Dog Boarding in Chestertown
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Chestertown dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I was nervous about boarding Mazie because she's never been away from home. She's older and has minor medical needs. I could not have been happier. Kennadi took such amazing care of my baby and sent lots of pictures. She even introduced her dogs to Mazie so she made friends! I would highly recommend her and I'll never be afraid to leave Mazie with her again. Love, love, love!!!”


“Elizabeth took great care of our dog, Macallan, over the Memorial Day weekend. We hope to make use of her services again the next time we need to use a dog sitter.”

“This was our second booking with Stephanie. She was very accommodating with our dog. It was so helpful that she dropped the dog at our home just as we arrived back home. Our dog arrived happy and well cared for. Stephanie has been reliable, a good communicator, and flexible with each of our bookings. We couldn't ask for a better fit!!”

“Alex and her family were wonderful!! We were a little nervous at first boarding our rescue of only 7 months. But once meeting her and seeing how much she loves animals we knew it was the perfect choice. Her home is perfect with comfy areas to relax and a huge fenced for you dog to run around. Alex is so kind that she sends updates with photos! Our dog River had the best time and highly recommended her to others!”

About: I have cared for dogs of every breed for more than 40 years. I frequently provide overnights in my home and pop in visits for friends & family dogs and have decided to start offering my services to all of you. I am a huge dog lover and will treat your babies like they are my own. Rest assure that you will be worry free while your fur-baby is enjoying their best life in daycare. You will receive updates and many photos while you are away Must be house-trained and not have to wear diapers or pee pads. I understand an accident can happen especially being in a new place. Must be friendly with people and all other dogs without having any aggression Must be up to date on their shots I currently work a full time job and I’m available for boarding on Friday evenings thru Sunday evening with the possibility of boarding during the week. The same goes for drop in visits I have a big yard but it’s not fenced in. I do have a very long lead that goes from one end of the yard to the other for the dogs that cannot be outside without a leash
“Shari and Connie were fantastic! Definitely recommend them. My 1yr old dog Olivia had a terrific time - they took her on great walks and gave her loads of attention, plus have a fabulous yard and great home that she felt very comfortable in. They also sent me regular updates, which I really appreciated. I think so highly of them that I’ve already booked another stint for Olivia in a few weeks!”

“Mikaela was really great! She was gracious to watch our pup while we attended a wedding nearby and was extremely communicative leading up and throughout his stay! We would absolutely book with Mikaela again.”

“A Big Shout Out to Brittney for taking care of our Finley for his first weekend away from home. We were a little nervous since our dog has some separation issues. But she kept us updated through text and photos and he looked like he had a great time with her and her cutie dog Pierre. Dogs got along well and our boy looked relaxed which in turn let us know we made the right choice when picking Brittney. We will definitely call her again for future help.. Thanks Brittney!!!”

“Inge was amazing with my pup! She sent picture updates to let me know how she was doing. Rosie had such a good time at her house that when I came to pick her up, she didn't want to leave! I am so glad I found Inge and we will certainly be back when needed!”

“Jacqueline was a wonderful sitter for Cory. She was great at communicating and scheduling. We appreciated her texts and flexibility. Next time we’re visiting upstate NY we will definitely contact her again!”
“We needed a quick overnight on a cross country trip. Our two goldens who just turned 2 we’re happy and loved with Hannah. We will be checking in with her next time we’re in the area for sure!”
About: I have pet and house-sat a lot through out my life, I love making new animal friends!! I have experience giving medication, bathing, walking, hiking and chilling with both 🐈 and 🐕. I live in Bomoseen and work in Middlebury, if you need a drop in while you go out on the lake or need to take a day trip, I’m your girl! I have time to get your pets outside and active, and to give them lots of attention. I’m an extremely reliable, punctual person. I’m also quite tidy, should you need an overnight sitter, your place will be almost identical to how you left it.
“This was was my senior cat’s very first boarding and it couldn’t have gone better! Dionna was so kind and gentle with him and checking in with me each day with pictures. When I brought my cat home he acted as if nothing ever happened, no stress, etc. I would definitely use Dionna’s services again!”

“Alissa and her family took my 13 year old dog in for two nights. She was kind enough to watch him with her dog and no other dogs so he would not be as stressed. It worked out wonderfully. She sent me updates with pictures which was helpful. If you need a dog sitter in the Lake George area I would not hesitate.”


About: I love all animals!!! I really enjoy coming to your house and playing with your precious babies. I have cared for a variety of animals including dogs, cats, hamsters, rabbits, birds, turtles, and yes even snakes. I’ve even experienced breeding and nurturing 11 golden retrievers (3 adults and 8 puppies) at one time. I will come to your house to LOVE, feed, water, play, brush, walk, talk to, and even car rides with your beautiful pets. I’ve also been known to mop, water your plants, retrieve your mail, and take your garbage to the street. On numerous occasions, I’ve taken on jobs in Massachusetts and Vermont as mini vacations! I have a bubbly and friendly personality that animals respond well too! Reasonable rates, flexible hours, and many satisfied customers! I am retired from the county, which allows me to provide full time care to all my fury friends! I travel distances to watch your babies and occasionally welcome your pet to stay at my house. My goal is to watch pups in their own environment. It’s always difficult when Mom and Dad go away, but they are definitely less stressed if they get to stay home. This way they can feel safe and comfortable in their own surroundings
Chestertown dog parents share their Rover experiences
From the first contact Kennadi was very responsive and accomodating. We are very selective about who we have watch our dog and were very comfotable with Kennadi and her husband Tyler. You can tell they are real animal lovers and very caring. We would definitely use them again.

Popular requests near you
Select a filter and find qualifying Chestertown sitters!How Rover works

1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
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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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Chestertown.
Rover makes it easy to find Chestertown dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 dog boarding 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.







