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.
“I highly recomend Michele. She was always quick to respnd. She sent many pictures every day so I could see that my boy was enjoying his stay. She has a beautiful backyard that my boy enjoyed running around. The best part of my boys stay at Michele's house is that he made a bunch of new playmates cand canine fcompanions.”
“My frenchie had the BEST time with Lindsay and her puppy!!!! Lindsay sent me pics daily, and whenever I asked for one. My baby literally had so much fun at her house, I think he sulked for a few days after ? Lindsay will be our go to for boarding in the future.”
“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!!”
“We’re so grateful for the great care Katelyn took of Hank! And appreciate all the communication - receiving pictures, videos, and updates on how well it was going. It was our first time entrusting Hank to a dog sitter so I was nervous but it went perfectly!”
“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.”
“Kelly and Maurice are more than awesome. I know that Zuri will be well care for and loved when I have to leave town. They treat her like family. They send videos and pics for reassurance that things are going well. I appreciate their professionalism and true dedication. They implemented some changes for their customers based on what they observed from my experience with them. That is more than customer service, that’s customer satisfaction. They are an A1 service all the way around.”
“Shuling always makes me feel so much better about leaving my needy dog, manny, when I go for vacation. He always comes back with a huge smile and has so much fun playing with her dog, Bear. Thank you so much, Shuling!!”
“Our first visit was so smooth. My dog seemed immediately comfortable with Katie. She sent pictures through the weekend and was flexible with pickup times. We are already looking to rebook her for next month. Thanks Katie?”
“Jasmine took wonderful care of our dog Hank over a long weekend for us. Hank came home happy and healthy and had a fun time with Jasmine! Jasmine is communicative, flexible, responsive, and a real animal lover. Your pets are in good hands here with her!”
“Marliez took amazing care of Ozzie. He walked with her Husky Wolf several times a day receiving plenty of needed exercise. Oz was received as part of her family. I could tell from the photos he was really enjoying his stay and looking forward to go back. Marliez paid attention to the nuance of my dog's antics to adjust to him. She is a wonderful sitter”
“Jillian and her family/animals were amazing! Happy loved playing with other dogs. She was very friendly and loving with our dog. We will definitely be back 😁”
“This was our first time boarding Black with a sitter, and Crystal provided a great experience for Black and for us. When we dropped him off, he didn’t even look back as she ushered him inside which told us he was comfortable with Crystal from the very beginning. When we picked Black up, he was excited to see us AND sad for his weekend with Crystal to come to an end. Black had a couple of behavioral issues during his stay and Crystal was very attentive taking great care of his needs and keeping us updated with great photos and detailed reports. We highly recommend Crystal.”
“Willow had the best time with Shelby and her pup Ellie. Instant best friends. I felt totally confident that our 4 year old dog was having a vacation all her own the entire weekend. Lots of time outside, on walks, playing, and snuggling. 100% would recommend and feeling so happy we have a go-to sitter :) thank you guys!”
“Celena was great! She sent tons pictures of our boy having a great time and she had plenty of updates. We also appreciate that she worked with us on our drop-off and pick-up times! We will definitely work with her again!”
“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!!!!”
Over 88 pet parents in Chester have booked dog boarding
Chester dog parents share their Rover experiences
Lindsay really treated Ruby like her own. Her family is fantastic and they took extraordinary care of my golden while I was out of town. She was receptive to my dogs needs, updated me regularly, loved on my girl and was overall the best pick I could imagine for boarding. I will use her services again in the future. Thank you so much!!
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
Select a filter and find qualifying Chester sitters!How Rover works
1. Search
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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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The median cost per night for dog boarding in Chester is $50
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 12 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, the median cost of dog boarding in Chester 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 Chester dog boarding rates can be found as low as $31 to as high as $61 per night.
As of Jun 2026, 710 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 17 years of experience. Dog boarding sitters with repeat customers have an average of 12 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 710 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 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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