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Windham Luxury Rentals

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Windham Pet Friendly Vacation Rentals

10.0 (42 Reviews)
Ski Chalet
Mountain chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Windham Large Vacation Homes

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Why Choose Rent By Owner for your Windham 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

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation here ensures you experience the region’s natural beauty and outdoor activities at their best, making your stay in Windham, Vermont, USA truly memorable and enjoyable.

Peak Season Highlights

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Winter (December to February)

During the peak winter months, this area transforms into a popular destination for snow sports enthusiasts seeking a scenic escape in Vermont.

Average Temperature Daytime: 20°F to 30°F - Nighttime: 0°F to 10°F
autumn
Fall (September to November)

Autumn draws many travelers with its vibrant foliage and crisp air, making it an ideal time to enjoy the natural beauty of the region.

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

Off-Season Highlights

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Spring (March to May)

In early spring, the quiet countryside offers a peaceful retreat before the busy summer season begins in this scenic destination.

Average Temperature Daytime: 45°F to 60°F - Nighttime: 25°F to 40°F
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Summer (June to August)

Lighter crowds and pleasant weather make summer a favorable time to explore outdoor activities and enjoy the lush landscape here.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°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 BBQ grill, perfect for savoring meals amidst scenic surroundings.
  • Take advantage of a spacious patio or deck area to relax and soak in the regional views.
  • Benefit from well-maintained garden spaces where you can unwind amid native flora.
  • Make use of convenient on-site parking facilities for easy access during your stay.
  • Experience scenic walking or hiking trails accessible directly from the property, ideal for exploring the area's natural beauty.
  • Utilize the available outdoor fire pit for cozy evenings under the stars.
  • Access to outdoor sports facilities such as tennis courts or volleyball areas often found in this destination’s rental properties.

Top Attractions Around Windham

What attractions are nearby?

During your stay, you'll have the opportunity to enjoy outdoor activities such as hiking and skiing in this region, making it an ideal destination for adventure seekers and nature lovers alike.

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Family Activities

  • Windham Hill Inn & Trails: Explore family-friendly trails for hiking and biking, offering scenic views that make outdoor adventures in this region memorable for all ages.
  • Windham Mountain Resort: Enjoy a variety of winter activities like skiing and snowboarding, perfect for creating fun-filled family days on the slopes close to your rental here.
  • Windham County Fairgrounds: Attend seasonal fairs and community events, providing engaging entertainment and local culture experiences suitable for children and adults alike.
  • Local Nature Centers and Parks: Discover open spaces and nature centers where you can picnic, observe wildlife, and participate in educational programs right in this area.
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Adult Activities

  • Skiing and Snowboarding: Take advantage of the area’s renowned slopes during winter for exhilarating skiing and snowboarding experiences amidst stunning mountain scenery.
  • Hiking and Nature Trails: Explore scenic hiking trails that wind through the region’s lush forests, offering a peaceful escape and breathtaking views for outdoor enthusiasts.
  • Local Art Galleries and Studios: Discover vibrant art scenes by visiting local galleries and studios showcasing works inspired by the area's natural beauty and cultural heritage.
  • Golfing at Scenic Courses: Play a round on picturesque golf courses that provide both a relaxing activity and panoramic vistas of the surrounding landscape.

Windham Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the region’s natural beauty by planning hiking, biking, or skiing adventures right from your Windham vacation rental.
  • Discover seasonal events: Check out the area’s calendar for festivals and community events that will enrich your stay and give you a taste of local culture.
  • Plan ahead for dining experiences: While here, explore nearby eateries and consider booking reservations in advance to enjoy the region’s best culinary offerings.
  • Utilize local resources: Reach out to local visitor centers or hosts for personalized tips on hidden gems and must-see sights during your stay.

Transportation Options

  • Windham County Transit Service: Provides reliable bus transportation across the area, making it easy to explore this scenic destination without the need for a car.
  • Regional Airport (Rutland Southern Vermont Regional Airport): Offers convenient flights from major cities, connecting you effortlessly to the region for a comfortable arrival or departure.
  • Taxi Services and Ridesharing: Local taxis and rideshare options like Uber are readily available here, providing flexible transportation around this peaceful spot in Vermont.
  • Car Rental Agencies: Numerous rental companies operate nearby, giving you the freedom to explore the region's natural beauty at your own pace with a rental vehicle.

Local Customs Options

  • Welcoming Community Spirit: Residents here take pride in their friendly and inclusive attitude, making newcomers feel like part of the local area from the moment they arrive.
  • Respect for Nature: The region values environmental preservation, encouraging visitors to participate in sustainable practices during their stay.
  • Local Food Traditions: Enjoy the region’s culinary customs, which emphasize farm-to-table ingredients and seasonal dishes that reflect the area's agricultural heritage.
  • Celebrating Seasonal Festivals: Participate in community events and festivals that highlight the area's rich cultural traditions throughout the year.

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. 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:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 75 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. 

4. What is the cancellation policy for vacation rentals in Windham, Vermont?

Cancellation policies vary by listing, so it’s important to review the specific terms on each property’s page. Some rentals may offer flexible cancellation options, while others may have stricter policies. Contact the owner directly if you need clarification.

5. How do I find the best vacation rental deals in Windham, Vermont?

To secure the best deals, compare listings based on price, amenities, and reviews. Booking early and checking for special offers or discounts can also help you find more affordable options here. Detailed descriptions and photos are available to assist your decision.

6. Are pets allowed in vacation rentals in Windham, Vermont?

Pet policies vary among individual rentals, with some properties welcoming animals and others not. Be sure to check the pet policy listed on the property’s page or contact the owner to confirm if traveling with your pet.

7. What amenities should I expect from vacation rentals in Windham, Vermont?

Amenities differ between properties but often include essentials like Wi-Fi, parking, fully equipped kitchens, and outdoor spaces. Review each listing carefully to ensure it meets your needs before booking.

8. How do I communicate with hosts for vacation rentals in Windham, Vermont?

Most listings provide a messaging platform or contact details to reach out directly to owners. Using these channels allows you to ask questions about the property, clarify policies, or request additional information before confirming your reservation.