Doggy Day Care Chesterville

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

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Chesterville, Find top rated doggy day care

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

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Sitter Profile Image: Jen C.
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Jen C.
Star Sitter
from
$30
per day
5.0 out of 5 stars
179 reviews
65 repeat clients
20 years of experience
SMYRNA, DE, 19977

Jen is so good with my dog. She communicates very well with us when he is with her. He gets so excited when he knows he is going to her house.

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Jennifer L.
Sitter Profile Image: Brittany F.
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Brittany F.
from
$29
per day
20 years of experience
Warwick, MD, 21912

About: My farm is a beautiful sanctuary that we love to share with all furry friends! Whether they want to splash in the pool, run outside in a safe CLEAN secure area, or just have a nice snuggle in their indoor kennel or maybe even stretch out on the couch- just know they’ll be wagging to come back! I have 6 horses on the property, 13 chickens, 2 turkeys, 2 outdoor barn cats, and my Friendly Laid back dog Archie. I provide love & care which is more important than anything else. But of course- I follow parents rules! My entire life revolves around my farm and caring for all of my animals. I am on the property 24/7 as this is my full time job. And luckily it’s my passion. We have a beautiful fenced in pasture with lots of space to run. We are in a very private and rural area. We also have a pool- only if parents are OK and the Pup chooses to take a dip! Your Pup will always be supervised. If there are restrictions we will always abide by them. We also have dog crates if needed or requested and a beautiful inside area as well. Basically your Pup is gonna have free range and feel a home away from home.

Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$35
per day
5.0 out of 5 stars
165 reviews
54 repeat clients
25 years of experience
Smyrna, DE, 19977

Emily was so attentive and confident. Her knowledge and expertise are unmatched! She is so in tune with my dog - it definitely made me feel like my dog was safe and in good hands. Would recommend Emily to anyone!

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Hannah C.
Sitter Profile Image: Tarina L.
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Tarina L.
Star Sitter
from
$40
per day
5.0 out of 5 stars
42 reviews
15 repeat clients
30 years of experience
Edgewood, MD, 21040

Our golden retriever puppy, Loki had the BEST time in Tarina’s care! He was extremely comfortable there and was treated like part of the family. We are excited to have Tarina watch him again soon! :)

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Maritta B.
Sitter Profile Image: Paris V S.
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Paris V S.
Star Sitter
from
$45
per day
5.0 out of 5 stars
248 reviews
57 repeat clients
17 years of experience
Edgewood, MD, 21040

my pup was so excited to see paris again! as soon as we turned down her street for drop off, his tail had already started wagging. i know he’s in great hands when he’s with paris!

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Britney N.
Sitter Profile Image: Jenny M.
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Jenny M.
from
$37
per day
5.0 out of 5 stars
183 reviews
71 repeat clients
9 years of experience
Dover, DE, 19901

Ollie had a good time playing at Jenny’s!

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J D.
Sitter Profile Image: Rackeem R.
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Rackeem R.
from
$55
per day
5.0 out of 5 stars
31 reviews
16 repeat clients
7 years of experience
Middletown, DE, 19709

Very professional and has a great relationship with dogs and knowledge of them. Provided pics and videos and walks. Will definitely use him again.

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Joseph L.
Sitter Profile Image: Elizabeth W.
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Elizabeth W.
from
$35
per day
5.0 out of 5 stars
6 reviews
13 years of experience
Centreville, MD, 21617

About: I've been around animals as long as I can remember. I currently have a puppy named Star and three cats Persephone (Purrsi), Odin and Loki. I foster for the local QA shelter and have worked in a vets office for a short time. I am lucky enough to work out of my house or remote so I am available seven days a week with enough notice. I can come to you or provide care in my house. I live in an end unit Duplex. I have a fenced in yard complete with a puppy pool and beds for lounging. I can provide care in my home or come to yours. Following directions and care requests provided is not a problem.

Sitter Profile Image: Gisel D.
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Gisel D.
Star Sitter
from
$35
per day
5.0 out of 5 stars
41 reviews
18 repeat clients
7 years of experience
Edgewood, MD, 21040

This was Finlay’s first visit with Gisel. Seems like he had a great time. He came home happy and tired. Thank you for being great with communication. Much appreciated.

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Teal C.
Sitter Profile Image: Dan K.
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Dan K.
from
$35
per day
15 years of experience
Middletown, DE, 19709

About: I’ve have been a dog owner all throughout my life. I currently have a golden retriever that is three year old named Steve. I know level 1 and level 2 dog training techniques. And enjoy taking dogs for long walks to get their energy out. I live five minutes from my job and can come home if needed and never work weekends. My wife works from home 3 out of 5 week days. I have a large fenced in yard (.75 acres) and a dog friendly golden retriever named Steve. I have an extra crate available if your pet needs crating.

Sitter Profile Image: Rachel B.
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Rachel B.
from
$50
per day
5.0 out of 5 stars
49 reviews
24 repeat clients
10 years of experience
Aberdeen, MD, 21001

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

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Laura W.
Sitter Profile Image: Candice M.
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Candice M.
Star Sitter
from
$40
per day
5.0 out of 5 stars
129 reviews
59 repeat clients
10 years of experience
South St. Georges, DE, 19709

Candice is a wonderful doggie caretaker. She was very attentive and patient with my fur baby, who is very needed and spoiled. I will be looking to have my fur baby do another stay soon. Thanks Candice!

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Otis S.
Sitter Profile Image: Jacob & Megan W.
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Jacob & Megan W.
from
$35
per day
5.0 out of 5 stars
78 reviews
48 repeat clients
10 years of experience
Bel Air, MD, 21015

Gunnar had a wonderful time and Jacob and Megan were super welcoming and on top of everything. Would definitely be using again, Gunnar had a blast and was well cared for.

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Chris A.
Sitter Profile Image: Pearl J.
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Pearl J.
Star Sitter
from
$30
per day
4.9 out of 5 stars
126 reviews
47 repeat clients
30 years of experience
Havre De Grace, MD, 21078

Pearl took great care of Angus at a last minute request and sent me pictures with updates throughout the day! I would definitely rebook with her.

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Lauren P.
Sitter Profile Image: Angela O.
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Angela O.
from
$38
per day
5.0 out of 5 stars
112 reviews
35 repeat clients
25 years of experience
havre de grace, MD, 21078

Our dog had a blast playing at Angela’s house. She took great care of him and we would highly recommend her to anyone looking for a dog sitter.

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Polly S.
Sitter Profile Image: Karen D.
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Karen D.
Star Sitter
from
$27
per day
4.9 out of 5 stars
161 reviews
78 repeat clients
30 years of experience
North East, MD, 21901

My pups change home happy and tired! Karen did an amazing job caring for them. She was very responsive and friendly! They will be going back soon!

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Valerie J.
Sitter Profile Image: Jen P.
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Jen P.
Star Sitter
from
$45
per day
5.0 out of 5 stars
76 reviews
22 repeat clients
25 years of experience
Middletown, DE, 19709

Liza had a great time with Jen!! Jen is really caring and was really attentive to put Liza at ease, not always a simple task as Liza has separation anxiety. Jen was very responsive, took a bunch of pictures, and sent me lots of updates. I really appreciated it and highly recommend her!

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Tatiana G.
Sitter Profile Image: Elena C.
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Elena C.
from
$40
per day
5.0 out of 5 stars
3 reviews
1 repeat client
7 years of experience
Belcamp, MD, 21017

Thanks for helping us out with a rushed schedule and for taking care of our little girl!

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Jackie E.
Sitter Profile Image: Cynthia M.
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Cynthia M.
from
$25
per day
5.0 out of 5 stars
7 reviews
40 years of experience
Middletown, DE, 19709

About: I own It takes a village animal rescue, though I am taking a 2 year break, I have had 451 dogs come through my rescue in the last 10 years. I can help with house training, and basic puppy skills. I have probably had about 100 plus puppies in the last 10 years. I have a facebook account for the rescue and you can see all that My Volunteers and I have done over the years. Dogs must be neutered or spayed. Pet care has been a way of life for me for the last 10 years, I own an animal rescue, but am taking a 2 year hiatus, but miss haveing dogs around all day. I am home 90% of the time so I am there to let dogs out who might not be potty trained or sometimes it is just for company, laying on the couch watching TV and getting rubbed. I have a fenced in yard with lots of room to roam. I also have Mr Donovan, 110 pound hound mix that lost his 2 playmates in the last 2 months, so he would love having anotherfriend to hang/ play with.

Sitter Profile Image: Elizabeth D.
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Elizabeth D.
Star Sitter
from
$45
per day
5.0 out of 5 stars
63 reviews
9 repeat clients
15 years of experience
Dover, DE, 19904

Elizabeth was fantastic!! Watched our girl Lylah on short notice, and was great about our time running long! It’s obvious she took great care of our baby! She was good with giving updates and pics! I would highly recommend her to anyone looking for a sitter ! We will definitely be using her again!

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Chris G.
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The median cost per day for doggy day care in Chesterville is $35

Dog parents share their Rover experiences - Chesterville

1 / 1
5.0 out of 5 stars

Everything worked out perfectly! Lincoln got two walks, played in a fenced in yard and even took a dip in the river. Great communication as well

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Chris Z.
Doggy Day Care
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Sitters in Chesterville average 4
repeat doggy day care clients

FAQs for Doggy Day Care - Chesterville

Frequently asked questions about Rover

As of July 2026, there are 703 sitters on Rover offering Doggy Day Care across Chesterville. Enter your ZIP code to see which available sitters are closest to your home.

Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Chesterville commute.

If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.

Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.

A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.

Here are tips for finding the ideal day care fit for your dog:

  • For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
  • For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
  • For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.

Play groups can be an option when you book with a day care sitter through Rover. Many sitters do host a small number of dogs at the same time. Smaller dog packs are generally safer, more fun, and ideal for dogs who enjoy playtime but also want to relax throughout the day. When looking for your dog’s pack, check the sitter’s profile to see if they "Accept multiple clients" or have their own dogs. Then during the Meet & Greet, you can see whether your dog is a good fit for their social circle!

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in MD ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 703 sitters in Chesterville, 88% respond to messages in under an hour.

You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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