Dog Boarding in Chester, MD
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Chester dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“This was our first time with Lindsay, and we couldn't be happier! We'll definitely be repeat customers. She took great care of our boys, and we felt completely at ease leaving them in her hands. Our dogs absolutely loved the interactions with the other dogs and her children, and it was clear they felt right at home. Lindsay provided a safe, loving, and fun environment, and we’re so grateful for her care. Highly recommend!”
“Michelle was able to accommodate caring for Molly quite last minute when a family member fell through on care- I reached out around midnight one evening and the next morning I was able to drop Molly off. She regularly sent me pictures and updates of Molly and I felt reassured knowing Molly was in good hands and able to lie on comfy couches and even sleep in Michelle's bed, it seemed! Thank you Michelle, and I'll definitely reach out again.”
“Elaine was WONDERFUL! Lots of updates and photos. Juniper was excited to come home, but also seemed a smidge sad to leave Elaine, which is wonderful :) 1,000% plan to book with Elaine again.”
“This was our first experience with Rover and it was absolutely wonderful! We have an older dog and she is both blind and deaf and Katelyn took such good care of her. She welcomed her into her home and treated her as if she were her own. Her communication was great. We received pictures/videos/updates several times a day. We will definitely use Katelyn again and highly recommend her!”
“Carlie and her family could not have been more loving and attentive. Arlo probably wanted to live there forever. She was incredibly kind about a mistake I made on pick up time.”
“Jessica & her family took such great care of Walter while we where out of town for Christmas. She even went out of her way to buy him presents for Christmas morning! She sent multiple pictures every time Walter played with the kids, went on walks, and at meal times. She was extremely flexible, she even extended Walters stay for another day so we could drive home safely. Thank you for everything Jessica!”
“As a first time user of Rover and first time search for a cat sitter, Elena definitely set the standard. From the first contact, Elena was incredibly responsive, very kind, and extremely welcoming of my babies. Elena and her children took such good care of my babies, as they allowed them space to adjust while being open to their affection as they warmed up. I had peace of mind that my babies were in good hands as she invited them into her home with open arms. When I picked Pocket and Rocket up, they were so soft from freshly brushed hair and calmer to get back into the car. I would absolutely recommend Elena to take care of your cats, as they will get plenty of cuddles, play time, and freedom to explore their new space. Thank you, Elena and kids!!”
“Candice was wonderful with our little gal pal, a 7 yo Shiba Inu female. She actively updated us the entire time, and we felt super confident knowing Candice was caring for her. Thanks Candice! We can’t wait to use her overnight services again. I highly recommend her! She’s really a superstar dog sitter & very nice, kind person :)”
“Celena was great with our 7 month old pup, Ace! He had so much fun at her house. She sent us many pictures and videos several times a day and for all of them he was playing and have the best time with her dog and her family. We would definitely book Celena again!”
“Kimberly and her family took great care of our dog Winnie while we were away over the holiday break! She sent pictures every day of her enjoying time inside and outside on her walks about the neighborhood. We are so grateful that we found them and will definitely use her in the future! Thank you, Kimberly!”
“Our pup had a wonderful stay! Amy made him feel right and home (I’m pretty sure he missed them when he had to come home with us lol). I’d definitely recommend Amy for any pet sitting!”
“Danielle took great care of my dog while I was away! Sadie was happy and well cared for when I picked her up. Danielle was responsive and sent me regular updates so I knew Sadie was happy and safe. I highly recommend Danielle!!”
“Kelly and Maurice are first rate and the best. They took care of our Mr . Biggie and did a fabulous job. They have a great system of walking and caring for the dogs. We got lots of pictures and videos. Do not hesitate in using Kelly and Maurice. We definitely will be using them again.”
“Dusty loved staying with Shelby! She took such good care of him, taking lots of walks, big yard to play, and loved making a new friend with Ellie!! Her home is lovely and very dog friendly. Will definitely rebook with Shelby!”
“Ducati loved his stay with Pam so much that when we went to pick him up, he came to the door and gave us a “oh, hey, you’re back” look vs the “OMG, I’m so excited to see you” look that we were expecting. Pam sent regular updates during Ducati’s stay so our guilt of leaving him behind was lessened. We would definitely recommend Pam!”
“Jillian was the best! She treated our pet just as her own, and continuously provided us with heartwarming updates. We will definitely be using her in the future.”
“Eli was awesome! My dog is somewhat shy but she took to Eli right away. Eli picked my furbaby up and once he was back to his home he sent a picture of my pooch and where she had her kennel setup. Skittles was able sit and stare out the windows, which she loves to do. I received plenty of pictures to put me at ease. Eli also had a camera setup so I could see my dog if I wanted!!! I’m super happy with Eli as he was on time for pickup and drop off and overall is a very nice person! I will definitely board my dog with Eli again!!!!”
“Sara was wonderful! She kept me updated on how my dog was doing every day and sent along a picture. My dog had a terrific time with Sara’s household and family. I highly recommend her services!”
Over 88 pet parents in Chester have booked dog boarding
Chester dog parents share their Rover experiences
Luna had such a great time with Lindsay and her family. Definitely exhausted after a whole week getting cuddled and loved on by the kids. Would definitely recommend her to anyone looking for someone loving and fun. She also sent plenty of updates/pictures which definitely made my day.
We couldn’t have asked for a better person to take care of our dog, Murphy, during our wedding weekend. Murphy was our ring bearer and Melanie brought him to and from the venue for us. She sent us pictures and videos of him enjoying play time and went above and beyond to make sure Murphy was ready for his ring bearer duties. When we picked him up, he could not have been a happier puppy! This was the first time he ever spent away from family and Melanie was the perfect option. Thank you for making our baby feel right at home. I know he loved his time with you!
Popular requests near you
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The median cost per night for dog boarding in Chester is $49
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.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Chester average 11 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Apr 2026, the median cost of dog boarding in Chester is $49 per night, including service fees. Boarding your dog for one week typically costs $343. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Chester dog boarding rates can be found as low as $31 to as high as $61 per night.
As of Apr 2026, 751 sitters provided dog boarding in Chester. 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, 91% of Chester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Chester have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 11 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 Chester.
Rover makes it easy to find Chester 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 751 dog boarding sitters in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 98% of sitters offer daily exercise, 97% offer medication administration, and 85% 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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