Winnetka Pet Friendly Vacation Rentals & PickleTrip Homes
Book a Dog-Friendly Rental in Winnetka for Your Next Adventure
10.0
(3 Reviews)
- Air Conditioner
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- Pet Friendly
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Villa
10.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
10.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
10.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
9.8
(10 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
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Hotel
9.0
(120 Reviews)
- Air Conditioner
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- Pet Friendly
New
- Air Conditioner
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- Pet Friendly
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Hotel
8.8
(707 Reviews)
- Air Conditioner
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- Pet Friendly
New
- Air Conditioner
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- Pet Friendly
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Hotel
7.6
(200 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
10.0
(1 Review)
- Air Conditioner
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- Pet Friendly
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Hotel
7.1
(91 Reviews)
- Air Conditioner
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- Pet Friendly
New
- Air Conditioner
- Pet Friendly
- TV
10.0
(7 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
New
- Air Conditioner
- Parking
- Pet Friendly
New
- Air Conditioner
- Pet Friendly
- Security/Safety
2.0
(1 Review)
- Air Conditioner
- Pet Friendly
- Wheelchair Accessible
New
- Air Conditioner
- Pet Friendly
- Laundry
New
- Air Conditioner
- Pet Friendly
- Security/Safety
New
- Air Conditioner
- Pet Friendly
- Security/Safety
8.8
(3 Reviews)
- Air Conditioner
- Pet Friendly
- TV
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About Winnetka Pet Friendly Vacation Rentals on PickleTrip
PickleTrip™'s pet-friendly rentals in Winnetka 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 Winnetka Pet-Friendly Rentals
There are a lot of options in Winnetka. If you plan on staying in the Winnetka 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 Winnetka:
- Updated Spacious Home -Near NWU- Hospitals+More
- Chicago NorthShore Luxury Private Vacation Rental
- Charming, light-filled 5br Wilmette home
- Updated Spacious Home Near Northwestern University
- Spacious Townhouse in Wilmette near lake and NW
- Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!
- Residence Inn by Marriott Chicago Wilmette/Skokie
- Hampton Inn & Suites Chicago North Shore
- Renaissance Chicago North Shore Hotel
- Sheraton Chicago Northbrook
There are more than 26 pet-friendly rentals available on PickleTrip. Check prices and availability in Winnetka and last updated on November 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 Winnetka. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Winnetka:
Most definitely! There are many luxury places to stay in Winnetka. 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 Winnetka. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $376. Find our pet-friendly accommodation near Winnetka.
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 Winnetka to find what works for you.
Finding the best prices in Winnetka
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