House Sitting in Chesapeake Beach

Find a loving house sitter to watch over your pets and your home.

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Top rated Chesapeake Beach house sitters

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: Faith M.
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Faith M.
Star Sitter
from
$40
per night
4.9 out of 5 stars
19 reviews
5 repeat clients
2 years of experience
Chesapeake Beach, MD, 20732

Our fur babies are family and not pets! She was attentive to their needs and gave them all the love and care in our absence! Our new go-to dog sitter!!

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Melinda J.
Sitter Profile Image: Leann D.
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Leann D.
from
$45
per night
5.0 out of 5 stars
5 reviews
1 repeat client
35 years of experience
North Beach, MD, 20714

Leann and Lola came to stay and took great care of my pets. They were very responsive and sent great reports on the dogs. Also took great care of the house!

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Darcy S.
Sitter Profile Image: Anna D.
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Anna D.
Star Sitter
from
$35
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
5 years of experience
North Beach, MD, 20714

Anna was awesome! She provided updates and responded to any inquiries within minutes. We've already rebooked her, just waiting on a response.

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Teresa I.
Sitter Profile Image: Grayson G.
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Grayson G.
from
$75
per night
4.9 out of 5 stars
17 reviews
6 repeat clients
13 years of experience
Chesapeake Beach, MD, 20732

Grayson was wonderful and loving with our older cat. She spent lots of time with him while we were away and was reliable, responsible and great with prompt communication and lots of pictures too. We felt safe and comfortable having her in our home and I’d recommend her for your pet needs any time.

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Tracy B.
Sitter Profile Image: Savanna B.
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Savanna B.
from
$89
per night
4.9 out of 5 stars
19 reviews
5 repeat clients
14 years of experience
Chesapeake Beach, MD, 20732

Savana was responsible in giving the medications on time even before I had time to check in about it. House was in perfect condition, would definitely recommend.

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John S.
Sitter Profile Image: Elizabeth G.
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Elizabeth G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
45 reviews
11 repeat clients
30 years of experience
HUNTINGTOWN, MD, 20639

Liz was an awesome pet sitter. She provided daily updates and photos and asked for information when a possible concern arose. My two dogs came home well cared for and happy!

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Leah M.
Sitter Profile Image: Drew F.
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Drew F.
from
$50
per night
5.0 out of 5 stars
4 reviews
5 years of experience
Chesapeake Beach, MD, 20732

Drew was an excellent experience for my Basset Hounds! I had a last second trip in which Drew was able to accommodate as well as a pre home visit to meet the dogs and get a feel of their environment. As I was out of town she sent consistent updates / pictures and followed all directions I left for feeding and overnight stay. Basset Hounds are a specific breed (needy & hard headed ) and she handled them perfectly!

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Matthew R.
Sitter Profile Image: Christina B.
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Christina B.
from
$25
per night
5.0 out of 5 stars
10 reviews
6 years of experience
Owings, MD, 20736

Christina was wonderful. Her communication was fantastic, we got lots of pictures, and she cared for our animals fabulously. She was everything we hoped for in a sitter, and more! We will definitely book her again.

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Becky S.
Sitter Profile Image: Amanda D.
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Amanda D.
from
$75
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
30 years of experience
North Beach, MD, 20714

About: Promo Code for $20 off first time booking for Pet Owners new to 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.

Sitter Profile Image: Jennifer D.
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Jennifer D.
from
$50
per night
15 years of experience
CHESAPEAKE BEACH, MD, 20732

About: I've had animals all my life! I love them all! I'm great with cats, dogs, pigs, and rabbits! I take special care of all my animals. I am self employed. I am available throughout the weekdays when most people are at work to be able to pop in and check on your pets as needed. Weekends as well. We have a fenced in yard. Cats would remain indoors unless stated otherwise. As long as your pets don't mind a toddler we should be great!

Sitter Profile Image: Jennifer S.
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Jennifer S.
from
$59
per night
5.0 out of 5 stars
53 reviews
20 repeat clients
25 years of experience
Churchton, MD, 20733

Jennifer was great with our babies. She sent lots of pictures and they really enjoyed all of the attention she gave them. We just booked her again for another visit.

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Kristin B.
Sitter Profile Image: Linda S.
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Linda S.
from
$60
per night
5.0 out of 5 stars
27 reviews
12 repeat clients
24 years of experience
Chesapeake Beach, MD, 20732

Linda was wonderful! She took great care of all our pets, kept us very well informed, and was very gracious and friendly as well! Will definitely work with her again

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Tyler S.
Sitter Profile Image: Jessica S.
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Jessica S.
from
$31
per night
4.8 out of 5 stars
11 reviews
3 repeat clients
9 years of experience
Owings, MD, 20736

Jessica was great with our dog Biscuit. We received updates and photos. She is very friendly and flexible with our schedule. I will use her again and highly recommend her.

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Melody F.
Sitter Profile Image: Jayden M.
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Jayden M.
from
$21
per night
10 years of experience
Huntingtown, MD, 20639

About: I have had animals my whole life, from chinchillas, birds, dogs, cats, and fish. I have also taken care of my neighbors animals in the past. Although I am only 18, I have grown up alongside big dogs my whole life, so I am no stranger to their difficulties. I also work as a home-healthcare CNA, so I am experienced in respecting other people’s homes. I also have other medical certifications, my BLS, CCMA, and GNA that I obtained in a 2-year program during my final two years of high school. I love spending time with my two huskies and my cat. While not professionally, I trained all my dogs current and past since childhood. I can’t say that I am a professional with dog training, but I’ve noticed that showing them respect allows them to respect me back. I have plenty of experience with taking care of my patient’s pets and I would love to meet yours! I am a full-time college student, and work part time as a home-healthcare CNA in annapolis and surrounding areas. I am busy sunday, monday, and wednesday, but I am available from 12-5 Tues & Thurs, and all day friday and saturdays. In my home, my dogs have a huge fenced in yard that they like to spend their time in. As they get older, they seem to love the couch just as much. I love to take them to dog parks and on hikes at Flag Ponds Park. I love walking with dogs and letting them see the world, so I will have no problem taking dogs on walks.

Sitter Profile Image: Tosawi L.
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Tosawi L.
from
$35
per night
5.0 out of 5 stars
1 review
5 years of experience
North Beach, MD, 20714

About: My goal is to take your spot as your pet’s best friend .. uhh I mean provide excellent care and service whenever duty calls :) My schedule is fairly flexible, and I am generally available each afternoon. I am sure that we can work out a reasonable time to get your pets situated! Owners rules are law. Whether it’s playtime, supper, potty time, etc I’ve got you covered. I am unable to provide services in my home at this time.

Sitter Profile Image: Kristina B.
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Kristina B.
from
$60
per night
5.0 out of 5 stars
2 reviews
2 repeat clients
15 years of experience
North beach, MD, 20714

About: I have grew up with my whole life with animals .They have always been a passion of mine! I am currently looking to pursue my career at an animal hospital and eventually start school for a veterinarian assistant ! One of my favorite child hood memories is looking back to all of our pets we had. We had dogs ,hamsters, iguanas, turtles ,cats,fish etc ! You name it we probably had it ! I am very compassionate, patient and friendly and i will make sure to treat your fur child like my own for sure! I have a daughter and also a 8 year old boxer who i adore so much so i absolutely know and understand how hard it can be to trust anyone with the ones we love the most but look no farther I will take care of them with no worries at all!! Your pets safety and needs will always be the number one priority at all times then the fun comes next! I cant wait to meet you and your furr kids soon to play and pamper them all!

Sitter Profile Image: Stephanie M.
Verified Enhanced Background Check
Stephanie M.
Star Sitter
from
$35
per night
5.0 out of 5 stars
45 reviews
16 repeat clients
10 years of experience
Huntingtown, MD, 20639

I have nothing but good things to say. Took care of my Atti like she was family. She will be so happy to go back in a couple weeks to play with Blaze again!

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Allyn F.
Sitter Profile Image: Tracey B.
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Tracey B.
from
$65
per night
5.0 out of 5 stars
4 reviews
30 years of experience
North beach, MD, 20714

About: I have over 30 yrs experience taking care of a wide range of furbabies & my furbabies say I’m the best mom ever! I love giving belly rubs and playing with the laser pointer. I work Monday through Friday as a full time government employee but I can do the evening checks and weekends for you and your furbaby I am able to come to you and your furbaby when you are away. If it’s a quick stop in the evening before you are able to get home or a weekend visit, I got your back!

Sitter Profile Image: Jenna M.
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Jenna M.
from
$40
per night
2 years of experience
Huntingtown, MD, 20639

About: I’ve taken care of puppies and dogs of all sizes and love animals through and through. Have raised puppies, to adult dogs. Am good with senior dog care etc I am a stay at home mom so I am able to meet your pet needs anytime of day, with one day of notice I am able to do in home pet care. Active in activities for animals and walks, meeting feeding requirements and taking care of animals of all sizes and specific needs. Available anytime of day

Sitter Profile Image: Lindsay J.
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Lindsay J.
from
$31
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
3 years of experience
Huntingtown, MD, 20639

About: Hi I’m Lindsay! I love spending time with our extroverted dog Zoomy 🐾 and with my cousin’s two cats Windex 🐈 and Squirt 🐈‍⬛. Zoomy would love to have some friends come over to play. I am a super responsible and clean person and would love to care for your fur babies while you’re away! Right now I have very flexible scheduling so send me a message! I can do daytime hours or evenings, just let me know. I’d be happy to work with you and your schedule. We have a big yard with an invisible fence for your dog to run around. Plenty of space inside the house to play too! I will make sure to give your dog plenty of water and potty breaks and meticulously follow any instructions you leave me!

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Over 68
pet parents in Chesapeake Beach have booked house sitting

Chesapeake Beach pet parents share their Rover experiences

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5.0 out of 5 stars

Faith was fantastic watching our 9 m old Golden puppy and 3 cats. She was responsive, attentive and timely. She house sit for us and left it looking better than ever. If she'll have us again we'll definitely be booking again.

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Brittany C.
House Sitting
5.0 out of 5 stars

Savanna house sat for us and gave such good care to our elderly house cat. She was extremely responsible, organized, and great with communication and photos too. I would highly recommend her for your pet needs.

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Tracy B.
House Sitting
5.0 out of 5 stars

Anna was awesome! She provided updates and responded to any inquiries within minutes. We've already rebooked her, just waiting on a response.

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Teresa I.
House Sitting
5.0 out of 5 stars

Leann is a wonderful pet sitter and so great with communication. She even took down our flags off our pier when we realized a nor'easter was coming. We will definitely use her again!

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Darcy S.
House Sitting
5.0 out of 5 stars

Drew was an excellent experience for my Basset Hounds! I had a last second trip in which Drew was able to accommodate as well as a pre home visit to meet the dogs and get a feel of their environment. As I was out of town she sent consistent updates / pictures and followed all directions I left for feeding and overnight stay. Basset Hounds are a specific breed (needy & hard headed ) and she handled them perfectly!

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Matthew R.
House Sitting
5.0 out of 5 stars

Victoria was great with Ferris - took him for little walks during n the evening and sent pics throughout the evening so felt really reassured. We were in town for a wddding and recommend anyone to Victoria for house sitting and cuddles for their pet!!!!

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Lotte J.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 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. 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 Beach is $50

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 Beach 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 Beach on Rover as of Mar 2026 was about $50 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.

If you’re searching for a Chesapeake Beach house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Mar 2026, there are 1,076 house sitters in Chesapeake Beach. 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 Beach house sitters respond in under an hour.

House sitters in Chesapeake Beach 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 Beach.

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 Beach 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.