Discover Your Perfect Windsor Vacation Homes

Why Choose Rent By Owner for your Windsor 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 Windsor

When should you plan your Vacation Rentals stay?

Choosing the right time to visit this destination ensures you experience its best weather and local events, making your stay in Windsor more enjoyable and memorable.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

This period offers warm weather ideal for exploring the area's outdoor attractions and enjoying local events. It’s a popular time to visit, so booking your vacation rentals early can ensure a comfortable stay.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
autumn
Early Fall (September to October)

Experience the region’s vibrant fall foliage and pleasant temperatures. This season attracts visitors seeking scenic beauty and outdoor activities, making it a prime time to secure your preferred accommodation options.

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Off-Season Highlights

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Winter (December to February)

During the colder months, fewer tourists visit this destination, so you can enjoy more tranquility in your vacation rentals while exploring the quiet charms of the area. Lower demand often translates to better rates and availability.

Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
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Early Spring (March to April)

Before the full bloom of spring, this is a quieter time to visit with fewer crowds. You can find cozy vacation rentals and explore the region's early seasonal changes at a relaxed pace.

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Weekly Weather Forecast for Windsor

How to Book Your Windsor 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 Windsor

More Top-Rated Vacation Rentals in Windsor 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 areas perfect for meals amid the fresh air of this destination.
  • Take advantage of spacious yards or gardens to relax or host outdoor gatherings.
  • Make the most of private patios or decks for sunbathing or evening relaxation.
  • Explore nearby walking trails or nature paths that allow you to enjoy the scenic surroundings.
  • Utilize outdoor grills or BBQ facilities for meals cooked under the open sky.
  • Relax by a swimming pool, if available, to cool off during warm days in the region.
  • Benefit from ample parking spaces with easy access to outdoor amenities and the surrounding area.

Top Attractions Around Windsor

What attractions are nearby?

During your stay, you'll find a variety of outdoor activities, cultural attractions, and local events nearby to enrich your visit in this charming destination.

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Family Activities

  • Windsor Nature Preserve: Explore scenic walking trails and enjoy birdwatching at this peaceful natural area perfect for family outings.
  • The Windsor Historical Society Museum: Discover local history through engaging exhibits that provide an educational experience for kids and adults alike.
  • Main Street Park: Relax and have fun in this family-friendly park featuring playgrounds, open green spaces, and picnic areas.
  • Connecticut Trolley Museum: Take a nostalgic ride on historic trolley cars and learn about transportation history here in the region.
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Adult Activities

  • Windsor Historical Society Museum: Explore local history and heritage through engaging exhibits that provide insight into the area's rich past.
  • Golf at Evergreen Walk Golf Course: Enjoy a round of golf on well-maintained greens, perfect for unwinding and connecting with nature in this scenic part of town.
  • Visit Windsor Arts Center: Engage with the vibrant arts scene through galleries and cultural events that showcase regional talent and creativity.
  • Shopping at Windsor Village Shops: Discover unique boutiques and stores offering a variety of products, ideal for leisurely browsing during your stay.

Other Places to Stay in Windsor, CT

SS&C SummerWind Performing Arts Center
SS&C SummerWind Performing Arts Center Vacation Rentals
Keney Park
Keney Park Vacation Rentals
Poquonock
Poquonock Vacation Rentals
Northwest Park
Northwest Park Vacation Rentals
Vintage Radio and Communications Museum of Connecticut
Vintage Radio and Communications Museum of Connecticut Vacation Rentals
Oliver Ellsworth Homestead
Oliver Ellsworth Homestead Vacation Rentals
Windsor Historical Society
Windsor Historical Society Vacation Rentals
Windsor Arts Center
Windsor Arts Center Vacation Rentals
More Places to Stay Near Windsor

Windsor Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of the region’s well-known cultural sites and outdoor spaces to enrich your stay in Windsor, Connecticut.
  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times can offer a more relaxed experience and better availability for your preferred vacation rentals.
  • Utilize Nearby Transportation Options: Use local transit or rental services to navigate easily around the area and reach key destinations efficiently.
  • Discover Dining and Shopping Spots: Sample local cuisine and browse unique shops to enjoy an authentic and memorable experience here.

Transportation Options

  • Windsor Locks Station: This regional train station offers convenient Amtrak and commuter rail services, making it easy to explore beyond this area.
  • Hartford-Brainard Airport: Located nearby, this small airport provides private and charter flight options for travelers seeking quick access to the region.
  • Local Bus Services: The region is served by bus routes that connect key points within Windsor and surrounding communities, facilitating budget-friendly transportation.
  • Car Rentals: Numerous car rental agencies operate here, giving you the flexibility to explore this destination and its scenic surroundings at your own pace.

Local Customs Options

  • Windsor’s Annual Apple Festival: You can experience the local tradition of celebrating the region’s apple orchards during this popular event, showcasing fresh produce and community spirit.
  • Historical Civil War Reenactments: The area honors its history through reenactments that bring to life significant moments from the Civil War era, providing an educational glimpse into the past.
  • Local Craftsmanship and Artisans: Exploring the craftsmanship scene reveals a strong tradition of handmade goods, which you might encounter at local markets and shops here.
  • Seasonal Community Events: The region hosts various seasonal festivals and parades throughout the year, reflecting the friendly and vibrant local culture that visitors often enjoy experiencing.

Frequently Asked Questions About Windsor?

1. What are the top vacation rentals in Windsor?

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

2. Which vacation homes in Windsor are best for families?

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

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 29 in the Windsor 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 Windsor. 

4. What is the cancellation policy for vacation rentals in Windsor, Connecticut?

The cancellation policy varies depending on the individual property listing. It is important to review the specific terms outlined in the listing details or contact the property owner directly to understand the cancellation options and any applicable fees.

5. How do I find a pet-friendly vacation rental in Windsor, Connecticut?

You can filter your search on the booking platform to display only pet-friendly options available here. Be sure to check each property's pet policy and any additional fees before completing your reservation.

6. Are there any minimum stay requirements for booking in Windsor, Connecticut?

Minimum stay requirements differ by property and are specified within each listing. To ensure your booking aligns with your travel plans, review these details carefully before confirming your reservation.

7. What amenities should I expect when staying at a vacation rental here?

Amenities vary among properties but often include essentials like Wi-Fi, parking, and kitchen facilities. Detailed information about what's included can be found in each listing’s description, so it’s advisable to read them thoroughly or contact the owner for clarification.

8. How can I ensure my safety and security when booking a vacation rental in Windsor, Connecticut?

Choosing well-reviewed listings with verified owner profiles helps ensure a trustworthy experience. Always communicate through the official booking platform, and review policies related to security deposits and property protections provided here for added peace of mind.