Dog Boarding in Chester, MD

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Calendar Recently Updated
Michelle M.
Beautiful back yard for your dogs!Annapolis, MD, 21409
Dog Boarding, Drop-In Visits

Michelle was very responsive for a last minute booking. She sends an end of the day summary with photos and comes outside to meet you right when you arrive! My … (more)

from
$35
per night
Confirmed availability: Labor Day
Brooke F.
2.
Pet Nanny by trade!Grasonville, MD, 21638
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking
1 repeat client
10 years of experience

About: I have been walking/sitting all sized dogs for 10+ years simply because dogs make me happier than anything else! I consider myself affordable so you … (more)

from
$33
per night
Elaine Y.
3.
Eastport Doggie B&B!Annapolis, MD, 21403
Dog Boarding, Drop-In Visits

Elaine took good care of my pets. She made sure my little Jessie couldn’t sneak under the fence. I will keep her in mind for my future vacations. (more)

from
$35
per night
Confirmed availability: Labor Day
Deborah M.
Playful human wants to watch petsStevensville, MD, 21666
Dog Boarding, House Sitting, Doggy Day Care

Deborah took wonderful care of our pup. We would recommend her to any pet owner and will plan to use her services again! (more)

from
$31
per night
Calendar Recently Updated
Kristen K.
Let us care for your dog!Annapolis, MD, 21403
Dog Boarding, Doggy Day Care

Kristen and Lucas were wonderful hosts for Tigger! We appreciated receiving photos and updates during his stay. Tigger got plenty of outdoor time in their fen… (more)

from
$45
per night
Calendar Recently Updated
6.
Big or Small. Love them all!Chester, MD, 21619
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
20 years of experience

About: I have been around dogs since the day I was born. I currently have a female black lab but have been around a variety of dogs through out my life. My … (more)

from
$35
per night
Calendar Recently Updated
7.
All pups and kitties welcome!!Stevensville, MD, 21666
Dog Boarding, Dog Walking

They took the best care of my Luna girl, she was so happy with them, they took her to the Beach, got her a treat from Starbucks, We received pictures and text m… (more)

from
$25
per night
Confirmed availability: Labor Day
The Dog Sitter For YouAnnapolis, MD, 21401
Dog Boarding, Doggy Day Care

I am delighted with the way Makhayla watched over my pup. She was kind and kept me updated the whole time. This was my first time leaving him, and she made me f… (more)

from
$35
per night
Calendar Recently Updated
9.
May 
Verified Enhanced Background Check
Responsible, dog lover!Annapolis, MD, 21409
Dog Boarding, Doggy Day Care

May did an amazing job caring for our fur babies while we were out of town! She sent daily photos and check ins to let us know how our pups were doing, and trul… (more)

from
$60
per night
“ Play, eat, nap, repeat!”Annapolis, MD, 21409
Dog Boarding, Doggy Day Care

Carolina gets an A+ in every category! She took great care of our pup, Lucy, sent us daily photos and updates, and was a great communicator. She's so kind, and … (more)

from
$40
per night
Confirmed availability: Labor Day
11.
Caring pet sitterAnnapolis, MD, 21403
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Laura was excellent! Kept my mind and heart at ease on my first experience using Rover. We will definitely ask her to watch our pup again. In addition to keep… (more)

from
$45
per night
Calendar Recently Updated
12.
Pet Care Operations Manager 15yrsArnold, MD, 21012
Dog Boarding, Doggy Day Care, Dog Walking

Natalie was fantastic. She's clearly someone who has a lot of experience working with dogs as she knew all of the right questions to ask and considered everythi… (more)

from
$60
per night
13.
Canine's Cozy CottageArnold, MD, 21012
Dog Boarding

Our first experience with Rover and we were able to do that for 2 nights for a short trip. We did a preliminary visit to talk to Sydney & Mike to see how thin… (more)

from
$50
per night
Calendar Recently Updated
14.
I enjoy the company of dogsArnold, MD, 21012
Dog Boarding, Dog Walking

Lauren was great! She was very responsive and our dog seemed to have a great time. We would definitely recommend her. (more)

from
$31
per night
Confirmed availability: Labor Day
15.
Puppy PawsitivityEdgewater, MD, 21037
Dog Boarding, Drop-In Visits, Dog Walking

My baby Banner is 75lbs of puppy energy. Chelsey has watched him numerous times. She treats him as if he were hers, and she has two VERY well cared for fur babi… (more)

from
$40
per night
Confirmed availability: Labor Day
16.
Home Away from HomeAnnapolis, MD, 21403
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

This was the first time we’d ever left our dog for the weekend. Obviously we were very concerned. Vanessa exceeded all of our expectations! We highly recommend … (more)

from
$47
per night
Calendar Recently Updated
17.
Experienced pet sitter with loveStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

I have known Emmy for a while now, and never once would I doubt leaving my dog in her care. She has a heart of gold when it comes to animals, especially dogs, a… (more)

from
$50
per night
Confirmed availability: Labor Day
18.
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
Calendar Recently Updated
19.
Professional pet lover/belly rubberAnnapolis, MD, 21401
Dog Boarding, Drop-In Visits, Doggy Day Care

Alexa did a wonderful job of looking after Luna. She would send us lots of pics so we were assured that our four-legged family member was on good hands. She res… (more)

from
$36
per night
Confirmed availability: Labor Day
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
$45
per night

Never beg a friend to watch your dog again, and no more dog kennels. With Rover, you can find your perfect Chester dog sitter in seconds. When you book dog boarding on Rover, your dog will enjoy a loving, relaxing stay in your dog sitter's home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers pet boarding for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care, right in their sitter's home. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach dog sitters in Chester, MD who can provide the care your dog needs, when they need it.

You'll also be able to relax when it comes to price, because the cost of dog boarding in Chester, MD is surprisingly reasonable. No matter your budget or lifestyle, there's a dog sitter on Rover to match your wallet. Wondering how much most people pay for Rover dog boarding services? The average dog boarding rates will give you a good sense of what to expect before checking out the individual dog sitters' hourly rates.

Looking for an on-demand solution to your dog boarding needs when you're short on time? Then you'll love the Rover dog boarding app. The Rover app features hundreds of highly-rated, trustworthy dog sitters, and you can scroll through the options or simply re-hire your regular dog boarder in no time. Your dog sitter can share real-time photo updates via the Rover dog boarding app, and with the app's cashless payment feature you'll be able to compensate your dog sitter quickly and safely, with no need for cash, checks or tips.

In short, when you book Chester 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.

Are you a dog lover who wants to know more about how to turn your passion into profit? There's lots of opportunity to earn money with dog boarding in Avon Crest, MD. If you're not sure where to start, visit our page about how to become a dog sitter. We're always happy to include new dog sitters in our dog boarding service listings, and the simple application process means you can start your own dog boarding business in no time. We also take the hassle out when it comes to paperwork, because all our Rover dog sitters have access to helpful benefits including premium pet insurance and cashless payment feature, so you don't have to worry about getting paid on time. Why not apply today?

Reviews from our dog sitters in Chester

Thanks Tabitha for taking our dog on a walk and giving her lots of love! Would recommend her to anyone!

Jess was very considerate of yiidi. They seemed to have enjoyed the walk and yiidi loved jess's company

Shunmarie was a great walker. She handled my big dog great. I will be using her again and recommend her