Dog Boarding in Chestertown

Find a loving dog sitter to watch your dog overnight at your sitter's home.

Confirmed availabilityEaster weekend
Tanya L.
1.
Your pet will be treated with careEdgewood, MD, 21040
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ms. Tanya L. Our dog sitter was excellent she took great care of my baby (baker). And she said that he was really good. I would use her again and definitely rec… (more)

from
$29
per night
Confirmed availabilityEaster weekend
Charell M.
My love for dogs grows daily.North East, MD, 21901
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Charell has been taking care of my little puppies a couple times, she is really friendly it seems that she love dogs and they love her too I get a hard time eve… (more)

from
$30
per night
Jeren C.
3.
Stay at home mom and animal loverCentreville, MD, 21617
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jeren has such a big heart for animals of all kinds! She was so kind to us and to our dog. We will definitely request her services again. (more)

from
$30
per night
Kelly L.
4.
Your dog gets its own vacation!Baltimore, MD, 21220
Dog Boarding

Can’t say enough about Kelly and the love and attention her entire family gives to our four legged child. We have 100% confidence in the care that Buster rece… (more)

from
$32
per night
Calendar Recently Updated
Pamela D.
5.
We have a HUGE ❤ for animals!!!Abingdon, MD, 21009
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Pamela was so wonderful with our Bella! Tons of pics and texts to assure us she was doing just fine. This was our first time leaving her somewhere other then ou… (more)

from
$40
per night
Confirmed availabilityEaster weekend
Beautiful back yard for your dogs!Annapolis, MD, 21409
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Michelle was absolutely wonderful! She was super easy to work with in advance of the booking and sent us daily, detailed updates with photos that made us feel l… (more)

from
$30
per night
7.
Dog lover extraordinaire!Belcamp, MD, 21017
Dog Boarding

I am so glad that I was referred to rover.com by a friend. like most pet parents I was a little reluctant to leave my girls with someone I didn't "know". we m… (more)

from
$33
per night
8.
I’ll love your pet like family!Rock Hall, MD, 21661
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Karly stayed at our house and took care of our dog and cat during a couple out of town trips my wife and I took in November 2018. She was responsible and commu… (more)

from
$25
per night
Calendar Recently Updated
Flexible Loving Pet CareArnold, MD, 21012
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Oreo had the best experience ever staying with Mikayla!!! The entire family loved and cared for Oreo just like he was their own dog. It was amazing! The picture… (more)

from
$35
per night
Calendar Recently Updated
10.
Amy 
Verified Background Check
Vet tech will love your baby!Kingsville, MD, 21087
Dog Boarding

Amy was absolutely wonderful and took such great care of our dog! She sent pictures every day of him and so I didn't worry at all and was able to enjoy vacatio… (more)

from
$37
per night
Confirmed availabilityEaster weekend
Oodles Of Poodles Doggy Sleep OverEdgewood, MD, 21040
Dog Boarding, Doggy Day Care

Great Job once again! Convenient and flexible drop off and pickup coupled with consistent communication and pics throughout the stay. I am a customer as long as… (more)

from
$30
per night
12.
Joy 
Verified Background Check
Can't imagine my life without a dogKennedyville, MD, 21645
Dog Boarding, Drop-In Visits, Dog Walking

About: I love dogs very much . Had them all of my life. I have 2 labs which are very spoiled. I would take very good care of your pet like it was my own. I … (more)

from
$25
per night
Calendar Recently Updated
Reliable & Responsible, Dog Lovers!Stevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jason and Tracy were AMAZING. They took wonderful care of our dog, Sunny. We left Sunny with them for a full week and I couldn’t be happier. Jason was very comm… (more)

from
$28
per night
Calendar Recently Updated
14.
Pam 
Verified Background Check
A Home Away from HomeBaltimore, MD, 21220
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: My husband and I love animals. Our home definitely has a pet friendly atmosphere! I am a recently retired teacher and am excited to be home full ti… (more)

from
$45
per night
Calendar Recently Updated
15.
A lass who loves animals!Annapolis, MD, 21409
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kathryn was wonderful and flexible with our crazy vacation schedule changes. She sent us updates every day and took great care of our Oliver while we were away.… (more)

from
$28
per night
Confirmed availabilityEaster weekend
16.
Stress-free environment🐶🐈Pasadena, MD, 21122
Dog Boarding, Doggy Day Care

Beni was so amazing! It was a last minute booking for my puppies. She sent me multiple photos throughout the day and put them at ease. Will definitely book ag… (more)

from
$32
per night
Calendar Recently Updated
17.
Reliable, mature, petcare providerHartly, DE, 19953
Dog Boarding, Doggy Day Care

Terri was amazing to my giant babies. She took care of them as if they were her own and sent me daily pics and updates. She has a great setup with a big yard an… (more)

from
$30
per night
18.
The Stay At Home Dog MomMiddle River, MD, 21220
Dog Boarding, Doggy Day Care

Katie did a wonderful job taking care of our 7 month old pup while we were away for the weekend! She sent updates/pictures on how he was doing and was quick to… (more)

from
$37
per night
Calendar Recently Updated
19.
A+ Home w Active Dog & Fenced InGrasonville, MD, 21638
Dog Boarding

Tommy has been a wonderful dog owner to his pal Tucker for the last 6 years. Tucker is sociable, well cared for, and much of that is owed to Tommy’s training an… (more)

from
$35
per night
Home Full Time + Fenced YardArnold, MD, 21012
Dog Boarding, Doggy Day Care

Luba and James were wonderful dog sitters! Our large dog stayed with them for a week and they took great care of her. She had some medical issues at the time a… (more)

from
$35
per night

Check out the Dog Boarding in your neighborhood:

    Rover also offers Dog Boarding in:


    Rover offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Chestertown, MD dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Chestertown, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

    If you need to book a great dog sitter on the go, you'll love the Rover dog boarding app. You can browse hundreds of pre-reviewed, trusted dog sitter in minutes from your phone, and rebook your favorite sitter with just a few taps. You'll get photo updates from your dog sitter which can be shared via the Rover dog boarding app in real time, and the app's cashless payment feature allows you to pay your dog sitter easily and securely, without worrying about cash, checks or tips.

    The price of dog boarding in Chestertown, MD might not be as much as you thought. Whatever your price range, you'll find a dog sitter on Rover for almost any budget. Interested in finding out what the typical Rover dog sitter expects as a dog boarding fee? Visit our average dog boarding rates report to see the general fees before checking out an individual dog sitter's hourly rates.

    Interested in what it's like on the other side? Do you think you have what it takes to become a dog sitter for Rover? We're always looking for people with a passion for pooches to join our dog boarding roster. If you've been thinking about starting up your own dog boarding business, or even if you've been doing it on your own for a while, you'll want to check out our easy application process and consider joining the hundreds of awesome dog lovers who use the Rover dog boarding platform. When you become a Rover dog sitter, you get access to great support, including premium pet insurance and immediate, cashless payment (no more worrying about whether you'll get paid on time). Why not apply today?

    In short, when you book Chestertown dog boarding on Rover, your dog gets the loving care they deserve, and you get to relax, knowing that your pet is in good hands.

    Reviews from our dog sitters in Chestertown

    Thank you so much for taking my fur babies for a walk and treating them really good!

    Tina is awesome. Mimi had a great time and can't wait for her next walk with Tina.

    Would definitely book with Briana for house visits and walks for my two dogs again.