Dog Boarding in Chestertown

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

Search Results

Confirmed availability: Labor Day
Dejah B.
1.
A young dog mom w/ a love for petsMiddle River, MD, 21220
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I really want to say thank you to Dejah for a job well done. My Lily never ever did this good for anyone. I was nervous about trying another sitter because Lily… (more)

from
$45
per night
Confirmed availability: Labor Day
Meme & Phil L.
Love To Care For Your Fur Babies!Essex, MD, 21221
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Best dog sitters ever! Meme took my dog with less than a weeks notice. My dog has only been to one sitter before so I was very nervous. I did a meet and gree… (more)

from
$35
per night
Confirmed availability: Labor Day
Connie K.
3.
Professional Sitter & GroomerRidgely, MD, 21660
Dog Boarding, Drop-In Visits, Doggy Day Care

Connie is great. She used to be my two chow chow’s hair dresser and they miss her dearly. It’s hard to find chow groomers anywhere and she took a chance on my c… (more)

from
$50
per night
Takiara W.
I love loving on dogsEdgewood, MD, 21040
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Takira did a great job caring for my Paw! He now has a new play date with Pablo! I appreciated the daily updates and pics. He always looked like he was having … (more)

from
$50
per night
Confirmed availability: Labor Day
Alessandra G.
Very passionate about pets !!!Edgewood, MD, 21040
Dog Boarding, Drop-In Visits, Doggy Day Care

Alessandra was AWESOME! She cared for Oli like he was a part of the family and she shared photos everyday to keep me informed! I will be using her again! THE… (more)

from
$40
per night
Calendar Recently Updated
Beautiful back yard for your dogs!Annapolis, MD, 21409
Dog Boarding, Drop-In Visits

Michelle has taken our dog Henry in twice now and we have zero complaints. Her and her family are dog lovers by nature and provide an ideal environment for dog… (more)

from
$35
per night
Confirmed availability: Labor Day
7.
Professional Pet LoversSmyrna, DE, 19977
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Deanna was amazing and gave regular updates with pictures. The dogs came back home and slept the entire afternoon. Thanks for taking such good care of them! (more)

from
$55
per night
Calendar Recently Updated
8.
Only 1 guest (family) at a time...North East, MD, 21901
Dog Boarding, Doggy Day Care

Always a wonderful time with Bill watching Maverick. He always goes above and beyond even this time meeting us halfway when we got in a bind with drop off logis… (more)

from
$50
per night
We love dogs and cats! APG Only.Aberdeen Proving Ground, MD, 21005
Dog Boarding, Drop-In Visits, Doggy Day Care

Matthew and Melissa were awesome and I can’t recommend them enough! Thanks for being so great to Caesar. (more)

from
$60
per night
Calendar Recently Updated
10.
Let me make your pet at home! 😍Edgewood, MD, 21040
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Bailey and her family was amazing from start to finish! She made sure we had a dog meet and greet to meet her pups to make sure everyone got along. Out of my pa… (more)

from
$40
per night
Calendar Recently Updated
11.
Reliable, mature, petcare providerHartly, DE, 19953
Dog Boarding

Terri was an excellent sitter for my 5 month old puppy! She has a wonderful farm with fenced in areas for lots of outdoor time. Belle came back happy and I rece… (more)

from
$35
per night
12.
A house is not a home w/o dog hairDundalk, MD, 21222
Dog Boarding, Drop-In Visits

Katie was WONDERFUL during the entire boarding process. She met with us beforehand to ensure it was a good fit and kept us updated throughout our weekend away. … (more)

from
$35
per night
Calendar Recently Updated
13.
Home Full Time & Large Fenced YardBel Air, MD, 21014
Dog Boarding

Amanda and family were amazing. Our pup looked so happy... I almost thought he didn't want to come home. Communication was amazing and there was flexibility.… (more)

from
$50
per night
Calendar Recently Updated
14.
Leave your pet and safe handsDundalk, MD, 21222
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Heather watched our dog Maya and was great and very communicative. She sent lots of adorable pictures and Maya was happy and comfortable when we picked her up. … (more)

from
$50
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
16.
i love all animals <3warwick, MD, 21912
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

I think that gabby is a very responsible and loving person when it comes to animals. She is always taking care of her bunnies and cat. She always plays with the… (more)

from
$50
per night
Calendar Recently Updated
College student, dog owner/loverRosedale, MD, 21237
Dog Boarding, Doggy Day Care, Dog Walking

Markayla was great! Took great care of our fur baby and kept us up to date with how she was doing & sent pics throughout her stay. Will definitely use her again… (more)

from
$40
per night
18.
Run, Play, Sleep. Make Pup Smile!Belcamp, MD, 21017
Dog Boarding, Drop-In Visits, Dog Walking

Robin did a phenomenal job watching our dog, Nora. She kept in touch by sending pictures and being very responsive to my text messages. Our dog came home happy … (more)

from
$42
per night
Calendar Recently Updated
19.
I love all fur babiesAberdeen, MD, 21001
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Linda was super sweet and accommodating. This was my dog's first night away from our family and Linda tried her very best to make him feel secure and taken care… (more)

from
$40
per night
Confirmed availability: Labor Day
20.
Friendly and caring home!Nottingham, MD, 21236
Dog Boarding, Doggy Day Care

Ruby was amazing with our little boy for the week! She communicated daily, sent frequent pics and videos, and even made him his own little toy. We immediately… (more)

from
$50
per night

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.