Windham, NY Short-Term Rentals

Windham Short Term Stay

House

Windham Townhouse - Base of Mountain

10.0

Exceptional

(14 Reviews)

3 Bedrooms 3 Baths 8 Guests

US $470/Night 7 Nights - US $3,289

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New

House

Spacious 4-bedroom house in tranquil Windham with AC big deck and fire pit BBQ

4 Bedrooms 1 Bath 8 Guests

US $640/Night 7 Nights - US $4,477

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House

Spacious 5-bedroom house in charming Windham centrally located in town.

10.0

Exceptional

(2 Reviews)

5 Bedrooms 3 Baths 14 Guests

US $5,881/Night 7 Nights - US $41,164

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House

4-bedroom country house in serene Windham with WiFi, AC

4 Bedrooms 1 Bath 8 Guests 2850 ft²

US $494/Night 7 Nights - US $3,455

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House

~ Alpine 5BR Chalet: 6 min to SKI | Sleeps 20 ~

10.0

Exceptional

(1 Review)

5 Bedrooms 4 Baths 20 Guests 2992 ft²

US $656/Night 7 Nights - US $4,593

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Highly Rated

Apartment

Cozy Caboose in the city

10.0

Exceptional

(107 Reviews)

1 Bedroom 1 Bath 2 Guests

US $200/Night 7 Nights - US $1,399

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Fantastic 2 family vacation home with EV charger

Ski Chalet

Fantastic 2 family vacation home with EV charger

10.0

Exceptional

(3 Reviews)

4 Bedrooms 2 Baths 10 Guests 1905.21 ft²

US $254/Night 7 Nights - US $1,779

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Highly Rated

Bed & Breakfast

Antique Rose Inn Windham

9.0

Exceptional

(129 Reviews)

1 Bedroom 1 Bath

US $146/Night 7 Nights - US $1,021

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Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ

Highly Rated

Cabin

Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ

10.0

Exceptional

(69 Reviews)

1 Bedroom 1 Bath 2 Guests 700 ft²

US $185/Night 7 Nights - US $1,292

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Luxury Home w/Deck: Explore the Catskill Mtns!

House

Luxury Home w/Deck: Explore the Catskill Mtns!

10.0

Exceptional

(2 Reviews)

4 Bedrooms 2 Baths 8 Guests 1797.57 ft²

US $687/Night 7 Nights - US $4,809

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Apartment

Gorgeous, First Class, 2 King apartment in downtown Windham

10.0

Exceptional

(15 Reviews)

2 Bedrooms 1 Bath 4 Guests 1 ft²

US $277/Night 7 Nights - US $1,942

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Mtn-View Home w/Deck on 4 Acres in Windham

House

Mtn-View Home w/Deck on 4 Acres in Windham

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests 1797.57 ft²

US $409/Night 7 Nights - US $2,865

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More Top-Rated Short Term Stay in Windham Area

Why Choose Rent By Owner for your Windham Short Term Stay?

What makes our Short Term Stay special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Windham

When should you plan your Short Term Stay stay?

Timing your visit to this picturesque area ensures you experience its natural beauty and outdoor activities at their best, whether you prefer the vibrant energy of summer or the serene charm of winter during your short term stays here.

Peak Season Highlights

Winter (December to February)

During winter, the area transforms into a winter wonderland, attracting visitors seeking snow-based outdoor activities and cozy retreats.

Average Temperature Daytime: 25°F to 35°F - Nighttime: 10°F to 20°F

Fall (September to November)

Autumn offers vibrant foliage and pleasant weather, making it an ideal time for scenic drives and outdoor exploration in the region.

Average Temperature Daytime: 55°F to 65°F - Nighttime: 40°F to 50°F

Off-Season Highlights

Spring (March to May)

Spring welcomes milder temperatures and blooming landscapes, perfect for exploring the area's natural beauty before the busy summer season begins.

Average Temperature Daytime: 45°F to 60°F - Nighttime: 30°F to 40°F

Summer (June to August)

Warm summer months draw visitors for outdoor activities and relaxation, though this is typically a quieter time compared to peak seasons.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 60°F

Weekly Weather Forecast for Windham

How to Book Your Windham Short Term Stay

What's our booking process?

Our platform allows you to browse a curated selection of short term stay. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Windham

More Top-Rated Short Term Stay in Windham Area

Common Short Term Stay Amenities

What amenities can you expect?

Our Short Term Stay are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

Enjoy outdoor dining or relaxing on a private deck or patio with scenic views of the surrounding landscape.
Take advantage of expansive yards ideal for outdoor games, picnics, or simply soaking up the fresh mountain air.
Relax around a cozy outdoor fire pit, perfect for evening gatherings under starry skies.
Make use of spacious balconies or verandas that offer a peaceful retreat after exploring the area.
Utilize well-maintained pathways or trails leading from the property for scenic walks or nature hikes.
Benefit from access to outdoor recreational facilities such as tennis courts, pools, or playgrounds often found in the region.
Discover nearby outdoor activities like fishing, kayaking, or mountain biking to enhance your stay here.

Top Attractions Around Windham

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities such as hiking, skiing, and scenic nature walks that showcase the region's natural beauty, making it an ideal destination for those seeking adventure and relaxation during their stay.

Family Activities

Windham Mountain Resort Experience outdoor fun with family-friendly activities such as skiing, snowboarding, and scenic chairlift rides that showcase the region’s natural beauty.
Windham Path Enjoy a leisurely walk along this scenic trail, perfect for families seeking an easy hike or bike ride amidst the area's picturesque landscape.
Zoom Flume Water Park Beat the heat with exciting water slides and lazy rivers designed to keep children entertained and cooled off during your visit here.
Windham Theatre Catch a family-oriented performance or seasonal event at the local theatre, offering cultural entertainment suitable for all ages.

Adult Activities

Windham Mountain Resort Experience the thrill of skiing or snowboarding during winter months or enjoy scenic mountain rides in the warmer seasons, making it a year-round destination for outdoor enthusiasts.
Windham Path Take a leisurely walk along this popular trail for stunning views and peaceful nature immersion, perfect for reconnecting with the outdoors in the region.
Windham Country Club Play a round of golf on this scenic course that offers a relaxing way to enjoy the area's natural beauty and improve your swing.
Hunter Mountain Visit nearby for exhilarating zip-lining adventures or explore the vibrant arts scene, adding an active cultural component to your stay here.

Other Places to Stay in Windham, NY

Windham Mountain Resort

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Windham Country Club

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Windham Vineyards and Winery

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Ashland

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More Places to Stay Near Windham

Windham Travel Tips

How Can You Make the Most of Your Stay?

Explore the natural surroundings: Take time to visit the scenic outdoor spots around this destination to fully enjoy the area's picturesque landscapes and outdoor activities.
Plan your activities ahead: Booking local tours or outdoor excursions in advance can help you make the most of your stay during peak seasons.
Choose accommodations wisely: Select a property that offers easy access to the region's main attractions and amenities for a more comfortable experience.
Embrace local dining experiences: Sample regional cuisine at local eateries to immerse yourself in the authentic flavors of this destination.

Transportation Options

Windham Bus Service With regular bus routes connecting to nearby cities, this option offers a convenient way to explore the region without the need for a car.
Local Taxi Services Available throughout the area, reliable taxi providers make short trips around Windham effortless and quick for visitors staying nearby.
Car Rentals Several rental agencies operate here, providing flexible transportation to suit your schedule while exploring beyond the immediate vicinity.
Airport Shuttle Services When arriving via regional airports, shuttle options offer a straightforward transfer to your accommodation in this scenic destination.

Local Customs Options

Community Gatherings: Participating in local events like seasonal festivals and farmers markets offers a glimpse into the area's vibrant community spirit.
Respect for Nature: The region values outdoor preservation, encouraging visitors to practice responsible recreation during hikes and outdoor activities.
Local Artisanship: Supporting regional artisans through craft fairs and galleries helps you connect with the area's rich artistic heritage.
Traditional Cuisine: Embracing local food customs by trying regional specialties fosters a deeper appreciation of the area's culinary traditions.

Windham Short Term Stay Frequently Asked Questions

1. What are the top Short Term Stays in Windham?

There are a lot of options in Windham. If you plan on staying in the Windham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Short Term Stays in Windham:

2. How many Short Term Stays are available in Windham?

Currently, the total number of properties listed by RBO in 2026 is over 5 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Short Term Stays in Windham. 

3. What is the cancellation policy for short term stays in this area?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the host directly to understand the terms and potential fees associated with cancellations.

4. How do I find available dates and book a short term stay here?

You can check real-time availability and make your reservation through the booking platform by selecting your desired dates and following the on-screen instructions to complete your booking process.

5. Are there any house rules or restrictions I should be aware of before booking?

Each property has its own set of house rules and restrictions, which are provided in the listing details. Be sure to read these carefully or reach out to the owner if you have specific questions.

6. What amenities are typically included in short term stays in this region?

Amenities vary between properties, but common features include Wi-Fi, parking, kitchen essentials, and outdoor space. Confirm the specific amenities listed for each property to ensure they meet your needs.

7. Is there local support if I encounter issues during my stay?

Hosts or property managers usually provide contact information for support. For urgent concerns, refer to the contact details provided in the listing or reach out directly to the property owner.