Dog Sitting Chesapeake Beach

Book a Chesapeake Beach dog sitter to watch your dog in your sitter’s home or yours.

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Over 67
pet parents in Chesapeake Beach have booked dog sitting

Chesapeake Beach, 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.

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Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$17
per visit
5.0 out of 5 stars
51 reviews
17 repeat clients
10 years of experience
Huntingtown, MD, 20639

Stephanie was fantastic this past week, doing drop-in visits with my usually shy dog. She was incredibly patient and gentle, making my dog feel comfortable, and my pup warmed up to her quickly. Stephanie is very responsive on the app and always sends detailed updates with photos after each visit. I’ll definitely ask her to look after my dog again. Highly recommend!

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Dusan I.
Sitter Profile Image: Cynthia H.
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Cynthia H.
from
$20
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
28 years of experience
Prince frederick, MD, 20678

About: I use to work for a boarding kennel when I was younger, but since my young teens I have been dog/cat/house sitting. I love animals I will be there new best friend. You will not regret if you choose me to watch your loved one, they will be well taken care of, well loved and spoiled! No request is to much, I have watched all different kinds of animals from dogs, cats, birds, hedgehogs, bunnies you name it I have probably watched them. I work at prince Frederick Safeway. I normally work 4-1pm, 5 days a week. My schedule does change from time to time due to what is going on but I will communicate my schedule prior to watching your babies. Some days are easier than others… Monday, Wednesday and Fridays I’m not normally available until 3pm. Tuesday and Thursdays I’m available anytime after 1pm. This could change just ask and we will work something out! I have a huge fenced in back yard! Lots of room to run and play! I will crate your animal if it is needed, just please bring your crate with you. If not crated during the day I keep all doors shut so they can’t get into anything they aren’t supposed to. I do also have indoor camera to keep an eye on them while I’m away at work. Due to apartment rules I am not allowed to have pit pulls at my apartment, I love the breed! I just have to make sure I am following my landlord rules, I would have to come to you!

Sitter Profile Image: Evangeline B.
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Evangeline B.
from
$15
per visit
15 years of experience
Huntingtown, MD, 20639

About: I’ve had a dog in my family for as long as I can remember, from my childhood husky Ginger to our current family pekingese Alley. I absolutely adore dogs and jump at every chance to hang out with any of my friends dogs as well. I have experience with dogs of all ages and sizes, including those with special medical needs. I currently work part time at a restaurant and will be dedicated to your pet’s care every second I am not at work. I would never accept a job that would require me to compromise a pet’s needs and they will always come first in my life. I am committed to following any and all instructions given for dog/cat care. I understand that being in someone else’s home means following their rules and I will respect any spaces I am invited into.

Sitter Profile Image: Elizabeth G.
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Elizabeth G.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
50 reviews
12 repeat clients
30 years of experience
HUNTINGTOWN, MD, 20639

Shes very accommodating and Jules loves her

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Lacey W.
Sitter Profile Image: Karlie M.
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Karlie M.
from
$20
per visit
5.0 out of 5 stars
1 review
14 years of experience
Prince Frederick, MD, 20678

Karlie did an excellent job of taking care of our fur-baby. We will definitely be using her services again. Kakes really liked her and how attentive she was with her. She took care of her like she was her very own. Great job all the way!!!

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Sarah P.
Sitter Profile Image: Savannah H.
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Savannah H.
from
$15
per visit
5.0 out of 5 stars
16 reviews
5 repeat clients
8 years of experience
Huntingtown, MD, 20639

About: I raised two bigs that I have trained years now and I grew up on a small farm so I have gotten the opportunity to care for animals for some time now! I also volunteer at animal shelters, getting the opportunity to work with all kinds of dogs as well. I am home from playing overseas and am available most days! During week days I can go to others homes to walk or check in pets normally any time of the day. I am comfortable with taking any size pet out for walks or stopping in to give them attention and have no issue taking them out to play and potty based on what the owner wishes!

Sitter Profile Image: Danielle E.
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Danielle E.
from
$12
per visit
5.0 out of 5 stars
7 reviews
1 repeat client
25 years of experience
Huntingtown, MD, 20639

Danielle was amazing! She was always on time, showed up for every check-in as scheduled, and was very reliable from start to finish. She left thoughtful updates with great notes and pictures, which gave us total peace of mind while we were away. I would highly recommend Danielle to anyone looking for a dependable and caring sitter. We’ll definitely be booking her again!

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Jenn H.
Sitter Profile Image: Ashley P.
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Ashley P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
49 reviews
16 repeat clients
15 years of experience
Huntingtown, MD, 20639

Ashley was amazing with Cocoa Bean! Cocoa is a 91 pound XL bully who is sweet but excitable and Ashley handled her perfectly. Our whole family loved the detailed updates and many pictures Ashley sent each day. It was clear that Cocoa and Ashley formed a real bond and Cocoa got endless pets and stick time in the yard. Ashley also thoughtfully brought in packages, took our garbage to the curb and back, and fed and watered our misanthropic hedgehog, Mister Bear.🤣 When our flight was rerouted Ashley stepped right up to add an extra visit for us with little notice. We 10/10 recommend Ashley!

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Jessica S.
Sitter Profile Image: Lindsay J.
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Lindsay J.
from
$15
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
3 years of experience
Huntingtown, MD, 20639

Lindsay did an excellent job keeping our kitties entertained while we were on our honeymoon and provided plenty of pictures and updates while we were gone.

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Allison S.
Sitter Profile Image: Jaicy D.
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Jaicy D.
from
$25
per visit
15 years of experience
Owings, MD, 20736

About: i grew up my whole life around dogs. when i was younger i had atleade 5 dogs and at time and even now that i am grown up i still have 5 dogs. i also have had multiple types of animals at time like pigs, bunnies, etc. i work 6:30-3:30 everyday but get a lunch break. so i can stop before work. during my lunch break and i can stop after work too! i always make sure your fur babies have extra water and stay hydrated. your fur babies will always have extra cuddles and treats. especially on hot days. and whatever you guys need me to do!

Sitter Profile Image: Amelia P.
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Amelia P.
from
$40
per visit
8 years of experience
Chesapeake Beach, MD, 20732

About: Dogs have always been a huge part of my life. Growing up with dogs taught me exactly how to read their body language and give them the care, attention, and love they deserve. I treat every furry guest just like my own, making sure they stay happy, active, and fully comfortable while you're away I’m currently working a full-time job, but I work remotely every other week which gives me some spare time and I’d love to use it to spend with some dogs. I do have two kids ages three and eight both love dogs. I don’t have any dogs in my own, but I plan to get one and then your future however I was in our home with four dogs at a time

Sitter Profile Image: Christina B.
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Christina B.
from
$15
per visit
5.0 out of 5 stars
13 reviews
6 years of experience
Owings, MD, 20736

Christina took great care of our two cats while we were away. she was very kind and her communication was great. Definitely will be using her again!

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Huston H.
Sitter Profile Image: Chris G.
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Chris G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
18 reviews
9 repeat clients
30 years of experience
Dunkirk, MD, 20754

About: I’ve had my knee replaced which has slowed me down a tad but also allows me be to home all the time. We recently lost our old boy (dog of 12 years) and while my cats have helped me to survive, I have so much more love to give! For now I want to spend time with others’ dogs to help fill the whole in my heart. I genuinely want to make every animal a friend of mine! I will always lead with love, care and respect. I work from home already which is usually stuff I take care of in the evenings anyway but I have the time, love and space to accommodate your furry family members. We have three lovable indoor cats. Two will stay away mostly and one will greet you at the door with friendly meows. We will spend the whole time snuggling on the couch or running around in our yard.

Sitter Profile Image: Kristy R.
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Kristy R.
from
$30
per visit
5.0 out of 5 stars
25 reviews
5 repeat clients
15 years of experience
Sunderland, MD, 20689

Kristy was wonderful with my kitties! She took time to make sure they had everything they needed and played with them too. Her communication was responsive and thorough. I highly recommend Kristy and will gladly use her again in the future!

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Denise L.
Sitter Profile Image: Lucy R.
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Lucy R.
from
$17
per visit
6 years of experience
Huntingtown, MD, 20639

About: Hi! I’m a dependable and caring animal lover with hands-on experience caring for dogs of all ages and personalities. I’ve walked my neighbor’s dog regularly, provided dog-sitting services for multiple family friends, and have experience training and caring for my own dog every day. I understand the importance of keeping pets safe, active, and comfortable while their owners are away. Whether your dog needs a fun walk, plenty of playtime, or patient, attentive care, I’ll treat them like they’re part of my own family. My goal is to make sure every pet feels happy, loved, and well cared for while giving owners peace of mind. I’m currently waiting for college to start, so I have a lot of availability! I can work any day Saturday through Sunday at anytime at the moment. When caring for your dog, I will make sure they receive plenty of attention, exercise, and affection while following their normal routine as closely as possible. I’ll take them on walks, provide fresh food and water, play with them, and make sure they have opportunities to go outside for bathroom breaks. I’ll also keep a close eye on their behavior to ensure they are happy, comfortable, and safe. My goal is to give your dog the same level of care and love they receive at home so you can have peace of mind while you’re away.

Sitter Profile Image: Savanna B.
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Savanna B.
from
$30
per visit
5.0 out of 5 stars
22 reviews
5 repeat clients
14 years of experience
Chesapeake Beach, MD, 20732

Savanna took such great care of our two cats will we were on vacation! Our older cat needed medication applied to her ears and fed wet food so I was nervous leaving her. Savanna was patient with her and made sure she ate and got her daily meds. I was able to enjoy the time away without worrying as Savanna updated me after each visit. She is awesome, thanks again, Savanna!!

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Holly M.
Sitter Profile Image: Denise S.
Verified Enhanced Background Check
Denise S.
Star Sitter
from
$45
per visit
5.0 out of 5 stars
40 reviews
12 repeat clients
25 years of experience
North Beach, MD, 20714

Denise did a fantastic job with my two Rotties. Thanks again Tammy

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Tammy ..
Sitter Profile Image: Kristina B.
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Kristina B.
from
$30
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
15 years of experience
North beach, MD, 20714

Kristina was fantastic! She came to our home everyday to take care of our two cats while we were away. She sent pictures of each visit and was very responsive. Definitely using her for all our pet care needs!

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Huston H.
Sitter Profile Image: Amanda S.
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Amanda S.
from
$17
per visit
5.0 out of 5 stars
13 reviews
2 repeat clients
15 years of experience
Huntingtown, MD, 20747

I have booked Amanda two times now. She has been the best! I am able to go away and feel confident my pets are safe, well loved and under amazing care.

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Naomi L.
Sitter Profile Image: Amanda D.
Verified Enhanced Background Check
Amanda D.
from
$30
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
30 years of experience
North Beach, MD, 20714

About: Promo Code for $40 off first time booking for Pet Owners that it is their first time using Rover- AMANDD61392 Friends and Family call me the animal whisperer. I have had a dog/dogs my whole life. I have taken care of dogs from brand new puppies, to babies that were at the end of their life. I'm currently not working full time away from home, so for any boardings that are on week days or weekends, you and your fur babies are good to go. I do have one small dog at home BUT, if you prefer your dogs to be alone while here, my dog is easily brought to his grandparents house:), which they are always happy about. I will update when my work schedule changes. I have a fenced yard (tall privacy wooden fence with sliding deadbolt), and can easily crate dogs if needed. Any animals would have free range of the house and the yard. Your babies are my babies while I am taking care of them.

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The median cost per visit for dog sitting in Chesapeake Beach is $20

Dog parents share their Rover experiences - Chesapeake Beach

1 / 1
5.0 out of 5 stars

Tosawi was a huge help for us when we were in a pinch. He took care of our 2 babies for 3 days with very attentive drop-in service. He was attentive, commucative and very accommodating. Our cuties are extremely opposite in both physical characteristics and temperament, one being a large pit mix who is very docile and a tiny yorkie pom, who is extremely high energy. Tosawi was able to navigate both personalities with ease. I would definitely use him again.

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Deanna J.
Drop-In Visits
5.0 out of 5 stars

Jake was awesome with my pooch! He was very communicative and helpful, sending lots of pics and updates. He’s my ‘go to’ from now on!😊

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Liz N.
Drop-In Visits
5.0 out of 5 stars

Beth was amazing with my pups! She was able to visit with very last minute notice, which is soo appreciated! Beth communicated quickly and shared lots of pictures of my babies. Will definitely reach out to Beth again if pet sitting is needed.

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Kelly B.
Drop-In Visits
5.0 out of 5 stars

Kristi is amazing! Our Maggie really seemed to have gotten lots of loving and play time for our drop in visit. We got lots of videos and photos and reassurance that Maggie was in good hands. We are so happy and excited to book Kristi again!

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Bianca M.
Drop-In Visits
5.0 out of 5 stars

Holly has been a life saver. We got our pup Zelda in summer of 2025 and needed someone during the fall and winter months to help with letting her out. I love coming home to all the doggie toys pick up and blankest folded (doggies are messy). Holly is very responsive, dependable and really cares for our pets. Would recommend Holly to anyone!!!

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Marsha M.
Drop-In Visits
5.0 out of 5 stars

Jen is excellent at what she does and always makes me feel at ease while we are out of town taking great care of our family pet.

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Jessie H.
Drop-In Visits
5.0 out of 5 stars

Brittany is the best. I am so thankful to be able to leave her with my new golden, and be confident she has my dog’s best interest at heart. And, this is one intelligent lady! Brittany remembers your habits, and acts according. I am very grateful for her.

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Denise B.
Drop-In Visits
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Sitters in Chesapeake Beach average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Chesapeake Beach

Frequently asked questions about Rover

The average cost for Dog Sitting in Chesapeake Beach on Rover is $22.2 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog 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 Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 6,814 sitters on Rover offering Dog Sitting across Chesapeake Beach. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Chesapeake Beach stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 Beach 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 short introductory meeting between you, your dog, 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.

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 Chesapeake Beach 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 Chesapeake Beach. On Rover:

  • 90% of sitters can help with special care needs
  • 95% 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.

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.

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