Discover Your Perfect Windham Vacation Homes

Windham Luxury Rentals

New
House
Wintertime
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
See More Windham Luxury Vacation Rentals
Find More Windham Villas, Resorts, & Rentals on BedroomVillas

Windham Large Vacation Homes

|
8.0 (8 Reviews)
Apartment
Townhouse W Private Deck & Mt View
  • Air Conditioner
  • Parking
  • Balcony/Terrace
View Availability
See More Family Vacation Rentals in Windham on FVR

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

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
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 Vacation Rentals stay?

Choosing the ideal time to visit here depends on your preferred activities and the season, allowing you to enjoy this destination's unique charm while making the most of your stay in the area.

Peak Season Highlights

winter
Winter (December to February)

Experience the region's snow-covered scenery and winter sports, making it an ideal time for outdoor enthusiasts seeking adventure and scenic beauty.

Average Temperature Daytime: around 25°F to 35°F - Nighttime: below freezing, often dipping into teens
autumn
Fall (September to November)

Enjoy the vibrant foliage and crisp air during this peak season, perfect for exploring the area's natural beauty and participating in seasonal festivities.

Average Temperature Daytime: mid-50s to mid-60s °F - Nighttime: low 40s to 50s °F

Off-Season Highlights

image
Spring (March to May)

Visit as the landscape awakens with blooming flowers and milder weather, offering a quieter escape with fewer crowds.

Average Temperature Daytime: mid-40s to mid-60s °F - Nighttime: 30s to 40s °F
image
Summer (June to August)

Relish warm days and longer daylight hours when the area becomes a peaceful retreat for outdoor relaxation and activities.

Average Temperature Daytime: 70s to 80s °F - Nighttime: mid-50s to mid-60s °F

Weekly Weather Forecast for Windham

How to Book Your Windham 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

More Top-Rated Vacation Rentals in Windham 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 outdoor dining with a private patio or picnic area to make the most of the scenic surroundings.
  • Relax by a cozy outdoor fire pit, perfect for unwinding after a day exploring the region’s natural beauty.
  • Take advantage of spacious yards or gardens ideal for outdoor activities or family gatherings.
  • Make use of a shared or private outdoor pool during the warmer seasons for refreshing relaxation.
  • Explore the area on hiking trails or nature paths directly accessible from your rental.
  • Utilize outdoor recreational equipment such as kayaks, paddleboards, or mountain bikes if available.
  • Enjoy panoramic views from a deck or balcony that overlook the picturesque landscape here in the region.

Top Attractions Around Windham

What attractions are nearby?

In this charming region, you can enjoy a variety of outdoor activities such as hiking, skiing, and exploring scenic trails that showcase the natural beauty of the area surrounding Windham, New York.

image
image

Family Activities

  • Windham Mountain Resort: Enjoy a day of family-friendly skiing, snowboarding, or tubing at this popular resort in the region that offers fun for all ages.
  • Windham Country Club: Spend quality time together playing a round of golf on the scenic courses nestled in this area known for its beautiful mountain vistas.
  • Hunter-West Kill Range: Explore the great outdoors with family hikes and picnics amid the stunning natural beauty of this nearby range, perfect for nature lovers staying here.
  • Windham Path: Discover an easy trail ideal for strollers and young children, offering a relaxing outdoor experience close to your vacation rental in Windham.
image

Adult Activities

  • Hiking and Nature Walks: Explore the scenic trails nearby, offering breathtaking views of the mountains and forests within this region.
  • Skiing and Snowboarding: During winter months, enjoy world-class slopes that cater to all skill levels, making it an ideal destination for snow sports enthusiasts.
  • Local Art Galleries and Studios: Discover the vibrant arts scene through visits to galleries showcasing local talent and handcrafted works unique to the area.
  • Farmers Markets and Culinary Tours: Experience the region's fresh produce and artisan creations firsthand by browsing local markets and enjoying authentic culinary tours.

Other Places to Stay in Windham, NY

Windham Mountain Resort
Windham Mountain Resort Vacation Rentals
Windham Country Club
Windham Country Club Vacation Rentals
Windham Vineyards and Winery
Windham Vineyards and Winery Vacation Rentals
Ashland
Ashland Vacation Rentals
More Places to Stay Near Windham

Windham Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Seasonal Activities: Take advantage of the area's seasonal events and outdoor activities by scheduling them early to ensure availability and a memorable experience.
  • Explore Local Dining Options: Discover the region’s cuisine by trying local restaurants or cozy cafes nearby your rental, immersing yourself in the area's culinary culture.
  • Pack Appropriately for the Climate: Prepare for varying weather patterns here by bringing suitable clothing and gear to stay comfortable during your stay in all seasons.
  • Utilize Nearby Outdoor Recreation: Maximize your trip by taking advantage of the region's outdoor pursuits such as hiking, mountain biking, or simply enjoying the scenic nature around your accommodation.

Transportation Options

  • Windham Bus Service: This reliable transportation option offers convenient local transit within the region, making it easy to explore centrally located vacation rentals.
  • Nearby Amtrak Stations: Connecting you to major cities and regional destinations, these stations provide comfortable rail travel options near this mountain town.
  • Rental Car Services: Numerous rental agencies in the area allow you to explore Windham and its scenic surroundings at your own pace with flexible vehicle options.
  • Taxi and Rideshare Options: On-demand taxi and rideshare services are readily available, providing quick and easy transportation from your vacation rental here to popular attractions.

Local Customs Options

  • Local Craftsmanship: Appreciating the region's rich tradition of handcrafted goods can enrich your experience in this area, where craftsmanship is an integral part of local culture.
  • Seasonal Festivals: Participating in seasonal festivals offers a glimpse into the area's vibrant community spirit and deep-rooted customs celebrated throughout the year.
  • Traditional Cuisine: Savoring traditional dishes highlights the region's culinary heritage and provides an authentic taste of local flavors during your stay.
  • Community Gatherings: Engaging in neighborhood events fosters a connection with residents and immerses you in the customary social practices here.

Frequently Asked Questions About Windham?

1. What are the top vacation 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 Vacation Rentals in Windham:

2. How many vacation rentals have private pools in Windham?

There are 15 vacation rentals with private pools near Windham. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Windham are best for families?

If you are looking for a family-friendly vacation home in Windham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windham:

4. How many Rentbyowner vacation rentals are available in Windham?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 398 in the Windham 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. 

5. What is the cancellation policy for vacation rentals in Windham, New York?

Cancellation policies vary by property, so it’s best to review the specific listing details or contact the owner directly to understand their terms before booking.

6. Are there any specific check-in and check-out times I should be aware of when staying in this area?

Check-in and check-out times are determined by each property owner; please refer to your reservation details or contact the host for precise timings.

7. How do I find out about additional fees, such as cleaning or security deposits, for my stay?

Additional fees are listed on the property page or can be confirmed by reaching out directly to the owner prior to booking.

8. Can I bring pets to a vacation rental here, and what are the pet policies?

Pet policies differ among listings, so it’s important to check the specific property details or contact the owner to confirm if pets are allowed.

9. What amenities should I expect from a vacation rental in this destination?

Amenities vary by property, including options such as Wi-Fi, kitchen facilities, and outdoor spaces; details are available on individual listings or through direct communication with the owner.