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Chestertown pet-friendly rentals

We found 18 pet-friendly rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any pet-friendly holiday rentals in Chestertown?
Select from 18 pet-friendly holiday rentals in Chestertown that feature perks like welcome treats and dog beds so that your pup can be just as comfortable as you. Consider houses in well-known areas such as Pomona, Edesville and Price.
How much does it cost to stay in a pet-friendly holiday rental in Chestertown?
To search for a pet-friendly holiday rental in Chestertown that suits your budget, take advantage of our comprehensive filters. Choose the maximum amount you want to spend and compare the prices of accommodation that have everything you need for an awesome getaway with your furry friend. Bigger properties with several bedrooms and lots of amenities generally cost more, so opt for something smaller if you want to save.
Where can I rent a pet-friendly holiday rental with great views?
Experience Chestertown from a new angle when you settle into a pet-friendly holiday rental with a view. Book one that's perfect for you by selecting the "Location" and "Recommended" filters. Another handy tip? Search for a property that features an outdoor area from where you can soak up the views while playing fetch with Fido.
Do any pet-friendly holiday rentals in Chestertown have a garden?
Some pet-friendly holiday rentals in Chestertown include an outdoor area for your four-legged pal to play in. Discover these stays by choosing "Garden or backyard" under the features and amenities section of our filters. Closely read the property details to find out more, such as whether they have an enclosed yard or are close to dog parks or pet-friendly hiking trails.
Can I book a pet-friendly cabin or lodge in Chestertown?
Get out into nature with your faithful furry companion at your side at one of our pet-friendly cabins or lodges in Chestertown. Use our handy "Pet-friendly" filter to look for stays that offer an unforgettable experience for the whole family — pooches included.
What are the top things to do in Chestertown?
It's easy to see why families love Chestertown, with popular attractions like Rock Hall Harbour, Betterton Beach and Rolphs Wharf Marina to explore. Discover this destination's wonders together and then return to the comforts of your pet-friendly holiday rental to curl up with your furry friend.
Why should I book my pet-friendly holiday rental with Stayz?
Besides having a fabulous space to kick back with your pup, there are many good reasons to book your pet-friendly holiday rental with us. From the second you book until you return home, our first-class customer support team will ensure that every step of your escape goes smoothly. Need to change plans? Check out our cancellation policies to find out if you're eligible for a complete refund.