Windham Luxury Rentals【 PREMIUM 】| Rent By Owner

Windham Luxury Rental

New

Windham Manor on 45 Acres - 5 Mi to Ski Resort!

10763.91 ft² 33 Guests 12 Bedrooms 10 Bathrooms

House

Fireplace/Heating
Parking
Internet

CA $6,793/Night For 7 Nights CA $47,552

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Luxury Mountain Log Home, Ski-In/Ski-Out to Windham Resort

10.0

Exceptional

(9 Reviews)

Luxury Mountain Log Home, Ski-In/Ski-Out to Windham Resort

11000 ft² 22 Guests 5 Bedrooms 7 Bathrooms

Family Friendly House

Hot Tub
Skiing
Fireplace/Heating

CA $5,708/Night For 7 Nights CA $39,955

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EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS

10.0

Exceptional

(25 Reviews)

EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS

10611 ft² 18 Guests 9 Bedrooms 7 Bathrooms

Ocean View House

Private Pool
Hot Tub
Fireplace/Heating

CA $5,208/Night For 7 Nights CA $36,458

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Luxurious ski in/out, 3-story chalet directly on the slopes of Windham Mountain

10.0

Exceptional

(1 Review)

Luxurious ski in/out, 3-story chalet directly on the slopes of Windham Mountain

12 Guests 7 Bedrooms 7 Bathrooms

Family Friendly House

Fireplace/Heating
Balcony/Terrace
Kitchen

CA $4,650/Night For 7 Nights CA $32,552

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Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

10.0

Exceptional

(1 Review)

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

16 Guests 6 Bedrooms 6 Bathrooms

Family Friendly Cabin

Fireplace/Heating
Balcony/Terrace
Kitchen

CA $4,476/Night For 7 Nights CA $31,332

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*The View* ski in/out modern luxury at Windham Mountain Resort

9.8

Exceptional

(10 Reviews)

*The View* ski in/out modern luxury at Windham Mountain Resort

7000 ft² 14 Guests 5 Bedrooms 6 Bathrooms

Family Friendly House

Private Pool
Hot Tub
Spa

CA $3,510/Night For 7 Nights CA $24,571

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New

Wintertime

721.18 ft² 22 Guests 8 Bedrooms 6 Bathrooms

House

Skiing
Balcony/Terrace
Parking

CA $3,488/Night For 7 Nights CA $24,414

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Family-Friendly Windham Estate, Swimming Pond, Spa

9.8

Exceptional

(37 Reviews)

Family-Friendly Windham Estate, Swimming Pond, Spa

6600 ft² 24 Guests 8 Bedrooms 6 Bathrooms

Family Friendly Ski Chalet

Private Pool
Hot Tub
Fireplace/Heating

CA $2,879/Night For 7 Nights CA $20,152

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New

Fireplaces, Home Theater, Ski-In Out Windham Lodge

6490.64 ft² 20 Guests 8 Bedrooms 6 Bathrooms

Free Cancellation House

Skiing
Fireplace/Heating
Pet Friendly

CA $2,541/Night For 7 Nights CA $17,785

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New

Alpine 5BR Chalet 6 min Away to SKI

3003.13 ft² 20 Guests 5 Bedrooms 4 Bathrooms

House

Fireplace/Heating
View
Pet Friendly

CA $2,469/Night For 7 Nights CA $17,284

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New

Condo on Windham Mountain - Greene County

8 Guests 3 Bedrooms 3 Bathrooms

Family Friendly Condo

Hot Tub
Fireplace/Heating
Pool

CA $2,443/Night For 7 Nights CA $17,098

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Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Highly Rated

10.0

Exceptional

(170 Reviews)

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

4000 ft² 30 Guests 9 Bedrooms 5 Bathrooms

Family Friendly Cabin

Hot Tub
Fireplace/Heating
Pool

CA $2,408/Night For 7 Nights CA $16,859

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More Top-Rated Luxury Rental in Windham Area

Why Choose Rent By Owner for your Windham Luxury Rental?

What makes our Luxury Rental 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 Luxury Rental stay?

Choosing the ideal time to visit here can enhance your experience, as seasonal variations in the region offer different opportunities for relaxation and adventure, making it the perfect setting for your luxury rentals in Windham, New York.

Peak Season Highlights

Winter (December to February)

During the winter months, you can enjoy the stunning snowy landscapes and winter sports, making this a prime time for a visit.

Average Temperature Daytime: 20°F to 35°F - Nighttime: 5°F to 20°F

Summer (June to August)

The warmest period offers perfect weather for outdoor activities and exploring the scenic beauty of the region.

Average Temperature Daytime: 70°F to 85°F - Nighttime: 55°F to 65°F

Off-Season Highlights

Spring (March to May)

As the area awakens with blooming flora, this is an ideal time for those seeking tranquility away from peak crowds.

Average Temperature Daytime: 50°F to 65°F - Nighttime: 30°F to 45°F

Fall (September to November)

Experience the vibrant foliage and cooler temperatures, perfect for enjoying the scenic views in a peaceful setting.

Average Temperature Daytime: 55°F to 70°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Windham

How to Book Your Windham Luxury Rental

What's our booking process?

Our platform allows you to browse a curated selection of luxury rental. 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 Luxury Rental in Windham Area

Common Luxury Rental Amenities

What amenities can you expect?

Our Luxury Rental 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 a spacious outdoor grilling area for preparing meals amidst scenic surroundings.
Relax in a private hot tub or whirlpool, perfect for unwinding after a day exploring the region.
Take advantage of well-maintained hiking trails directly accessible from your rental property.
Benefit from a large outdoor patio or deck ideal for entertaining and soaking up the mountain views.
Make use of a fire pit for cozy evenings under the stars with family or friends.
Discover outdoor recreational facilities such as tennis courts or volleyball courts if available.
Experience direct access to nearby lakes or swimming ponds for warm-weather water activities.

Top Attractions Around Windham

What attractions are nearby?

Explore a variety of outdoor activities, local dining experiences, and scenic attractions right in the vicinity, offering you an ideal blend of adventure and relaxation during your stay in Windham, New York; this destination’s natural beauty and vibrant community provide the perfect setting for memorable moments in the region.

Family Activities

Windham Mountain Resort Experience family-friendly skiing, snowboarding, and outdoor activities suitable for all skill levels at this renowned regional ski destination.
Windham Path Explore scenic nature trails perfect for family walks, biking, or leisurely hikes amidst the stunning natural beauty of this area.
The Windham Theatre Enjoy live performances, cultural events, and engaging entertainment tailored to keep the entire family entertained during your stay.
Local Farms and Markets Visit nearby farms and markets where you can pick fresh produce, learn about regional agriculture, and enjoy farm-to-table experiences in the region.

Adult Activities

Wine Tasting Tours Explore local vineyards and enjoy guided wine tasting experiences that showcase the region's renowned viticulture.
Skiing and Snowboarding During winter months, take advantage of the area’s world-class slopes for an exhilarating day of skiing or snowboarding.
Hiking Adventures Discover scenic trails through lush forests and mountain vistas, perfect for outdoor enthusiasts seeking both challenge and tranquility.
Golfing Experiences Play a round at championship courses nestled within the region, offering stunning views and top-tier amenities.

Other Places to Stay in Windham, NY

Windham Mountain Resort

Explore 448 Properties

Windham Country Club

Explore 436 Properties

Windham Vineyards and Winery

Explore 127 Properties

Ashland

Explore 96 Properties

More Places to Stay Near Windham

Windham Travel Tips

How Can You Make the Most of Your Stay?

Explore local outdoor activities: Take advantage of the scenic surroundings by engaging in outdoor pursuits unique to this region, making your stay both exciting and memorable.
Plan ahead for peak seasons: Book your luxury rentals well in advance during popular times to ensure you secure the best accommodations and enjoy a seamless experience.
Discover hidden gems locally: Seek out less crowded spots and local favorites that offer an authentic taste of this destination’s charm and natural beauty.
Utilize personalized services: Opt for properties that provide tailored amenities and concierge options to elevate your visit and make it truly relaxing.

Transportation Options

Private Car Services: You can easily arrange for a private car service to explore the area or reach nearby destinations in comfort and style, ensuring a seamless travel experience within this scenic region.
Rental Cars: Renting a vehicle provides flexibility and convenience for visiting local attractions and enjoying the picturesque surroundings at your own pace.
Public Transit: Local bus routes and shuttles operate throughout the area, offering an economical way to explore without the need for personal transportation.
Taxi and Ride-Sharing: Taxis and ride-sharing options are readily available here, providing quick and reliable transportation around this popular destination.

Local Customs Options

Greetings and Handshakes: When visiting, you'll notice that a firm handshake is a common way to greet locals, reflecting their friendly and respectful nature.
Seasonal Festivals: Participating in seasonal festivals offers insight into the area's rich cultural traditions and community spirit.
Local Cuisine Etiquette: Respect for traditional dining customs, such as sharing family-style meals, enhances your authentic experience here.
Respecting Natural Landscapes: Preserving the region's scenic beauty by adhering to outdoor guidelines demonstrates your appreciation for the local environment.

Frequently Asked Questions About Windham Luxury Rentals

1. What are the top Luxury Rentals 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 Luxury Rentals in Windham:

2. How many Luxury Rentals are available in Windham?

Currently, the total number of properties listed by RBO in 2026 is over 436 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Luxury Rentals in Windham. 

3. What is the cancellation policy for luxury rentals in Windham, New York?

Cancellation policies vary depending on the property listing. You should review the specific terms outlined on the listing page or contact the property owner directly for detailed information.

4. Are there any additional fees I should be aware of when booking a luxury rental here?

Additional fees such as cleaning, security deposits, or service charges may apply. Details are provided in the listing description or can be clarified by reaching out to the owner before booking.

5. How do I ensure my reservation for a luxury rental is secure and confirmed?

Reservations are typically secured through the platform's trusted booking system. Confirm your booking once you receive the confirmation email, and check the listing for any specific requirements or verification steps.

6. What amenities are generally included with luxury rentals in this destination?

Luxury properties often feature high-end amenities like private pools, fireplaces, modern kitchens, and scenic views. For precise details, refer to the property listing or contact the owner directly.

7. Is there a minimum stay requirement for luxury rentals in this region?

Minimum stay requirements vary by property and season. Please review the specific listing or contact the owner to confirm the policy for your intended travel dates.