+
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Gorgeous, First Class, 2 King apartment in downtown Windham - Windham - Bedroom
Gorgeous, First Class, 2 King apartment in downtown Windham
Windham, NY
10Wonderful(14)
Apartment
$472+
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Condo with Loft 2 Mi to Windham Mountain Ski! - Windham - Building
Condo with Loft 2 Mi to Windham Mountain Ski!
Windham, NY
9.2Wonderful(14)
Condo
$321+
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Homey Windham Condo Hike and Ski the Catskill Mtns! - Windham - Living room
Homey Windham Condo Hike and Ski the Catskill Mtns!
Windham, NY
8.5Very good(4)
Condo
Free Wi-Fi
$294+
Check availability
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski - Windham - Balcony
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski
Windham, NY
8.8Very good(7)
Apartment
Free Wi-Fi
Spa
$249+
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Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham - Windham - Patio
Luxurious,spacious 4500 sq ft home,hot tub & sauna,in center of downtown Windham
Windham, NY
10Wonderful(11)
House
$1,100+
Check availability
Catskills Home, 5 Mins to Windham Mtn Resort! - Windham - Living room
Catskills Home, 5 Mins to Windham Mtn Resort!
Windham, NY
9.2Wonderful(18)
House
Free Wi-Fi
Spa
$242+
Check availability
Townhouse W Private Deck & Mt View - Windham
Townhouse W Private Deck & Mt View
Windham, NY
6.6Okay(36)
Apartment
Parking
Free Wi-Fi
$221+
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Grand Windham Retreat with Fire Pit and Game Room - Windham
Grand Windham Retreat with Fire Pit and Game Room
Windham, NY
8.6Very good(3)
House
Free Wi-Fi
$664+
Check availability
Useful Info

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

July
September
$593
$426
Cheapest month to stay with an average 63% drop in price.
Most expensive month to stay with an average 107% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Windham vacation rental deals

  • Vacation rentals in Windham are around 72% more expensive than hotels on average. Search here to compare prices for all accommodation types in Windham.
  • The best vacation rental properties in Windham are Cozy Caboose in the city (9.9, 59 reviews), Redwood Retreat in Windham - minutes to Mtn! (9.6, 30), and Townhouse-Slp 8 Mt View/6 Beds. Downtown Windham. Walk To Restaurants And Stores (8.3, 23), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Windham, you should consider visiting during the low season. The cheapest vacation homes in Windham can be found in July and November.
  • The cheapest night for renting a vacation home in Windham is Sunday. In contrast, the most expensive is Monday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Windham for 1 days.

FAQs when booking a vacation home in Windham

  • What types of vacation rentals are available in Windham?

    There are loads of different property types that you can make your vacation home in Windham. You’ll find apartments, cabins, chalets, condos, houses and villas.

  • Are there any pet-friendly vacation rentals in Windham?

    There are a number of dog and pet-friendly Windham vacation rentals, with around 8% allowing you to bring your pet along with you.

  • How much is a vacation rental in Windham for this weekend?

    In the last 72 hours, users have found Windham vacation rentals for this weekend for as low as $517 per night. Search here for similar prices

  • How can I find vacation rentals near me in Windham?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Windham?

Our map will help you find the perfect place to stay in Windham by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Windham