Discover Your Perfect Windham Country Club Vacation Homes

Best Vacation Homes in Windham Country Club

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10.0 (1 Review)
Cabin
Windham NY Espace
  • Air Conditioner
  • Parking
  • Bedding/Linens
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10.0 (1 Review)
Apartment
Windham Ridge Chalet
  • Air Conditioner
  • Parking
  • View
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9.4 (285 Reviews)
Bed & Breakfast
Mountain Treasure B&B
  • Air Conditioner
  • Parking
  • TV
View Availability

Why Choose Rent By Owner for your Windham Country Club Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Windham Country Club

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, with each season offering unique opportunities to enjoy the region’s natural beauty and outdoor activities at its best.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, this destination experiences warm weather perfect for outdoor activities and exploring the scenic region.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Fall (September to November)

Autumn brings colorful foliage and mild temperatures, making it an ideal time to enjoy the natural beauty of the area.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Off-Season Highlights

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Winter (December to February)

The winter months see fewer visitors, offering a quieter stay with opportunities to enjoy peaceful scenery and winter sports nearby.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 15°F to 25°F
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Spring (March to May)

Early spring features cooler weather and less crowded conditions, ideal for those seeking tranquility and the start of local seasonal changes.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Windham Country Club

How to Book Your Windham Country Club Vacation Rental Home

What's our booking process?

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

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

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

Explore and book the perfect rental in Windham Country Club

More Top-Rated Vacation Rentals in Windham Country Club Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 access to scenic outdoor spaces perfect for picnicking and relaxation amidst the natural beauty of the area.
  • Take advantage of well-maintained golf courses, ideal for enthusiasts seeking a round of golf during your stay.
  • Utilize spacious yards or gardens for outdoor activities or family gatherings in the fresh air.
  • Benefit from convenient parking areas for easy access to your outdoor adventures around the destination.
  • Make use of designated outdoor seating or patios to unwind while soaking in views of the surrounding landscape.
  • Explore nearby hiking trails that provide a great way to experience the region’s picturesque scenery.
  • Access recreational facilities such as tennis courts or swimming pools commonly available in upscale outdoor settings here.

Top Attractions Around Windham Country Club

What attractions are nearby?

While staying here, you'll have the opportunity to enjoy outdoor activities such as hiking, golfing, and exploring scenic trails in the nearby region of Windham County, ensuring a relaxing and adventurous getaway.

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Family Activities

  • Windham Mountain Resort: Enjoy a day of family-friendly skiing or snowboarding at this popular winter destination in the region, perfect for creating lasting memories.
  • Windham Path: Explore scenic hiking and biking trails along this easy-to-navigate path, offering picturesque views suitable for all ages.
  • Windham Historical Society Museum: Discover local history through engaging exhibits that provide an educational experience for children and adults alike.
  • Windham Country Club Golf Course: Spend quality time together by playing a round of golf at the well-maintained course nestled in the area’s lush landscape.
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Adult Activities

  • Golf at Windham Country Club: Experience a round of challenging and scenic golf at the local course, perfect for adult enthusiasts seeking a relaxing day on the greens.
  • Wine Tasting Tours: Explore nearby vineyards where you can enjoy tastings and learn about the region's distinguished wine-making tradition.
  • Hiking in the Area: Discover scenic trails around here that cater to different skill levels, offering breathtaking views and outdoor exercise for adventure lovers.
  • Local Dining Experiences: Indulge in the area's culinary scene by visiting restaurants that serve regional cuisine, ideal for savoring delicious meals after a day of activities.

Windham Country Club Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Outdoor Activities: Take advantage of the area's natural beauty by engaging in outdoor pursuits like hiking or mountain biking to fully experience the scenic landscape surrounding Windham.
  • Plan Your Visit During the Off-Peak Seasons: Visiting during quieter times can give you a more relaxed experience and access to local attractions without the crowds.
  • Discover Exclusive Dining Options: Savor regional flavors at nearby eateries to enhance your stay while enjoying the authentic tastes of this destination.
  • Choose Well-Located Vacation Rentals: Opt for accommodations close to key attractions and outdoor spots to maximize your sightseeing and recreational time in the region.

Transportation Options

  • Windham Railway Station: The nearby train station provides convenient rail service, allowing you to explore the region comfortably and efficiently.
  • Local Bus Services: Reliable bus routes operate throughout the area, making it easy to access local attractions and amenities without a car.
  • Car Rentals: Several car rental agencies in Windham offer flexible options for exploring the scenic surroundings at your own pace.
  • Taxis and Rideshare Services: Taxis and popular rideshare platforms are readily available here, providing quick and dependable transportation within the area and beyond.

Local Customs Options

  • Greeting and Hospitality: When visiting the area, it’s customary to greet locals warmly and with politeness, reflecting the friendly community atmosphere that defines this destination.
  • Respect for Nature and Outdoor Etiquette: As outdoor activities are popular here, respecting natural spaces by adhering to local guidelines is an important custom to uphold during your stay.
  • Local Dining Traditions: Supporting local eateries and trying regional specialties demonstrates appreciation for the area's culinary heritage and enhances your cultural experience.
  • Community Engagement: Participating in or observing community events showcases a respectful interest in the local culture and fosters meaningful connections here in the region.

Frequently Asked Questions About Windham Country Club?

1. What are the top vacation rentals in Windham Country Club?

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

2. How many Rentbyowner vacation rentals are available in Windham Country Club?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 427 in the Windham Country Club area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windham Country Club. 

3. What is the cancellation policy for booking vacation rentals in Windham?

Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the terms applicable to your reservation.

4. Are there any extra fees or charges associated with staying in Windham vacation rentals?

Additional fees such as cleaning, service charges, or taxes may apply. Please check the listing details or reach out to the host for a complete fee breakdown before booking.

5. How do I ensure my reservation in this area is secure and confirmed?

Reservations are typically secured through the platform's verified booking process. For added confidence, verify the property’s reviews and contact the owner if needed before finalizing your booking.

6. Can I modify or cancel my booking in Windham once it’s confirmed?

Modification and cancellation options depend on the property's policies; please refer to the listing or contact the property owner directly to understand the flexibility available for your reservation.

7. What amenities and features can I expect from properties here?

Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. To ensure your needs are met, review the detailed amenities list on each listing or communicate directly with the host.

Best Vacation Homes in Windham Country Club