Doggy Day Care in Chester

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

Search Results

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Alexis A.
Verified Background Check
Sitter Profile Image: Alexis A.
Verified Background Check

1. Alexis A.

Star Sitter
Dog Lover Available to Help!!
Millersville, MD, 21108
17.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
369 reviews
126 repeat clients
from
$55
per day

After just recently moving to the area, we found Alexis on Rover. She was very responsive to our messages, and took great care of our pups! Thank You Alexis!!!

Calendar Recently Updated
Sitter Profile Image: Jenna C.
Verified Background Check
Sitter Profile Image: Jenna C.
Verified Background Check

2. Jenna C.

Star Sitter
Loving Petsitter Welcomes All
Annapolis, MD, 21401
11.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
58 reviews
22 repeat clients
from
$35
per day

Super flexible and wonderful experience! Ozzy enjoyed getting to play with another dog and he was well taken care of and received a picture update during his time!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jessica M.
Verified Enhanced Background Check
Sitter Profile Image: Jessica M.
Verified Enhanced Background Check

3. Jessica M.

Star Sitter
Because it deserves the best 🫶
Annapolis, MD, 21401
12.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
3 repeat clients
from
$40
per day

Junie had a great day with Jessica. Will definitely use her again

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dory T.
Verified Enhanced Background Check
Sitter Profile Image: Dory T.
Verified Enhanced Background Check

4. Dory T.

Star Sitter
Kind flexible and experienced care
Severna Park, MD, 21146
14.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
93 reviews
34 repeat clients
from
$30
per day

Thank you Dory for caring for our pup for the day! We loved the fact she had other friends to run with & according to her collar activity, she was BUSY! We were able to book with short notice & Dory immediately responded back w/her flexible availability. Drop off & pick up couldn’t have been easier. She even offered to keep her overnight if we needed, which was super thoughtful! Thank you again for your hospitality! We definitely recommend Dory:)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Carolyn M.
Verified Enhanced Background Check
Sitter Profile Image: Carolyn M.
Verified Enhanced Background Check

5. Carolyn M.

Rover 101
Star Sitter
Animal lover w/ flexible schedule!
Annapolis, MD, 21403
11.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
62 reviews
16 repeat clients
from
$45
per day

Carolyn took amazing care of Bixby and provided updates throughout the day. So thankful to have him in such caring and loving hands. Jax is a great play and nap mate!

Calendar Recently Updated
Sitter Profile Image: Vanessa R.
Verified Enhanced Background Check
Sitter Profile Image: Vanessa R.
Verified Enhanced Background Check

6. Vanessa R.

Home Away from Home
Arnold, MD, 21012
11.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
5 repeat clients
from
$75
per day

Duke our papillon was right at home. He took to Vanessa instantly. This was Duke's first time with any pet sitter, and it could not have gone more perfect. Thank you, Vanessa!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Makhayla D.
Verified Background Check
Sitter Profile Image: Makhayla D.
Verified Background Check

7. Makhayla D.

Star Sitter
The Dog Sitter For You
Annapolis, MD, 21401
11.2 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
33 reviews
5 repeat clients
from
$40
per day

Bella had a great day with Makhayla! She sent pics throughout the day and I received constant updates. It put my dog mom heart at ease knowing she was taken care of. Thanks so much!!

Sitter Profile Image: Christian J.
Verified Enhanced Background Check
Sitter Profile Image: Christian J.
Verified Enhanced Background Check

8. Christian J.

Star Sitter
Kind and Compassionate Animal Lover
Arnold, MD, 21012
10.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$25
per day

Thank you! Jester has a nice first day.

Calendar Recently Updated
Sitter Profile Image: Alex K.
Verified Enhanced Background Check
Sitter Profile Image: Alex K.
Verified Enhanced Background Check

9. Alex K.

Star Sitter
Pooch palace in Annapolis!
Annapolis, MD, 21401
12.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$38
per day

Alex has been wonderful with my puppy. She brings him on lots of walks and sends lots of updates/pictures throughout the day. My pup loves her dogs and always has a good time.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Susan S.
Verified Enhanced Background Check
Sitter Profile Image: Susan S.
Verified Enhanced Background Check

10. Susan S.

Star Sitter
Dr. Dolittle- talks,walks, cuddles
Annapolis, MD, 21403
10.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
9 repeat clients
from
$55
per day

Susan is a wonderful and caring person & caretaker. She is trustworthy, accountable, and empathetic. Any pet under her care would be nurtured and taken care of like they are part of the family. I am happy to expand further on Susan’s capability if needed!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Melissa & Zachary H.
Verified Background Check
Sitter Profile Image: Melissa & Zachary H.
Verified Background Check

11. Melissa & Zachary H.

Family of 5 with love to give!
Annapolis, MD, 21402
11.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
25 reviews
6 repeat clients
from
$35
per day

Melissa was very responsive to my texts. Definitely seems like Lulu had a great day spending the day with them and Rosie. I'd recommend booking a day care or boarding with Melissa and Zach anyday!

Calendar Recently Updated
Sitter Profile Image: Martin N.
Verified Enhanced Background Check
Sitter Profile Image: Martin N.
Verified Enhanced Background Check

12. Martin N.

Trustworthy & reliable caretaker
Annapolis, MD, 21401
12.3 mi. away
Doggy Day Care
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$35
per day

Our golden retriever Murphy had an amazing two days with Martin and his dog Waffle!! Martin sent us many photos, videos and updates throughout his stay. They went on several walks and played in the backyard. Murphy was exhausted when he got home from all of the playing! Martin was extremely responsive, responsible, and flexible. We will definitely use Martin again in the future!

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
2.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
9 repeat clients
from
$39
per day

Mary and her family were absolutely wonderful! I received multiple picture updates throughout the day. My puppy had a great time!

Calendar Recently Updated
Sitter Profile Image: Victoria H.
Verified Enhanced Background Check
Sitter Profile Image: Victoria H.
Verified Enhanced Background Check

14. Victoria H.

Furry hair. Don’t care.
Annapolis, MD, 21409
9.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$25
per day

Victoria is an amazing person to care for your pet. If you’re looking for a trustworthy, consistent, and responsible pet sitter, she’s a great choice. She has taken care of my dog in the past and has never failed to show her love and support.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashley & Bob B.
Verified Background Check
Sitter Profile Image: Ashley & Bob B.
Verified Background Check

15. Ashley & Bob B.

Rover 101
Star Sitter
Pet Care When You're Not There!
Annapolis, MD, 21409
9.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
137 reviews
75 repeat clients
from
$25
per day

Ashley was great to communicate with. I think our dog was happy to be in a home with other dogs, and people who know how to care for them. Ashley was also easy to work with and patient, given this was our first time using Rover!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Mari H.
Verified Enhanced Background Check
Sitter Profile Image: Mari H.
Verified Enhanced Background Check

16. Mari H.

Dog Lover extraordinaire
Chester, MD, 21619
0.7 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
1 review
1 repeat client
from
$24
per day

About: Ever since I could walk I have been around dogs. I have been pet sitting for people since I was 10. I love every animal and will treat them like my own. I work part time and am off on the weekends. I can stop by in the mornings, some afternoons, and any evening you need to check on the sweet animals. I will make sure they are well loved and have everything they need. My home is a very safe space for animals. I have an open space behind my home that they can run around and play in.

Sitter Profile Image: Jenny H.
Verified Enhanced Background Check
Sitter Profile Image: Jenny H.
Verified Enhanced Background Check

17. Jenny H.

4-legged friends welcome!
Queenstown, MD, 21658
6.9 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$25
per day

Jenny creates an awesome space for Charlie, who loves her and her pups. She's attentive to his needs and makes sure that he gets plenty of play time. Jenny is completely trustworthy... I recommend her without reservation!

Confirmed availability: Memorial Day Weekend
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
3.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
6 repeat clients
from
$20
per day

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!

Calendar Recently Updated
Sitter Profile Image: Jason & Tracy Y.
Verified Enhanced Background Check
Sitter Profile Image: Jason & Tracy Y.
Verified Enhanced Background Check

19. Jason & Tracy Y.

Rover 101
Reliable & Responsible, Dog Lovers!
Stevensville, MD, 21666
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
65 reviews
28 repeat clients
from
$25
per day

I cannot recommend Jason and his mom Tracy enough! I received daily reports, and their care and attention to my pup was stellar! Will be using them again.

Sitter Profile Image: Emily A.
Verified Enhanced Background Check
Sitter Profile Image: Emily A.
Verified Enhanced Background Check

20. Emily A.

Compassionate Pet Care Provider
Chester, MD, 21619
2.9 mi. away
Doggy Day Care
2 reviews
1 repeat client
from
$36
per day

Emily took care of our two guinea pigs last summer while my family was away for a week and a half. She and her two kids provided the best care for our guinea girls! Before leaving for our trip, I asked if they could stop by just once a day to make sure the piggies had food and water. Emily and the kids made sure to stop by at least once a day (some days it was twice) and they stayed awhile each time to give the girls lots of attention. One day they put the piggies on FaceTime so my daughter (the piggies’ mommy) could interact with them from our location across the country. We are going on a trip this summer and I will definitely be asking Emily if she is available to care for the girls again.

Search Map

Chester Doggy Day Care ratings

Overall Rating:
5.0 out of 5 stars

Doggy Day Care sitters in Chester are rated on average 5 out of 5 stars based on 3 reviews.

Rover also offers Doggy Day Care in:

Rover also offers other services in Chester:

Doggy Day Care