Windham, NY Summer Home Rentals

Windham Summer Rental

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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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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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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Condo

Windham Mountain Village - Walk to Slopes - 2 Bedroom/2 Bathroom Condo

10.0

Exceptional

(10 Reviews)

2 Bedrooms 2 Baths 8 Guests

US $459/Night 7 Nights - US $3,213

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House

Cozy, Modern Cabin Retreat 8 min to Windham mtn

10.0

Exceptional

(1 Review)

1 Bedroom 2 Baths 11 Guests 7879.18 ft²

US $413/Night 7 Nights - US $2,892

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Condo

Windham getaway!

10.0

Exceptional

(10 Reviews)

2 Bedrooms 2 Baths 8 Guests

US $199/Night 7 Nights - US $1,396

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Beautiful Windham Chalet 2 minutes to the Mountain

Ski Chalet

Beautiful Windham Chalet 2 minutes to the Mountain

9.8

Exceptional

(8 Reviews)

4 Bedrooms 2 Baths 11 Guests 2002.09 ft²

US $410/Night 7 Nights - US $2,873

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Cabin

Lake view Cabin on Lake Heloise

10.0

Exceptional

(8 Reviews)

1 Bedroom 1 Bath 5 Guests

US $194/Night 7 Nights - US $1,361

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Apartment

Windham Ridge Chalet

9.5

Exceptional

(2 Reviews)

3 Bedrooms 2 Baths 5 Guests 1517.71 ft²

US $257/Night 7 Nights - US $1,801

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Cabin

Cozy Mtn-View Chalet < 2 Mi to Windham Slopes

10.0

Exceptional

(7 Reviews)

2 Bedrooms 1 Bath 6 Guests 960 ft²

US $338/Night 7 Nights - US $2,363

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House

Georgian Garden

9.3

Exceptional

(20 Reviews)

6 Bedrooms 4 Baths 12 Guests 226.05 ft²

US $149/Night 7 Nights - US $1,043

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House

Cozy Cabin Condo by the Mountain, 5mins to skiing!

10.0

Exceptional

(7 Reviews)

1 Bedroom 1 Bath 4 Guests 1 ft²

US $131/Night 7 Nights - US $920

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More Top-Rated Summer Rental in Windham Area

Why Choose Rent By Owner for your Windham Summer Rental?

What makes our Summer 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 Summer Rental stay?

Timing your vacation in this charming region ensures you experience the best of what the area has to offer, making it essential to consider the optimal months for summer rentals when planning your stay here.

Peak Season Highlights

Summer (June to August)

During the peak summer months, you can enjoy warm days and lively outdoor activities in this scenic area, making it ideal for booking summer rentals that provide a comfortable retreat amidst nature.

Average Temperature Daytime: 78°F - Nighttime: 55°F

Fall (September to October)

This season offers stunning foliage and crisp air, perfect for those seeking a peaceful getaway while enjoying the vibrant colors typical of the region during this popular time to visit.

Average Temperature Daytime: 65°F - Nighttime: 45°F

Off-Season Highlights

Winter (December to February)

In winter, the area becomes a tranquil retreat with snowy landscapes, ideal if you prefer a quiet stay with cozy indoor amenities as fewer travelers venture here during these colder months.

Average Temperature Daytime: 32°F - Nighttime: 20°F

Spring (March to May)

Early spring brings mild weather and blooming flora, offering a serene environment for your vacation while avoiding the busier summer period in this destination.

Average Temperature Daytime: 50°F - Nighttime: 33°F

Weekly Weather Forecast for Windham

How to Book Your Windham Summer Rental

What's our booking process?

Our platform allows you to browse a curated selection of summer 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 Summer Rental in Windham Area

Common Summer Rental Amenities

What amenities can you expect?

Our Summer 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 outdoor dining opportunities with a spacious picnic area or deck, perfect for summer meals surrounded by scenic views.
Take advantage of a private or shared outdoor pool to cool off and relax during warm summer days.
Make the most of a well-maintained patio or porch equipped with comfortable seating for enjoying the fresh air and sunsets.
Explore the region's natural beauty with access to hiking trails directly from your rental property.
Benefit from outdoor fire pits or fireplaces ideal for evening gatherings under the stars.
Utilize outdoor sports amenities such as volleyball courts, badminton sets, or basketball hoops to stay active.
Appreciate landscaped gardens or yards that provide a peaceful environment for outdoor lounging and family activities.

Top Attractions Around Windham

What attractions are nearby?

In the area around Windham, New York, you can enjoy a variety of outdoor activities such as hiking, mountain biking, and scenic nature walks, all easily accessible from your summer rental, making it an ideal destination for outdoor enthusiasts seeking adventure and relaxation in this welcoming region.

Family Activities

Windham Mountain Resort Enjoy a family-friendly day on the slopes or participate in summer activities like mountain biking and scenic chairlift rides, perfect for outdoor recreation in this vibrant area.
Windham Riding Stables Experience guided horseback riding tours suitable for all ages, offering an authentic way to explore the region's beautiful natural scenery.
Windham Path Take a leisurely walk or bike along this scenic trail that meanders through the town and surrounding forested areas, ideal for family outings and outdoor exploration.
Windham Public Library Engage in family-friendly programs, storytimes, and activities that foster community connection and provide educational entertainment during your stay here.

Adult Activities

Hiking Trails Explore scenic hiking routes through the lush landscapes surrounding this destination, perfect for outdoor enthusiasts seeking adventure and breathtaking views.
Local Wineries Visit nearby wineries and enjoy tastings that showcase the region’s finest wines amidst picturesque vineyard settings.
Art Galleries and Studios Discover local art by touring galleries and studios that highlight the creative spirit of the area’s vibrant community.
Golf Courses Play a round at acclaimed golf courses nestled within the region, offering challenging fairways and stunning mountain scenery for adult golfers.

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?

Plan Your Activities in Advance: To maximize your experience here, research local events and outdoor activities early, ensuring your summer rental time is filled with enjoyable excursions.
Choose a Centrally Located Property: Selecting a rental close to the area's main attractions allows for easier access and more flexibility during your stay.
Pack Appropriately for the Season: Make sure to include essentials for warm weather, outdoor adventures, and any specific planned activities to stay comfortable throughout your visit.
Engage with Local Resources: Take advantage of community information and recommendations available in the region to discover hidden gems and enhance your trip.

Transportation Options

Car Rentals: Renting a car provides you with the flexibility to explore Windham and its scenic surroundings at your own pace, making it an ideal transportation option for your summer stay.
Taxi Services: Reliable taxi services in the area offer convenient point-to-point transportation, ensuring you can easily reach local attractions from your rental property.
Local Shuttle Services: Shuttle options operate between popular destinations and accommodations, providing an affordable way to get around without the hassle of driving.
Public Transit: Buses serve certain routes in the region, offering an economical choice for travelers who prefer to use public transportation during their visit.

Local Customs Options

Respect for Local Landmarks: Visitors typically observe a tradition of respecting the area's historic landmarks and natural sites, ensuring they remain pristine for future generations.
Community Gatherings: Participating in local events such as seasonal festivals or town meetings demonstrates appreciation for the close-knit community atmosphere.
Environmental Conservation: The region emphasizes eco-friendly practices, encouraging visitors to minimize their ecological footprint during their stay.
Traditional Crafts and Artisanship: Supporting local artisans by purchasing handcrafted goods reflects a deep respect for the area's cultural heritage.

Windham Summer Rental Frequently Asked Questions

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

2. How many Summer Rentals are available in Windham?

Currently, the total number of properties listed by RBO in 2026 is over 307 in the Windham area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Summer Rentals in Windham. 

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

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

4. Are there any additional fees I should be aware of when booking summer accommodations here?

Additional fees such as cleaning, service charges, or security deposits are specified in each listing. For precise information, refer to the property details or reach out to the host before confirming your reservation.

5. How do I find the best summer rental options in this region?

To find the most suitable options, use search filters to narrow down your preferences and read reviews carefully. Details about amenities and location are available on each listing to help you make an informed choice.

6. Can I verify the safety and cleanliness standards of summer rentals in this destination?

Property listings often include information on cleanliness protocols and safety features. For further assurance, contact the host directly to ask about their procedures and any specific health guidelines they follow.

7. What should I do if I encounter problems during my stay in a summer rental?

If issues arise, contact the property owner or local support team listed on your booking. Specific contact details are provided in your reservation confirmation to ensure prompt assistance.