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
“Ivy and I were very pleased with the care Paris provided. Updates and photos were perfect. We will definitely be using her again in the future. If she is available.”
“Mimi had a blast. Michelle was wonderful. She sent daily updates and pictures of Mimi everyday. Mimi loved playing with her new dog friends. She was so happy and we are so excited we found Michelle. I know Mimi was well taken care of. Thank you so much”
“Fulton truly enjoyed his stay there for the week. The pictures received showed how much fun he had in a new pack. I’ll definitely use Rachel and Ryan in the future.”
“Theresa was great! She seemed very knowledgeable about dogs and provided updates throughout the stay. She also gave some advice for addressing my dog's separation anxiety which was helpful.”
“Gisel did an awesome job accommodating my last minute emergency need to board my dog for a few days. She was patient, responsive and flexible given this was the first time I ever used this service. I would definitely use her again.”
“Jean & Romeo are great sitters for Bear & Benny! For the first time we enjoyed our vacation with little anxiety about our boys being cared for! Until next time…”
“Briyonna provided excellent service to my dog. She updated me daily regarding my dog’s status and also sent me pictures. Her efforts reassured me that my dog was being treated well. She was courteous and polite. I definitely plan to use her services again in the near future.”
“Outstanding with the care that was given to our dogs Tempest and Peanut. I received updates everyday with pictures! They certainly looked happy and made themselves right at home even jumping on Janice’s lap ! We will definitely use them again whenever we decide to go away for even a weekend ! Thank you for all the love and care you gave Tempest and Peanut !♥️♥️”
“He did amazing with Thor .He took him on amazing potty breaks and play time .He supported him well as he was recovering from being neutered and needed medicine and a blocking pillow.He sent updates daily with pictures.Definitely recommend.”
“Rich was amazing and took great care of my Shiba Inu! He has a fenced in yard, my boy got lots of time outside, Rich was very communicative and sent pictures, I picked up a very happy dog! Overall 1000/10 would recommend and will be in touch with Rich again in the future! I appreciate you Rich!”
“We have not met Brianna but her husband Isaiah was very nice. They were very accommodating with pick up of our dog when our flight got delayed. They sent us few pictures of tanner being walked, he looked happy!”
“These folks are amazing. They were born to board pets - my boy Marvin had the best time! You will not regret leaving your precious pooch with them!”
“Katharine was amazing with our pup Mac! We could tell by all of her updates and pictures that he was having fun and being taken care of. We will definitely be trusting her with our dog again. 😊”
“We loved having Gina watch our dog, Camden. She sent lots of pictures and videos which made us feel so comfortable. He’s been sleeping ever since we picked him up so I know he had a great time! Would definitely rebook with her and highly recommend.”
“Andy boarded our two boys for a night and was very responsive, keeping us updated with pictures, and playing with them. Our dogs got along great with his dog Luna. When our dogs had behavioral problems Andy was honest and understanding about it. I trusted him completely to take good care of them. They seemed relaxed and happy to have been there.”
“Rachel and her partner took great care of Loop and were super communicative. He was tired and happy heading home from their place. Thank you to you both - I will definitely book again!”
“This was first time using the service and also first time leaving my Callie overnight. We were super nervous and had no one to help us with her so thankful to have found this service. Erin was very nice and even sent me pictures of my girl 😊 Would love to book with her again. Thank you for taking good care of my baby 😊”
“Molly was an amazing sitter! Vienna is elderly with multiple medical problems, and Molly couldn’t have been more patient, understanding, and attentive regarding her needs. I felt so relaxed having her with Molly for her overnight stay and Vienna was so happy and comfortable with her stay. Thank you Molly!”
“Such a great experience. We had 3 dogs stay with them. Our dogs were treated great and with love. We definitely recommend using Kari & Joseph”
“Ceil took care of my dog for a few overnights and I could not be more happy with the care he gave. From the time I dropped him over I knew right away my dog was in good hands. He kept me updated with pictures and videos which was very warming. If there were 10 stars I woukd of gave all 10”
Loving dog sitters in your neighborhood
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1. Paris V S.
“Ivy and I were very pleased with the care Paris provided. Updates and photos were perfect. We will definitely be using her again in the future. If she is available.”
2. Michelle M.
“Mimi had a blast. Michelle was wonderful. She sent daily updates and pictures of Mimi everyday. Mimi loved playing with her new dog friends. She was so happy and we are so excited we found Michelle. I know Mimi was well taken care of. Thank you so much”
3. Ryan P.
“Fulton truly enjoyed his stay there for the week. The pictures received showed how much fun he had in a new pack. I’ll definitely use Rachel and Ryan in the future.”
4. Theresa C.
“Theresa was great! She seemed very knowledgeable about dogs and provided updates throughout the stay. She also gave some advice for addressing my dog's separation anxiety which was helpful.”
5. Gisel D.
“Gisel did an awesome job accommodating my last minute emergency need to board my dog for a few days. She was patient, responsive and flexible given this was the first time I ever used this service. I would definitely use her again.”
6. Jean L.
“Jean & Romeo are great sitters for Bear & Benny! For the first time we enjoyed our vacation with little anxiety about our boys being cared for! Until next time…”
7. Briyonna E.
“Briyonna provided excellent service to my dog. She updated me daily regarding my dog’s status and also sent me pictures. Her efforts reassured me that my dog was being treated well. She was courteous and polite. I definitely plan to use her services again in the near future.”
8. Janice & Charles B.
“Outstanding with the care that was given to our dogs Tempest and Peanut. I received updates everyday with pictures! They certainly looked happy and made themselves right at home even jumping on Janice’s lap ! We will definitely use them again whenever we decide to go away for even a weekend ! Thank you for all the love and care you gave Tempest and Peanut !♥️♥️”
9. Patrick & Bahiya A.
“He did amazing with Thor .He took him on amazing potty breaks and play time .He supported him well as he was recovering from being neutered and needed medicine and a blocking pillow.He sent updates daily with pictures.Definitely recommend.”
10. Rich B.
“Rich was amazing and took great care of my Shiba Inu! He has a fenced in yard, my boy got lots of time outside, Rich was very communicative and sent pictures, I picked up a very happy dog! Overall 1000/10 would recommend and will be in touch with Rich again in the future! I appreciate you Rich!”
11. Briana & Isaiah S.
“We have not met Brianna but her husband Isaiah was very nice. They were very accommodating with pick up of our dog when our flight got delayed. They sent us few pictures of tanner being walked, he looked happy!”
12. Tarina L.
“These folks are amazing. They were born to board pets - my boy Marvin had the best time! You will not regret leaving your precious pooch with them!”
13. Katharine D.
“Katharine was amazing with our pup Mac! We could tell by all of her updates and pictures that he was having fun and being taken care of. We will definitely be trusting her with our dog again. 😊”
14. Gina M.
“We loved having Gina watch our dog, Camden. She sent lots of pictures and videos which made us feel so comfortable. He’s been sleeping ever since we picked him up so I know he had a great time! Would definitely rebook with her and highly recommend.”
15. Andy & Lydia M.
“Andy boarded our two boys for a night and was very responsive, keeping us updated with pictures, and playing with them. Our dogs got along great with his dog Luna. When our dogs had behavioral problems Andy was honest and understanding about it. I trusted him completely to take good care of them. They seemed relaxed and happy to have been there.”
16. Rachel O.
“Rachel and her partner took great care of Loop and were super communicative. He was tired and happy heading home from their place. Thank you to you both - I will definitely book again!”
17. Erin I.
“This was first time using the service and also first time leaving my Callie overnight. We were super nervous and had no one to help us with her so thankful to have found this service. Erin was very nice and even sent me pictures of my girl 😊 Would love to book with her again. Thank you for taking good care of my baby 😊”
18. Molly Q.
“Molly was an amazing sitter! Vienna is elderly with multiple medical problems, and Molly couldn’t have been more patient, understanding, and attentive regarding her needs. I felt so relaxed having her with Molly for her overnight stay and Vienna was so happy and comfortable with her stay. Thank you Molly!”
19. Kari & Jospeh M.
“Such a great experience. We had 3 dogs stay with them. Our dogs were treated great and with love. We definitely recommend using Kari & Joseph”
20. Cecil J.
“Ceil took care of my dog for a few overnights and I could not be more happy with the care he gave. From the time I dropped him over I knew right away my dog was in good hands. He kept me updated with pictures and videos which was very warming. If there were 10 stars I woukd of gave all 10”
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1. Search
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2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
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Why Choose Rover?
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Reservation protection
It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
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Dog Boarding FAQs
Frequently asked questions about Rover
As of Apr 2025, the median cost of dog boarding in Chestertown is $45 per night, including service fees. Boarding your dog for one week typically costs $315. 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 $25 to as high as $49 per night.
As of Apr 2025, 228 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, 94% of Chestertown dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chestertown have an average of 18 years of experience. Dog boarding sitters with repeat customers have an average of 14 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 228 dog boarding sitters in Chestertown on Rover, so you’re sure to find the perfect match for your dog! In Chestertown, 97% of sitters offer daily exercise, 100% offer medication administration, and 87% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care 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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