House Sitting Chesapeake City
Find a loving house sitter to watch over your pets and your home.

Chesapeake City, 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.

“Nina was great! She collected a lot of written information about our dog Daisy prior to our vacation and used it to guide her care. Nina's written log of play activities and treat rewards was remarkable and assured us Daisy was always in good hands. She updated us regularly while we were away with texts and photos. As part of our arrangement, we had requested a few extra tasks involving the watering of house plants (quite a few) and these were carried out to perfection. Not to mention, the house looked great when we returned! We will not hesitate to request our new friend and pat-sitter the next time we need to go away.”

About: Hey, pet parents! I’m a proud Animal Science student at Penn State with years of experience caring for all animals great and small including dogs, cats, horses, cows, and more! With 2 dogs and 3 cats of my own, I totally get how much love our pets bring into our lives. Whether your pup needs a walk or your cat needs cuddles, I bring knowledge, reliability, and lots of tail wags. I treat every animal like family because that’s exactly what they are! As a dedicated pet owner and Animal Science student, pet care is already a major part of my daily routine! I care for my own 2 dogs and 3 cats every day, which includes feeding, walking, grooming, playtime, and managing any health or behavioral needs. I naturally structure my schedule around animal care, and it’s something I truly enjoy and prioritize. Whether it’s early morning feedings, mid-day walks, or evening cuddle sessions, caring for animals is second nature to me and I’m always happy to make space in my week to care for others’ pets with the same love and attention I give my own. When caring for pets in my own home or a client’s, I focus on creating a calm, safe, and engaging environment that matches each animal’s personality and routine. In client homes, I always follow their care instructions closely whether that’s feeding schedules, medication, preferred walking routes, or favorite toys. I keep pets on their normal routines to reduce stress and make them feel comfortable while their owners are away. For cats, I make sure litter boxes are clean, water is fresh, and they have a mix of playtime and quiet time, depending on their temperament. For dogs, I provide plenty of exercise, enrichment, and affection along with structured potty breaks and walks. I’m also experienced with senior pets and those needing medication or extra TLC. Whether I’m staying overnight, dropping in for visits, or out for a walk, I care for every pet like they’re my own attentively, gently, and with lots of love and respect!
“Matt stayed overnight with our dogs while we were away for a week. Matt arrived around dinner time and stayed overnight. After feeding them breakfast, he'd leave for a few hours and then come back mid-day for a play break. We got proactive daily communication and pictures. Which was great! Matt even accommodated an unusual request when a family member needed access to our home while we were away, which was much appreciated. We would definitely use (Jenni &) Matt again.”

“SUPER🤩 This was our first time using Michaela, and she was absolutely wonderful! She watched our 5 year old lab at our home for a week and did a fabulous job with her. Cali is a very active and energetic lab. She followed her schedule and met Cali’s needs. Michaela made sure that her needs were met by getting her outside a few times during the day to play fetch with her frisbee and tennis ball, along with taking her on her walks. And not only that, Cali has a bit of anxiety at times and Michaela made sure she was loved and got the attention she needed while we were away. Michaela did check-ins and sent pictures daily( morning and evening). Michaela is very professional, caring and super friendly plus, she actually had more questions for us about Cali then we did for her, which was super impressive. She took notes about Cali starting with what her daily routine is like, her eating schedule, activities she likes, her behaviors etc. You name it, she asked it. My husband and I just knew after meeting with her, that she would be perfect taking care of Cali because you could just tell that she genuinely cares about your pet and their needs. We also felt super comfortable allowing her care for Cali and be in our home. We were so happy to find a kind, friendly, professional and trustworthy person to take care of Cali. Also, I am a bit of a clean freak and I can tell you, that my house was left the same way I left it….looked like she was never there, spotless! We were also having bad storms while we were away, so I texted Michaela about a few outside things on our deck that needed to be taken care of and she made sure it was all taken care of as well. A breaker tripped while she stayed with Cali, so she texted us the issue and we were able to call her and help get it resolved. Like I said before very professional, caring and kind. Her communication and dedication of care not only for our dog but our home was truly amazing. We will definitely be using Michaela’s services again and highly recommend.”

“Look no further - Reid is the man! We had Reid dog sit our 2 relatively new to us bonded pair rescue dogs. The poochies had spent 2 months in a kennel waiting to be adopted, so we wanted in home care while we went away. Our flight schedules changed several times coming and going, and Reid was always available to accommodate those changes. The poochies were still adjusting to us and their new home, and were having some anxiety issues. Reid was so patient and really worked with them while we were away. When we arrived home it was obvious that they loved him and he loved them. I would not hesitate to have Reid house sit for us again, and already have plans to have him back for day visits when we are out for the day. 5 stars all the way!”

“Christine was exceptional and took such great care of our home and our pup. She provided frequent updates with photos and videos. We scheduled last minute so finding such great care was a huge relief for us. Would recommend her and use her again in the future.”

“Our dog has so much anxiety and Kathleen was amazing with him! He warmed up to her with her patience and it was a great weekend! She kept us updated and in turn we had a great time away, not worrying at all. She communicates well and quickly, she kept our house clean and in great condition. We would love to have her stay and take care of our dog again. Definitely recommend her to anyone else looking.”


About: I am compassionate, caring and loving to all cats. My cat is my best friend because she listens better than humans. Cats are my go to for unjudgmental opinions I work full time, so I would be available to care for your furbabies after 4pm. I would also be available on the weekends to provide checkin n needed care. I have 1 cat , our apartment is cat friendly and quiet with 2 adult caretakers. I have had 3 cats previously. They can be such good companions. She eats 3 meals, has regular water changes and litter box changes and plays good solo .

About: I've Been an avid animal lover since birth. Always have had animals in the house since I can remember. I started my first dog walking/sitting job at 10, made flyers and all. Flash forward 23 years and im still taking care of loved friends fur children. I'm a mother of 2 french bulldog/Boston terrier mixes, 2 beautiful black cats & an energetic 1 year old babygirl. I've worked with animals of all types, I'm not just your adverage cat and dog sitter (ducks, geese, chickens, goats) Can't wait to meet you and your precious fur babies. We have a very flexible routine typically our day starts with potty and breakfast for everyone. In the afternoon we have a snack and playoutside for 20-30 minutes. the evening is filled with cuddles relaxing and dinner. At bed time we all go potty and the pups get locked up in their create. Everyday is different but we are easy adapt to what ever the day may bring. We have a large yard which my pups are trained to stay in, with being frenchies they are practically my shadows. For bedtime and when we are away from home they are create trained for their safety. I would follow what ever rules are set in place to take care of your fur babies as well I understand all the dangers pets can get into when not leashed, fenced in, or created for their safety.
“I was going to be away on a 15 day vacation in Europe and concerned I wouldn’t be able to find a someone I could trust to care for my two young cats for such a long time. Any and all worries melted away when I met Jen! She is very personable, very reliable and caring. Jen sent me daily updates on my kitties interactions with her and lots of photos . I highly recommend her to care for your pet. I will definitely continue with Jen for taking care of my fur babies 😊”

“Amber took care of my dog and cat with so much care and attention! She kept me updated and was able to easily follow my dogs routine. Absolutely would recommend her services and will be booking again!”

About: I have been around and taken care of different pets since I was young. Often I pet/house sit for family/friends while they are on vacation but I have recently started watching dogs in my own home while the owners are away. I have watched dogs ranging from Cane Corso to Shih Tzu as well as several cats, hamsters and fish. I prefer to pet sit in the owners home so the pets are less stressed but will do everything I can to make them feel comfortable in my own home. I live on 4 acres that are not fenced in so if you or your dog are not okay with that I will make sure they are leashed anytime they are outside. I do have cats but they are in a separate part of the house where your pet will have no access with. I am always open to any questions or suggestions! I work full time typically from Monday to Friday. It’s usually 8-4 but can range from 4am to midnight. I will always let you know ahead of time what my schedule is or if you require something specific I’m willing to try to work something out. I have a lab that is crate trained if your dog is lonely they can go together or be in crates next to each other. The dogs will also never be alone or outside together without supervision. As for your own home I have no issue with pictures/FaceTime or cameras being in the house. I have a law enforcement background and my only concern is to care for your pets and make sure the house is secure when I leave.
About: I've raised 5 of my own dogs, cared for family members' dogs, and neighbors' dogs since I was 15. I love them and treat them like my own children. Puppies and seniors are not an issue. I can care for multiple dogs at a time. All breeds. As of now, I'm pretty flexible. My daughter moved out, so it's just my husband and me. We have an 8 year old Beagle and a 4 year old dachshund. I'm available weekdays, weekends, and holidays for up to 2 weeks at a time to give your dogs plenty of attention and affection. First of all, I ask the owner if there's any special instructions for their pet. My availability allows me to be there to attend to and play with pets in the comfort of their own home. I give them lots of love, just like they deserve! They are family!
“Raven did a wonderful job with our pup! This was our first time having someone (not family) stay at our house to watch him, so we were a little nervous on how it would go. Spice is an 85 pound mixed breed dog that can be pretty quirky and anxious with new people. It took a little bit to warm up, but once he was comfortable, he did great! Raven was very patient with him and understood his quirks quickly. She was very responsive, sent multiple updates (with pictures), played with him and took him on walks daily. I truly appreciated having her stay with him.”

About: From caring for 10 senior dogs at a rescue, to bathing dogs that got sprayed by skunks, to training and taking dogs on their own outings to parks and nature hikes, you name it I’ve done it! Even flying with dogs! ✈️ I have experience with all breeds, ages, and like to keep pet parents informed with notes & pics. Growing up in farm country taught me to love and care for all animals, but dogs and cats are by far my favorite. I also have experience in administering medications to our furry friends. I left my career of being a nanny in CA to move to the east coast to marry my husband. That was 2019, and I’ve been boarding/caring for animals since then. I’m currently a stay-at-home wifey so the dogs get 100 percent of my attention when they are with us. We live in a 3 story townhouse with a small unfenced yard in front of our home, to a large grassy area on the side of our home, to a giant green grass patch directly behind us just out our back door. The neighborhood is VERY dog-friendly with lots of sidewalks and comes complete with a dog park in walking distance. Our home is dog-friendly meaning dogs are allowed on all furniture and we even have doggie steps for little pooches to get up on our bed if they wish. We also have a 2mile + walking path near us. So we have plenty of activity options. We even have Pluto cartoons for your pet to watch! Pets get 100 percent of my attention when they stay with us. Their comfort and safety is my priority as I do pet care full-time. Our home has no place that’s off limits to your pets. If they want to snuggle on our bed or relax on our couch or even be in our guest room - they are more than welcome wherever they are most comfortable. We even have a massive bean bag most animals love thinking it’s a giant dog bed 😂.
“Terry is absolutely amazing!! I can’t say enough good things about her and how she went above and beyond in taking care of our two dogs while we were out of town. She loved and cared for them like they were her own, sending us updates and videos each day. We had an amazing vacation and was able to not worry a bit about how the dogs were adjusting - they were so happy and got so much attention with Terry!! She will be the first person we call whenever we need a sitter! Thank you Terry!!”

“Rebecca did an excellent job staying at our home with Pippin! She was really prepared with questions to help the weekend good smoothly and to understand his needs. She was very responsive to messages and sent detailed updates and pics. Our pup had a great time!”

About: Pet lover ready to provide your pets with all of the needs and love they need! I have been dog sitting consistently for the past 4 years and have my own two kitties since then as well! I have taken care of horses, fish, snakes. Etc! Depending on the location I can care for pets during the week and make sure they get their potty needs out of the way during lunch time and once I am done at work. Afternoons and weekends are also super doable! My cats are indoor kitties and are only allowed on the deck, however I will care for the owners pets as they would like me to care for them. Some dogs are better cared for on a leash others are free to roam and others have fences! That all depends on the pet owner but I will respect whatever they choose.

About: With over six and a half years of hands-on pet care, I bring a rare blend of experience, attentiveness, and heart. I’ve worked with dogs of all sizes, temperaments, and ages—from energetic puppies learning the ropes to senior pets needing gentle, attentive care. What truly sets me apart is my ability to read and respond to animals’ unique personalities. I create a calm, consistent environment where pets feel safe, loved, and understood. Whether it’s administering medication, offering leash training for puppies, or providing low-stress companionship for older pets, I bring patience and skill to every interaction. I also have experience caring for a diverse range of animals beyond just dogs and cats. From chickens and birds to hamsters and other small pets, I understand that every species has its own rhythm, needs, and comfort cues. I’m confident and compassionate with unique, exotic, or less-common animals, always prioritizing their safety, emotional well-being, and daily routines. Pet care is a built-in part of my weekly life. I’m highly flexible and genuinely enjoy working around each pet’s needs and schedule. Whether it’s early mornings, midday visits, evenings, or even late nights, I’m available and committed to making your pet’s care seamless and stress-free. I’m also happy to accommodate weekend bookings and unique timing requests whenever possible—just let me know what works best for you and your pet, and I’ll do my best to make it happen. Reliability, consistency, and clear communication are at the heart of everything I do. In clients’ homes, I prioritize maintaining their pet’s normal routine and environment. I follow all instructions closely—feeding schedules, walking routes, medication routines, and preferred playtime activities—so your pet experiences as little disruption as possible. I also make sure the space stays tidy and respected while I’m there. If I’m hosting pets in my home, I provide a calm, safe, and welcoming space. I separate animals as needed, keep food and water fresh and clean, and ensure they have access to cozy rest areas and supervised play. I never leave pets unattended, and I’m mindful of their comfort, especially in a new setting. In both cases, I focus on creating a low-stress, high-trust atmosphere, and I keep pet parents updated with messages, photos, and honest communication throughout the stay.
The median cost per night for house sitting in Chesapeake City is $55
Pet parents share their Rover experiences - Chesapeake City
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- 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.

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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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Meet local sitters who will treat your pets like family

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Popular requests for house sitting - Chesapeake City
Select a filter and find qualifying sitters offering house sitting.Sitters in Chesapeake City average 4 repeat house sitting clients
FAQs for House Sitting - Chesapeake City
Frequently asked questions about Rover
As of September 2026, there are 1,035 sitters on Rover offering House Sitting across Chesapeake City. 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 Chesapeake City 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 Chesapeake City 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 Chesapeake City 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 Chesapeake City. On Rover:
- 97% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 93% 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.


