House Sitting Annapolis
Find a loving house sitter to watch over your pets and your home.
Over 234 pet parents in Annapolis have booked house sitting
Annapolis, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Leigh Ann was amazing taking care of our dogs and cat while we were on vacation. She sent us regular updates of time spent with our pets. Her attention and care was as if they were her own dogs.”
“Jerad was amazing and I’m so glad we had him watching over our two fur babies while we were away! He kept in contact with daily updates and did everything we asked from giving the dogs plenty of play time as well as walks. We felt completely at ease being away on vacation and we will definitely being booking Jerad again in the future when we need to be away!”
“Leticia was wonderful with our two large dogs! She was punctual, communicative, followed all directions, and took good care of the house too. We’re looking forward to having her watch our dogs more in the future!”
“Jacqueline was a wonderful sitter! She was responsive, understanding, and communicative. She listened to our care instructions and left our house very neat and tidy. We will definitely work with her again in the future.”
“Cheri was a wonderful sitter! She filled in last minute when we had another sitter cancel on us, which was very helpful. She was communicative and our girls seemed happy and healthy when we got home. She left our house in great shape. We will definitely contact her again!”
“Courtney was great! We felt very comfortable being away knowing that our pets were getting so much love and attention. We had clear and frequent communications and a plenty of pictures confirming all the good things happening. We'd (and our critters) would be very happy to see Courtney again.”
“Cassandra took impeccable care of our senior pup and we would highly recommend her to anyone! She was proactively communicative and provided lots of updates and photos. Her stay was seamless and it was as if we had never been away. Thank you Cassandra!”
“Ava is consistently wonderful with our cat snd our anxious, senior dog. She’s super communicative, and puts us at ease. We never worry about leaving town if Ava is with our pets!”
“Karen took wonderful care of our dogs, Sam and Tito, for a full week while we were on vacation. She was incredibly responsive, always sending updates and photos when we asked, which gave us so much peace of mind. It was clear our boys were happy, comfortable, and well cared for the entire time. She also left our home in perfect condition, which we really appreciated. We would absolutely book with Karen again and highly recommend her to anyone looking for a reliable, thoughtful sitter!”
“Lucille was fantastic!! She kept us informed on their day and the administration of his medications. When she was concerned about something she called us and gave us updates every day. She also took care of the house by removing the trash etc! It was also so obvious that she loves animals. I will definitely book her again!! Thanks Lucille for making my trip so much more enjoyable knowing that my dog was in such good hands!!”
“Margriet was a wonderful dog sitter. Rory took to her immediately (and she to him). We were able to go on vacation knowing that he would be fed, walked, cuddled, and let outside to run around in the backyard. Rory was not completely house trained when we left, but Margriet finished the job for us. Margriet also brought in packages from Amazon, and left the house clean and sheets laundered. We highly recommend Margriet for all dog sitting needs.”
“Olivia stayed at our house and took care of our cat while we were away. She was very attentive and sent us photos and updates throughout her stay. We will definitely book her again in the future.”
“Gabrielle housesat for me and my golden retriever Dora for a week. She was wonderful with Dora. She handled Dora's medication and dietary restrictions with no problem. Every picture Gabrielle sent throughout the week showed Dora happy and healthy on her walks and getting her snuggles. Gabrielle was also an excellent house guest, leaving the house clean and tidy. She even watered my plants and vacuumed up copious amounts of dog hair so I didn't have to come home to that! She was very communicative and checked in with me in regularly or if anything was out of the ordinary. I would definitely use Gabrielle again and highly recommend her!”
“Violet took great care of our pup (and our home). She was very responsive, highly communicative, and followed all of our care requests. Not too mention she provided plenty of snuggles for our boy. Would recommend and hire again.”
About: I've had dogs my whole life. Grew up in a house with 2+ dogs near constantly. All family dogs were 60+ lbs each with the largest being 110lbs. My 75lb dog crossed the rainbow bridge Sept 2025, I am not ready for a dog full time but I do miss the company. I will spoil your dog. I do not care about breed. I am looking for weekends. I work full time, so I am ready to go around noon on Friday and depending on the needs can be around all weekend. Generally I do leave the house during the weekend for a couple hours during the day to do chores and stuff but other than that can be a total home body. If the dog is good on leash I have a great neighborhood to take walks. If you are looking for me to stay at your house over the weekend, I can provide as much potty coverage as you request. If you want me to stay over the week, I do have a day job with my schedule being 7-3. I have a 8ft privacy fence the whole way around my backyard with a dog door. I do not have a crate, but I can use yours if you want your dog crated. I follow your food rules. I used to make hot breakfast/dinner for my dog. I do keep some dog treats in the house but I will check with you if your dog can have that specific treat first and if there are any dietary needs. If you want me to stay in your house, lets write the rules down and I'm happy to do whatever. If you have poor cellphone service, it'd be great to get a wifi password.
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 night for house sitting in Annapolis is $50
Pet parents share their Rover experiences - Annapolis
Margriet was a wonderful dog sitter. Rory took to her immediately (and she to him). We were able to go on vacation knowing that he would be fed, walked, cuddled, and let outside to run around in the backyard. Rory was not completely house trained when we left, but Margriet finished the job for us. Margriet also brought in packages from Amazon, and left the house clean and sheets laundered. We highly recommend Margriet for all dog sitting needs.
Ezekiel is a wonderful, dependable, & communicative person. We have quite the menagerie at our house and he takes care of our 2 dogs, cat, birds, frogs, gecko & guinea pig as well as our house. We feel fortunate that he is so responsible & caring with our pets. We will have him pet/house sit again to be sure!!!!!
Jamie once again did great with the fur babies. I felt so comfortable leaving my reactive cattle dog. She also watched my cat and watered the plants. There was a big storm the night before we came back and a neighbors tree fell in our yard and she sent pictures and told us about the situation. We will use Jamie again in the future!!!
Ellie did a wonderful job of watching our dog, Camden! She was incredibly communicative and kind and treated him just like we would have if we were there. It is clear that Ellie has a passion for animals and that her responsible nature and kind disposition will make her a staple for watching our sweet boy in the future. Ellie really did go above and beyond in caring for Camden and watching our home while we were away, she really has a way with pets, even large and very playful dogs like ours. We are so glad we've found a great option for care for future needs with Ellie.
I just took a quick long weekend and Makayla made it so seamless for me. Cooper felt so loved in his own environment with her and the updates and pictures allowed me to enjoy my time. Makayla is fantastic, I almost don’t want to share how good she is because she will get to busy!!
Julia was amazing with Barker! She was really quick to respond to our request, she communicated clearly and was very punctual. She sent updates regularly during her stay in our home which gave me so much peace of mind, she took care of Barker following all our detailed instructions and we came back to a very happy pup. I’ll definitely work with her again!
5 stars! We are are new dog pawrents to a rescue pup. He’s a Pyr mix and is pushing 60 lbs and still growing! He has some separation issues and we feel more comfortable leaving him with someone while we are gone. Henriette was great and we will absolutely use her again. We chatted a few days prior to the appointment so that we were all on the same page. She is very easy to communicate with. Einstein, our pup, took to her and they had a great time. She kept us informed on how he was doing and what they were up to. They went on a lot of walks (he was conked out by the time we got home!) and kept busy! We definitely recommend Henriette and will will use her in the future.
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?
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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 pets like family
1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for house sitting - Annapolis
Select a filter and find qualifying sitters offering house sitting.Sitters in Annapolis average 4 repeat house sitting clients
FAQs for House Sitting - Annapolis
Frequently asked questions about Rover
The average cost for House Sitting in Annapolis on Rover is $44.4 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .
As of August 2026, there are 8,448 sitters on Rover offering House Sitting across Annapolis. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Annapolis walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Annapolis maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
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!
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.
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 .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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.
Yes, you can find sitters who have experience with handling special pet needs in Annapolis. On Rover:
- 91% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 96% 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.
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