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 90
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: Faith M.
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Faith M.
from
$20
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!

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Jacqueline A.
Sitter Profile Image: Aleah J.
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Aleah J.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
12 reviews
4 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: 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: 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 and cat 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: Laura L.
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Laura L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
19 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: 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
Annapolis, MD, 21403

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: 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: 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: Isabella G.
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Isabella G.
from
$18
per visit
8 years of experience
Chesapeake Beach, MD, 20732

About: I grew up walking dogs at the humane society and have had a dog all my life. I now have had my dog, Lou, for 7 years. He is a huge German Sheppard mix, he’s full of anxiety, but communicative in his cues to me and has taught me a lot. My friends have always had dogs and I loved being able to take care of them while they were away! I am currently working part time, so I have plenty of time to care for your fur babies! I have an incredibly flexible schedule and can dedicate as much time as needed. I am here for what you need! I can walk, feed, watch, and hangout with your dog. I love taking walks and meeting new fur babies, their needs are my priority

Sitter Profile Image: Kaylee H.
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Kaylee H.
from
$16
per visit
4 years of experience
Lothian, MD, 20711

About: I have over 3 years of professional pet care experience through my roles at PetSmart, where I cared for pets, assisted pet parents, monitored animal health and behavior, and maintained high standards of safety and cleanliness. I have experience with dogs of all sizes, breeds, and temperaments and understand the importance of providing reliable, loving care. Whether your pet needs walks, playtime, feeding, medication reminders, or companionship, I will treat them like my own and keep you updated while you’re away. Pet care fits naturally into my daily routine. I have a flexible schedule and can provide consistent care, whether that’s feeding, playtime, walks, litter box cleaning, medication reminders, or simply keeping your pet company. I understand that every pet has different needs and will do my best to follow their normal routine to help them feel comfortable and stress-free while you’re away. Your pet’s safety and comfort are my top priorities. With over 3 years of experience working at PetSmart, I’m familiar with a variety of pet personalities and behaviors. I carefully follow all care instructions, provide regular updates, and take the time to build trust with each pet. Whether caring for your pet in your home or during drop-in visits, I’ll treat them with the same love, patience, and attention that I give my own cat, Luna.

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: 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: 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: Dana H.
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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: 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: Marilyn B.
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Marilyn B.
from
$20
per visit
3 years of experience
Lothian, MD, 20711

About: I provide dependable, attentive care for both dogs and cats, making sure each pet feels safe and comfortable while you’re away. I’m experienced with different personalities, from energetic and playful to calm or shy, and I adjust my care to fit their needs. I handle feeding, walks, litter cleaning, and playtime while sticking closely to your pet’s routine. I’m responsible, observant, and genuinely enjoy caring for animals, which helps me build trust quickly with every pet I meet. I’m available every day from 10am to 5pm, which allows me to provide consistent and reliable care for your pets. I can easily fit into your pet’s routine for walks, feeding, playtime, and check-ins during the day. I’m dependable, flexible within those hours, and focused on making sure your pet feels safe, comfortable, and well cared for while you’re away. priorities. I make sure to follow your instructions closely and keep your pet in a secure, clean, and calm environment. I pay attention to behavior, routines, and any specific needs to reduce stress and keep them happy. In your home, I respect your space while providing attentive, reliable care. I’m patient, responsible, and focused on building trust with both you and your pet.

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: Antavia G.
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Antavia G.
from
$15
per visit
6 years of experience
Upper Marlboro, MD, 20772

About: I have always had a deep love for animals and understand how important it is to find someone you can truly trust with your pet. As a pet parent myself, I know that pets are family, and they deserve care that feels safe, loving, and personalized. My experience includes caring for dogs in a home environment, supporting daily routines, providing walks, feeding, playtime, potty breaks, companionship, and giving pets the patience and attention they need while their owners are away. I pay close attention to each pet’s personality, comfort level, habits, and care instructions so their routine feels as familiar and stress-free as possible. I am also the founder of Lovebugs & Co. Pet Care, a boutique pet care service created for pet parents who want reliable, thoughtful, and loving care. My approach is calm, attentive, and detail-oriented. I believe in clear communication, regular updates, and treating every pet with the same care and affection I would want for my own. Pet care fits very well into my daily routine. I currently work from home in a flexible remote environment, which allows me to be present, attentive, and available throughout the day. This makes it easy for me to provide regular potty breaks, walks, meals, playtime, companionship, and a calm home environment. Because my schedule is flexible, I can build pet care around each pet’s normal routine and make sure they receive consistent attention and care while their family is away. Safety, trust, and comfort are very important to me. For pets cared for in my home, I provide a calm, cozy, and supervised environment where they can feel comfortable and loved. I follow each pet’s routine as closely as possible, including feeding schedules, potty breaks, walks, playtime, rest time, medication instructions if needed, and any special care notes provided by the pet parent. Before boarding, I like to learn about each pet’s personality, behavior, comfort level, triggers, and routine so I can make sure my home is a good fit. I keep the environment clean, peaceful, and secure, and I provide regular updates and photos so pet parents feel confident while they are away. For walks and drop-in visits in a client’s home, I treat the home with care and respect. I make sure pets have fresh water, food if requested, potty breaks, litter box care if needed, playtime, companionship, and a quick check of their overall comfort and behavior. I also make sure doors, gates, crates, and leashes are secure before leaving. My goal is always to provide dependable, loving care while keeping pets safe, comfortable, and on a routine that feels familiar to them.

Sitter Profile Image: Alayna B.
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Alayna B.
from
$25
per visit
5.0 out of 5 stars
6 reviews
12 years of experience
Friendship, MD, 20758

About: Hi, I’m Alayna I’m 23 I’ve been taking care of dogs/cats since I was 10. I’ve worked at shelters in my free time helping out dog walking, cleaning the crates. I love watching senior dogs and giving them all the lovings, I love all dogs small, big, medium sized. My schedule is very flexible, I’m a business owner I make my own schedule. I’m available for just about everything else . Drop ins, walks. Overnights. We have a fenced in play pin and I have a dog frenchies one is named Tucker & Finn. They love to play and meet new friends.

Sitter Profile Image: Alexandria F.
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Alexandria F.
from
$25
per visit
5.0 out of 5 stars
3 reviews
30 years of experience
Upper Marlboro, MD, 20716

Alexandria was a great sitter for our pup. She provided excellent care for the 4 days we were gone. I would highly recommend her to watch your furry friend.

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Bradley P.
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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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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • 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?

  • 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 sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

How Rover works

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet & Greet

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

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 $13.32 per visit (as of July 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 July 2026, there are 12,921 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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