Dog Sitting Shady Side

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

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Over 71
pet parents in Shady Side have booked dog sitting

Shady Side, Find top rated dog sitting

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: Snowden C.
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Snowden C.
from
$35
per visit
5.0 out of 5 stars
17 reviews
4 repeat clients
13 years of experience
Edgewater, MD, 21037

Snowden could not have been better for us! She has amazing energy and our dog took right to her. Incredibly respectful of our home & managing while we were away. We'll become regulars :)

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Abigail C.
Sitter Profile Image: Aleah J.
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Aleah J.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
14 reviews
5 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: Ella M.
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Ella M.
from
$25
per visit
5.0 out of 5 stars
1 review
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: Kevin W.
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Kevin W.
from
$14
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
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: Jai B.
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Jai B.
from
$10
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
1 year of experience
Bowie, MD, 20716

Jai was very sweet and kind, taking the time to get to know my Laidi. She's very attentive and good at troubleshooting any issue; I recommend her 10/10!

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Jessica C.
Sitter Profile Image: Tosawi L.
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Tosawi L.
from
$15
per visit
5.0 out of 5 stars
3 reviews
5 years of experience
North Beach, MD, 20714

Tosawi was a huge help for us when we were in a pinch. He took care of our 2 babies for 3 days with very attentive drop-in service. He was attentive, commucative and very accommodating. Our cuties are extremely opposite in both physical characteristics and temperament, one being a large pit mix who is very docile and a tiny yorkie pom, who is extremely high energy. Tosawi was able to navigate both personalities with ease. I would definitely use him again.

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Deanna J.
Sitter Profile Image: Savannah P.
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Savannah P.
from
$50
per visit
4 years of experience
Edgewater, MD, 21037

About: I have 4 years of pet experience. I have a 4 year old Maltese and have helped my family with their dogs for many years when they go on vacation. I walk the dogs, feed them, play with them, I do take them on car rides etc to make sure they’re happy and healthy. Dogs say I have a good sense of humor they really warm up to me. I’m currently working as a babysitter part-time so I have lots of time on my hands to help watch the little and big dogs and play with them and watch them for families who are going away. I go to many peoples homes to babysit who have dogs and I treat them like my own. I have have a dog myself and will treat the dog as if it was my own and take it on lots of walks and make sure the water is filled and the food is filled as well and make sure everything is done for their routine.

Sitter Profile Image: Uduak U.
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Uduak U.
from
$20
per visit
5.0 out of 5 stars
14 reviews
5 repeat clients
12 years of experience
Upper Marlboro, MD, 20772

Uduak was wonderful! She was communicative with my husband and I, and very patient with my pup who is not comfortable with new people. Uduak followed instructions to a tee, and also used her discernment in caring for Mozzy (even cleaning up an accident he had without us requesting she do so). 10 out of 10 would recommend. We will definitely be using her services again in the future.

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Loren H.
Sitter Profile Image: Jessica S.
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Jessica S.
from
$20
per visit
4.8 out of 5 stars
12 reviews
5 repeat clients
10 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!

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Mallory L.
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
9 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: Laura L.
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Laura L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
20 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: 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: Avery R.
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Avery R.
from
$20
per visit
5 years of experience
North beach, MD, 20714

About: I have had dogs my entire life. My mom always watched dogs when I was younger and at some points had up to 5 dogs in the house. I have walked dogs over the past few summers. I am reliable, safe, and friendly with pets kinds but especially dogs. I am a current college student and in my time of break I have a pretty clear schedule. I am available everyday during the week and most weekends at this time until I go back to school. I can do anything requested from walking dogs to staying with them for a few hours. I will make sure to abide by your schedule. I can be there when your animals need me.

Sitter Profile Image: Alyssa B.
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Alyssa B.
from
$20
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
10 years of experience
North Beach, MD, 20714

Alyssa did an awesome job caring for my puppies. She was a great communicator and sent great pictures. I requested her pretty last minute but she was very responsive and I would recommend her to anyone!

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Caroline J.
Sitter Profile Image: Lena M.
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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: 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: Alexandra G.
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Alexandra G.
from
$20
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
18 years of experience
Davidsonville, MD, 21035

Alex was fantastic and shared all the updates with our pups. She didn’t hesitate to ask questions when she thought something was off with the pups. We felt very confident that our dogs were in safe hands.

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Alexandria O.
Sitter Profile Image: Meghan C.
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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: Crystal J.
Verified Enhanced Background Check
Crystal J.
from
$20
per visit
1 repeat client
20 years of experience
Dunkirk, MD, 20754

About: I was an owner of a 8yr old Cane Corso who has now passed away from bone cancer. She has had 2 litters whom I cared for. 7 puppies each litter for 8 weeks was such an amazing experience! We have 4 sons and she was always attached to our 3rd son’s hip. We also rescued a beautiful cat, Misaki, who is now 1 1/2. My youngest son begged us for her and she has claimed me. She is the most sweetest thing and loves to cuddle. She follows me everywhere which we should have named her Shadow. If I could bring all the animals into my home I truly would! Myself and my youngest boys ages 16 & 15 would love to care for your animals as we would our own! We now have Briahs grandson Deuce is now 1 1/2 and is huge and a ball of fun! I’m currently a homeschool mom for I’m very flexible. I work part time but I’m available at anytime. I will make sure your babies are well taken care of! I am available three times a day for services and anytime you need your babies needs met. If they need play time we can do that or even just a belly rub after dinner :)

Sitter Profile Image: Elena D.
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Elena D.
from
$40
per visit
5.0 out of 5 stars
12 reviews
6 repeat clients
10 years of experience
Churchton, MD, 20733

We love Elena! This was our second time using her services, and we can’t say enough great things. She is wonderful with our dogs and was willing and able to handle our very energetic puppy. We love having someone we trust in the area!

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Keri V.
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The median cost per visit for dog sitting in Shady Side is $20

Dog parents share their Rover experiences - Shady Side

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!!!!

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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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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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

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

Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - Shady Side

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Sitters in Shady Side average 7
repeat dog sitting clients

FAQs for Drop-In Visits - Shady Side

Frequently asked questions about Rover

The average cost for Dog Sitting in Shady Side on Rover is $16.05 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 12,909 sitters on Rover offering Dog Sitting across Shady Side. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Shady Side stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Shady Side choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Shady Side with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Shady Side. On Rover:

  • 90% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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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