Windham Pet Friendly Vacation Rentals & PickleTrip Homes
Book a Dog-Friendly Rental in Windham for Your Next Adventure
10.0
(74 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
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Ski Chalet
10.0
(4 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
New
- Parking
- Pet Friendly
- TV
10.0
(6 Reviews)
- Air Conditioner
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- Pet Friendly
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Apartment
10.0
(1 Review)
- Parking
- Pet Friendly
- Accessibility
10.0
(3 Reviews)
- Air Conditioner
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- Pet Friendly
10.0
(1 Review)
- Parking
- Pet Friendly
- View
10.0
(2 Reviews)
- Air Conditioner
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- Pet Friendly
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House
8.7
(3 Reviews)
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- Pet Friendly
- Accessibility
10.0
(1 Review)
- Pet Friendly
- Security/Safety
- Bedding/Linens
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House
8.5
(2 Reviews)
- Parking
- Pet Friendly
- Accessibility
9.8
(11 Reviews)
- Pet Friendly
- Pool
- Balcony/Terrace
7.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
9.4
(6 Reviews)
- Air Conditioner
- Pet Friendly
- TV
8.0
(2 Reviews)
- Parking
- Pet Friendly
- TV
8.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
8.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
7.6
(5 Reviews)
- Air Conditioner
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- Pet Friendly
6.0
(1 Review)
- Pet Friendly
- Security/Safety
- Child Friendly
5.0
(2 Reviews)
- Air Conditioner
- Parking
- Pet Friendly
4.0
(1 Review)
- Air Conditioner
- Parking
- Pet Friendly
New
- Parking
- Pet Friendly
- TV
New
- Air Conditioner
- Parking
- Pet Friendly
New
- Air Conditioner
- Parking
- Pet Friendly
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About Windham Pet Friendly Vacation Rentals on PickleTrip
PickleTrip™'s pet-friendly rentals in Windham 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 Windham Pet-Friendly Rentals
There are a lot of options in Windham. If you plan on staying in the Windham 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 Windham:
- Windham Log Cabin on 35 Acres. Family friendly.
- Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
- DREAM LOG CABIN 110 Acres/Hot Tub/5 Minutes to the slopes/pond/river/internet
- Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
- Windham Family Getaway
- EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS
- Ski Ridge Golf farmhouse
- Serene Catskills Escape: Hot Tub, Pond & Game Room
- Condo in Windham Mountain Village
- Blue Spruce Chalet — Hot Tub, Pet Friendly
There are more than 148 pet-friendly rentals available on PickleTrip. Check prices and availability in Windham 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 Windham. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Windham:
Most definitely! There are many luxury places to stay in Windham. 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 Windham. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $687. Find our pet-friendly accommodation near Windham.
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 Windham to find what works for you.
Finding the best prices in Windham
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