House Sitting Choptank Overlook

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Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Pamela A.
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Pamela A.
from
$65
per night
5.0 out of 5 stars
• 40 reviews
12 repeat clients
31 years of experience
Hillsboro, MD, 21641

“We LOVED Pamela! She was responsive, flexible, and loving to our boys! We were so lucky to find her in such a timely manner. She sent lots of pictures and videos of our dogs while we were gone, which was so loved and appreciated. She left our home in perfect condition! Thank you again, Pamela! We look forward to using you again!”

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Hannah D.
Sitter Profile Image: Emily W.
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Emily W.
from
$40
per night
5 years of experience
Denton, MD, 21629

About: I love dogs and I love spending time with them and playing with them! I love to snuggle or lay close with them and make sure they are comfortable at all times. I love playing with them and wearing them out so they sleep good at night! I love walking them and seeing how excited they get when someone comes to see them! I have dog sat many of dogs from very small to very big and I don't have a type, I love all sizes, shapes, and more! I have had a dog my whole life and I can't ever get enough of them. I have been told that I am good at dog sitting and their pets are always great when they return!

Sitter Profile Image: Kelly C.
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Kelly C.
from
$65
per night
4.9 out of 5 stars
• 13 reviews
3 repeat clients
10 years of experience
Preston, MD, 21655

“This was a last minute arrangement on our part, so we were a bit nervous, as we did not get a chance to meet Kelly before allowing her in our house to care for our dogs. She was great! She let us know as soon as she arrived, sent us pics and videos several times in just two days. The dogs were very happy and so were we. We would certainly invite her back in the future.”

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Stephen W.
Sitter Profile Image: Ashley C.
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Ashley C.
from
$70
per night
5.0 out of 5 stars
• 13 reviews
2 repeat clients
10 years of experience
Centreville, MD, 21617

“Ashley is a wonderful dog and house sitter! She took great care of Sadie for a week while we were out of town. She did everything I requested and was always very kind and courteous. The house looked exactly how we left it. Not a thing out of place. She is very trustworthy and highly dependable. I would recommend her to anyone!”

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Anne H.
Sitter Profile Image: Aliciya M.
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Aliciya M.
from
$40
per night
1 repeat client
15 years of experience
Queenstown, MD, 21658

About: I’ve lived with dogs and cats my entire life and have over 15 years of hands-on experience caring for pets. Growing up, my mom had five dogs—some of which had puppies—and I helped raise and care for them. I’ve also cared for cats in multi-pet households, including feeding, litter box maintenance, and creating calm, safe environments for shy or senior cats. Neighbors, friends, and family have trusted me for years to walk, feed, bathe, and care for their pets while they’re away. I now have a black Yorkie of my own, and I treat every animal I care for like part of the family—whether they bark or purr! I currently work part time- and have lots of free time! I will send out a daily schedule of what I’ll be doing with the pets! I will take your dog out on walks on our neighborhood trail outside! I also have a few ring cameras, and will send a lot of pictures/videos throughout the day.

Sitter Profile Image: maranda c.
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maranda c.
from
$65
per night
5.0 out of 5 stars
• 16 reviews
4 repeat clients
10 years of experience
Centreville, MD, 21617

“Maranda was fantastic. I really can’t say enough positive things about our experience with her. She was quick to learn and work with the idiosyncrasies of our two cats, took care of our house which was immaculate when we returned and communicated with us while away as much/or as little as we requested. She is very personable, respectful and responsive.”

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Stephanie N.
Sitter Profile Image: Claire A.
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Claire A.
from
$55
per night
3 years of experience
Dover, DE, 19904

About: Taken care of many of my neighbor’s, family’s, and other’s pets over the years. I’ve done overnight stays as well as drop ins and walks. I have pretty wide availability so just let me know what you need! I’m in a graduate program so I can do overnight stays & walks/drop ins. I’m pretty flexible so just let me know when you need me and we can likely make it work! I maintain a safe environment and closely follow instructions from the owner! I’ll always reach out if I’m unsure of something to make sure I can give your babies the best care!

Sitter Profile Image: Rachael B.
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Rachael B.
from
$80
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
10 years of experience
Queen anne, MD, 21657

About: I have 8 animals of my own, both dogs and cats. I also work part time as a Kennel Technician so I am very familiar with different animal personalities and how I’m expected to care for them! Neighbors, friends, family & clients have relied on me to care for their furry friends and I’ve loved getting to know each one. I am pet CPR & First aid Certified. I work as a nanny from 11-5 as well as dog sitting overnights frequently. I work as a nanny from 11-5 in Southampton. College is online so that won’t be a problem right now. My scheduled days can change but shifts are no longer than 6 hours at a time, Mon-Fri. I live in Sayville. I have plenty of time in the morning & afternoon for long walks and fetch! My weekends are completely free. I will take wonderful care of your pets as if they were my own. My pups love to play outside and get lots of attention so I want to share the love!! It’s always fun getting to know your dogs and cats. I have built a trusted clientele over the last 3 years of being on Rover. I am very responsible and will care for your house just as well as your pets! I know it takes a lot to entrust someone in your home so I won’t let you regret it.

Sitter Profile Image: Aaron C.
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Aaron C.
from
$25
per night
5.0 out of 5 stars
• 8 reviews
1 repeat client
20 years of experience
Greenwood, DE, 19950

About: My wife and I love being with our dogs, we have 3 adopted dogs and 1 dog we received as a newborn puppy, and love meeting other owners and their pets. We take our dogs for walks at our lovely park across the street or to the dog park to let them run free with the other dogs. We also have a 5 acre yard for any animal to do what they please. We take our dogs on hikes on the red rock trails, have lots of toys for them to play with, spoil them with the right amount of dog treats. We have a specialized dog food brand we use and cook our dogs fresh meat for them to eat, they don't seem to mind.

Sitter Profile Image: Teresa D.
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Teresa D.
from
$45
per night
5.0 out of 5 stars
• 99 reviews
36 repeat clients
Frederica, DE, 19946

About: Hello! My name is Teresa! I work full-time on the weekdays but I have weekends free for dog sitting. I have been a dog sitter for a few of my neighbors in the past for fun. Your dog(s) will have a nice house to run around in, we'll take long walks around the neighborhood, going to the Bowers beach, playing in the sand. Since its only me in the house, they will have my undivided attention and love. In the summer, they will be cool, and in the winter, they will be warm by the fireplace. I truly enjoy the company of pets and I look forward to providing you peace of mind and the utmost in care for you and your four legged family members!

Sitter Profile Image: Kayla J.
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Kayla J.
from
$90
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
10 years of experience
Milford, DE, 19963

“Penelope and Charlie loved spending time with Kayla 😍 always takes great care of them both!”

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Cathleen T.
Sitter Profile Image: Jordan M.
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Jordan M.
from
$35
per night
4 years of experience
Smyrna, DE, 19977

About: Hello everyone! I am an animal lover, I grew up around animals all my life. Our furry friends are extended family members. I hope you entrust me with your furry loved ones. I am currently an active college student, but I have somewhat situated myself with a work-life balance. I am available and flexible for weekdays and weekends! I currently have a kitten almost a year old. Having him has taught me patience, and having complete responsibility. Milo is my profile picture! I feel as though I am completely up to any challenge, I hope I can help with your furry loved ones!

Sitter Profile Image: Alexxis E.
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Alexxis E.
Star Sitter
from
$165
per night
5.0 out of 5 stars
• 35 reviews
9 repeat clients
15 years of experience
Annapolis, MD, 21409

“Alexxis was wonderful with our dog Maddie. She was very communicative with planning and sharing photos/updates and flexible when our drop off time changed and with dropping of Maddie at our home. Would recommend and use again!”

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Chelsea K.
Sitter Profile Image: Alyssa M.
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Alyssa M.
from
$20
per night
4.5 out of 5 stars
• 2 reviews
2 repeat clients
12 years of experience
Seaford, DE, 19973

“Alyssa was great with our fur babies, and sent pictures often while we were away. You could tell the pups were happy by the big smiles on their faces in every picture! We will definitely be asking Alyssa to watch them the next time we go away.”

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Jennifer S.
Sitter Profile Image: Amanda M.
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Amanda M.
from
$40
per night
5.0 out of 5 stars
• 1 review
15 years of experience
Grasonville, MD, 21536

About: I love playing with dogs and walking them. I've grown up around all types of dogs small and large. I'm very fun and outgoing as well as criminal justice trained ensuring your pets safety. I have taken care of our families dogs as well as watching other family friends pets. I have watched animals with allergies and medication needs. Dogs of all ages are welcome. I will meet any needs of the dog/dogs and ensure to have them back to you safe worn out and happy. I work part time so most of my day is running errands or cleaning the house. If they love car rides they are more than welcome to drive around with me. I will adjust my schedule to meet the needs of the dog or animal. Also absolutely love my kitties. Open to all animal requests just ask! Im a full time optician and part time cook. With plenty of notice I will take off my parttime job to care for your babies. Your pet will be loved as family. Your pet will be able to sleep with me and get full access of my apartment. Toilet bowl lids will always be closed

Sitter Profile Image: Jacqueline G.
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Jacqueline G.
from
$85
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
14 years of experience
Crownsville, MD, 21032

“Jacqueline was the BEST for my highly needy anxious dog!”

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Meredith C.
Sitter Profile Image: Danielle D.
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Danielle D.
from
$80
per night
5.0 out of 5 stars
• 4 reviews
3 repeat clients
5 years of experience
Salisbury, MD, 21804

About: Im familiar with giving medication, and providing exceptional care for all animals. I've cared for pets most of my life, and I have 5 years of experience in an animal shelter caring for cats and dogs. It's very rewarding, and it's the best part of my day when I see the happy tails, hear the purring and receiving those kisses. I dont live in Denton, I live in Salisbury. I do travel for my clients,[up to 50 miles] only if youre in need of a sitter for more than 3 days. We can discuss even further during a meet n greet. My full time work is as a gig worker. I make my own schedule, so I am able to care for your pets at any time. I love animals! I provide a safe, and caring environment when I care your pets. I love them like they're my own. Care would be in your home, and I usually stay overnight, unless you would like daily care, then I would come a couple times per day to provide meals, scoop litter boxes, take daily walks, etc.

Sitter Profile Image: Chelsi M.
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Chelsi M.
from
$90
per night
5.0 out of 5 stars
• 9 reviews
3 repeat clients
5 years of experience
Bear, DE, 19701

About: I am here to take of your dog and to provide them the love they long when it’s vacation time for owners (or anytime you need to yourself). Provide exercise for dogs (usually in half-hour or one-hour increments). Pick up and dispose of dog droppings during walks. Check dogs' food and water supply to make sure basic needs are met after walks. I am very patient and show a lot of compassion towards dog. I just want them to feel at home away from home! I am also a very active person, so your dog will be able to have all of their fun they usually have or more when they are with me! I hope to walk your dog soon! Prices are non negotiable I am working from home currently. This will allow me to give your first baby all of the attention they desire. Please ask me any questions on any accommodations that we may be able to work out. I don’t have any pets of my own so if your fur baby isn’t fond of other pets they can feel secure being over my home. My I am close with my neighbors who do have friendly pets as well, so if your pet loves company, they can be easily accommodated. We also have a dog park walking distance from the complex

Sitter Profile Image: Alexis, Tammy & Jamie A.
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Alexis, Tammy & Jamie A.
Star Sitter
from
$110
per night
5.0 out of 5 stars
• 596 reviews
203 repeat clients
15 years of experience
Millersville, MD, 21108

About: 👋 Meet Your Caregivers: ❤️ Alexis I’ve had a big heart for dogs all my life—starting with my very first dog, Spencer, a Yorkie who lived to be 18.5 years old despite being medically challenged! Caring for him throughout his long life inspired me to pursue a career in the veterinary field. I am currently a remote student studying to become a Veterinary Technologist. Because I complete my coursework online from home, I have an extremely flexible schedule and spend the vast majority of my time dedicated to caring for pets. Whether going on neighborhood walks, playing fetch, or simply relaxing together, I am committed to keeping your fur-baby safe, happy, and loved. 📋 What We Need to Know Before the Stay To help us provide the absolute best individualized care, please share: Any preexisting medical conditions, medication schedules, or dietary needs. Behavioral quirks, triggers, or leash-pulling tendencies. Your pet's regular daily routine, potty schedule, and comfort preferences. When your pet stays with us, they get the benefit of a dedicated, full-time care team! ❤️ Tammy I’m a lifelong dog owner and shelter volunteer who understands how stressful it can be to leave your fur-baby behind. I provide 24/7 loving, home-style care so your pet never has to deal with the stress of a commercial kennel. I have extensive experience with oral medications, all ages of pets including senior pets, and dogs with separation anxiety. Whether it's playing fetch in the yard, going on walks, or cuddling on the couch, I treat every visiting pet like family! 🏡 Jamie — House Sitting Specialist As a retiree with a lifelong passion for animals, I specialize primarily in in-home house sitting for both dogs and cats. My goal during house sits is to keep your pet's daily routine as normal and stress-free as possible in the comfort and security of their own home. I am attentive, trustworthy, and meticulous about following your exact instructions. When assisting with boarding or outdoor activities, I love taking pets for peaceful walks through nearby Kinder Farm Park or letting them explore our secure, backyard! 24/7 Full-Time Supervision: Someone is always home to monitor, feed, and interact with your pets. 100% Secure & Supervised Outdoor Play: Pups are strictly supervised outdoors and will never be left unattended. Individualized Attention: We match our daily routine to your dog's energy level, from high-energy fetch to peaceful senior relaxation. 🐾 Services Include Boarding: A safe, loving environment for your pet's home away from home. Doggy Daycare: A fun-filled day of play and socialization. Dog Walking: Give your pup the exercise and potty break they need! House Sitting: Keep your pet safe and comfortable in their own home. Drop-in Visits: Quick check-ins for feeding, playtime, or medications. We offer 24/7 support and a FREE In-Person Meet & Greet to ensure the perfect fit for your pet! We're here for YOU (and your best friend)! Advanced & Specialized Care With my professional and personal background, I am uniquely equipped to manage pets with complex health needs, including: Medical Conditions: Diabetes, blindness, neurological conditions, cardiac issues, liver disease, heart and kidney disease, and medically challenged pets. Mobility & Recovery: Specialized care for pets with limited mobility, including those recovering from or living with CCL injuries. Age Groups: Safe, patient, and tailored care for dogs of all ages including young puppies and senior dogs. Treatments: Proficient in administering oral and injectable medications. 🏡 Our Home & Safety Commitments Prime Location: Located right across from Kinder Farm Park great for engaging daily walks! 24/7 Full-Time Supervision: Someone is always home to monitor, feed, and interact with your pets. 100% Secure & Supervised Outdoor Play: Pups are strictly supervised outdoors and will never be left unattended. Individualized Attention: We match our daily routine to your dog's energy level, from high-energy fetch to peaceful senior relaxation.

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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.

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 house sitting

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

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Popular requests for house sitting - Choptank Overlook

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FAQs for House Sitting - Choptank Overlook

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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 Choptank Overlook 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 Choptank Overlook 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.

<b>Tip:</b> 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 Choptank Overlook 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 , 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 .

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 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 .

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.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.

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