Dog Walking Chestertown
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Chestertown, Find top rated dog walking
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: As a long-time volunteer with a local dog rescue, I have cared for, helped train and loved on dogs of all sizes, ages, needs and personalities! Being commited to these pups has taught me more about dogs and life than ever imaginable, and I cherish every connection made with both the animals and people along the way. Family and friends who have trusted me with caring for their animals can guarantee your pets will be spoiled just like my pittie girl, Addy! My schedule tends to be sporadic, but is quite open through the winter season! I understand the need for scheduling around your plans and the needs of your pets. I prefer to keep dogs on leash at all times while outside unless otherwise specified, and a safe enclosed environment is present. I'm happy to spend time in your pet's favorite places with them! I will follow any instructions given by owners to guarantee the safety and comfort of you and your animals. I currently have a hybrid work schedule in the Saratoga area, but reside in Chestertown and make trips to my hometown, Oswego, and to see friends near Buffalo. With enough notice, I can usually be wherever I'm needed! I always want what is best for the animals, and will do whatever I can to make sure owners are happy and comfortable with the care being provided!
About: I grew up surrounding myself with animals, since I was seven I spent all of my time at our horse farm and I learned to take care of animals big and small. This grew into my life passion which is animals. I studied animal science at UMASS Amherst and UNLV and also have worked at various animal clinics with different roles as a kennel technician and a veterinarian assistant learning so many skills along the way. Yet my favorite thing I have done so far is taking care of animals while their families enjoy a vacation away! It takes the stress out of going to the kennel, the animals get to show me the ropes and the owners always have daily updates and pictures! I currently work part time at a local restaurant, and my shifts are typically mid afternoon to the evening, but I am flexible upon request!! I am more comfortable coming to a clients home. I own two cats and unfortunately do not have a fenced in yard. But there are parks around my neighborhood that are great for walks.
About: Life can be hectic, and we always want what's best for our animals, including a reliable sitter! I have been taking care of dogs most of my adult life, from my own rescue pup to family and friend drop-ins visits with their loveable four-leggeds. I specialize in walks and drop-in visits. I would love to meet your happy pup! I'm currently working seasonally, so I'll have plenty of time to play with your pup(s)! I'm available Tues-Fri 11am-6pm, and Sat-Mon during these same hours on occasion. If your pup is in need of a drop-in visit, I will make sure to give them some active play time (weather inside or out), use the potty, and feed if he/she is in need of some kibble. If your pup is in need of some outdoor walk time, just show me the leash and we'll head right out the door with poop bags ready - just in case :)
The median cost per walk for dog walking in Chestertown is $22
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 walking
1. Search
Browse profiles of walkers near you who offer dog walking.
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 walking - Chestertown
Select a filter and find qualifying sitters offering dog walking.Sitters in Chestertown average 3 repeat dog walking clients
FAQs for Dog Walking - Chestertown
Frequently asked questions about Rover
As of November 2026, there are 195 sitters on Rover offering Dog Walking across Chestertown. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in Chestertown. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Chestertown after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the walk begins.
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 walker 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.
Yes, you can find walkers who have experience with handling special pet needs in Chestertown. On Rover:
- 94% of walkers can help with special care needs
- 94% can help with giving oral medications or injections
- 97% 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.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.
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