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.
“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!”
“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!”
“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!”
“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: I have experience caring for dogs of different breeds, sizes, and personalities. I’m dependable, patient, and always make each pet’s safety and comfort my top priority. I understand that every pet has its own routine, so I follow feeding schedules, medication instructions, exercise needs, and any special requests exactly as provided. Pet care fits well into my daily routine, and I have a flexible schedule that allows me to provide reliable care throughout the week. Whether it’s morning walks, midday check-ins, evening visits, or overnight stays, I’m committed to making sure pets receive the attention, exercise, and companionship they need. I also make it a priority to stick to each pet’s normal routine so they feel comfortable and well cared for while their owner is away. I treat every pet with patience and respect, paying close attention to their behavior and needs. Whether they enjoy active play, long walks, or simply relaxing with company, I adapt my care to help them feel happy and comfortable while their family is away.
“This was our first experience using Rover for our pet. Alex was timely and thorough with our dog. Photos, videos and reports of meals / bathroom. The house was left in great shape. Definitely worth the price for not having to coordinate a bunch of days with neighbors for pet care.”
“Tiffany was a real trouper to come visit our 3 month old puppy. She is knowledgeable, organized and loves dogs. Communicates promptly, and is open to changing circumstances. I highly recommend her.”
“When Sophie , CoCo and I first met Katherine we knew immediately that the girls were in great hands. The moment we met Katherine we knew she loves dogs and that is really important. Wayne and I went on a vacation with no worries at all . We would highly recommend Katherine for your next dog sitter. We were completely satisfied with Katherine’s care of our doggies!”
About: I have had two small family dogs, both of which have been spoiled rotten. I have experience with senior dogs since our Gizmo lived to be 17 1/2. I have dog sat for friends and neighbors before and love snuggling with pups. I have patience for slow walkers and the energy for the fast ones. I have volunteered twice with BARCS for Dogs Day out, where I spent the day with a shelter dog, giving them the best day ever! I am a teacher, so my availability in the summer is pretty open. During the school year, I am available most afternoons and evenings for walks. I am typically available each week day after 3:30 during the school year. I love taking dogs on walks. I have experience with fast walkers and those who pull. I also have patience with slow walkers or senior dogs too. I can easily crate dogs if necessary.
“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.”
About: Mostly I grew up with pets I had many dogs and cats I have patience I also like to play with them walk, run and I got attached easily For now I have a full-time job, but I have time in the afternoons and I usually go for a walk and I would like to take them for a walk to play or distract themselves so they are not bored The truth is I don't have much space to take care of him in my house but I can take him for a walk or take care of him instead it would be great
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: 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.
“Carolyn did an amazing job looking after our cat Chance for the past week. She is very reliable and we always received great pictures and updates for every visit. Will definitely work with her again.”
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: 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
“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 have grown up with medium to large sized dogs my whole life. I have experience with very friendly dogs and dogs that cannot play with others as well as puppies to older dogs. I have cared for my own pets and friends while growing up and can be trusted with any task to ensure your pets needs and safety! I can offer dog walking in the mornings (7-9am) or afternoons (4-7pm) during the week or anytime during the weekends. I am available on the weekends to check-in or stay with your animal overnight as well. I can check-in and care for your animal during the day or overnight at clients homes. I will ensure your pet is fed, walked, bathed, played with and let outside for their needs. I am comfortable with any specific instructions from the owners as well (medication that needs to be taken, crate training, etc).
The median cost per visit for dog sitting in Annapolis is $20
Dog parents share their Rover experiences - Annapolis
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!
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.
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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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 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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