Dog Sitting Leonardtown
Book a Leonardtown dog sitter to watch your dog in your sitter’s home or yours.
Over 80 pet parents in Leonardtown have booked dog sitting
Leonardtown, 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.
“John was fantastic! He kept us updated on what was going on at home and sent us pictures of the pets each day. He made sure the cats and Guiana pig didn’t miss a step in their routine while we were out of town. Fantastic experience! We will use him again.”
About: I have been pet sitting for about 5 years now! With lots of experience with senior dogs and animals in need of more attentive care! I am fully available to housesit along with pets! I work a wonky schedule but the animal or persons baby also comes first! I am fully available 7 days a week! I am much more able to give my upmost priority and attention when staying with the animal in their home. I am not able to host animals at the moment. Not until I move. If that was not going on I would absolutely be able to host.
About: Very experienced 20 plus years dog owner and dog lover! We bread our KCC and now have 2 beautiful small gentle dogs. Your pet is welcome in our home. Or I can visit them in yours. I have two children age 9 and 13 who have had dogs all their lives. Love all dogs and are very good at caring and playing with them! I am a stay at home mum. Originally from Ireland and live in Wildewoods. I have flexibility to cater for your Dogs needs. Communication will be first class to reassure you on your time apart. Large home. My two small dogs will offer company or indeed I can visit your home if your dog prefers solo walks and to stay in familiar surroundings. We have a fenced back garden and live in a quiet neighbourhood.
About: I’ve cared for animals my entire life and truly love being around pets of every size and personality. I’m patient, gentle, and confident with all breeds from small dogs and seniors to high-energy pups and big lovable goofballs. I live with dogs and a cat of my own, so I understand how important routine, comfort, and trust are. I give every pet the same love, attention, and care I give my own. Caring for pets is naturally built into my day because I already have animals of my own. I plan my mornings, afternoons, and evenings around walks, feeding, playtime, and check-ins. I’m very flexible, so I can adjust my schedule to match your pet’s routine and needs Safety and trust come first. In your home, I follow your routines exactly—feeding schedules, walk routes, crate rules, and any house preferences. I always keep doors locked, double-check leashes and harnesses, and never rush a pet. I give each animal a calm, loving environment where they feel safe and understood.
“Thank you so much for taking such great care of my pups. They are my family and knowing you were taking such great care of them while I was away was such a relief! Thank you again!!”
About: I’m already someone who loves being home, going on peaceful walks, and keeping things cozy, so adding a furry friend to the mix just makes everything better. I treat pets like little VIP guests and I make sure they get plenty of attention, affection, and a routine that feels calm and predictable for them. I always try to match whatever your pet is used to so they feel safe and comfortable. If I’m watching your pet in your home, I keep their routine exactly how you have it. They will have their meals on time, daily walks, play breaks, and plenty of cuddles. I’m very detail-oriented, so I pay attention to the small things like their favorite toy, how they like to be greeted, or where they prefer to nap. If I’m caring for them in my home, they get a clean, cozy environment, lots of love, and a peaceful space to relax. Whether your pet is energetic, shy, or somewhere in between, I adjust to what makes them feel happiest. I genuinely treat every pet like they’re my own and give them spoiled-in-a-good-way kind of love. I’m patient, observant, and good with pets who may be a little shy or anxious. I have a patient personality and animals tend to trust me quickly. I’m also extremely reliable and communicative, so you’ll always know how your pet is doing. I’ve cared for a variety of pets from rambunctious puppies to senior dogs. I tailor my care to each pet’s personality and needs.
“Benjamin took great care of my 2 cats. He always sent a picture, whether of the cats (if he saw them), or of a full food and water bowl. He also checked in to let me know the cats were doing well. I absolutely recommend him and would have him watch my cats again!”
About: My time working a the trading and boarding kennel had allowed me to handle sometimes over a 100 dogs in a day, each one with different personalities and needs. Each time I would take them on their potty breaks I would make sure to lavish them in attention and play chase if they felt inclined. I also have monitored up to 10+ dogs together in group play, being very careful to watch behavior and know when a dog has had too much or needs a better playmate. I am also an experienced feeder that can create highly individualized meals and medicate dogs through pilling or hiding meds in food/treats. This also includes non-oral meds like ear and eyes drops as well as topicals. Before the kennel, I walked many neighborhood dogs, taking them for long 30+minute walks and ensuring they were fed and had water. I would stay and give them attention after their walks to keep them company if I was not spending the night. I have experience in using E-collar and commands as well. I mostly used commands for feeding purposes but I can also use them to stop bad behavior. Injuries can also occur not matter how careful one is, be it a broken nail, ear inflections, or cuts and scrapes. I have experienced this many times at the kennel and am apt at tending to said injuries should they occur. I’m currently between jobs and while applying to new ones I have all the time in the world to see your babies! No matter the time, my attention is theirs. I work hard to slowly build trust with nervous dogs and give them all play time, pets, and treats (owner approved of course). If there are any special needs, like age or aggression, I take extra care to ensure everyone and dog is safe and secure around me.
“Callie did a fantastic job taking care of our cat while we were away. Very good with communication during her visits and included daily pictures. Was very helpful to collect our mail and packages as well. We will definitely use Callie again in the future!”
About: Moved to California, MD area from being stationed in Japan! With a lifetime of experience caring for cats and dogs, I know that pets are more than just animals—they’re family. I’ve raised three dogs and currently have both a poodle and a cat. My skills include puppy training, crate training, basic command training, and managing pets with medical needs, including medication administration. I’m also experienced with reactive dogs, allergies, and maintaining breed-specific grooming standards. As a passionate pet lover, I volunteered with the Red Cross animal visitation program while Active Duty & St Mary Animal Humane Society. You can trust me to treat your pets with the same love and attention I give my own! I work part-time and live 10 minutes from my house. I always check in on my pets during lunch. My husband works nights so he is home while I’m at work and we switch. I have a fenced yard, and lots of dog friendly walking areas. I have two friendly pets who do very well with other animals. I crate my dog when I leave home for safety & use cameras to check in on them.
About: I have loved animals for as long as I can remember, and I would be honored to care for your pet friends! I currently have two sweet cats that I adore, and I frequently watch my family’s Havanese dog. I also have experience pet sitting and walking larger dogs, so I am comfortable with pets of all sizes. I have experience working with all ages, from helping with puppy and kitten training to providing gentle care to elderly pets. I tailor care to each pet’s needs, making sure they feel loved, safe, and happy while you’re away. My pets have big personalities, so I understand pets’ unique quirks and am happy to follow any special routines. Just let me know how I can help! My schedule is very flexible right now, so I have plenty of time to care for your pets! My Rover calendar is up to date with my availability, so don’t hesitate to reach out for any pet sitting, dog walking, or drop in visits. During visits, I focus on making pets feel safe and comfortable in their familiar environment. I carefully follow each pet’s routine for feeding, playtime, litter box care, or walks. I’m attentive to their behavior and needs, and I always respect my clients’ homes while providing loving, reliable care.
“Vanessa is AMAZING! If I could give 10/5 stars, I would. She sent pictures and an update during every visit with our cat and is just so pleasant! I'm a nervous mama who hates leaving her furbabies, and Vanessa made me feel completely at ease. I highly, highly recommend her!”
About: Ive taken care of different kinds of dogs since childhood. Family, friends, and locals have trusted me to feed, watch, or walk their dogs. I also can bathe dogs and brush them if needed. I work a part time job but I can stop in or help whenever needed. I typically work 4 hours a day and can care for animals before or after. I have a fenced in yard for my dog, and have multiple beds, towers, and scratching posts for my cats. I also have boxes of toys for both along with treats.
“Amazing dog sitter!! Emilie kept us updated at every visit with our dogs. She really went above and beyond for our dogs and we can't thank her enough for all that she did while we were away. Also, the pictures were so great to receive. Thanks again for putting our worries at ease. Would definitely recommend her and rebook with her!”
About: What sets me apart is the genuine care and attention I give every pet. I treat each one like family and tailor my care to their unique personality and needs. I’m patient with puppies, helping reinforce routines like potty breaks and basic training, while also providing gentle, attentive care for senior pets who may need a slower pace, medication reminders, or extra comfort. I prioritize safety, reliability, and communication, and I’ll always keep you updated with photos and messages so you can feel confident your pet is happy and well cared for while you’re away. Pet care fits into my routine very easily because I plan my day around being consistent and responsible. I’m able to schedule visits in the morning, afternoon, and evening depending on what each pet needs. I make time daily for feeding, walks, playtime, and litter box cleaning, and I stay flexible for any special routines or medication schedules. Weekly, I organize my availability so I can give each pet enough attention without rushing, making sure they feel cared for and not alone for long periods of time I care for pets by keeping their environment clean, safe, and familiar. I follow routines closely, provide food, water, walks, playtime, and give consistent attention and comfort.
“Raymond did an amazing job with our cat and dog while we were out of town. He was very attentive, and gave constant updates everyday. It’s always never wracking to leave your animals with someone you do not know, but Raymond truly put all our nerves to rest with his exceptional communication and daily pictures. We will definitely be using Raymond again in the future!”
The median cost per visit for dog sitting in Leonardtown is $20
Dog parents share their Rover experiences - Leonardtown
Rileigh is the perfect person to chose to take care of your pets! She cared for our two small dogs, one of them being older and a little bit of a pain. She was prompt on every visit, sent pictures and updates of babies. It had rained and she even went out of her way to clean up the muddy paw prints. We had the biggest peace of mind knowing Rileigh was caring for our dogs while we were away. Will definitely be booking her again in the future!
Good first experience using Rover and Susanne. We met prior to the drop in to ensure a good fit. She asked questions and if we had any. Showed in the drop in window, played with the dogs and wrote a thorough check in with pictures. We appreciate Susanne being able to drop in & how quickly our pets took to 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 dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog sitting - Leonardtown
Select a filter and find qualifying sitters offering dog sitting.Sitters in Leonardtown average 5 repeat dog sitting clients
FAQs for Drop-In Visits - Leonardtown
Frequently asked questions about Rover
The average cost for Dog Sitting in Leonardtown on Rover is $22.2 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 631 sitters on Rover offering Dog Sitting across Leonardtown. 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 Leonardtown 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 Leonardtown 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 Leonardtown 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 Leonardtown. On Rover:
- 98% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 100% 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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