Dog Sitting Annapolis
Book a Annapolis dog sitter to watch your dog in your sitter’s home or yours.
Over 507 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.
“Karen was great for our drop-in visit with Chicken. She’s a great communicator, and keeps us in the know about dog behavior. She took a charming photo of chicken enjoying the outside. Much thanks Karen!”
About: I have owned dogs my whole life, and know how to take care of them. I also have experience with cats, I have helped my grandfather with a stray cat that chose him! I'm openly available, as of today. I like to volunteer, but that usually only takes about 4 or 5 hours. I will give your pet the time it needs. You make sure that they have plenty of fresh water, eat on time, and walk them every day when the sun is not too hot, eg in the morning or evening.
“Leah was a huge help to us over Labor Day weekend, dropping in to let out and feed our three dogs. My husband and I are both small business owners, so we jumped at the chance to take a brief overnight trip together and Leah’s help made it possible. She was on time and engaging with the dogs and they were well cared for in our absence. We would definitely recommend Leah!”
About: The Cockapoo I rescued from a horrible shelter in Oxford, NC lived to be 21yrs old. Had dogs all my life, friends have often entrusted me to watch their pets while they vacationed. Now happily married (we got married at the Senior Dog sanctuary in Severn), my wife Lydia has rescued and cared for many dogs since childhood. While I get to work from home (i.e will be able to tend to your dogs' every need, she has to run out to "make money" for milk bones and will assist during the evenings and on weekends. We love to take our dog to Quiet Waters park and with your permission, will take yours as well. Our home (albeit small) has a fully fenced yard. Tips are greatly appreciated - we provide much better service than any kennel! I am fortunate to be able to work from home and will be able to tend to your dogs' every need (while also caring for my 4yr old Chocolate Lab). We have a fenced yard, there will be a friendly 4yr old Chocolate Lab here for company. My friends consider me to be the dog whisperer, known to be reliable, loveable and patient. Your dog can come along on walks, visit Quiet Waters, and could even come to the family farm - which our dog loves.
“Jessica did a great job checking in on our puppies while we are out of town. She was able to assist us with last minute request! Our pets love her and she provides timely updates and pictures on how they are doing. Jessica has become our go to provider for pet sitting and check ins.”
“We truly couldn’t have asked for a better sitter than Ally! She stayed at our home for 6 days while we were away and took incredible care of our French Bulldog who was recovering from an IVDD flare-up. Frenchies can definitely be little forever babies with lots of quirks and extra needs, but Ally handled everything perfectly! She kept us updated every day with thoughtful messages and pictures, paid close attention to Bella’s routine, made sure she stayed comfortable and kept up with administering her medications. Coming home to a happy, relaxed dog was the greatest peace of mind! I would recommend Ally without hesitation, especially if you have a dog with medical needs or one who needs a little extra love and attention. We’ll absolutely be booking with her again. Thank you so much, Ally! ❤️🐾”
“Jazmin has been highly communicative, very proactive, and sent me a lot of photos of the fur babies, which put me at great ease. She’s also been very punctual and checked in with me during the visits. I so appreciate that kind of thoughtful support and strong communication! Will be reaching out to her for future pet care. Thank you, Jazmin!”
About: For 18 years I have cared for my own dogs and dog sat for friends and family. I worked at a vet clinic for 4 years ending 13 years ago. Familiar with many breeds and comfortable with them as well. I currently working full time but my husband works from home completely so we always have a person around, including my kids who are great care takers. I work from home usually a day or two. I have a 6 foot fence and 2 friendly dogs to keep your furbaby company. No other pets are in the home. We are great with giving meds and love to all animals.
About: I’ve been caring for dogs of all sizes and personalities since I was young. I grew up with dogs in my home and currently have two dogs of my own, so I know how much our pets mean to us and how important it is to find someone you can trust with them. I love getting to know each pet’s unique personality and making sure they feel safe, comfortable, and loved while their owners are away. I truly love all fur babies and would be so excited to care for yours! 🐾❤️ I am currently a part time student at Anne Arundel community college. I also have a part time job. My weekends are available. Weekdays I have a lot of free time during the day between classes before I head to work at 2:30-5:30 (usual hours). Safety is my top priority when caring for your pets. I will always make sure they are supervised, secure, and comfortable, whether we are out on a walk, during a drop-in visit, or staying overnight. I follow each pet’s routine and any instructions you provide, including feeding schedules, medications, walks, and anything else that helps them feel at home.
“I was a little nervous to use rover for the very first time but as soon as my animals met Catherine they loved her. Catherine is so wonderful with animals -we have a very shy great Dane who just immediately loved her. She kept in contact with us the whole time and sent us pictures of the dogs playing. After our meet and greet we felt completely at ease leaving her the keys to our house and our precious dogs with her. We will 100% be calling again to use Catherine.”
“Allison took care of my cat for 3 days over Thanksgiving, including Thanksgiving day itself, which I really appreciated. She texted photos when the reclusive cat made an appearance, otherwise she texted a photo of the cat food & water bowl. The cat seemed just fine upon my return. All went as scheduled.”
About: I’ve always grown up in a pet loving household with multiple pets. I’ve been not only babysitting but pet/house/farm sitting since I was 12 years old. I am very comfortable in all different environments and love to walk, run, & snuggle! I’m currently a part time pediatric nurse and have fallen in love with the Annapolis area. On my off days I am very willing to accommodate all your pet needs as early/late and as many times as needed! I have cared for pets in multiple different environments. I’ve cared for pets who have a fenced in yard and others who needed to be walked on a leash. I am comfortable with whatever your preferences are.
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.
About: I love all kinds of animals!! I have grown up around dogs my whole life. I used to walk my neighbors dogs all throughout high school and college. I treat every animal I take care of as my own dog, with lots of care and love!!! I have undergone a routine of caring for my own dog, with walking multiple times a day, playing with a bunch of toys, and making her entertained. I am open to caring for other pets and giving them the love I give my own dog. I work in the restaurant business so I have a good amount of free time! I love reaching out to owners when I am watching your dog. I will send lots of updates, photos, and everything in between while you're away!! After years of taking care of pets, I have come to understand that every animal is different and needs their own routine and care!
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!
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!
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.
How to book dog sitting
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 - 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 is $22 per visit as of October 2026. Most bookings cost between $16 and $33 per visit. On Rover, 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 12,494 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 .
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 , 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 .
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:
- 85% of sitters can help with special care needs
- 91% can help with giving oral medications or injections
- 94% 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 , 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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