Dog Boarding in Chestertown
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Top rated Chestertown dog boarders
“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.”
“We have a very anxious 12 year old black lab dog and going away is always a problem. We had a very pleasant experience with Alexandria. Her patience and personal attention was just what our dog needed. We recently went away for a week and Grace had a wonderful experience. I would highly recommend Alexandria's services.”
“I absolutely love Inge!! She treated my boy like he was her own! Many pics and texts! Will not be using anybody else in the future! Thank you for taking such good care of my Henry boy!! ❤️❤️❤️”
“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!”
“Andrea was wonderful with our dog Denali. We feel so fortunate to have connected with her for our trip to Lake George. She was flexible with us when we hit unavoidable travel delays and had to meet up later than expected and at a different location. She communicated with us by text when something worried her (very reassuring!) She sent us happy dog pictures. And Denali was so happy when we picked her up. We will definitely use her again when we’re back in the area!”
“Jesse was great! He was able to accommodate our Bode on very short notice for the whole weekend. He sent daily updates with pictures and was very communicative. Thank you Jesse!”
“Lexy is an amazing girl! Truly a pet lover, who knows how to deal with them! My skittish 2 "Covid present" cats don't trust other people. It was their "out of the house" 1st experience.... And Lexy earned their trust...Thank you Lexy! I will definitely recommend you and your service!”
“Our beagle (Sunny) had a great time with Lydia and her dog, Maxine. Lydia sent several pix and updates during the 3-day stay, and when we went to pick up our pup to go home, she was in no hurry to leave — she obviously enjoys being there. Lydia loves dogs and it shows. We’ve already booked two more stays this summer.”
“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.”
“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!!!”
“Johanna was terrific with my dog. Very welcoming and accommodating. He enjoyed his time there and completely at ease when I returned. Very much appreciated the updates throughout his long weekend stay.”
About: I have owned and taken care of dogs for my entire life. Currently, I own a small 9lb rescue, who is 11 yrs old. In the past, I have owned medium and large dogs as well, including beagles, labs, retrievers. I have professionally and personally walked and fed dogs for neighbors and friends, our furry ones are the very best!! I am a self-employed yoga instructor, with a flexible schedule. With this flexibility, I can accommodate most days and times, both weekdays and weekends. I am organized, punctual, reliable, trustworthy, and communicative. I really enjoy walking every day and it's always better with a dog! My dog, Bodhi, fetches sticks in our backyard and stills plays like a puppy, even at 11yrs old! I take him hiking regularly, as well as to the surrounding parks, which are numerous and all within walking distance from where I live.
Loving dog boarding sitters in your neighborhood
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Kennadi G.
“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.”
Alexandria P.
“We have a very anxious 12 year old black lab dog and going away is always a problem. We had a very pleasant experience with Alexandria. Her patience and personal attention was just what our dog needed. We recently went away for a week and Grace had a wonderful experience. I would highly recommend Alexandria's services.”
Jacqueline L.
“Jacqueline took such great care of my girl. She sent lots of updates and accommodated my hectic flight delays. Mavis will be visiting again!”
Stephanie P.Star Sitter
“Our Luna was well taken care off and very happy! Thank you Steph!”
Inge K.
“I absolutely love Inge!! She treated my boy like he was her own! Many pics and texts! Will not be using anybody else in the future! Thank you for taking such good care of my Henry boy!! ❤️❤️❤️”
Mikaela L.
“Good with communication and photos of my pup, kept him happy while I was away!”
Shari G.
“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!”
Andrea W.
“Andrea was wonderful with our dog Denali. We feel so fortunate to have connected with her for our trip to Lake George. She was flexible with us when we hit unavoidable travel delays and had to meet up later than expected and at a different location. She communicated with us by text when something worried her (very reassuring!) She sent us happy dog pictures. And Denali was so happy when we picked her up. We will definitely use her again when we’re back in the area!”
Jesse B.
“Jesse was great! He was able to accommodate our Bode on very short notice for the whole weekend. He sent daily updates with pictures and was very communicative. Thank you Jesse!”
Hannah D.
“Hannah was great! Great bog sitter and great gal! Very knowledgeable and sweet. Sent me multiple pics of my Finn when he stayed overnight for the first time.”
Lexy C.
“Lexy is an amazing girl! Truly a pet lover, who knows how to deal with them! My skittish 2 "Covid present" cats don't trust other people. It was their "out of the house" 1st experience.... And Lexy earned their trust...Thank you Lexy! I will definitely recommend you and your service!”
Lydia G.
“Our beagle (Sunny) had a great time with Lydia and her dog, Maxine. Lydia sent several pix and updates during the 3-day stay, and when we went to pick up our pup to go home, she was in no hurry to leave — she obviously enjoys being there. Lydia loves dogs and it shows. We’ve already booked two more stays this summer.”
Alissa V.
“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.”
Mollie M.
“Mollie was great with Cheddy! He loved staying with her and we'd leave him with her anytime.”
Kerrie B.
“Kerrie was so pleasant and accommodating for my two pups. They warmed up well with her pup and the three of them really had a great time together!!”
Sara S.
“Sara was very accommodating for our lil pup. She has a nice backyard and great windows (our buddy likes to”
Brittney R.Star Sitter
“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!!!”
Johanna D.
“Johanna was terrific with my dog. Very welcoming and accommodating. He enjoyed his time there and completely at ease when I returned. Very much appreciated the updates throughout his long weekend stay.”
Laura P.
“Laura is an amazing pet caregiver! I highly recommend her services, as she is responsible and passionate dog lover. Laura has taken care of my senior small dog many times. My pup has high anxiety and needs plenty of love. Laura consistently takes Bodhi on walks, plays fetch, and gives him plenty of love! She is reliable, trustworthy, and communicative in her time caring for Bodhi. You will be happy with the care that Laura provides you pet!”
Colleen D.
“Colleen took great care of our lab mix, Maisie, on two separate visits. She got tons of attention and cam home happy!”
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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
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?
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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.
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We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Chestertown is $50 per night, including service fees. Boarding your dog for one week typically costs $350. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chestertown dog boarding rates can be found as low as $32 to as high as $42 per night.
As of Aug 2025, 27 sitters provided dog boarding in Chestertown. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 96% of Chestertown dog boarding sitters respond in under an hour.
Dog boarding sitters with repeat customers have an average of 5 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters 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
There are 27 dog boarding sitters in Chestertown on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
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.
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