Dog Sitting in Shady Side

Book a Shady Side dog sitter to watch your dog in your sitter’s home or yours.

End Date
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Shady Side dog sitters

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

1 / 1
Sitter Profile Image: Milanni B.
Verified Enhanced Background Check
Milanni B.
from
$20
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
6 years of experience
Bowie, MD, 20716

Goldie Loves Milanni! Milanni is someone I can count on for drop-ins or boarding when I’m traveling around the world. I appreciate how easy it is to communicate with her and she confidently takes care of business without any worry. Goldie appreciates Milanni being part of her caregiving community when I am away. I recommend Milanni for your pet and caregiving needs.

Profile image
Matthew G.
Sitter Profile Image: Nicki J.
Verified Enhanced Background Check
Nicki J.
from
$25
per visit
5.0 out of 5 stars
1 review
3 years of experience
Deale, MD, 20733

About: I have been taking care of dogs and cats for the last 6 years. I have had to feed, walk, scoop litter boxes, give medicine, and give ALL of my attention to them :) I have had a dog all of my life and have been around animals every single day. I will care for your for baby like my own. I will send pictures/videos to make you feel like you are there watching them :) I do have a full-time job, but it is remote, so I am very flexible. I do not have assigned hours, so I am able to care for your animal at any point of the day, whether be walks, or just stop in to say hey and play for a while! I will be able to care for your fur baby at your house making sure everything is cleaned up and safe for your animal. I am very accommodative and if you need or want anything else done just let me know!

Sitter Profile Image: Jennifer S.
Verified Enhanced Background Check
Jennifer S.
from
$45
per visit
5.0 out of 5 stars
53 reviews
21 repeat clients
25 years of experience
Edgewater, MD, 21037

Jennifer was great with our dog who is 13. I have had to be away more than he is used to and when I get back he is relaxed and happy to see me. Which means Jennifer's time with him has been fun. I highly recommend her.

Profile image
Melanie K.
Sitter Profile Image: Kevin W.
Verified Enhanced Background Check
Kevin W.
from
$14
per visit
5.0 out of 5 stars
2 reviews
8 years of experience
Annapolis, MD, 21402

About: As stated, I have an 8 almost 8 year old German Shepherd myself. I’ve trained him myself to be quite obedient off leash, to listen well, and overall he’s very well behaved. I’ve grown up with dogs, cats, turtles and more so I know my way around animals. I’m currently enlisted in the United States Navy. I work at the Naval Academy typically from around 9 in the morning to about 3pm most days. I’m also married with two kids and my wife is a stay at home mom who can also look after your furry friends as well. I don’t work weekends so I’m always available during the weekends and can be flexible throughout the week as well. At my home my dog is never crated he is always out and house trained. However, when looking after your fur babies if they need to be crated I have no issue catering to your needs. I don’t have a yard but we have a massive field and live in a circle so long walks are always a must. Whatever the needs of your fur babies, I can take care of those from daily dog walking, spending and playing time with your animals, staying over night at yours/my place, and giving g medicine if needed.

Sitter Profile Image: Faith M.
Verified Enhanced Background Check
Faith M.
Star Sitter
from
$24
per visit
4.9 out of 5 stars
20 reviews
5 repeat clients
2 years of experience
Chesapeake Beach, MD, 20732

Faith has watched our Shiba Inus multiple times now, and we couldn’t be happier with the care she provides. She’s reliable, responsive, and truly great with our dogs—even administering medication to our elderly Shiba with no issues. Most recently, she helped us out while we were in the hospital for the birth of our son. We weren’t sure how many drop-ins we’d need or how long we’d be gone, but she was incredibly flexible and quick to respond. It gave us so much peace of mind knowing our pups were in good hands. Highly recommend!

Profile image
Jacqueline A.
Sitter Profile Image: Aleah J.
Verified Enhanced Background Check
Aleah J.
from
$25
per visit
5.0 out of 5 stars
10 reviews
2 repeat clients
10 years of experience
Chesapeake Beach, MD, 20732

About: I’ve been caring for cats and dogs for about 10 years now, through my friends, family, neighbors and my own 2 puppies! I’m a college athlete who’s very active, so I’m happy to run/play and keep energetic dogs exercised while also making sure they feel loved, safe, and cared for! Pet care has always been a part of my daily routine, caring for my own two dogs! However, I’m a college student now, who lives an hour away from home, but I’m back for weekends and have plenty of free time to care for pets! I provide a safe, fun environment for pets. I have a fenced yard for running around outside, and two friendly dogs who would love to make friends! I closely supervise pets and will follow all instructions/special requests strictly from owners!

Sitter Profile Image: Amanda J.
Verified Enhanced Background Check
Amanda J.
from
$25
per visit
25 years of experience
Annapolis, MD, 21403

About: Lifelong animal lover with years of hands-on experience caring for dogs and cats for friends, family, and neighbors. I grew up with two family dogs and now have a 6-year-old “super mutt” named Mija who completely runs the household (and honestly, I’m okay with that). I’m responsible, trustworthy, attentive, and genuinely happiest when I’m around animals. Whether your pet loves long walks, belly rubs, playtime, or just a calm comforting presence, I’ll care for them like they’re my own. I know how important it is to trust the person watching your pets, and I take that responsibility seriously — while still making sure your furry family member has a fun, loving experience. I currently work part time in e-commerce and my availability is very flexible. I’m working towards a real estate license and my long-term goal is to retire my mom! I have experience caring for and walking dogs of all breeds and sizes, including large breeds that require confidence, awareness, and strong handling skills. Safety is always my top priority, and I have exceptional risk assessment when it comes to walks, environments, and interactions with other animals. I’m also comfortable administering medications and following specific care instructions and routines. As a lifelong dog owner, I understand how important structure, consistency, and enrichment are for pets. My own dog thrives on her daily routines and knows exactly when it’s time for walks, dinner, and her nightly “search and find” game. I genuinely love building trust with animals and making sure they feel safe, happy, and cared for while their owners are away.

Sitter Profile Image: Kristina B.
Verified Background Check
Kristina B.
from
$30
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
15 years of experience
North beach, MD, 20714

Kristina was fantastic! She came to our home everyday to take care of our two cats while we were away. She sent pictures of each visit and was very responsive. Definitely using her for all our pet care needs!

Profile image
Huston H.
Sitter Profile Image: Emilee A.
Verified Enhanced Background Check
Emilee A.
from
$15
per visit
15 years of experience
Annapolis, MD, 21401

About: I’ve taken care of dogs of multiple sizes and ages. I grew up with dogs, cats, hamsters, a bunny, you name it. I’m the go to family member for when it comes to pet sitting! I work full time between M-F 8:30am to 5:30pm I can always find time on my lunch break or after work or weekends to help out! I can help out with whatever is needed. It doesn’t matter if they need a leash or can free roam. I will take care of them just like you would!

Sitter Profile Image: Dana H.
Verified Enhanced Background Check
Dana H.
from
$30
per visit
5.0 out of 5 stars
22 reviews
5 repeat clients
30 years of experience
Tracys Landing, MD, 20779

Dana was very communicative and instilled a sense of trust that my cat would be well cared for. She was accommodating and flexible with pick up times. My cat always looked happy and comfortable in the pictures she sent throughout his stay!

Profile image
Brigette D.
Sitter Profile Image: ClaRissa M.
Verified Enhanced Background Check
ClaRissa M.
from
$25
per visit
20 years of experience
Deale, MD, 20751

About: I've had dogs since I was a kid an have pet sit for people since I was about 13 years old. In my own life I have had and trained 3 puppies of my own (Tootsie is still currently in the training works). The most dogs I've watched in one household was four, one golden retriever rescue, one Labrador rescue, and two beagle mix rescues. I've worked with several different breeds of dogs over the years including pit bull mixes, pugs, labs, retrievers, beagles, great danes, etc. I currently am taking some time off from working as a Senior Accountant so have availability all day everyday for the most part, when im not spending time with my pets and hubby that is. 🥰 When I do drop in visits I follow what is requested for dogs regarding feeding time/walking habits. I normally talk to them because well idk, I talk to my pets because thats what you do as a pet person. 😂

Sitter Profile Image: Emily B.
Verified Enhanced Background Check
Emily B.
from
$18
per visit
4.9 out of 5 stars
23 reviews
8 repeat clients
4 years of experience
Arnold, MD, 21012

Emily was amazing with my dogs. She was on-time and great at sending photos, especially since she had a late night and early AM request from me. I will definitely use again and highly recommend.

Profile image
Christine A.
Sitter Profile Image: Meghan C.
Verified Enhanced Background Check
Meghan C.
from
$14
per visit
8 years of experience
Edgewater, MD, 21037

About: I’m a lifelong dog lover and have been a veterinary technician for 8 years, so your pup will be in knowledgeable, experienced hands. I’m comfortable with feeding schedules, administering medications, recognizing signs of stress or illness, and handling dogs of all sizes and temperaments. I stay home with my toddler, which means your dog will receive plenty of supervision, structure, and love throughout the day. I also have two very friendly, well-socialized dogs of my own who love making new friends. I treat every dog like part of the family and understand how important it is to have someone you fully trust caring for your pet. Pet care fits seamlessly into my daily routine because I’m home full-time and already structured around consistent schedules. Our days include regular potty breaks, walks, playtime, and rest periods, so adding another pup into that rhythm is easy and intentional. I plan my day around the dogs’ needs — whether that’s supervised outdoor time, enrichment activities, or quiet crate breaks — making sure each pet feels comfortable, safe, and included. Because I’m home, your dog will never be left alone for long periods and will always have attentive, hands-on care. I have a fenced yard for free roaming with my dogs or play time. I also have space for crates if you dog needs to be crated during the night or any specific time.

Sitter Profile Image: Lillymae K.
Verified Enhanced Background Check
Lillymae K.
from
$30
per visit
3 years of experience
Edgewater, MD, 21037

About: As I have had a love for animals for as long as I can remember I’m also a veterinary technician in the Edgewater/Annapolis area and can provide services for you and your pet as needed!! Im currently in college online for Veterinary medicine as i wish to go further in my medical career so I have plenty of time to give your furry friends playtime, snuggles and the proper care I treat every pet as I would my own, with love, care and respect. No animal will be unloved ,unhappy or hungry if left with me!

Sitter Profile Image: Laughlin M.
Verified Enhanced Background Check
Laughlin M.
from
$20
per visit
23 years of experience
Annapolis, MD, 21401

About: I've had dogs my entire life and couldn't imagine life without them. I have dog sat for a few friends as well. I'm an active person, so I would love to take them on walks as long as it's a safe area. I don't have pets here, so I would love to hang out with yours. I work in college athletics, but I love animals and want to spend time with them which is why I want to do this and make a little extra money. My hours are 8:30-6:30 depending on the day and week message me and I will try to make it work! I show them so much love, but I respect their space and their personality. I think it's good to be firm with them, especially depending on how the owner is training them. But the silly moments are always a blast

Sitter Profile Image: Lena M.
Verified Background Check
Lena M.
from
$38
per visit
4.9 out of 5 stars
23 reviews
7 repeat clients
18 years of experience
Edgewater, MD, 21037

About: Hi there! My name is Lena, I'm 38 years old, and have been pet sitting professionally on and off for the last eighteen years. I started officially petsitting out in San Francisco and after moving back east, I professionally pet sat for a local company in the DC area for two years. I have experience in taking care of dogs, cats, rabbits, birds, turtles, guinea pigs, chickens, ducks, and pigs. I love animals and enjoy taking care of them, so your pet will be in very safe and capable hands! My wife, who also works remotely full time helps me on occasion with taking care of your pets. You can check out her Rover profile at: https://www.rover.com/sit/sheiip87322 We guarantee that your pet will always be taken care of no matter what! I require meet and greets before confirming bookings with new clients. This is so we can both make sure that we’re a good fit, so please keep this in mind when choosing me as your sitter and allow sufficient time for this. I will not take new clients without meet and greets! *Pictures are of my cats and some of my dog walking and petsitting clients. I currently work as a freelance videographer/photographer and live in Edgewater. I have a very flexible schedule and mostly work remotely. I currently have three cats, so I’m used to having fur babies by my side 24/7. At the moment, I’m not accepting boarding clients. When I do stay at your home, I follow whatever routine your pet is used to. I know animals tend to stick to routines and try to be mindful of their daily schedules.

Sitter Profile Image: Rebecca W.
Verified Enhanced Background Check
Rebecca W.
from
$15
per visit
5.0 out of 5 stars
3 reviews
10 years of experience
North Beach, MD, 20714

I have used Rebecca "Chloe" for 3 drop-in visits recently. I appreciate her ability to navigate my old man cat, who can be very antisocial at times. I also appreciate her updates and photos that are sent to keep me updated! I would highly recommend Chloe for your pet care needs.

Profile image
Wanda R.
Sitter Profile Image: Amanda D.
Verified Enhanced Background Check
Amanda D.
from
$30
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
30 years of experience
North Beach, MD, 20714

About: Promo Code for $20 off first time booking for Pet Owners that it is their first time using Rover- AMANDD61392 Friends and Family call me the animal whisperer. I have had a dog/dogs my whole life. I have taken care of dogs from brand new puppies, to babies that were at the end of their life. Someone trusting you with their fur babies is a big compliment that I take seriously. I'm currently not working full time away from home, so for any boardings that are on week days or weekends, you and your fur babies are good to go. I do have one small dog at home BUT, if you prefer your dogs to be alone while here, my dog is easily brought to his grandparents house:), which they are always happy about. I will update when my work schedule changes. I have a fenced yard (tall privacy wooden fence with sliding deadbolt), and can easily crate dogs if needed. Any animals would have free range of the house and the yard. Your babies are my babies while I am taking care of them.

Sitter Profile Image: Jessica S.
Verified Enhanced Background Check
Jessica S.
from
$20
per visit
4.8 out of 5 stars
12 reviews
4 repeat clients
9 years of experience
Owings, MD, 20736

Jessica took great care of our pup while we were out of town! She's very communicative and great with dogs. I will definitely be using her again!

Profile image
Mallory L.
Sitter Profile Image: Sally D.
Verified Enhanced Background Check
Sally D.
from
$30
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
26 years of experience
Edgewater, MD, 21037

About: I will treat your pet as my own with care, welcoming hugs, and one on one attention. I’m not in the position to have a pet right now but find much joy from being with animals. I’ve had both small and large dogs. I have experience providing dogs with medications as both of my previous dogs needed multiple medications in their older years. I’ve lived with my partner’s cat for a few years and enjoy cats. However, I have less experience with higher needs cat care. I’m open to cat care though. I once watched 10 cats and a goose during grad school. I would go into the house several times a day to change litter and play with the cats and goose. I’m currently work part time three days a week. This allows me to provide individual attention and spend quality time with the pets I care for. I integrate my visitor pets into everything I do. I will primarily walk your pet but I do have a small fenced yard (20x7). The yard has payers and some a small flower bed/dirt area. It is connected to my work area and I can watch your pet in the yard should fresh air breaks be needed. I would not leave your animal in the yard alone as I think that not okay. If I am inside, they will be inside. I have experience crating pets should that be preferred. However, I’m fine with pet’s being able to roam my home.

1 / 1
View more sitters

Shady Side dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Remy loves his daily visits from Samantha! She is so sweet and makes Remy feel extremely comfortable. We are lucky to have her as our sitter! If you are looking for a pet sitter, we highly recommend!!!!

Profile image
Tyler C.
Drop-In Visits
5.0 out of 5 stars

Once again, Sarah was the best! She sent lots of updates and was so sweet with our River girl. So happy to have her close by when we need help!

Profile image
Cassie W.
Drop-In Visits
5.0 out of 5 stars

Wenda did an excellent job taking care for our pets in our home with twice a day visits. She became their new best friend! She took care of all of their needs as we asked.

Profile image
Janice B.
Drop-In Visits
5.0 out of 5 stars

Chasity is always amazing. She takes such good care of our dos and always plays with our cat even though we don’t even ask for her to care for her. She sends lots of pics and always goes the extra mile. We really appreciate her.

Profile image
Mari H.
Drop-In Visits
5.0 out of 5 stars

Ashley was great with the pups again! She kept us updated on her drop in visits and sent photos. We amd the pups look forward to her taking care of them in the future.

Profile image
Victoria
Drop-In Visits
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!

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.

Dog Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Shady Side dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

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

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.

Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Shady Side.

Rover makes it easy to find Shady Side dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

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

Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.