House Sitting Shady Side
Find a loving house sitter to watch over your pets and your home.
Over 6 pet parents in Shady Side have booked house sitting
Shady Side, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: Hi! I’m Renee — a lifelong animal lover who’s been caring for pets since I was a kid. I’m experienced with feeding, walking, playtime, and making sure every pet gets the love and attention they deserve. I’ve also cared for pets through house sitting for friends, including homes with multiple dogs and cats. I’m comfortable managing different personalities, routines, and making sure each pet gets the attention they need I currently work full-time in Annapolis Monday through Friday from 7:45 AM to 4:15 PM. I’m available for walks, drop-in visits, and care in the Annapolis area after 4:15 PM. I live in North Beach and typically arrive back around 5:00–5:30 PM, so I’m also available for evening care in that area. I am generally available throughout the week and weekends, with the exception of Wednesdays and Thursdays in the evenings due to a part-time job. I have reliable transportation and am happy to travel between Annapolis and North Beach. On weekends, I have open availability for walks, drop-ins, house sitting, or extended care. I’m also available for house sitting during the week, with the understanding that I’ll be at work during daytime hours (7:45 AM–4:15 PM), and unavailable Wednesday and Thursday evenings. I make sure pets are fed on schedule, get plenty of walks and playtime, and feel happy and comfortable. I’m also happy to give baths and trim nails if requested. I’ll always keep you updated and make sure your pet feels safe, loved, and well cared for while you’re away.
“Courtney was great! We felt very comfortable being away knowing that our pets were getting so much love and attention. We had clear and frequent communications and a plenty of pictures confirming all the good things happening. We'd (and our critters) would be very happy to see Courtney again.”
About: Hi guys! My name is Emily, I’m a 27 year old who loves animals. I really like to read, go to concerts with my friends, and spend time with my family. I’ve been house sitting and pup sitting for over 10 years now. My availability is very open at the moment considering I’m doing school virtually. Please feel free to contact me anytime for all of your dog, cat, fish, bird, turtle, hamster, cow, horse, etc needs! I also have a huge vegetable/flower garden so have plenty of experience with that if necessary. Look forward to hearing from you! I currently am working part time and doing school virtually so I have a very flexible schedule that would allow me plenty of time to help care for your babies! I’ve had 10 plus years experience with pet sitting so have had to handle many different situations that have made me a better sitter. I’m prepared for anything and love these pets as my own!
About: Caring, dependable, and eager to earn your trust. I’m attentive, responsible, and truly love providing safe, loving care. New to this service, but have been taking care of family pets for years. I'm available for pet walks or drop-in visits anytime after 4 PM on weekdays and most of the day on weekends. Whether it's an evening stroll or a quick check-in, I'm here to help! I provide respectful and reliable care by closely following the owner’s instructions. During walks or visits, I make sure pets feel safe, happy, and comfortable. I stick to their routine, give them attention and affection, and always keep their owners informed of any eventuality.
About: I have taken care of dogs for over 20 years, including having my own dogs. I am a travel nurse and I usually volunteer to walk dogs at shelters when I’m on assignment. I work full time as a nurse, but I only work 3 days a week. My schedule is usually free on the 4 days a week that I’m off of work. I am currently living in an apartment while on assignment in North Beach, Md, so I can only take car of pets in your own home.
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
About: Hi! I'm a lifelong dog lover who grew up with 3 dogs, and regularly pet sit for friends and family before deciding to make it official. Friends often call me an animal whisperer because even shy or nervous pets tend to warm up to me quickly. I work remotely, and am very active, so I have a flexible schedule and can give your pet plenty of attention (and activity)! I work remotely and have very flexible hours, so your pet will have plenty of time, walking, snuggling, and being active. I also attend run clubs where pets are allowed, so if your fur baby is social, I’ll happily take them! I have a backyard, and live in a community with plenty areas to walk and sniff. Pets are welcome to be on furniture and in bed! I’m an excellent communicator, and will work collaboratively with you to determine the best care plan for your pet.
About: My goal is to take your spot as your pet’s best friend .. uhh I mean provide excellent care and service whenever duty calls :) My schedule is fairly flexible, and I am generally available each afternoon. I am sure that we can work out a reasonable time to get your pets situated! Owners rules are law. Whether it’s playtime, supper, potty time, etc I’ve got you covered. I am unable to provide services in my home at this time.
“Faith is a fantastic petsitter! We were out of town for 8 days and didn't have to worry about a thing back home. It was wonderful to find a caring person who could spend this much time with our pets. Boarding can be so stressful on our big dogs, but Faith was able to do overnights and wasn't intimidated by our Dobermans in the slightest. She was a perfect fit, and we were so blessed to find her on Rover. It was our first experience with the service platform being new to Southern Maryland, but we will be repeat customers for sure.”
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.
“Jessica was very responsible and extremely caring and hands-on with our senior cat (and hamster too). She did several check-ins a day and spent many overnights which requires a high level of trust and Jessica went above and beyond. She communicated constantly with updates, pictures and videos (seriously, top-notch communication) and she left our home in perfect condition. Our animals took right to her and I am grateful to have found someone so kind and committed.”
“Anh was amazing with Pico. She jumped in last minute and handled everything so thoughtfully - including some unexpected tummy issues and his occasional puppy chaos. She kept me fully updated the whole time and sent lots of great photos, which I really appreciated. It made such a difference being able to see how he was doing. Pico is used to being with me all the time, so social interaction is really important for him. Anh adjusted to Pico’s needs and routine and also made him part of hers - giving him so much extra love and attention. You can’t always guarantee that level of care when you’re away, and I’m so grateful I never had to worry. I would absolutely recommend Anh to anyone without hesitation!”
About: I’ve cared for my own dog for the past 3 years, giving me daily, real‑world experience with feeding routines, walks, training, and managing anxiety. I’m patient, attentive, and committed to keeping pets safe, comfortable, and happy while their people are away. I work during the day, but I’m available for pet care in the afternoons, evenings, weekends, and on most holidays. I make time to ensure every pet gets plenty of attention, exercise, playtime, bathroom breaks, and companionship while they’re in my care. I’ve owned my own dog for the past three years and have experience living with two dogs and three cats, so I’m comfortable caring for pets with different personalities and needs. I prioritize their safety by following your care instructions, maintaining their feeding and potty schedules, keeping a clean and secure environment, and providing plenty of supervision, affection, and exercise. I’ll also keep you updated with photos and messages so you know your pet is happy and well cared for.
About: I’ve been a huge animal lover my entire life! I grew up with a family dog for 14 years, and for the last 2 years, I've been a cat parent to my own kitty, so I understand both dog and cat personalities. I’ve been the sitter for my friends and family whenever they go out of town. Plus, giving back to animals is super important to me; I've been volunteering at animal shelters since high school and still do today. Whether your fur baby needs lots of playtime, long walks, or just some cozy cuddles, I'll treat your baby like my own! My work gives me flexibility throughout the week. From Monday-Friday, I normally work in the office from 12-6pm. So, I am available for early morning and late morning walks before I leave, and I am back in time for dinner and evening care. My weekends are pretty open, so I have plenty of time for extended visits and walks. I follow all the rules and instructions you give me for both your house and your pet's care. Whether your pet has a specific feeding schedule, strict house boundaries, or a precise medication routine, I will make sure everything is done exactly the way you want it. Your home and your pet’s comfort and safety are my top priorities while you are away
The median cost per night for house sitting in Shady Side is $50
Pet parents share their Rover experiences - Shady Side
We feel so incredibly lucky to have Jennifer to look after our puppies. She took such great care of them. They are older and have some health issues and I fully trusted her to treat them as her own. She was attentive and very responsive, sharing photos and updates often. I could not be happier and would highly recommend her!
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.
Meet local sitters who will treat your pets like family
1. Search
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Select a filter and find qualifying Shady Side sitters!Sitters in Shady Side average 4 repeat house sitting clients
FAQs for House Sitting - Shady Side
Frequently asked questions about Rover
The average cost for House Sitting in Shady Side on Rover is $36.08 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .
As of July 2026, there are 8,682 sitters on Rover offering House Sitting across Shady Side. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Shady Side walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Shady Side maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
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!
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.
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 .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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.
Yes, you can find sitters who have experience with handling special pet needs in Shady Side. On Rover:
- 92% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 97% 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.
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