Dog Sitting Annapolis
Book a Annapolis dog sitter to watch your dog in your sitter’s home or yours.
Over 315 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.
“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!”
“Lee did a fantastic job taking care of our kitty! They were always timely, helped in all of the ways we asked, and most importantly bonded very quickly with our cat who is usually quite skittish with new people. We will definitely look to rebook with Lee for future trips!”
About: My wife and I had a dog for 13 years and enjoyed taking her hiking and swimming throughout her active years and snuggling on the couch when she became a senior. I'm familiar with the whole life cycle of dog care. From helping puppies get all the wiggles out to carrying seniors whose legs are arthritic and no longer at their best. Now that our girl, Nala has passed away, we are enjoying connecting with others' pets. I have an unconventional schedule for work and am available to let your dog out from 9 am until noon on Monday, Tuesday, Friday, and Saturday. Wednesdays and Thursdays are my days off and I'm free to hang with your pup any time! I'm very committed to pet safety and will want to understand all situations in which your dog may become reactive so that we avoid putting your pet in a situation that will make him or her uncomfortable. I also have a tracker that I like to put on all dogs in my care just in case they get spooked or something unexpected happens while we are together.
About: Hello! I am a teacher and parent who is reliable and trustworthy. I have always had a dog of my own and currently have 2 dogs, one 6 month old dachsund mix and the other is a 4 year old cattle dog mix. I am very passionate about helping others care for their dogs! When I was a teenager, I worked as a vet clean up tech at my local veterinarian. Everyone who knows will tell you that every time I see a dog, I always want to go pet it right away! I’m a true dog lover and would love to help people out caring for their pets! I am available in the early mornings and afternoons for walking and pet sitting! Holidays are also a great time for me because I’m off work then! I look forward to taking care of your fur babies! I am a teacher, so I'm available on the weekends and have more availability in the summer months to take care of dogs. I prefer to take care of dogs and cats in the mornings, but can do mid-day or afternoons if needed. I have a fenced in yard and a great neighborhood to walk dogs around. I also have a crate that can be used for small and large dogs if needed.
About: Hi there! I have been caring for animals since a very young age. Growing up, we always had at least 2 dogs and raised litters of puppies at times. I had a sweet boy of my own (Nixon, in my profile photo) who I raised from a pup, but sadly passed away this year. I am an active person and love caring for animals, taking them for ample walks and pup cups, or just good company! Having a pet by my side is natural for me and would love to care for yours! I work from home full time and have a flexible schedule so I have ample time to take pets for walks, play, and they will never be lonely if staying with me! We have a townhome in Eastport which is a very walkable area and there is a backyard of green space for easy access potty breaks. Always will be leashed. I previously had a husky that wasn’t trusted off leash so I am overly cautious on that! Pets are allowed on furniture/ beds if owners allow. We have several decks if they like to look out and the boat action or sunbathe!
About: I have always had 2 dogs of my own and a cat once. I pet sit frequently and am super excited to meet your pet/pets! I am a local Annapolitan and hard working girl seeking extra, flexible, work to help pay for my new car, future rent, and moving expenses. I live at home with my parents and 2 dogs and work in Downtown Annapolis. I am frequently around to walk your pets and play with them as needed!
“Kayla did a great job with Chip, and I was super appreciative of her last minute availability! Chip seemed happy and tuckered out when I got home, so it seems like they had a fun time. Thanks Kayla!”
“Snowden could not have been better for us! She has amazing energy and our dog took right to her. Incredibly respectful of our home & managing while we were away. We'll become regulars :)”
About: I have taken care of family and friends dogs most of my life. Love both dogs and cats! Always looking to make new furry friends I work from home so I am very flexible with my schedule and weekly routine. Reliable for last minute requests as well as long term ones Very flexible with different environments. I have a lot of experience with animals of different temperaments and always respect the owners wishes concerning how they would like their animals taken care of
“Emma came for a midday drop-in visit for my dog, Rizzo, while I went into my office. She gave Rizzo a potty break out in the backyard. Played fetch h with her, and gave her a snack. The house was left just as she found it. 😊 We will definitely use Emma again, whenever the need may arise.”
About: I grew up on a farm so I have lots of experience with all kinds of animals. I currently volunteer with BARCS and SPCA and frequently take on high needs medical fosters. I will happily care for your animals based on their individual needs no matter how complex. I'm free most weekday afternoons and weekends, I have a pretty flexible schedule so I can work around your needs in a lot of cases I'm available for drop in visits and some overnight stays. I'll treat your home and pets with the same care and consideration as my own.
“Jessica is a superstar! My puppies get so excited when she comes every day. She's been so reliable and flexible with my chaotic schedule. She's dealt with some incidents (mangled pillow, an accident in the crate, to name a few) with grace, care, and patience. I couldn't be more thrilled to have her watching my dogs every day. I know she loves them as if they were her own!”
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.
“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.”
“Sofia is the warmest dog lover who cares for your pet with grace, attentiveness, and love. She came for a drop-in visit and soothed our dog who has been diagnosed with cancer. Our family is lucky to have found her! ❤️”
“Our cats felt very comfortable with Michael, and so did we! He's reliable, kind, and respectful of animals, and also very intuitive with them. Their personalities are very different, but he gave Bagheera plenty of active play and made friends with the very shy Laska. We highly recommend Michael and will use him again. Great Rover cards, by the way!”
The median cost per visit for dog sitting in Annapolis is $20
Dog parents share their Rover experiences - Annapolis
Allison is such an attentive and caring dog care giver!! Always on time, conscientious and full of love to give our sweet old girl. Allison helped take the worry out of leaving our aging pup and allowed us to enjoy our trip, confident that our furry family member was in great hands. Thank you!!
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!
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 $23 per visit as of November 2026. Most bookings cost between $16 and $29 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 November 2026, there are 12,428 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:
- 85% of sitters can help with special care needs
- 90% 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 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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