Madison Pet Friendly Vacation Rentals & PickleTrip Homes
Book a Dog-Friendly Rental in Madison for Your Next Adventure
10.0
(8 Reviews)
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- Pet Friendly
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House
New
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10.0
(2 Reviews)
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New
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- Pet Friendly
- Balcony/Terrace
10.0
(262 Reviews)
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- Pet Friendly
10.0
(88 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(78 Reviews)
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- Pet Friendly
10.0
(51 Reviews)
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10.0
(23 Reviews)
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10.0
(5 Reviews)
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10.0
(4 Reviews)
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10.0
(4 Reviews)
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9.8
(74 Reviews)
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9.8
(74 Reviews)
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- Pet Friendly
9.6
(89 Reviews)
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- Pet Friendly
9.6
(4 Reviews)
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9.4
(20 Reviews)
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9.4
(15 Reviews)
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9.4
(6 Reviews)
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9.4
(6 Reviews)
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9.2
(5 Reviews)
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- Pet Friendly
9.0
(15 Reviews)
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- Pet Friendly
6.4
(5 Reviews)
- Air Conditioner
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- Pet Friendly
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About Madison Pet Friendly Vacation Rentals on PickleTrip
PickleTrip™'s pet-friendly rentals in Madison 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 Madison Pet-Friendly Rentals
There are a lot of options in Madison. If you plan on staying in the Madison 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 Madison:
- Family and Pet-Friendly, Waterfront with Pier
- Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
- Year Round Waterfront Estate/Family Reunions/Retreats - Sleeps 28
- Waterfront Getaway with Dock
- A Beautiful Waterfront Retreat for Family Gatherings!
- Quarterdeck at Swan Cove Manor
- About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!
- "Endless Summer" Waterfront on the Chesapeake Bay!
- About Time-Main House
- About Time-Bunkhouse Only
There are more than 31 pet-friendly rentals available on PickleTrip. Check prices and availability in Madison 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 Madison. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Madison:
Most definitely! There are many luxury places to stay in Madison. 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 Madison. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $747. Find our pet-friendly accommodation near Madison.
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 Madison to find what works for you.
Finding the best prices in Madison
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