396+ Vacation Rentals & Holiday Homes in Windham |
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Windham Accommodations - Hotels & Rentals

About Windham Vacation Rentals

Discover More than 396 Incredible Getaway Rentals Available in Windham. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Windham.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Windham, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Windham. The Average Size of Places to Stay Near Windham is 1508.95 ft², with Prices Averaging US $719 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Windham. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Windham

Type Count
Vacation Homes 243
Holiday Apartments 19
Villas 7
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Windham

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Windham with Online Reservations.

Weather in Windham, NY

View the weather forecast for Windham before booking your Windham Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities WindhamGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World WindhamGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Windham Mountain Resort
Windham Vineyards and Winery
Windham Country Club
Hunter Mountain
Catskill Mountains
Belleayre Mountain
Kaaterskill Falls
Plattekill Mountain
Copperhood Retreat & Spa
Zoom Flume
Emerson Place Kaleidoscope
Belleayre Beach at Pine Hill Lake
Bethel Woods Museum
Karma Triyana Dharmachakra Monastery
Pine Hill Community Center
Woodstock Golf Club
Woodstock Public Library
Hobart Book Village
Bailiwick Ranch and Discovery Zoo
Giant Ledge Trailhead

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Windham Mountain Resort 384 Properties
Windham Country Club 358 Properties
Windham Vineyards and Winery 107 Properties
Ashland 72 Properties

Frequently Asked Questions About Windham?

What are the top hotels, lake houses & vacation rentals in Windham?

We provide an array of great vacation destinations in Windham. If you are looking to stay in or around the Windham area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windham:

How many Hotels & Vacation Rentals have private pools in Windham?

We have 11 Hotels & Vacation Rentals featuring a private pool in and near Windham. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Windham is best for families?

Searching for a family-friendly getaway in Windham? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Windham?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 396 in the Windham area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Windham.


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