Doggy Day Care in Chester

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Chester doggy day care sitters

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Jason & Tracy Y.
Verified Enhanced Background Check
Jason & Tracy Y.
from
$25
per day
4.9 out of 5 stars
78 reviews
31 repeat clients
10 years of experience
Stevensville, MD, 21666

About: We are very personable, friendly, responsible, and I love animals! My schedule is very flexible; I can accommodate all of your and your pet's needs. We are familiar with various pet health problems. we have experience walking and caring for and dog sitting for neighborhood pets. When my neighbors or friends go out of town for any reason, we always offer to pet sit for them. We like to know the dog's history, including any known behavioral issues (good or bad) or special needs to help identify appropriate activities, such as walking. We truly love dogs of all kinds, this is a dream job for me. Your pet's well-being is our number one concern. we are looking forward to meeting you all and your dogs! Pet Care Fits Into My Life Because I Am Home A Lot Trying To Earn My High School Diploma And Saw This As An Opportunity To Do What I Love Taking Care Of Dogs To Make Money I Do Not Have A Fenced In Yard And I Do Not Own Any Dogs But I Love What I Do It Is Big Fun Due To Personal Injury I Do Not Use Retractable Leashes And They Are Not Recommended I Work For Rover as my soul's means of income, and I Really Enjoy What I Do For A Living. I work for Rover as my primary source of income, and I truly enjoy what I do for a living. All the animals are like my own kids. I work for Rover as my primary source of income, and I truly enjoy what I do for a living. All the animals are like my own kids. All The Animals Are Like My Own Kids I will do whatever is necessary to meet my clients' animals' needs, be it medication or whatever it takes to make sure the animals in my care are well cared for.

Sitter Profile Image: Elena K.
Verified Enhanced Background Check
Elena K.
from
$30
per day
5.0 out of 5 stars
11 reviews
1 repeat client
10 years of experience
Annapolis, MD, 21409

Elena was absolutely phenomenal with our pup!

Profile image
Chanel R.
Sitter Profile Image: Lena M.
Verified Enhanced Background Check
Lena M.
Star Sitter
from
$60
per day
5.0 out of 5 stars
17 reviews
5 repeat clients
20 years of experience
Stevensville, MD, 21666

Lena is great! She is flexible, knows dogs and is very communicative

Profile image
Connor T.
Sitter Profile Image: Sydney T.
Verified Enhanced Background Check
Sydney T.
from
$40
per day
5.0 out of 5 stars
8 reviews
5 repeat clients
17 years of experience
Chester, MD, 21619

Sydney is so great! She took lots of photos and I could tell my dog enjoyed spending time with her! She's really responsive, easy to talk with, and very friendly!

Profile image
Drew J.
Sitter Profile Image: Celena W.
Verified Enhanced Background Check
Celena W.
from
$40
per day
5.0 out of 5 stars
10 reviews
3 repeat clients
4 years of experience
Annapolis, MD, 21409

Sooo easy to work with her under flexible conditions. My hound is a rescue from a nine-year life of abuse. Celena allowed Miguel and me to do a met and greet ahead of time so that it wouldn’t be a shock for him. He was treated as a visiting family member and enjoyed his stay.

Profile image
Patricia B.
Sitter Profile Image: Lucy & Daniel M.
Verified Enhanced Background Check
Lucy & Daniel M.
Star Sitter
from
$35
per day
5.0 out of 5 stars
16 reviews
4 repeat clients
15 years of experience
Annapolis, MD, 21403

Lucy and Daniel are a great team for the best doggy daycare you could ever want/need for your dog! My dog is extremely needy and they gave him nothing but love. We look forward to next time!

Profile image
Meredith C.
Sitter Profile Image: Luba & James H.
Verified Background Check
Luba & James H.
from
$40
per day
5.0 out of 5 stars
238 reviews
51 repeat clients
45 years of experience
Arnold, MD, 21012

Luba and James are great. They have a beautiful home with a nice fenced in backyard. Lilly received lots of love and had a lot of fun playing with their dog Nellie.

Profile image
Laura K.
Sitter Profile Image: Laura T.
Verified Enhanced Background Check
Laura T.
from
$40
per day
5.0 out of 5 stars
36 reviews
11 repeat clients
20 years of experience
Annapolis, MD, 21403

Laura is fantastic! Our pup Luna had a great time and loved playing around in the yard and with her two lovely pups. Laura was great to work with and sent pictures during Luna’s daycare session. Thanks!

Profile image
Mike H.
Sitter Profile Image: Jenna C.
Verified Background Check
Jenna C.
Star Sitter
from
$50
per day
5.0 out of 5 stars
224 reviews
60 repeat clients
10 years of experience
Annapolis, MD, 21401

Jenna is amazing! She was so accommodating with our early drop off time, and our pup had a blast! You know it was a good day when he comes home and snoozes the rest of the evening :)

Profile image
Madeline B.
Sitter Profile Image: Alex K.
Verified Enhanced Background Check
Alex K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
61 reviews
15 repeat clients
30 years of experience
Annapolis, MD, 21401

Alex took care of Pepe like he was her own. I very much appreciate the videos, photos, and updates. She was very good at trying to bring Pepe out of his shell. I will book with Alex again!

Profile image
Louise J.
Sitter Profile Image: Kacie B.
Verified Background Check
Kacie B.
Star Sitter
from
$45
per day
5.0 out of 5 stars
73 reviews
27 repeat clients
12 years of experience
Annapolis, MD, 21401

Kacie was awesome! She took great care of Queen while I was away at work. Kacie is very easy to communicate with and was extremely accommodating when my schedule was switched up at work last minute. Multiple videos were sent of their daily adventures. Kacie took Queen to the park or on a hike multiple times throughout the day. I 100% recommend Kacie if you need a dog sitter!

Profile image
Jance S.
Sitter Profile Image: Lindsay M.
Verified Enhanced Background Check
Lindsay M.
Star Sitter
from
$55
per day
5.0 out of 5 stars
42 reviews
10 repeat clients
40 years of experience
Annapolis, MD, 21401

Lindsay did an amazing job with our Daisy who has separation anxiety. Photo during the day and a fun video to watch. We will book again next time we are in town!

Profile image
Debra R.
Sitter Profile Image: Andy & Lydia M.
Verified Enhanced Background Check
Andy & Lydia M.
Star Sitter
from
$55
per day
5.0 out of 5 stars
63 reviews
17 repeat clients
41 years of experience
Annapolis, MD, 21403

Roxy had a wonderful time playing with Andreas and his dog Luna. She was reluctant to leave in order to come home. The rest of the day she was happy and tired. Andreas was very pleasant to deal with. His fenced-in yard is a big plus.

Profile image
David C.
Sitter Profile Image: Taylor Grace T.
Verified Enhanced Background Check
Taylor Grace T.
from
$55
per day
5.0 out of 5 stars
8 reviews
1 repeat client
7 years of experience
Capitol Hill, Annapolis, MD, 21401

They were sweet with Kodi and sent picture updates during the day. I look forward to using them again!

Profile image
erin t.
Sitter Profile Image: Aliciya M.
Verified Enhanced Background Check
Aliciya M.
from
$25
per day
15 years of experience
Queenstown, MD, 21658

About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.

Sitter Profile Image: Amy D.
Verified Enhanced Background Check
Amy D.
from
$45
per day
5.0 out of 5 stars
27 reviews
11 repeat clients
7 years of experience
Arnold, MD, 21012

Ed and Amy are pleasant and attentive to their pet guests. Plus, they are very good about making sure animals get bathroom breaks and exercise. In addition, Gunner’s warm demeanor always makes people feel welcome.

Profile image
Matthew H.
Sitter Profile Image: Michelle M.
Verified Background Check
Michelle M.
Star Sitter
from
$38
per day
5.0 out of 5 stars
551 reviews
255 repeat clients
25 years of experience
Annapolis, MD, 21409

Michelle took excellent care of my baby. We are getting used to a new area, and new people, and she made it that much easier for my Boston Terrier!

Profile image
Howard W.
Sitter Profile Image: Carmel S.
Verified Enhanced Background Check
Carmel S.
from
$35
per day
5.0 out of 5 stars
16 reviews
2 repeat clients
5 years of experience
Grasonville, MD, 21638

Carmel was awesome with my pup, Dakota! I am so grateful that she let her come hang out for a few days and she took such great care of Dakota! Highly recommend!!!

Profile image
Chrissy B.
Sitter Profile Image: Elaine S.
Verified Background Check
Elaine S.
from
$50
per day
5.0 out of 5 stars
68 reviews
37 repeat clients
20 years of experience
Annapolis, MD, 21403

Elaine takes such good care of our dog, Ellie. I'm so glad she was available to watch her when I had to be away for a work trip. I know she's in good hands! Thank you Elaine!

Profile image
Jessica A.
Sitter Profile Image: Brooke F.
Verified Enhanced Background Check
Brooke F.
from
$20
per day
5.0 out of 5 stars
76 reviews
17 repeat clients
10 years of experience
Grasonville, MD, 21638

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!

1 / 1
View more sitters

Over 14
pet parents in Chester have booked doggy day care

Chester dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Sydney is so great! She took lots of photos and I could tell my dog enjoyed spending time with her! She's really responsive, easy to talk with, and very friendly!

Profile image
Drew J.
Doggy Day Care
5.0 out of 5 stars

Brianne and her daughter were wonderful sitters. Communication was great and they were very flexible as we were coming from out of town. Will definitely use them again if we are in MD.

Profile image
Glenn D.
Doggy Day Care
5.0 out of 5 stars

Melanie was excellent. Communication was great and really gave us confidence. Most importantly Melanie and her husband have wonderful personalities. We could see Duke took to them both right away and was very happy with them when we came back. Really made us comfortable that we could trust them with Duke.

Profile image
Eran R.
Doggy Day Care
5.0 out of 5 stars

Cait took such great care of our pup, Lemonade. It was our first time doing doggy daycare and it couldn’t have gone better. Thank you again for everything and accommodating our last minute request. Lemmy seems very happy and I know she will sleep solid tonight!

Profile image
Erin G.
Doggy Day Care
5.0 out of 5 stars

Dogs know best! When we move to the area my dogs interviewed several dog sitters. They growled at one, said okay with another, but with Jason and Tracy they licked their faces (which they never do) which told us they wanted to spend time with Jason and Tracy. Voila! We found our new dog sitters!!! Jason and Tracy are dependable and they are loved by my dog Jack, and by my husband in me. I've always hesitated to give a good review because I was afraid they would get too booked. But they deserve a positive and encouraging review. Thank you, Tracy and Jason!

Profile image
Kay E.
Doggy Day Care
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per day for doggy day care in Chester is $39

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Chester average 4
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Chester on Rover as of Jun 2026 was about $39 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Chester doggy day care sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, 488 sitters provided doggy day care in Chester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 87% of Chester sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Chester have an average of 15 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Chester.

Chester doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Chester sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 488 sitters offering doggy day care in Chester on Rover, so you’re sure to find the perfect match for your dog! In Chester, 98% of sitters offer daily exercise, 98% offer medication administration, and 91% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your doggy day care sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.