Dog Sitting Annapolis
Book a Annapolis dog sitter to watch your dog in your sitter’s home or yours.
Over 503 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.
“Liza is the BEST! This was the first time Liza visited Ruby and we will definitely request her again when we need a sitter. She was understanding of my concern for Ruby’s care. I appreciate her attention to details, her communication with photos and her interaction with Ruby. We came home to a very happy pup.”
“Heather is absolutely wonderful with our 5 dogs. She takes great care of them and communicates very well. We have 1 skittish dog that she’s been very patient with and he’s slowly coming around. Definitely recommend her.”
“Thomas is great with our pups, and very reliable; even last minute! He’s pleasant, kind and responsible. I really enjoy seeing the Rover Cards with his notes, pictures and activities. We look forward to using him again!”
About: Hi, I’m Hannah! I’ve grown up with dogs my whole life and can’t remember a time when I didn’t have a furry companion by my side. Since my teenage years, I’ve been the go-to pet sitter for friends and family, and I still love helping out whenever I can. I also foster dogs, so I’m experienced with pups of all sizes, temperaments, and needs. Your dog will be in caring, capable hands with me! I am currently working remotely, so I am free most of the day to care for your dog and be there as a friend and make sure they are not left alone. I have a fenced in backyard that your pup can run around in. I also have two sweet and loving dogs of my own that will keep your pup company! If coming to your house, I will respect your space, and let you tell me how to manage your pet and home.
“Margriet is fabulous. She is always punctual, reliable, and responsible, which gives me great peace of mind when I’m away. Most importantly, I can tell that she really cares about my dog and treats her with kindness and affection. I feel very blessed knowing my dog is safely in her care. Highly recommend!”
About: As someone who loves to travel, I know the importance of having trusted and communicative pet care. I have had two cats for 12 years and was lucky enough to become a dog mom when my husband I met 4 years ago. I have experience with walking and caring for our friends pets as well. I have a hybrid work schedule, so my availability is flexible for you and your fur baby’s needs. I can do early mornings, lunchtime, evenings, and overnights. We have a fenced in backyard that our dog enjoys and a covered porch that our cats enjoy. We can accommodate any animal and separate all the animals if feeding time is an issue.
“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.”
“Ellie was absolutely amazing! She took marvelous care of our cats and provided detailed notes as to how the cats were doing during each visit. The pictures she provided were adorable. We would gladly re-book her and recommend her for pet sitting.”
About: I get a lot of pleasure assisting busy professionals with their pet sitting needs. I provide a nurturing and loving environment for your special pets in a very tranquil setting. Your pets will be treated as if they were my own. My husband and I will treat your pet with the utmost care and attention. References available upon request.
About: I have been pet sitting since I was a freshman in highschool for members in my community. I have always loved pets and used to knock on my neighbors’ doors in elementary school offering to walk their dogs (and cats lol). I’ve taken care of pets of all sizes, ages, and breeds, and even multiple pets at once. I love to take long walks in general and would love to have a pup come with me! For house calls, I’m happy to spend some quality time with your pet and play with them. I am currently a highschool senior who starts school at 8am and is done by around 2:30pm. I am happy to wake up early to take care of a pet’s needs in the morning and am usually available after school to do so in the afternoon as well. I occasionally work from 3-6 after school or for a couple hours on weekends but will communicate with a pet’s owner if that comes up. I will be sure to pay close attention to your pet when taking them on a walk, feeding them, playing, or letting them outside to make sure they are safe.
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.
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: I’m a mature woman with professional and life experience. I’ll treat your pets and home with great integrity, thoughtfulness and care. As a former pet mom of 20 years, I can promise your beloved will be in trusted and experienced hands! I love walking and I love dogs- your pup will enjoy his or her time with me! Big or small doesn’t matter- just looking for friendly, loving pups! Also a total cat lover and can’t wait to give yours some pets and cuddles! I am confident in doggy commands and very tidy in another’s home and spaces. I look forward to caring for your pet as if they were my own- making their time away from you as fun and engaging as it can be- so you’ll return home to a happy and well-cared-for 🐶 or 🐱 ! I have a small clothing line and do freelance work. I love dogs and the park so thought I’d try offering my service here again! (Haven’t since 2019!) I have tons of experience with dogs and cats and they tend to really trust me. I am always overly cautious with allowing dogs to interact while on a walk just to keep everyone 🐾 safe! ❤️
The median cost per visit for dog sitting in Annapolis is $20
Dog parents share their Rover experiences - Annapolis
Thomas was EXCELLENT with Sheena!! He is very attentive and conscientious in his care. Communication is superb and timely, and he was consistent with the times of his visits. Our old girl did well with Thomas in charge. We will be contacting you again when we need care for Sheena. Thank you!
Margriet is fabulous. She is always punctual, reliable, and responsible, which gives me great peace of mind when I’m away. Most importantly, I can tell that she really cares about my dog and treats her with kindness and affection. I feel very blessed knowing my dog is safely in her care. Highly recommend!
Megan was absolutely amazing with Oreo! She was incredibly kind, reliable, and made us feel completely comfortable leaving Oreo in her care. She kept us updated throughout the stay and sent plenty of pictures, which we really appreciated. Oreo looked happy, relaxed, and right at home with her. It was clear that Megan genuinely cared about her and treated her like one of her own. We would absolutely book with Megan again and highly recommend her to anyone looking for a trustworthy and caring sitter!
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!
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!
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
1. Search
Browse profiles of sitters near you who offer dog sitting
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Schedule a free in-person Meet & Greet to find the perfect fit
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Popular requests for dog sitting - Annapolis
Select a filter and find qualifying sitters offering dog sitting.Sitters in Annapolis average 7 repeat dog sitting clients
FAQs for Dog Sitting - Annapolis
Frequently asked questions about Rover
The average cost of Dog Sitting in Annapolis on Rover is $22 per visit as of October 2026. Most bookings cost between $16 and $33 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 12,637 sitters on Rover offering Dog Sitting across Annapolis. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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