Dog Boarding Chester
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 33 pet parents in Chester have booked dog boarding
Chester, Find top rated dog boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Our dog sitting experience with Shuling was wonderful. Lucky, our 4-year old mini goldendoodle, and his 2-year old beagle cousin looked like they were having a great time running around outside then relaxing inside. Shuling sent us lots of pictures. We would definitely contact her again if we need dog sitting coverage the next time we are in Annapolis.”
“Michelle is reliable, kind and deeply cares for dogs, I will return anytime! Bailey came back home happy and even made some friends at her house. With daily picture updates and text message she kept us up to date with our puppy. He temporary became part of her family.”
“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!”
“If I could give 10 stars, I would. Katelyn is very kind and helpful, in addition to being understanding of HoneyBee's blindness and separation Anxiety. I appreciate all the pictures and videos of my pup while I was away, and especially all the attention given to my pup as well as flexibility of scheduling. Would highly recommend to anyone in the area.”
“Yukia was awesome! My dog left her house very happy. She took him on walks and he got to play with other dogs. She also worked with me and added an extra day when I realized I messed up the schedule. I highly recommend Yukia.”
“Kelly and Maurice were absolutely wonderful. They accepted my pup Khori on very short notice. Their home and neighborhood are beautiful and made for great walks and play time. Kelly made sure that I had more than enough pictures, and she is an excellent photographer! Truly thankful to have found them on Rover!”
“Janice and Stalio were great hosts to our dog Diego. When Diego needed daily medicine after we made the booking they were happy to assist. They were communicative and helpful. They treated our dog like he was their own.”
“We had another great experience with Luba and James! Biscuit came home relaxed and happy. It is clear that he is treated with kindness and love when he stays here. Our pets are our family, so it is a blessing to find someone you can trust to treat your fur baby like their own. We are forever grateful for your service!”
“I wish i could gate keep them, but they’re always great and i can tell how well my dog gets taken care of with them. She anyways has friends to play with as well. Highly recommended!”
“This was Tytus' first time away from us since his birth almost 5 years ago. Angela gave us a since of peace and comfort by providing us daily updates via text, photos, and videos. She and her daughter took great care of Tytus with giving him lots of love and hugs, which his very spoiled sweet spirit demands. I've already booked my next appointment and I would highly recommend her multiple services, which are flexible and reasonable. Thank you Angela for your exceptional service!”
“This is the second time that Diana has kept my little one and once again I was very happy with her level of communication and care when it came to him. When he is with her, I literally do not worry about him because she has demonstrated she is an awesome pet sitter. I will continue to use her in the future.”
“Erin and Casey were a dream come true for me! They were very accommodating and showed our Lilly lots of love. I was very worried about leaving my pup for three weeks but Erin put me at ease from the minute I met her. She sent videos and photos regularly and helped my very shy Lilly to be at ease. I hope to use them whenever we need a sitter and highly recommend them to others❤️❤️❤️”
“Dana is the perfect fit for our little nervous Annie. Dana respected my wishes and took extra time to make Annie comfortable. She even allowed our pup to sleep with her. I loved getting pictures and updates. We have been doing a few trial visits and now I have NO hesitation in using her for the week we go on vacation. Thank you Dana!”
“Hester is great. Very good communication. Follows up quickly. Keeps me in the loop during my dogs stay. And I usually get a tired and happy dog after the stay. Very happy I found Hester!”
“They took care of our 11 month old puppy for a short stay. The care they provided was truly exceptional. We plan to use them again for a longer stay later this spring. The were caring, professional and very communicative. We highly recommend Liz and Jeff.”
“Brigid took care of my senior girl, Chloe, for 4 nights. She was open to a last minute meet and greet. She accommodated Chloe’s senior needs, sent updates, and gave a nice verbal summary at how Chloe’s time went and included things she will miss about her. Chloe seemed content when I arrived, often going over to Brigid several times while we packed up all of her things into the car. Being a dog sitter myself, I found comfort in that, considering they were strangers just days before. I would recommend Brigid!”
“Jason and Tracy were wonderful. Our dog is a rescue and has some anxiety issues. They understood and were so patient with her. They also sent me pictures every day. I knew that she was completely safe and happy while we were away. Thanks to both of you!!”
The median cost per night for dog boarding in Chester is $50
Dog parents share their Rover experiences - Chester
Brigid took care of my senior girl, Chloe, for 4 nights. She was open to a last minute meet and greet. She accommodated Chloe’s senior needs, sent updates, and gave a nice verbal summary at how Chloe’s time went and included things she will miss about her. Chloe seemed content when I arrived, often going over to Brigid several times while we packed up all of her things into the car. Being a dog sitter myself, I found comfort in that, considering they were strangers just days before. I would recommend Brigid!
Lindsay is amazing. She took such great care of my dog this weekend. From the moment I met her, she put my mind at ease that Comet would be well taken care of. I got several updates throughout the weekend that confirmed just that. If you need a dog sitter in our area, I highly recommend her and will be using her again in the future when I go away.
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!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family
1. Search
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Popular requests for dog boarding - Chester
Select a filter and find qualifying sitters offering dog boarding.Sitters in Chester average 12 repeat dog boarding clients
FAQs for Boarding - Chester
Frequently asked questions about Rover
The average cost for Dog Boarding in Chester on Rover is $31.08 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Boarding. For more information on service fees, click here .
As of August 2026, there are 2,321 sitters on Rover offering Dog Boarding across Chester. Enter your ZIP code to see which available sitters are closest to your home.
Every sitter on Rover has their own rhythm and routine, but most will follow the flow that keeps your dog happiest. Sitters can give meals on your dog's regular schedule, provide a comfortable place for sleep, and plenty of one-on-one attention.
92% of Chester sitters also include daily walks in the neighborhood during dog boarding stays. You can also request photo and message updates throughout the stay so you can see which Chester landmarks or neighborhoods your dog is enjoying.
If your dog is a little shy, consider booking a one-night trial stay! This practice run can boost your and your dog’s confidence before your trip.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chester home-away-from-home, we recommend packing:
- Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
- Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
- Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Chester.
Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.
You and your Chester sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in MD ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
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