Winter Pet Friendly Vacation Rentals & PickleTrip Homes
Book a Dog-Friendly Rental in Winter for Your Next Adventure
10.0
(17 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
10.0
(11 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(2 Reviews)
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- Pet Friendly
10.0
(2 Reviews)
- Pet Friendly
- Balcony/Terrace
- Security/Safety
10.0
(1 Review)
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- Pet Friendly
- TV
9.8
(59 Reviews)
- Air Conditioner
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- Pet Friendly
9.8
(19 Reviews)
- Air Conditioner
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- Pet Friendly
9.8
(14 Reviews)
- Air Conditioner
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- Pet Friendly
9.8
(6 Reviews)
- Pet Friendly
- Bedding/Linens
- Wellness Facilities
8.8
(5 Reviews)
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- Pet Friendly
- Balcony/Terrace
8.6
(7 Reviews)
- Air Conditioner
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- Pet Friendly
8.4
(27 Reviews)
- Air Conditioner
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- Pet Friendly
8.0
(6 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(67 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(21 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(7 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(1 Review)
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- Pet Friendly
9.8
(41 Reviews)
- Air Conditioner
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- Pet Friendly
9.2
(5 Reviews)
- Parking
- Pet Friendly
- TV
9.0
(2 Reviews)
- Air Conditioner
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- Pet Friendly
8.6
(8 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(4 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(10 Reviews)
- Air Conditioner
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- Pet Friendly
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About Winter Pet Friendly Vacation Rentals on PickleTrip
PickleTrip™'s pet-friendly rentals in Winter 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 Winter Pet-Friendly Rentals
There are a lot of options in Winter. If you plan on staying in the Winter 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 Winter:
- 5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
- Cabin in the Woods Near Big Chip and Hayward
- Pets & kid Friendly ,direct access to ATV& snow trails, private dock
- Cozy cabin on Island Lake
- Pfaff Winter Retreat on Lake Winter. Minutes from Tuscobia trail.
- Exclusive PRIVATE ISLAND for your group on Lake Winter
- Bobbers Cabin on Perch Lake
- Right on the Tuscobia Trail Cozy 2-bedroom cabin in Winter with WiFi, AC
- Haven Island on Lake Winter - Private Island!
- Classic Rustic Lakeside Cabin Retreat. Sleeps 6. Pets allowed.
There are more than 36 pet-friendly rentals available on PickleTrip. Check prices and availability in Winter 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 Winter. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Winter:
Most definitely! There are many luxury places to stay in Winter. 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 Winter. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $221. Find our pet-friendly accommodation near Winter.
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 Winter to find what works for you.
Finding the best prices in Winter
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