Windsor Pet Friendly Vacation Rentals & PickleTrip Homes
Book a Dog-Friendly Rental in Windsor for Your Next Adventure
10.0
(10 Reviews)
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9.8
(4 Reviews)
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- Pet Friendly
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10.0
(5 Reviews)
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House
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10.0
(3 Reviews)
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New
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9.8
(10 Reviews)
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5.4
(71 Reviews)
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- Pet Friendly
- Wheelchair Accessible
9.4
(36 Reviews)
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- Pet Friendly
9.4
(9 Reviews)
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10.0
(14 Reviews)
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10.0
(10 Reviews)
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10.0
(7 Reviews)
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10.0
(5 Reviews)
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10.0
(2 Reviews)
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10.0
(1 Review)
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9.8
(19 Reviews)
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9.6
(7 Reviews)
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9.2
(159 Reviews)
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8.0
(4 Reviews)
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7.8
(8 Reviews)
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- Pet Friendly
New
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- Pet Friendly
New
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- Pet Friendly
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About Windsor Pet Friendly Vacation Rentals on PickleTrip
PickleTrip™'s pet-friendly rentals in Windsor are perfect for pet owners who want to bring their furry friends and enjoy their next pickleball game on vacation. You can rest easy knowing that your pet is welcome and comfortable in your rental. With a variety of options to choose from, you can find the perfect accommodation that fits your needs and budget. Whether you're looking for a cabin in the woods, a beachfront villa, or a luxury resort, PickleTrip™ has a pet-friendly rental that will suit your needs.
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Frequently Asked Questions About Windsor Pet-Friendly Rentals
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 Pet Friendly Vacation Rentals in Windsor:
- Nancy Kentucky 1800s log cabin
- Farmhouse in the Lake Cumberland area
- Sandy Acres Cabins (Big Cabin) - by Galilean Home
- Sandy Acres Hobbit - Near Galilean Home - Liberty
- Lake Cumberland Cabin Getaway! Quick Local Lake Access!
- Great place to gather near Lake Cumberland
- Big Foot's Retreat- is in walking distance of Cumberland Point Recreation Area
- Green Acres by the water
- Beautiful Cubby Cabin On The Mountain
- Cozy Family Fishing Cabin, with Sauna, Near Lake 1/2mile beautiful walk/view!
There are more than 75 pet-friendly rentals available on PickleTrip. Check prices and availability in Windsor and last updated on October 2025. Check an individual property if they have restrictions on the size or numbers of pets.
There are many dog-friendly vacation homes available in Windsor. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Windsor:
Most definitely! There are many luxury places to stay in Windsor. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Windsor. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $338. Find our pet-friendly accommodation near Windsor.
At PickleTrip, many of our accommodations are perfect for families and allow dogs too. Check out the complete list of pet-friendly holiday rentals in Windsor to find what works for you.
Finding the best prices in Windsor
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