House Sitting Shady Side
Find a loving house sitter to watch over your pets and your home.
Over 10 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.
“Having Ev take care of our dogs provided great peace of mind! Ev did a great job - and clearly loves animals - and the dogs barely missed us (which, if you knew our dogs, you'd know that is extremely rare!). Highly recommend.”
About: While most of my experience pertains to cats, I also grew up with several dogs over my life! Most of them were larger breeds - labs, huskies, malamutes, dobermans and one carolina dog. I did train the malamute to pull me on my bike when I was a teenager, and taught the doberman basic obedience and good manners. I work from home/freelance, so my schedule is very open! In fact, I often find myself needing to get the heck out of my house! My own home has a fenced in yard (4ft high chain link, so if your pet is a jumper, this might not be a good fit!) and I also own my home, so there'll be no issues with landlords or whatnot. I do also have three cats, so cat friendly pets are preferred if you're looking to board. If I am visiting or staying at your home, things will be kept neat and clean, and any and all instructions will be followed (same for if you board with me!)
About: I have many years of hands on experience caring for dogs, cats, and other animals of all breeds, sizes, ages, and personalities. I’ve worked in animal shelters and have been working at Beechnut Kennels for the past 3 years, caring for pets daily through feeding, exercise, playgroups, cleaning, and monitoring their health and behavior. I also foster cats and kittens and have experience with shy, fearful, reactive, and feral animals. I’m comfortable administering medications and using Fear Free handling techniques to keep pets as comfortable and stress-free as possible. I truly love animals and treat every pet in my care like they’re my own! I currently work part-time at Beechnut Kennels, which gives me flexibility to provide dependable pet care throughout the week. I offer drop-in visits, walks, and overnight care, and I’ll do my best to accommodate your pet’s routine. I understand the importance of consistency and will always keep you updated with photos and messages while you’re away. Your pet’s safety and comfort are my top priorities. With years of experience working in shelters and at Beechnut Kennels, I’m comfortable caring for pets of all ages, sizes, temperaments, and medical needs. I have experience using Fear Free handling techniques, administering oral medications, and caring for shy, fearful, and senior pets. I’ll always follow your pet’s routine and instructions closely to help them feel safe, relaxed, and loved while you’re away. Communication is important to me, so you can expect regular updates and pictures during every visit.
“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: Growing up, we always had some kind of a pet, from turtles to baby chicks, puppies to kittens! We used to foster kittens as well growing up & since living on my own, I've fostered dogs and pet-sat any time we could. Love all animals & trying to make them feel happy & comfortable :) I work 7:30-2:30 or 8-3 in DC but after work & on the weekends, I'm always willing to help in any way they I can! We have a dog of our own, medium in size, who loves making new friends and two kids that adore giving love whenever they can.
“Christianna was so great with my babies. We have a usual dog sitter but he was unavailable due to a family issue and I was so nervous to try someone new but knowing she has animals of her own and has been doing this for so long, really helped ease my anxiety. She came to do a meet and greet and right away they loved her. She sent pictures and updates the whole time we were gone and they looked so relaxed with her!”
About: I have been walking and sitting dogs for over 20 years, starting at age 11 when I realized dogs just made sense to me. I have owned hounds my whole life and currently share my home with a spirited beagle/jack russell mix named Tate who keeps me well-practiced with high-energy breeds. I recently lost our beloved 11-year-old foxhound mix Juniper, a gentle 70-pound soul who reminded me daily why this work matters. I am a firm believer in Cesar Millan's calm, assertive approach to dog handling. Dogs respond to confident, consistent leadership, and I bring that to every walk and every stay. I am comfortable with all breeds, large and small, and experienced administering medications and hands-on therapy when needed. I work from home in central Annapolis, which means flexible scheduling and plenty of attention for your dog during the day. Your pup is a member of your family and I always treat them like a member of my own. I own a design firm that I run out of my home. My work varies as a creative from video work to graphic design and more but it all comes from my home office located right next to my dog's food and water bowls (my hound dog Tate is currently asleep at my feet- exactly where he loves to be, and right where I love to have him). My workdays typically start around 7am and I work through the early afternoon, occasionally in the evenings. Though I have a full office setup, I also have a laptop that travels with me during house/dog sitting sessions if I need to be away for an extended period of time. As my work is on the creative spectrum, I can always adapt my schedule to fit around yours (and your pup's). Whether it's daily walks or stays with your dog, you can rest assured that they will be looked after with love, care, and the attention they deserve. I live in an apartment in Annapolis so we don't have a fenced in yard. Instead, I take my boy out in the neighborhood on short and extended walks and in the community dog park. Sniff spots and local trails are always on our schedule as our dog is high-energy so he thrives on long walks with lots of smells. Depending on your dog's needs and routine, I'm happy to take them on long walks in and around your neighborhood and parks they're comfortable with, or just playing with them in your own backyard. I'm also open to taking them further out to nature hikes and trails as long as you're comfortable with that. I tend to have Blue Buffalo, Newman's Own, and Charlee Bear treats at the ready (but of course that's up to your discretion) for good dogs and I always adhere to any diet or medication requirements to ensure a happy and healthy experience. I treat your dog like I treat my own and I've always had a great experience with every breed and personality.
“Lena is absolutely awesome. We are so grateful to have found Lena and she did a wonderful job pet sitting and house sitting. Her communication is great, and she kept us posted with thoughtful updates. We were extremely comfortable and confident while out of the country.”
“Vanessa was fantastic to work with. She arrived promptly, kept me updated on my pup Morgan with pics and notes. I’m felt very comfortable having Vanessa house/dog sit. Would highly recommend here. Patty”
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.
About: Growing up in a animal filled household, taking care of pets has always been something natural to me, I’m able to watch any dog you have I’m almost always readily available and would love to give pets some company while their owners are away Im currently taking care of my grandparents after surgery, and don’t have too much on my schedule until college in spring, which leaves plenty of time for me to stop by and look after pets I’ve been around animals practically since I was born, and I’ve been watching them on my own since I was 13, I can work with almost any breed of dog, as well as cats
About: When I was young I was entrusted with the keys to several of my neighbors homes and took care of dogs, cats, and even fish. I have owned serveral dogs in my lifetime and enjoy taking care of cats as well as other pets! I understand that every pet is different and many have very specific needs, therefore, I am prepared to receive instruction and tailor my care to each pet accordingly to make sure everyone stays happy and healthy. I currently walk dogs and overnight sit for my neighbors and friends but would love to branch out these services for others as well! I currently do not have a full time job, I have an odd job schedule that would always prioritize your pets care above all else. i care for your home as if it is my own!, I am able to water the garden if requested, and i always take the trash out as i leave to assure you come back to a fresh smelling home. doors remain locked when i am not present on the premises, animals will not be left outside unsupervised.
“Brittanny was great with our two dogs - they really loved her. She spent so much time with them and stuck to their normal schedule. We will definitely be booking Brittanny again!”
“Jamie is the best dog sitter! She took such great care of Adam. She was patient with him and got to know him really well. I didn’t stress about him at all when on vacation :) and she took lots and lots of pictures. Also, she left my apartment super clean. Would definitely recommend!”
“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.”
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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2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for house sitting - Shady Side
Select a filter and find qualifying sitters offering house sitting.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 $42.18 per night (as of September 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 September 2026, there are 8,617 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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