Windsor vacation rentals

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August 2025

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Scroll through and select from vacation rentals in Windsor to find one that's perfect for your trip. Vacation rentals offer the best amenities for your stay with friends, family, or just your pet, such as a hot tub and garden. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Windsor

Showing deals for:Nov 7 - Nov 14

Excellent

(5 reviews)

Walking distance to Wellspan York Hospital, York College. Comfortably sleeps 8.

York, PA

8% off

All fees included

Exceptional

(35 reviews)

Welcome to Maple Lane a beautiful farmstead in Western Lancaster County, PA

Conestoga, PA

9% off

All fees included

One of 3 gas-log fireplaces in the Wrightsville cabin rental.

Exceptional

(152 reviews)

Wrightsville Cabin: Outdoor Fire Pit: Hammock by the creek: Long Level Marina

Wrightsville, PA

6% off

All fees included

Exceptional

(40 reviews)

Cozy Family Sized Cottage in the Country! 15 minutes to Lancaster City!!

Conestoga, PA

8% off

All fees included

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Windsor

Highville Hideaway - 2 bed, 1 bath, country views

Sleeps 4 · 2 bedrooms · 1 bathroom

Wrightsville Cabin: Outdoor Fire Pit: Hammock by the creek: Long Level Marina

Sleeps 4 · 1 bedroom · 1 bathroom

Top rated rentals - Windsor

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York State Fair

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Find out more about Windsor

Find the perfect vacation rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a private vacation home. There's no shortage of things to see and do in the area.If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Windsor

Are you hoping to discover things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Windsor a fun spot to vacation. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

Heritage Hill Golf Course (5.4 mi / 8.7 km)
Moon Dancer Winery (6.4 mi / 10.3 km)
Rocky Ridge Park (7.6 mi / 12.2 km)
Corn Cob Acres Field of Fun (11.9 mi / 19.2 km)
Field of Screams (12 mi / 19.3 km)
Nissley Vineyards and Winery Estate (12.4 mi / 20 km)

Exploring the natural landscape of Windsor

Whether you're looking for fun outdoor activities or just want to take in the scenery, Windsor is a great place to get outside. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city center:

Rocky Ridge Park (7.6 mi / 12.2 km)
Susquehanna River (27.8 mi / 44.8 km)
Chickies Rock Park (10.2 mi / 16.4 km)
Brunner Island (14 mi / 22.6 km)
Lakewood lake (15.3 mi / 24.6 km)
Dallastown Lions Club Community Park (4.4 mi / 7 km)

Traveling to and around Windsor

The nearest airport is in Lancaster, PA (LNS), located 20.5 mi (32.9 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Harrisburg Intl. Airport (MDT), which is 21.5 mi (34.6 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Windsor?

Prices for vacation rentals in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Windsor to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.

Are there any discounts for Windsor vacation house rentals?

You can find great discounts on house rentals in Windsor on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I find long-stay vacation rentals in Windsor?

A long-stay vacation rental in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Are there any Windsor vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Windsor with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

When is the best time to visit Windsor for a vacation rental?

The best time to visit Windsor for a vacation rental is during the peak season, which spans from March to May. This period is particularly enchanting as spring blooms fill the landscape, creating a picturesque setting for outdoor activities and sightseeing. With mild temperatures averaging in the mid-50s to mid-70s Fahrenheit, it's an ideal time for visitors to explore the charming local parks and nearby historical sites.

October is another popular month, especially for those who appreciate the beauty of fall foliage. The vibrant colors of autumn make walks through Windsor's scenic areas truly memorable. This month also offers a more relaxed pace, allowing travelers to enjoy the local culture and seasonal events without the hustle and bustle of peak tourist crowds.

For those looking for a more budget-friendly option, consider visiting in August, when rental prices are typically lower.

How early should I book a Windsor vacation rental?

Book your Windsor vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Can I change or cancel my Windsor home rental booking on Vrbo?

To find Windsor vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Windsor vacation rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.