Dog Sitting Annapolis
Book a Annapolis dog sitter to watch your dog in your sitter’s home or yours.
Over 568 pet parents in Annapolis have booked dog sitting
Annapolis, 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.
“Katie is polite & quick to respond! She did a drop in visit with my 1 year old black lab in my home. She sent pictures & updates. Would definitely recommend & would use her in the future again!”
“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.”
About: I grew up taking care of multiple dogs, cats, hamsters, fish, even feeding and rescuing some wild animals in my neighborhood. I’v always had a strong connection to animals and care deeply for them. I have multiple years of experience with pet sitting, ensuring pets are taken well care of. Animals have taught me so much and I just love to be around them, I think everyone deserves to know their animals are being well taken care of, safe and happy! I am an incoming graduate student at the Pratt Institute in NYC starting in August. I am taking the summer to work on my art, travel, and enjoy some downtime between working full time at a law firm and starting classes. I would love to take care of some animals over the summer for some extra income and to have some structure in an otherwise loose summer! When I take care of animals, I like to make sure they are comfortable with me being around them, ensuring they have amble time to get used to my presence. I like to take my time with this, allowing them to build confidence around a new person and so that we can form a real bond! For dogs, I like to have a variety of activities including walks, runs in the backyard if possible, playing with toys, and sometimes even hikes! But if I'm being honest, my favorite part is just hanging out and getting to cuddle with the furry creature! In my previous experiences, I have done 2-4 check in's a day as needed for non-live in clients and these visits can vary in length. I have also had live-in/over night clients.
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.
“My cats love Courtney! Especially my super shy boy comes out of shell when he sees her. I’m super happy with her taking care of my two little ones, she spends quality time with them and doesn’t cut her visits short. I also really appreciate the detailed write up and the cute photos. Thank you, Courtney!”
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: I have been caring for animals my entire life and currently help care for two energetic golden retrievers and two cats. Through years of pet ownership, I have experience with feeding, walking, playtime, and maintaining daily routines. As a UCLA student with a flexible schedule, I am available for dog walking, drop-in visits, and pet sitting. I love animals of all kinds and am committed to providing attentive, reliable care while treating every pet like my own. I am a college student home for the summer and available take care of your pets most anytime! I am happy to do early mornings or late nights I am happy to spend as much time as needed with your pet and take care of any special needs they might have! I am highly attentive and love bonding with new pet friends
About: Hi! I’m Liz — an animal lover with a flexible hybrid work schedule and years of experience caring for friends’ and family members’ dogs. I’ve also fostered before, so I’m comfortable with dogs of all breeds, sizes, and personalities. As a dog owner myself, I know how important it is to find someone you can count on. I take that trust seriously and always aim to make things stress-free while you’re away — with regular updates, photos, and plenty of care and attention. Whether it’s daily walks, drop-in visits, or overnight stays, I’m dependable, patient, and genuinely enjoy spending time with dogs. Your pup will be in great hands with me. I currently work a hybrid schedule. I work in the office on Wednesdays and Thursdays, and I’m home the rest of the week, which gives me plenty of flexibility for walks, drop-ins, and overnight stays. When I’m caring for pets in a client’s home, I always treat it with the same care and respect as my own. I stick to your pet’s normal routine — walks, meals, and downtime — to keep them comfortable and relaxed. I make sure doors and gates are secure, follow all instructions closely, and leave your home just as I found it. You’ll get regular updates and photos so you always know how your pet’s doing while you’re away.
About: Adopted 2 Newfoundlands over 20 years, groomed so much fur I could knit a sweater! I understand what Dogs need! Making canines happy until you get home. Availability all week as I am currently not working and would love to walk your dog and make sure they have water and food during the day Experienced in socializing and training pups. I can help keep the manners in check for your pet, whether walking or sitting or staying. Treats are encouraged
“Bella- was wonderful! I never worried about my dogs the entire time I was on the other side of the country. She sent me regular updates and pictures and reassured us that Sadie were being well cared for. I would definitely hire her again!”
“This was our first experience with Rover. Ava was professional, timely, and provided great communication during pet sessions. We came home to a happy dog, and a clean home ( Ava even pulled the trash cans down the night before needed due to our late return!!). Definitely worth the price for not having to corral several neighbors to coordinate pet care.”
About: Ive been dog sitting, walking, and have done overnights for 2 owners the last few years. Reason being is the town I moved away from is super small and not many dog places around where I lived. I’ve always loved animals and have such a soft spot for them. I always keep owners updated with things and love taking pictures. I’m someone who’s very organized and doesn’t want to mess anything up. I know your pets mean the world to you, and that 100% means taking the best care of them and spoiling them! My dad owns two of our family dogs. Murray & Jojo. I love them both entirely with my whole body and couldn’t imagine my life without them. Since my dad recently moved to California a few months ago with them, when I visit I take them on walks, play with them, love on them, it’s one of my favorite things that get me through daily life. Caring for animals and making other people happy is something I want to achieve in life. I want to make the owners satisfied and happy with what I can do for them, and there fur babies! I do both cats and dogs! I did a cat for my video production teacher last year up until around now. I went in, fed her, cleaned her litter box, and watered my teachers plants for her. She didn’t seem like I had to stay (her cat is kinda scared of everyone) so I’d hang around sometimes, but mostly just dropped in and left. But I’ve loved cats so much as well, and think I’d love dropping in and taking care of them too. For my own dogs or other dogs of my own, I always make sure I’m giving the right amount on what owners write down. I never want to make a mistake so I’m very careful with instructions. I think it’s super important to be mindful of that, and I’m pretty good at updating with texts, pictures, etc.
“Marley was absolutely fantastic with our 5-month-old puppy, Goose! He’s definitely a handful, but everything went incredibly smoothly. Her quick and consistent communication before, during, and after her visit gave me complete confidence that he was in great hands. I also loved the pictures she shared and appreciated the updates throughout her time with him. I would happily have Marley watch Goose again and highly recommend her!”
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.
“Leticia did a great job taking care of my cat Madison. Madison is a loner and doesn't warm up to people but he trusted Leticia from the start. I loved the photos and videos that she forwarded to me. It gave me peace of mind to know that he was well cared for. I hope that Leticia will be available the next time I need to be away from home for an extended period of time.”
The median cost per visit for dog sitting in Annapolis is $20
Dog parents share their Rover experiences - Annapolis
Halsey was amazing! She took great care of our big, but sweet dog, Camden and provided lots of pictures and details of all their walks. She was very communicative and I knew our boy was in great care with her! We would love to have Halsey come back and care for Cam!
Leigh Ann was an absolutely fabulous pet sitter! Not only was she available with fairly short notice, she spent extra time with our pets to make sure they were comfortable with her. She walked our dog when she only needed to let him out back, she checked on the cats multiple times each day when she only needed to check on them once a day, and she thoroughly cleaned up their accidents in the house when she didn’t have to. It was great to find someone so responsible with our pets. We will definitely be using Leigh Ann’s services again!
Jacqueline is kind, reliable and professional. She also communicates well and is very patient. She took detailed notes on my dogs’ specific needs and quirks, which helped me to feel very confident that they would be in good hands. She took the time to send photos and notes after her visits. I was so surprised by how quickly my rescue dogs got comfortable around her! I feel that anyone would be lucky to have her help with their fur-babies :) We look forward to her helping us out again!
This is our second time working with Shelby, both times we needed last-minute assistance and she stepped in happily. She took great care of our dogs, gave them their medicine, let them frolic in the yard, and even brought in our packages and kindly turned off our oil diffuser that we had left on in a rush so we didn’t have to come back. We cannot recommend her enough, especially if you are looking for a sitter who is patient with skittish/anxious dogs.
Camilla was amazing with my dogs! She checked on them regularly, made sure they were fed and walked, and handled their timid personalities with so much patience. Even though they were initially skittish even after a meet‑and‑greet. She took her time and let them warm up at their own pace. Her communication was excellent. She sent consistent updates and photos, which gave me total peace of mind and confirmed I’d made the right choice. By the end of the stay, my dogs were completely comfortable with her. I’m truly appreciative of the care she provided and will absolutely book Camilla again.
Leilani was amazing with my dog Cade. He’s almost 12 and he’s picky about who he likes and he loves her! She worked with how anxious he can be at first and sent wonderful updates and pictures! She took the best care of him. She gave me such peace of mind while I was away and is super sweet! I hope to rebook with her again soon!
Sarah did an amazing job with Oreo during the 30-minute visit. She was punctual, attentive, and made sure Oreo was well taken care of the entire time. I really appreciated the updates and photos as it gave me peace of mind while I was away. Oreo seemed happy and comfortable, which says a lot. I’d definitely book with Sarah again and highly recommend her to anyone looking for a reliable and caring sitter.
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
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Select a filter and find qualifying Annapolis sitters!Sitters in Annapolis average 7 repeat dog sitting clients
FAQs for Drop-In Visits - Annapolis
Frequently asked questions about Rover
The average cost for Dog Sitting in Annapolis on Rover is $23.54 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 12,591 sitters on Rover offering Dog Sitting across Annapolis. 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 Annapolis 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 Annapolis 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 Annapolis 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 Annapolis. 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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