Dog Sitting in Shady Side

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

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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.

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Sitter Profile Image: William B.
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William B.
from
$20
per visit
15 years of experience
Riva, MD, 21140

About: I provide calm, attentive, and reliable care tailored to each pet’s personality and routine. I have experience with dogs of all sizes and temperaments, including energetic puppies, senior dogs, and pets that need extra patience or reassurance. I’m comfortable with feeding schedules, administering basic medications, reinforcing training routines, and making sure pets get plenty of exercise, playtime, and affection. What sets me apart is my focus on consistency and communication. I keep owners updated with photos and messages, pay close attention to details, and make sure pets feel safe and comfortable while you’re away. Whether your pet loves long walks, quiet companionship, or structured routines, I adapt my care to match their needs and help reduce stress for both pets and owners. I am currently a junior at covenant college studying biology. I plan on applying to med school and becoming a doctor in a field where I can be an asset in medicine. I am currently a Vet Tech at Great Scottie Veterinary Clinic. I am a lover of animals and will do all that I can to provide the joy and satisfaction your pet needs! I take safety and trust seriously when caring for pets in my home or a client’s home. I always follow the owner’s instructions for feeding, walks, and routines so pets feel comfortable and secure. I make sure pets are supervised, kept in safe areas, and never put in situations that could be unsafe. In my home, I keep a clean and calm environment where pets have fresh water, regular bathroom breaks, and plenty of attention. I always use leashes on walks and make sure dogs are secure when outside. In a client’s home, I respect their space and try to keep the pet’s routine the same as usual. I also provide updates and photos so owners know their pet is safe and happy. My goal is to make pets feel comfortable and cared for while giving owners peace of mind.

Sitter Profile Image: Milanni B.
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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.

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Matthew G.
Sitter Profile Image: Alexandra R.
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Alexandra R.
from
$15
per visit
10 years of experience
Annapolis, MD, 21403

About: I’ve owned 5 dogs through my life & have always loved caring for others’ pets as well. Being around animals is my happy place 🥰 I work part time on a charter boat & would love something besides gardening to keep me busy during the week. Also trying to save up for an Rv to travel I’ve been around all types of different kinds of dogs and know how to deal with different personalities and needs ❤️ from weeks old to golden days I love them all

Sitter Profile Image: Bianca T.
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Bianca T.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
140 reviews
82 repeat clients
15 years of experience
Sunderland, MD, 20689

Bianca did a great job with all of our pets!

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Charlie M.
Sitter Profile Image: Amanda J.
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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: Ella M.
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Ella M.
from
$25
per visit
2 years of experience
Annapolis, MD, 21401

About: As a dedicated dog walker and in-home pet sitter with over two years of experience, I know how important it is to find someone you can truly trust with your pet. I care for every dog (and cat!) as if they were my own — with patience, love, and attention to their unique needs and routines. What You Can Expect: ✅ Safe, fun, and tailored walks ✅ Home visits that follow your pet’s schedule ✅ Clean water, food, meds (if needed), and lots of affection ✅ Daily photo updates and messages so you never have to wonder how things are going ✅ Respect for your home and your pet’s space I’m trained in basic pet first aid and always check collars, leashes, and gates before heading out. Whether it’s a quiet walk or an energy-burning play session, your pet's safety and happiness are always my top priority. Let’s schedule a meet-and-greet! I’d love to learn more about your pet and how I can help make your time away stress-free for both of you. 🐶🐾 Pet care fits naturally into my daily routine because of how flexible and rewarding it is. Since I set my own schedule, I can book pet care clients around my part-time job shifts and study blocks, which helps me stay balanced and productive. Walking dogs gives me a much-needed mental reset from screen time and studying, and it keeps me active throughout the day. It’s also a great way to supplement my income without taking on another traditional job. Most of all, spending time with animals brings me a lot of joy and motivation — it breaks up long study days and reminds me why I love what I do Whether you’re at work or away for a few days, I provide reliable, in-home care that keeps your pets safe, happy, and stress-free in their familiar environment. From daily walks to feeding, playtime, and medication routines, I tailor every visit to your pet’s unique needs. 🔐 Safety & Professionalism Equipped for pet first aid always carrying a kit Detailed home-entry and security protocols Leash and harness checks before every walk Weather-conscious and always alert to potential hazards Respectful of your home, your pets, and your time 📸 Peace of Mind After each visit, you’ll receive a photo and short update so you know how your furry friend is doing — because trust is built on communication

Sitter Profile Image: Chris G.
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Chris G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
18 reviews
8 repeat clients
30 years of experience
Dunkirk, MD, 20754

About: I’ve had my knee replaced which has slowed me down a tad but also allows me be to home all the time. We recently lost our old boy (dog of 12 years) and while my cats have helped me to survive, I have so much more love to give! For now I want to spend time with others’ dogs to help fill the whole in my heart. I genuinely want to make every animal a friend of mine! I will always lead with love, care and respect. I work from home already which is usually stuff I take care of in the evenings anyway but I have the time, love and space to accommodate your furry family members. We have three lovable indoor cats. Two will stay away mostly and one will greet you at the door with friendly meows. We will spend the whole time snuggling on the couch or running around in our yard.

Sitter Profile Image: Taylor P.
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Taylor P.
from
$15
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Upper Marlboro, MD, 20774

About: With 15 years of dedicated pet care under my belt, I've honed a deep understanding of both canine and feline needs. From playful puppies to senior sweethearts—and from curious kittens to laid-back lap cats—I’ve cared for dogs and cats of all breeds, ages, and personalities. As a dog owner myself, I’ve also supported a pup with aggression issues through his stressful times, giving me valuable experience in patience, awareness, and calm handling. My background includes administering medications, maintaining clean and comfortable litter boxes, and providing specialized care to ensure every pet feels safe, loved, and understood. Trust me to bring expertise and genuine affection to every walk, cuddle, and visit with your furry family members. Pet care seamlessly fits into my daily routine, with availability after my 8-4 job Monday through Friday, and all day on weekends. I'm dedicated to providing consistent, reliable care that complements your schedule and ensures your pets are happy and well-looked after. When caring for pets in their home, I prioritize creating a safe, comfortable, and stress-free environment. I follow your specific instructions for feeding, medication, and exercise, ensuring consistency with their regular routine. I also provide plenty of love, attention, and playtime, maintaining open communication with you to keep you updated on your pet's well-being.

Sitter Profile Image: Kylie R.
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Kylie R.
from
$20
per visit
4 years of experience
Edgewater, MD, 21037

About: I have helped take care of my dog for the past 5 years, along with occasionally taking care of and walking friends and families pets for years! I’m recently graduated from Jacksonville University, and am living with some family in Edgewater this summer! While I plan for grad school, I’m nannying, but am looking for some extra money and thought taking care of some pups would be perfect! I’m very flexible and am available most weekdays and weekends this summer. I will not be able to boards your pups, but am an extremely responsible 22 year old, who will play with and give your pups all the love!

Sitter Profile Image: Rebecca W.
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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.

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Wanda R.
Sitter Profile Image: Kevin W.
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Kevin W.
from
$14
per visit
5.0 out of 5 stars
3 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: 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: Laura L.
Verified Enhanced Background Check
Laura L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
18 reviews
7 repeat clients
10 years of experience
Chesapeake Beach, MD, 20732

Laura was fantastic when I went out of town for the holidays. She was very communicative and took excellent care of our cat. I would highly recommend!

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Chelse H.
Sitter Profile Image: Kristina B.
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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!

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Huston H.
Sitter Profile Image: ClaRissa M.
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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: Elizabeth "Phoenix" P.
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Elizabeth "Phoenix" P.
from
$20
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
20 years of experience
Lothian, MD, 20711

Thanks Phoenix. Reliable, got the job done well and a caring person to trust with my cat visits. I appreciate you watching my kitty kid and will be in contact again for your great services ASAP.

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J C.
Sitter Profile Image: Anna D.
Verified Enhanced Background Check
Anna D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
5 years of experience
Owings, MD, 20736

About: With years of experience caring for dogs, I stand out as a pet sitter due to my ability to also look after my clients’ plants/garden from time-to-time. My lifelong passion for animals includes providing special care for young and senior dogs, ensuring their health and happiness. My current schedule varies, but I typically work 7-hour shifts on Sundays and Mondays. On the these dates, I can manage pet care for all dogs that have a wait period to be let out 4-8 hrs. If necessary, I have the flexibility to call off work to ensure your pets are well taken care of. From Tuesday to Saturday, I have open availability, allowing me to dedicate ample time to pet care activities, such as walks, feeding, and playtime. This arrangement helps me balance work commitments while ensuring your pets receiving the attention and care they need. In caring for pets in my clients’ homes, I prioritize safety, trust, and a comfortable environment. I ensure to follow detailed instructions provided by the client to meet the specific needs of their dog. For instance, if a dog is anxious during thunderstorms, I am proactive in reaching out via call or text to discuss calming strategies. Additionally, I always clarify any boundaries regarding what I can handle or access in the home and to build a stronger rapport, I will arrange pre-sitting meetings with clients to better understand their preferences and to bond with their dog(s).

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: 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!

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Brigette D.
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.

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Shady Side dog parents share their Rover experiences

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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!!!!

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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!

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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.

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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.

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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.

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Victoria
Drop-In Visits
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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.