Chester Pet Friendly Vacation Rentals & PickleTrip Homes
Book a Dog-Friendly Rental in Chester for Your Next Adventure
10.0
(43 Reviews)
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- Pet Friendly
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Bed & Breakfast
9.5
(16 Reviews)
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- Pet Friendly
10.0
(23 Reviews)
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- Pet Friendly
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House
9.5
(2 Reviews)
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- Pet Friendly
10.0
(14 Reviews)
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Apartment
9.0
(5 Reviews)
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- Pet Friendly
10.0
(12 Reviews)
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- Pet Friendly
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Hotel
8.8
(233 Reviews)
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- Pet Friendly
10.0
(4 Reviews)
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- Pet Friendly
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Hotel
8.7
(187 Reviews)
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- Pet Friendly
10.0
(3 Reviews)
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- Pet Friendly
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8.5
(200 Reviews)
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10.0
(1 Review)
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8.2
(214 Reviews)
- Air Conditioner
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- Pet Friendly
9.8
(34 Reviews)
- Air Conditioner
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- Pet Friendly
7.8
(329 Reviews)
- Air Conditioner
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- Pet Friendly
9.8
(9 Reviews)
- Air Conditioner
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- Pet Friendly
6.9
(369 Reviews)
- Air Conditioner
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- Pet Friendly
9.4
(28 Reviews)
- Pet Friendly
- Security/Safety
- Child Friendly
9.4
(3 Reviews)
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- Pet Friendly
New
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- Pet Friendly
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New
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4.0
(1 Review)
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- Bedding/Linens
- Kitchen
New
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- Pet Friendly
- TV
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About Chester Pet Friendly Vacation Rentals on PickleTrip
PickleTrip™'s pet-friendly rentals in Chester 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 Chester Pet-Friendly Rentals
There are a lot of options in Chester. If you plan on staying in the Chester 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 Chester:
- Little Blue Cabin
- The Homestead - 3 bedroom House in the Heart of Chester
- The Westland Suite - Historic Lodging, Contemporary Comforts
- ENTIRE LOWER LEVEL - Mountain Lakeview Lodge
- Entire home in Valier, Montana
- THE RANCH ROOM - Mountain Lakeview Lodge ~ Enjoy your stay!
- Make memories at our unique & family/pet-friendly log home in historic Ft Benton
- FOOTHILLS LOOKOUT INN -Come home to Montana!
- Great northern bed and breakfast
- Great Northern Bed & Breakfast
There are more than 26 pet-friendly rentals available on PickleTrip. Check prices and availability in Chester 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 Chester. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Chester:
Most definitely! There are many luxury places to stay in Chester. 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 Chester. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $234. Find our pet-friendly accommodation near Chester.
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 Chester to find what works for you.
Finding the best prices in Chester
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