Dog Boarding in Chester, MD
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 70 pet parents in Chester have booked dog boarding
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Loving dog sitters in your neighborhood
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1. Michelle M.
“Michelle has been caring for our dog, Lucy, for years now... and we have been nothing but pleased with her loving care for Lucy, her great communication, and dependability. Lucy loves her vacations with Michelle, and we always feel 100% confident in the care we know she will receive. Definitely 5 stars in every area!”
2. Andy & Lydia M.
“First time using a sitter for my two dogs who are now seniors. Andy was responsive and met with us first in person so we felt comfortable. During out trip, he kept us up to date with what was happening and sent lots of pictures. We will use Andy in the future!”
3. Lindsay G.
“Lindsay is absolutely amazing! She treated our furr baby like her own. We are so grateful to have came across her. We will definitely be booking with her in the future. ??”
4. Jean L.
“Jean was awesome! She sent daily photos and messages updating us about our dog. Would not hesitate to use her again in the future, and will definitely be booking again! Thank you again Jean!”
5. Katelyn M.
“Katelyn is amazing and helped our family on short notice when we had to fly to another state for a funeral. She took amazing care of Gary and he was well-loved by her children and her husky, Balto. I highly recommend her!”
6. Sophie P.
“Very accommodating and her dogs were great playmates.”
7. Jenna C.
“She was awesome! Very communicative and very thoughtful! Really appreciated her asking times I was going to be dropping them off and picking them up!”
8. Amy D.
“I was so nervous boarding our two dogs with a Rover sitter vs a facility, but both Amy and her husband took SUCH good care of our babies. I had a family emergency and had to leave them for five days. They went on tons of walks, got ample amounts of snuggles, and I was updated with pictures every step of the way. I could focus on family knowing they were in excellent hands, and we will certainly be using them again!”
9. Ashley H.
“Ashley was an absolute lifesaver! She came to our rescue at the last minute, and took excellent care of my Rebel. Ashley sent pictures everyday, and Rebel came home a happy boy.”
10. Makhayla D.
“From the time I pulled up, my chihuahua was welcomed so cheerfully! Makhayla was wonderful, and stayed in communication with me the entire overnight stay. I loved the pics and video! My dog is my baby, and I do not just leave her with anyone. I will definitely be using Makhayla in the future if she will have Gracie.”
11. Kelly & Maurice G.
“This family gets an A plus for professionalism. I felt like I was really leaving my dog with a family member. They kept us up to date with all my dogs daily fun. I would book again in a heartbeat”
12. Ryan P.
“Rachel and Ryan are by far the best dog sitters we’ve had. They looked after Mac, our goldendoodle and I loved seeing him come home excited and very tired from a fun weekend with Rachel and Ryan. Definitely recommend them for your pet needs.”
13. Lisa B.
“Neyland really enjoyed her stay with Lisa! We were happy to get many updates and pictures throughout the stay! Thanks again for taking great care of our pup.”
14. Toby G.
“Second time for Kona staying with Toby. He and his family are awesome, attentive and great with our pup. Looking forward to booking with him again!”
15. Candice W.
“Can not find a better lover of dogs ! She took the best of care with our two dogs, one puppy and one an older dog. They each got so much love and attention, and I loved the pictures and videos while we were away :)”
16. Cait B.
About: I have been a dog mom for more than 9 years but have grown up with a house full of animals, so I feel my experience with animals goes far beyond a decade. I have crate trained multiple puppies, and litter box trained kittens and rabbits. I am now learning senior care for my own fur-baby, a Yorkie mix. I have experience with dogs of all sizes, from the smallest baby to the biggest, bestest pups. You can trust your pup will be in excellent hands. When boarding at my house, your pup will get lots of outdoor playtime. Or, for senior dogs or tiny babies who prefer to a cushy indoor life, snuggles would be on the schedule! Whatever the need is! I spend all my weekend time at home, so your pup would not be left unattended for any length of time. I have two dogs of my own, but there is plenty of space for new friends in my home. My 9-year-old pup, Daisy, is more cat than she is dog, and tends to seek out high places to avoid new fur friends. But my 1-year-old Australian shepherd, Dax, is always eager to play and greets. Dax is submissive, and will lay on his back to play no matter the size of your pup. Both of my doggies are also good with cats. I guarantee that stays with me are far more comfortable, safe and fun than any traditional boarder or kennel -- all of which means less stress for nervous pet parents! I am available almost every weekend. I have two dogs that I have built my schedule around. Working out of the home most week days means I spend all my weekend time at home. My hours are flexible and bend entirely at the will of what my pets need -- the same would be true for any fur-babies I am trusted to sit. My home offers a nice sized, mostly private yard. It is not fenced. Dogs with off-leash training have plenty of space to run without leaving the yard. Leashed play time is also not a problem. I am very active with my dogs, running alongside them to play outside or going for long walks on our quiet street. Pets are always 100% supervised when outside.
17. Ashley & Bob B.
“Ashley was wonderful with our 3 very energetic dogs! She was very laid back and sent daily updates and pictures. We felt great leaving our dogs with her and they were well cared for! Will definitely use her again!”
18. Mary L.
“They were absolutely amazing with Nellie. We couldn't of have had a better experience. Nellie enjoyed her time with them and they treated her very well. It was our first time leaving Nellie with anyone and the random updates on her with pictures and videos helped ease our minds during our time away. We would definitely recommend them to anyone who is looking for pet care/boarding.”
19. Alexis A.
“Alexis was amazing! This was our first experience with a Rover sitter and I was a little nervous, but Alexis was incredibe and communicated with us throughout our pups visit and sent a lot of great photos! She was so sweet and our pups really enjoyed their stay! I'd recommend her to any of our friends!”
20. Alina L.
“Alina was great and took care of Mishka as if she were her own. She sent lots of pictures and asked for my permission before taking my dog to a dog park. We will definitely be coming back.”
The median cost per night for dog boarding in Chester is $45
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1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
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Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
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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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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 2025, the median cost of dog boarding in Chester 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 Chester dog boarding rates can be found as low as $29 to as high as $46 per night.
As of Apr 2025, 705 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, 93% 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 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 705 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, 98% 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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