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Top rated Chesapeake house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Chelsea was great with our 2 energetic Yorkies! She was very responsive with texts and pictures. I was so impressed with how well she left the house. She even washed the sheets and put them back on the bed. Above and beyond! Thanks Chelsea we will be booking you again.”
“Vivianna stayed with my zoo for the weekend. She was incredibly communicative and sent updates and pictures. I knew they were in great hands the entire time”
“We couldn’t have asked for a better sitter than Alyssia! She stayed overnight in our home for a week while we were on vacation in the OBX and took fantastic care of our three cats. She sent daily updates with funny photos and videos that gave us total peace of mind (and some good laughs). Alyssia also took excellent care of our home—bringing in the mail and packages, taking out the trash, and cleaning up after herself. Everything was spotless when we returned. Most importantly, our cats were calm, happy, and well-fed. In the past, they’ve seemed stressed or even lost weight while we were away, but not this time. They warmed up to her quickly! We’ve already rebooked her and wouldn’t hesitate to recommend her to anyone looking for a reliable, caring sitter. Thank you, Alyssia!”
“I cannot say enough great things about Rayna! I would give her 10 stars if I could! She is one of the sweetest people on the planet and did a PHENOMENAL job watching our dogs when my family was away for 10 days. She was extremely communicative and kept us up to date on our dog’s wellbeing and went out of her way to make sure they were well cared. For the record, I have a very anxious pup and Rayna went above and beyond to make sure she was comforted, especially at night. She gave us so much piece of mind. Additionally, she left my house so immaculately clean I was shocked! She also did an amazing job of watering the plants, garden, and collecting the mail. Do yourself a favor and book Rayna! She is a gem and one in a million!!! Rayna, you are always welcomed back! Tuna and Nelson miss you already!”
“London is AMAZING!!! She took care of Baxter and Boscoe like they are her own babies. She sent me tons of updates and pictures that showed me how much she cares. We will definitely be using London in the future!!!”
“Jillian was great! Communicative, caring, responsive...she sent lots of pictures and kept me updated on all the goings on around the house. Would recommend her for anyone, and will definitely use her services again!”
“Damian was fantastic with our pups and rabbit. He was responsive and shared daily pics/updates. He not only cared for our pets, but our house too!! We highly recommend working with him if you are looking for someone you can trust to take good care of your fur babies.”
About: I have always been around various animals and have had multiple dogs/cats/rabbits - my entire life. I have tons of experience watching either friends or family members dogs/cats during extended periods of time. (Vacations/ out of town) . Long walks and play time are always a top priority. Dogs are part of your family, and they should be treated as such when work or vacations come into play. Endless snuggles and attention will be given while your pets are in my care. *** Update for AUGUST - Extra availability *** Tuesday, August 26th I have early morning availability ( 6am-9:30 am ), Thursday, August 28th I will have evening availability ( 6:30pm - 10:30 pm ) and Sunday, August 31st I will be available from 2:30pm - 10:30pm ) Monday, September 1st ( Labor day ) I am available all day *** I have a full time position working from home. My availability is 5:15pm - 10pm , Monday through Fridays. Every Saturday and Sunday I have open availability besides my blocked dates. Most holidays I will be available also! Looking to add in morning time availability during the week in the near future. I am available to house sit, dog walk, or do drop in visits. I will follow your pets daily routine as closely as I can whether it be feeding times, walk schedule, playtime. I will provide plenty of attention and affection to your pets while you are away! I always have my watch or phone on me for constant communication. Due to me adopting a new German Shepard puppy I cannot board in my home yet.
“Hannah was great with my crew of 2 cats and 2 dogs on an overnight stay at our home. I was nervous to leave them for the first time but Hannah's professionalism and attention to detail eased my mind. The babies loved her right away. She was able to keep up with all of them and gave great updates along the way. We are so glad to have found Hannah and would definitely recommend her to others.”
“Naja was awesome. Super accommodating and communicative. She came over beforehand to make sure the dogs were comfortable around her and didn’t have any issues throughout the booking. Awesome rover that has skill and patience!!”
About: Hi there! I'm a lifelong animal lover and experienced dog caregiver, and I truly understand the importance of finding someone you can trust with your furry family member. I'm currently a proud pet parent to two high-energy dogs, so I know firsthand how to keep pups engaged, exercised, and happy. Whether your dog loves long walks, tug-of-war, or just some good belly rubs, I'm here to give them the attention they deserve.I work a traditional 9–5 job, but I’m flexible and can schedule around that to make sure your dog is well cared for during mornings, evenings, and weekends. I offer drop-in visits, walks, and overnight care that fit comfortably around my work hours, ensuring your pup gets the love and attention they deserve! Let's set up a meet and greet, and hopefully had your pup to my extended family! I work a traditional 9–5 job, but I’m flexible and can schedule around that to make sure your dog is well cared for during mornings, extended evenings, and weekends. I have a fenced in yard with two friendly dogs who can keep your fur baby company! I have 2 large crates that can house both of my dogs if individual play time is needed!
“I took my precious and shy Nina Simone to Raymond on a whim, I needed an immediate sitter. The fact that he was willing to fit me in at the last minute, spoke volumes. Nina enjoyed herself so much that when we got home, she barely finished her dinner before racing upstairs to jump in her bed! She was knocked out immediately! He mentioned that he took her to the neighborhood dog park, and played tug-of-war with one of her toys I left with him. The dog park is located in the older neighborhood of Berkley, which I love because it reminds me of back home, in Georgia. The residents all know one another and seem highly respectful towards Raymond and his Rover dogs, lol. I saw a difference in Nina with him, regarding her being more outgoing, with just that one day, then the days she has been at an actual doggie day care center. I will definitely be bringing Nina S. back to Raymond!”
“We were so fortunate to have found Breezy for our weekend getaway. She was absolutely amazing with our doggo. Gideon has severe anxiety, so we are always a bit nervous leaving him for extended periods. But Breezy was truly perfect with Giddy. She was so patient with our sweet boy and cared for him like her own. We were able to enjoy our trip to the fullest knowing she was taking such good care of Gideon. I will most definitely be reaching out to her to rebook in the future. Thank you so much!”
“Brittany is awesome and she is my new go to when I need my dog looked after. I recently moved to the area and have been looking for someone to look after my dog when I have to travel. She kept in constant communication with me; provided photos and videos daily; and even picked up an Easter gift for him.”
“Taylor is the best house and dog sitter there is! She gives updates, sorted mail and left the house perfectly clean. And our dogs absolutely adore her! I would rate her 10 stars if I could.”
Loving house sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Jazmin C.Star Sitter
“Jazmin came through at the last minute and was amazing help! She even cleaned up after the puppy had an accident In her crate. Thank you Jazmin!”
Chelsey M.
“Chelsea was great with our 2 energetic Yorkies! She was very responsive with texts and pictures. I was so impressed with how well she left the house. She even washed the sheets and put them back on the bed. Above and beyond! Thanks Chelsea we will be booking you again.”
Vivianna & Reyna A.Star Sitter
“Vivianna stayed with my zoo for the weekend. She was incredibly communicative and sent updates and pictures. I knew they were in great hands the entire time”
Alyssia J.
“We couldn’t have asked for a better sitter than Alyssia! She stayed overnight in our home for a week while we were on vacation in the OBX and took fantastic care of our three cats. She sent daily updates with funny photos and videos that gave us total peace of mind (and some good laughs). Alyssia also took excellent care of our home—bringing in the mail and packages, taking out the trash, and cleaning up after herself. Everything was spotless when we returned. Most importantly, our cats were calm, happy, and well-fed. In the past, they’ve seemed stressed or even lost weight while we were away, but not this time. They warmed up to her quickly! We’ve already rebooked her and wouldn’t hesitate to recommend her to anyone looking for a reliable, caring sitter. Thank you, Alyssia!”
Rayna H.
“I cannot say enough great things about Rayna! I would give her 10 stars if I could! She is one of the sweetest people on the planet and did a PHENOMENAL job watching our dogs when my family was away for 10 days. She was extremely communicative and kept us up to date on our dog’s wellbeing and went out of her way to make sure they were well cared. For the record, I have a very anxious pup and Rayna went above and beyond to make sure she was comforted, especially at night. She gave us so much piece of mind. Additionally, she left my house so immaculately clean I was shocked! She also did an amazing job of watering the plants, garden, and collecting the mail. Do yourself a favor and book Rayna! She is a gem and one in a million!!! Rayna, you are always welcomed back! Tuna and Nelson miss you already!”
London N.
“London is AMAZING!!! She took care of Baxter and Boscoe like they are her own babies. She sent me tons of updates and pictures that showed me how much she cares. We will definitely be using London in the future!!!”
Jillian E.
Star Sitter
“Jillian was great! Communicative, caring, responsive...she sent lots of pictures and kept me updated on all the goings on around the house. Would recommend her for anyone, and will definitely use her services again!”
Damian H.Star Sitter
“Damian was fantastic with our pups and rabbit. He was responsive and shared daily pics/updates. He not only cared for our pets, but our house too!! We highly recommend working with him if you are looking for someone you can trust to take good care of your fur babies.”
Ava D.Star Sitter
“She’s a great sitter! I have an anxious dog and she did great with him, was always available when I reached out and sent me daily updates! Would recommend her any time.”
Miranda T.
“Miranda is a excellent person with animals. She is very responsible and always on time! She is amazing pet giver and always goes out her way for any animal. She always been great when she watches my dogs”
Zara M.Star Sitter
“Zara was amazing staying with our anxious little dog! We were able to book her at the last minute and she was so responsive and friendly. She was amazing!!!!”
Jacqueline R.Star Sitter
“I felt confident in leaving my furbaby for a weekend in her care. Super thorough with her meet and greet and sends plenty of pictures while you’re gone.”
Hannah W.
“Hannah was great with my crew of 2 cats and 2 dogs on an overnight stay at our home. I was nervous to leave them for the first time but Hannah's professionalism and attention to detail eased my mind. The babies loved her right away. She was able to keep up with all of them and gave great updates along the way. We are so glad to have found Hannah and would definitely recommend her to others.”
Naja D.
“Naja was awesome. Super accommodating and communicative. She came over beforehand to make sure the dogs were comfortable around her and didn’t have any issues throughout the booking. Awesome rover that has skill and patience!!”
De'Ara G.
“Cannot recommend Deara enough! She’s super friendly, professional and just loves dogs! From the moment she met Roxie, we knew it was right! She sent us many update pictures and vids throughout her stay which was so comforting! 10/10!”
Jordan C.
“Jordan was wonderful! She took great care of our dog which included multiple oral medications. We will absolutely see if she is available in the future!”
Raymond C.
“I took my precious and shy Nina Simone to Raymond on a whim, I needed an immediate sitter. The fact that he was willing to fit me in at the last minute, spoke volumes. Nina enjoyed herself so much that when we got home, she barely finished her dinner before racing upstairs to jump in her bed! She was knocked out immediately! He mentioned that he took her to the neighborhood dog park, and played tug-of-war with one of her toys I left with him. The dog park is located in the older neighborhood of Berkley, which I love because it reminds me of back home, in Georgia. The residents all know one another and seem highly respectful towards Raymond and his Rover dogs, lol. I saw a difference in Nina with him, regarding her being more outgoing, with just that one day, then the days she has been at an actual doggie day care center. I will definitely be bringing Nina S. back to Raymond!”
Brieana R.Star Sitter
“We were so fortunate to have found Breezy for our weekend getaway. She was absolutely amazing with our doggo. Gideon has severe anxiety, so we are always a bit nervous leaving him for extended periods. But Breezy was truly perfect with Giddy. She was so patient with our sweet boy and cared for him like her own. We were able to enjoy our trip to the fullest knowing she was taking such good care of Gideon. I will most definitely be reaching out to her to rebook in the future. Thank you so much!”
Brittany B.
“Brittany is awesome and she is my new go to when I need my dog looked after. I recently moved to the area and have been looking for someone to look after my dog when I have to travel. She kept in constant communication with me; provided photos and videos daily; and even picked up an Easter gift for him.”
Taylor G.
“Taylor is the best house and dog sitter there is! She gives updates, sorted mail and left the house perfectly clean. And our dogs absolutely adore her! I would rate her 10 stars if I could.”
Over 1,069 pet parents in Chesapeake have booked house sitting
Chesapeake pet parents share their Rover experiences
Our dog isn't used to being left alone for more than 3 hours at a time. So Taylor either brought Pepper with her or stayed at the house. She updated me with pictures and messages letting me know how our dog reacted to meeting her animals, and let us know when Pepper needed her special meds.
Hannah is the best! I will definitely rebook her in the future. My Yorkie and Morkie immediately warmed up to her. She is dependable and trustworthy. She has a genuine interest in the care and welfare of animals and her beautiful, attentive personality conveyed that. Read and believe all of her reviews. Again, she is the best!
I cannot say enough great things about Rayna! I would give her 10 stars if I could! She is one of the sweetest people on the planet and did a PHENOMENAL job watching our dogs when my family was away for 10 days. She was extremely communicative and kept us up to date on our dog’s wellbeing and went out of her way to make sure they were well cared. For the record, I have a very anxious pup and Rayna went above and beyond to make sure she was comforted, especially at night. She gave us so much piece of mind. Additionally, she left my house so immaculately clean I was shocked! She also did an amazing job of watering the plants, garden, and collecting the mail. Do yourself a favor and book Rayna! She is a gem and one in a million!!! Rayna, you are always welcomed back! Tuna and Nelson miss you already!
Tori is simply amazing! To ensure my pup and Tori would be a good fit, she facilitated a meetup before hand to ensure I felt comfortable as well as ensuring my pup was comfortable. Tori stayed in my home to watch my Goldendoodle. Tori provided daily updates, with lots of pictures! I felt so relaxed knowing someone who deeply cares about animals was watching my dog. Tori was also incredibly respectful of my home. When I returned, it was as if no one had stepped inside! I highly recommend Tori to anyone in need of a pet sitter! I will most certainly be reconnecting in the future! Tori is the best!
This was the first time Brieana took care of our dog and hopefully it won’t be the last. Brieana and her partner took great care of our dog Zeke while we were out of town. They kept him company pretty much the entire time. This was special to us since our older dog passed away very recently, and Zeke has never been alone before. They followed our instructions, they brought in the mail, and even watered the plants for us. We are truly grateful ☺️
Danielle was amazing and the perfect sitter for our little one! She sent us pictures throughout her stay and she was very friendly with our pup. I think he may have even found a new friend! Our pup was only 5 days out of the shelter and she handled his crazy self perfectly and was so helpful for us!
My dog had some unexpected health issues arise between booking and Marissa’s stay that ended up requiring a lot more work for her, but she did great and my dog was in much better condition when we got home. I’m very grateful Marissa has some vet tech experience. I did have to ask for updates a few times, and the communication wasn’t always the clearest, but the specialty care for my dog was my priority and she did great with that.
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Chesapeake is $40
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 house 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.
Sitters in Chesapeake average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Chesapeake on Rover as of Aug 2025 was about $40 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Aug 2025, there are 1,227 house sitters in Chesapeake. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 89% of Chesapeake house sitters respond in under an hour.
House sitters in Chesapeake have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Chesapeake.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Chesapeake house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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