Doggy Day Care in Chestertown

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Jen C.
Verified Enhanced Background Check
Sitter Profile Image: Jen C.
Verified Enhanced Background Check

1. Jen C.

I just wanna love on all the dogs!!
SMYRNA, DE, 19977
24.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5.0 out of 5 stars
49 reviews
22 repeat clients
Profile image

Amazing experience! We couldn’t have asked for better top notch care and service for our pup. Thank you Jennifer! We would recommend her to anyone and will use her services again!

Availability updated 8 days ago
Sitter Profile Image: Theresa C.
Verified Enhanced Background Check
Sitter Profile Image: Theresa C.
Verified Enhanced Background Check

2. Theresa C.

Star Sitter
Small dog expert, puppies & seniors
Baltimore, MD, 21221
23.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5.0 out of 5 stars
24 reviews
5 repeat clients
Profile image

Theresa was awesome with my pup. She made me feel at ease with leaving my dog with someone for the first time. Knowledgeable, Friendly, and pleasant to the both of us. I highly recommend Theresa to care for your dogs.

Availability updated 4 days ago
Sitter Profile Image: Athena M.
Verified Enhanced Background Check
Sitter Profile Image: Athena M.
Verified Enhanced Background Check

3. Athena M.

Experienced & reliable animal lover
Smryna, DE, 19977
26.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5.0 out of 5 stars
11 reviews
1 repeat client
Profile image

It was lovely to meet Athena. I asked her to watch my dog, and she immediately said yes. My dog had a lot of fun. I highly suggest her and will absolutely bring my dog to her again.

Availability updated 9 days ago
Sitter Profile Image: Alana C.
Verified Enhanced Background Check
Sitter Profile Image: Alana C.
Verified Enhanced Background Check

4. Alana C.

Rover 101
Star Sitter
will love your pets like my own
Havre de Grace, MD, 21078
23.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per day
5.0 out of 5 stars
227 reviews
40 repeat clients
Profile image

Alana was great! She was very patient and had a fast response time. 30 looked like he had a great time with her. He was exhausted by the time he got home from having such an amazing time!

Availability updated 8 days ago
Sitter Profile Image: Paris S.
Verified Background Check
Sitter Profile Image: Paris S.
Verified Background Check

5. Paris S.

Star Sitter
Dogs paradise away from paradise
Edgewood, MD, 21040
18.5 mi. away
Boarding, Doggy Day Care
from
$38
per day
5.0 out of 5 stars
113 reviews
25 repeat clients
Profile image

Paris was awesome she took Bear last minute for doggy daycare and I couldn’t be more happier with how his stay was. She updated me throughout the day which was great. Overall seemed like bear had a great day with her and her dogs while I’m working on his separation anxiety. Will def use again if needed and would recommend!! Thanks Paris!

Availability updated today
Sitter Profile Image: Rachel B.
Verified Background Check
Sitter Profile Image: Rachel B.
Verified Background Check

6. Rachel B.

Rover 101
Love. Cuddle. Exercise. Repeat!
Aberdeen, MD, 21001
22.0 mi. away
Boarding, Doggy Day Care
from
$40
per day
5.0 out of 5 stars
43 reviews
20 repeat clients
Profile image

Rachel is a great sitter and dog lover. She is true to her word of taking great care of our furry family member. She has this thing on point!! Great job Rachel

Availability updated yesterday
Sitter Profile Image: Nalia C.
Verified Enhanced Background Check
Sitter Profile Image: Nalia C.
Verified Enhanced Background Check

7. Nalia C.

Rover 101
Star Sitter
Lots of love for your fur baby!🐶🐩
Dundalk, MD, 21222
24.0 mi. away
Boarding, Doggy Day Care
from
$28
per day
5.0 out of 5 stars
307 reviews
160 repeat clients
Profile image

Nalia was great with my puppy! She was very welcoming and her response time was very quick. She took lots of pictures and kept updates on everything throughout the visit!

Availability updated today
Sitter Profile Image: Jill & Chad H.
Verified Enhanced Background Check
Sitter Profile Image: Jill & Chad H.
Verified Enhanced Background Check

8. Jill & Chad H.

Rover 101
Star Sitter
We LOVE dogs!!!
Abingdon, MD, 21009
23.4 mi. away
Boarding, Doggy Day Care
from
$35
per day
5.0 out of 5 stars
30 reviews
8 repeat clients
Profile image

Cal had a great day with Chad! We received pictures and videos of Cals stay. They even took him on a walk! Chad was great at communicating and flexible with pick up time. We already have another stay booked!

Availability updated today
Sitter Profile Image: Katie M.
Verified Background Check
Sitter Profile Image: Katie M.
Verified Background Check

9. Katie M.

Rover 101
Your local professional Dog Aunt!
Middle River, MD, 21220
21.8 mi. away
Boarding, Doggy Day Care
from
$40
per day
5.0 out of 5 stars
74 reviews
28 repeat clients
Profile image

Katie is amazing! This was the first time I left my puppy with anyone. She sent pictures and updates all day. Winston had a blast. He can’t wait to come back tomorrow ?

Availability updated yesterday
Sitter Profile Image: Angelene H.
Verified Background Check
Sitter Profile Image: Angelene H.
Verified Background Check

10. Angelene H.

Rover 101
Paws and Claws Doggy Sleep Over!
Edgewood, MD, 21040
20.6 mi. away
Boarding, Doggy Day Care
from
$36
per day
5.0 out of 5 stars
439 reviews
186 repeat clients
Profile image

Angelene always does a great job with Bailey!! Bailey is always excited when she gets in the car with me in the morning during the week, because she knows she will have a fun filled day with Angelene!!

Availability updated 15 days ago
Sitter Profile Image: Katharine D.
Verified Enhanced Background Check
Sitter Profile Image: Katharine D.
Verified Enhanced Background Check

11. Katharine D.

Check us out!
Centreville, MD, 21617
14.2 mi. away
Boarding, Doggy Day Care
from
$30
per day
5.0 out of 5 stars
13 reviews
1 repeat client
Profile image

Thanks for giving our girl a try!

Availability updated 61 days ago
Sitter Profile Image: Janice & Charles B.
Verified Enhanced Background Check
Sitter Profile Image: Janice & Charles B.
Verified Enhanced Background Check

12. Janice & Charles B.

We’d love to welcome your pets!
Clayton, DE, 19938
21.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per day
5.0 out of 5 stars
20 reviews
8 repeat clients

Janice is a very caring person and truly loves animals. She has experience caring for large, small and exotic pets. She is responsible and reliable.

Availability updated yesterday
Sitter Profile Image: Mary L.
Verified Enhanced Background Check
Sitter Profile Image: Mary L.
Verified Enhanced Background Check

13. Mary L.

Star Sitter
Chickens Squirrels Dogs & Kitties!
Stevensville, MD, 21666
18.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$39
per day
5.0 out of 5 stars
26 reviews
12 repeat clients
Profile image

Mary was great, she just incorporated Allie into her family and daily life. She sent photos of Allie totally chilling out and interacting with people. It made me feel better knowing she was safe and content. I could see that in her face and body language.

Availability updated 5 days ago
Sitter Profile Image: Melissa A.
Verified Enhanced Background Check
Sitter Profile Image: Melissa A.
Verified Enhanced Background Check

14. Melissa A.

No dog is too big or too small!
Chester, MD, 21619
20.1 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$25
per day
5.0 out of 5 stars
4 reviews

About: I have had a pet of some sort for my entire life, my love for animals continues to grown as I have become older. I have also recently fostered animals and over the course of a few months have had about 5 additional dogs at different times. I work from home full time, I have three dogs of my own, a 5 pound Yorkie, 60 pound red fox lab and a 3 month old GSP, lab mix. I am also a sports mom so I know how important it is to exercise our dogs. We spend plenty of time in our yard throughout the day. We recently lost our Cane Corso to epilepsy so I understand the need for dog care when you have to be away from your pet for however long that may be. If your dog is not in a fenced yard they will stay on a leash at all times. Safety while providing proper exercise is my number one concern. My goal is to love your pet for the time that you are away. I have my own pets so I understand how difficult it can be to be away from them.

Availability updated 18 days ago
Sitter Profile Image: Briana & Isaiah S.
Verified Background Check
Sitter Profile Image: Briana & Isaiah S.
Verified Background Check

15. Briana & Isaiah S.

Dog Lover & Dog Parents x2
Abingdon, MD, 21009
20.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5.0 out of 5 stars
16 reviews
3 repeat clients

Briana and Zae love their pups with everything they have, and they treat the dogs they sit just as equally. They kept me posted on how my dog Malcolm was doing and sent pictures of him on adventures. Without a doubt my mind and heart were at ease knowing Malcolm was being taken care of while we were on vacation. 10/10 would recommend them!

Availability updated 15 days ago
Sitter Profile Image: Tania H.
Verified Enhanced Background Check
Sitter Profile Image: Tania H.
Verified Enhanced Background Check

16. Tania H.

Pet lover 💓
Edgewood, MD, 21040
20.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5.0 out of 5 stars
36 reviews
6 repeat clients

About: I have taken care of dogs off and on for the last 7 years. They play and walk and really keep me good company. Its been the best part time job ever. Who knew I'd be spoiling pets and watching over them like my own. Yes. I am home all day. I spent my days that I am not pet sitting hiking. The outdoors is where I enjoy exploring. Also just got into some bird watching I do not have a fenced in yard. I do enjoy walking dogs in my neighborhood. We have alot of friendly trails to walk on and plenty of trees to mark.

Availability updated 33 days ago
Sitter Profile Image: Ryan P.
Verified Enhanced Background Check
Sitter Profile Image: Ryan P.
Verified Enhanced Background Check

17. Ryan P.

Doggy Play Care
Centerville, MD, 21617
12.8 mi. away
Boarding, Doggy Day Care
from
$20
per day
5.0 out of 5 stars
26 reviews
12 repeat clients
Profile image

I'm thankful and felt like my dogs were in good hands and safe. I can

Availability updated yesterday
Sitter Profile Image: Brooke F.
Verified Enhanced Background Check
Sitter Profile Image: Brooke F.
Verified Enhanced Background Check

18. Brooke F.

Star Sitter
Pet Nanny by trade!
Grasonville, MD, 21638
18.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per day
5.0 out of 5 stars
21 reviews
7 repeat clients

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 can work away from home with ease knowing your dog won't be in a kennel all day long! I also dog sit/house sit if you need to go away for business or vacation and can not take your 4 legged friends with you. I am trustworhty and dependable so you do not have to worry about a stranger coming in for your dog but more so your dogs BFF coming in to let the out for a little and play and to use the bathroom for a potty break! I hope to talk to you soon and meet your furry friend(s)! I am home almost all day everyday so my schedule is pretty open and I am extremely flexible to accommodate your schedule as well if needed! I have a fenced in big back yard and a very friendly 3 year old lab to accompany your dog! Frequent let outs and frequent cuddle seshs!

Availability updated 4 days ago
Sitter Profile Image: Madison P.
Verified Enhanced Background Check
Sitter Profile Image: Madison P.
Verified Enhanced Background Check

19. Madison P.

Pet loving couple saving for house!
Chestertown, MD, 21620
1.4 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5.0 out of 5 stars
4 reviews
1 repeat client

Madison is a dream with dogs! I have a very shy German Shepherd/husky mix who is 2 years old. Madison was patient with him-talked in a soft voice, didn’t stand over him, but sat down so they were on the same level and let him warm up to her. By the time she was leaving he was sitting in her lap. She is responsible, warm hearted, and loves all animals like they are her own! 15/10 would recommend!!

Availability updated 34 days ago
Sitter Profile Image: Lisa R.
Verified Background Check
Sitter Profile Image: Lisa R.
Verified Background Check

20. Lisa R.

I LOVE ANIMALS
Kennedyville, MD, 21645
7.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$29
per day
12 years of experience

About: The first time I cared for an animal I was in kindergarten and my class was raising chicks. After that moment I valued life and I became infatuated with animals of all kinds. I am free in the mornings one the weekends for pet sitting and for pet boarding I am available on the weekends for overnight care. There are a number of close by parks for playtime and potty time. I enjoy teaching easy tricks and giving a lot of attention. So you won’t have to worry about a sad pup!

Availability updated 4 months ago

Search Map

Doggy Day Care FAQs

Frequently asked questions about Rover

Rover also offers other services in Chestertown:

Doggy Day Care