Dog Boarding in Chester, MD

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

Confirmed availabilityEaster weekend
Chris W.
1.
PuppyDog Resort-Fenced in back yardStevensville, MD, 21666
Dog Boarding

Miles loves going to Chris's and I love the level of comfort I have when dropping him off. Chris cares for Miles as I would and it brings me peace in knowing h… (more)

from
$30
per night
Mikayla M.
Flexible Loving Pet CareArnold, MD, 21012
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

amazing care was given to our golden retriever Duncan! Mikayla and Angela sent lots of pictures and stayed in touch over the 2 days Duncan stayed with them. L… (more)

from
$35
per night
Calendar Recently Updated
Jason & Tracy Y.
Reliable & Responsible, Dog Lovers!Stevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Thank you so much for taking excellent care of Cupid! It was great to see pictures throughout her stay. I know my family and I can count on you next time she ne… (more)

from
$28
per night
Confirmed availabilityEaster weekend
Michelle M.
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
Calendar Recently Updated
Elaine Y.
5.
Eastport Doggie B&B!Annapolis, MD, 21403
Dog Boarding, Drop-In Visits

I came home to a happy, healthy, obviously well cared for pup! My dog was with Elaine for over two weeks. She made him feel part of the pack! Will use her servi… (more)

from
$33
per night
Calendar Recently Updated
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
“ Play, eat, nap, repeat!”Annapolis, MD, 21409
Dog Boarding, Doggy Day Care

We are repeat customers, and our pup Lucy loves her time at Carolina's! She and her husband are fantastic; very loving and caring with Lucy, and take great care… (more)

from
$40
per night
Calendar Recently Updated
8.
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
9.
yard, next to the park and dog parkAnnapolis, MD, 21403
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Tango loved her stay at Alina’s! She sent pictures of Tango and was very quick to reply every time I reached out! I will definitely use her again as I was so pl… (more)

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

Luba and James took care of Blitzen like he was their own! They made the meet and greet easy, drop off was a piece of cake, and communicated well with me throu… (more)

from
$35
per night
Confirmed availabilityEaster weekend
11.
Honest, gentle and friendlyGrasonville, MD, 21638
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Joe enjoyed (more)

from
$40
per night
Calendar Recently Updated
12.
A loving ‘second home’ for your dogAnnapolis, MD, 21401
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Sally was amazing with our fur baby! She was accommodating and so sweet. We got pictures and updates during the stay. I would highly recommend her. (more)

from
$38
per night
13.
All breeds welcomed and lovedStevensville, MD, 21666
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

What a fantastic experience! Kasey was great! This was my first time leaving my rescue pup and I was totally put to ease thanks to the care she received. (more)

from
$28
per night
Calendar Recently Updated
Home all day great at spoiling!Shady Side, MD, 20764
Dog Boarding

I think my dogs liked Elizabeth's house more than mine! They had fun with the resident dogs and were well looked after. Elizabeth sent photos throughout our tri… (more)

from
$40
per night
15.
Jen 
Verified Enhanced Background Check
Life-long animal lover!Annapolis, MD, 21409
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jen was the perfect sitter! She sent daily updates and was super responsive the entire time we were gone. Our dog, Auggie, had a great time with her and the res… (more)

from
$50
per night
Confirmed availabilityEaster weekend
16.
Loving your pets as my own!Annapolis, MD, 21402
Dog Boarding, Drop-In Visits, Dog Walking

Megan was wonderful with my two senior girls. They have special dietary and medication needs and she made sure they were comfortable and very well taken care of… (more)

from
$40
per night
17.
Canine's Cozy CottageArnold, MD, 21012
Dog Boarding

Woody had a great stay with Sydney! You could tell he was well taken care of and Sydney was so great sending daily pictures of Woody. We definitely recommend he… (more)

from
$43
per night
Confirmed availabilityEaster weekend
18.
Let us care for your dog!Annapolis, MD, 21403
Dog Boarding, Drop-In Visits, Dog Walking

I've known Kristen all her life and she's a kind-hearted, animal-loving person. She's owned and cared for dogs since she was a child and has always had shelter… (more)

from
$28
per night
Confirmed availabilityEaster weekend
Stay at home Mom and animal lover!Annapolis, MD, 21409
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Ashley was great! Kashi had a great time and seemed to feel right at home when I left him. Great fenced back yard with plenty of room to run around. (more)

from
$30
per night
Confirmed availabilityEaster weekend
20.
Stress-free environment🐶🐈Pasadena, MD, 21122
Dog Boarding, Doggy Day Care

This is the second time we have used Beni and she is one of my favorites! Ellie always has such a good time and Beni sends me photos throughout the stay and sen… (more)

from
$32
per night

Check out the Dog Boarding in your neighborhood:

    Rover also offers Dog Boarding in:


    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