House Sitting in Chestertown
Find a loving house sitter to watch over your pets and your home.
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Top rated Chestertown house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Jonathan is the BEST! He always goes above and beyond with our Buddy. It is so comforting to know that while we are away, Buddy is in such good hands. We highly recommend Jonathan!!!”
“Brandy housesat our 5 month old pup while we were visiting Johnsburg for a wedding! She was super responsive and flexible! She met us the day before to get to know the pup, the requirements etc. She was dependable and on time! She was kind and it was easy to see that she loves animals! She sent us pictures every few hours and kept us updated! Great experience!”
“Tara-Lynn is the best dog sitter I've ever had. She took excellent care of my dog Lola and sent me plenty of pictures. She also did not leave any trace of a mess in my place.”
“Thank you Lillian, for taking Finley at the last minute for us. Finley seemed to really like you and you kept us updated throughout your visit with him including pics!! We will definitely call on you again to watch Finley!! Many thanks!”
“Jaimi is wonderful! My dog gets anxious when we leave for extended periods of time. I reached out to Jaimi and we did a meet and greet beforehand and talked about what would be best for Finn for a day we needed to be away. Jaimi came to our house twice to take Finn out for a walk, playtime, and snuggle time. She sent me lots of pictures and updates. We came home to a more relaxed Finn and I was able to relax when we were away because I knew he was in great hands! I will definitely be rebooking with Jaimi in the future!”
“This was our first time using a house/dog sitter in this area and I was nervous. My very active dogs love Alissa. We were updated frequently with pictures and our house was just as we left it.”
“Trustworthy and meticulous, Karen spent five days with my two big labs and gave them endless love and attention. Since we have no fence, she had to leash and walk the dogs a lot, and modify for the old limpy dog versus the young bouncy one. She left my house looking beautiful and even did the laundry! I want her back next time I'm going out of town.”
About: Hello there, my name is Riley and i love pets of all shapes and sizes, big, small you name it. i have a ton of experience pet sitting and would be more than happy to dog sit in your home and stay there as needed also willing to do drop ins to feed and water. I also do walks around your neighborhood as well if needed. i am a honest, hardworking and trustworthy person and i will treat your pets as if they were my own, because really isn't that what every pet owner wants? to know that their pets are taken care of and loved when they are away for long periods of time or just for the day while your at work. I always make time for clients and there pets no matter what. I will treat your dog as my own, and i am available 24/7. I always listen to instructions and follow them to a T, always make sure everything is locked up when I leave and the dogs are in crates if you crate them.
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
House Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, house sitters on Rover respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Chestertown.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chestertown house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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