Dog Boarding Chestertown
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Over 7 pet parents in Chestertown have booked dog boarding
Chestertown, 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.
“This was my first time using Rover. So fortunate to have Michelle watch my sweet dog Pippi. Your dog will be in excellent care. Michelle was very responsive, sent cute pics and kept me posted each day. I highly recommend her for your pets. Thank you again Michelle!”
“Jeren did an amazing job with my dog! She was even flexible with my pick up time when my flight got delayed. Would definitely recommend if your dog likes other dogs and is very shy like mine”
“My lab Ruby had a wonderful time with Jacob and Megan. She was super excited that she would be able to play with other dogs and lounge on their deck. She was exhausted when she came home. I definitely recommend Jacob and Megan as dog sitters and would take Ruby back again!”
“Tarina is absolutely fantastic! My pup always comes home exhausted from a well spent time away playing with friends and getting lots of snuggles and love. Not only is she amazing with my baby but she’s incredibly flexible and understanding. Twice my husband and I have had to ask her for last minute changes to our booking and she was super kind and accommodating, seeing to our every need. Highly recommend Tarina to anyone in her area, she is the best!”
“Paris is excellent in every way! She really helps us out on short notices.She is caring with our big boy Deuce and sends us multiple photos & videos.Paris is incredibly nice and accommodating, and communicated with us frequently. We vacation often so Paris and the fam is Deuce second family lol .Thanks so much ❤️”
“Marliez was great with my Bentlee. She sent plenty of pics and videos. I’m always worried about him being around other dogs because he’s so young but she handled him so well. Def would recommend.”
“Gus had a great stay! He came home happy and healthy. I felt very comfortable with Jill and her family. Very very nice folks. Gus warmed up quickly. Jill kept me updated with pictures and messages. And they were very accommodating of my strange schedule. I wouldn't hesitate to use them again and I highly recommend them.”
“Our dog spent two nights with Rich, and he absolutely fell in love with him. When I came to pick him up, he was thrilled to see me but clearly reluctant to leave Rich's place. I’m confident that Rich took wonderful care of him and kept him entertained the entire time. Rich is kind, considerate, and genuinely the best sitter we’ve ever met.”
“Justin and Stephanie will absolutely be our new go- to pet sitters. The pictures updates they sent said more than a thousand words! Our pup was loved and exercised daily. They followed all instructions and kept us in the loop with everything. 100/10 amazing.”
“Veronica and her husband were exceptional. It was my first time booking with Rover and they exceeded my expectations. They looked after my 2 Pomeranians for a week, sent me the cutest pictures every day and I could see how comfy and laid back the poms were. They spoiled them with tv time and cuddles and even hand fed Theo, who can be picky to eat 🤣. I definitely recommend.”
“Benjamin is an excellent dog sitter! We could really tell he cared about our dog Chewy. He has a lovely home in a nice quiet neighborhood with plenty of outdoors space for our dogs. Chewy looked really happy during his stay and didn’t give us any attitude after his pickup.”
“Kendall and her family helped me in a bind and proved to be reliable, friendly and incredibly welcoming to my dog, Shoto. I’d highly recommend her for anyone who needs pet sitting, and I’d definitely book her again.”
“Steph couldn’t have been any more perfect for our dog, Remy! It was the first time we left a pet with a non-family member but I felt completely comfortable. Steph even has a doggie-sofa in her living area. I could tell from our first meet and greet that she was in tune with dog behavior. Her dogs are the sweetest hosts too! When we picked up Remy, I could just tell that she had a wonderful weekend. I really appreciate having a reliable, loving place to take Remy when needed.”
“Melissa was a perfect fit for our pup. Her two dogs are wonderful, and our dog had a great time. I’m not even sure she missed us!! Would definitely have Melissa watch our dog in the future.”
“Karen and her husband were the absolute best this was my first time boarding my dogs with anyone . But when I first met them on day 1 I was very comfortable that they were in the best of hands . She updated us and sent pics of the dogs I’m so happy with her care for the dogs for 4 days !!! Kudos to Karen and her husband.”
“Im always nervous to drop off Adonis with anyone because he is very unpredictable meaning nervous. But Lia was great to him. Leaving for my daughter nationals so many miles away and she was great! Definitely will book again.”
“My dog Luna seemed to have enjoyed her time at Linda’s home and playing with the other dogs. Linda was communicative and flexible.i appreciated the daily photos and sometimes even videos. I will be booking with her again.”
“Latoya was very kind and compassionate. She took great care of my dog and was very pleasant to meet with overall. Our dogs got along really well, she has a lovely home and even gifted my dog a little toy that she enjoyed during her stay!! I'd recommend Latoya to everybody and you can be sure that your dog will be loved and will be in great hands!”
The median cost per night for dog boarding in Chestertown is $50
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.
How to book dog boarding
1. Search
Browse profiles of sitters near you who offer dog boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog boarding - Chestertown
Select a filter and find qualifying sitters offering dog boarding.Sitters in Chestertown average 12 repeat dog boarding clients
FAQs for Dog Boarding - Chestertown
Frequently asked questions about Rover
The average cost of Dog Boarding in Chestertown is $44 per night as of November 2026. Most bookings cost between $37 and $62 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 1,474 sitters on Rover offering Dog Boarding across Chestertown. Enter your ZIP code to see which available sitters are closest to your home.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.
94% of sitters in Chestertown can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.
During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.
Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Chestertown 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 Chestertown.
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.
Yes, you can find sitters who have experience with handling special pet needs in Chestertown. On Rover:
- 90% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 94% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
You and your Chestertown 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.
Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.
Connect anywhere with the Rover app
