House Sitting in Windward Cove

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Top rated Windward Cove house sitters

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Sitter Profile Image: Louise D.
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Louise D.
from
$28
per night
5 out of 4.9 stars
34 reviews
15 repeat clients
6 years of experience
Easton, MD, 21601

Louise left the house tidy and did a great job caring for our pack! We received many photos while away and she was quick to communicate if an issue arose.

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Colleen D.
Sitter Profile Image: Seth G.
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Seth G.
from
$50
per night
30 years of experience
Easton, MD, 21601

About: I’ve had different types of dogs since I was young. I’ve trained dogs for all types of reasons. I’m a lover of all pups and can handle your dogs needs. I own a large property specifically for the environment, which is perfect for dogs. I look forward to meeting your doggie and returning a happy pup back to you. Please message for any details. I’m available on weekends and weeknights. I work full time M-F, so weekends are primarily open. While I can do many activities during the work week, I am gone about 8 hours for my primary job. Weeknights and weekends are available. I have a large property with plenty of room to roam. Chickens in the yard (in coop). I have a 6 year old pup of my own that is very docile, loves other animals and gets along with them easily, and is my number two. I don’t have a fence because my dog is perimeter trained. However, I can perimeter train your dog too or walk them on a leash if that is preferred. I plan to add a fence soon and will update this once I do.

Sitter Profile Image: Wendy B.
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Wendy B.
from
$60
per night
5 out of 5.0 stars
30 reviews
7 repeat clients
54 years of experience
Queenstown, MD, 21658

Wendy was so great with our two dogs, 8 chickens, and fish! I highly recommend her! She responds quickly and sends lots of updates. This was the best Ive ever felt leaving my animals! Thank you Wendy!

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Abbey M.
Sitter Profile Image: Jordan D.
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Jordan D.
from
$60
per night
5 out of 5.0 stars
3 reviews
1 repeat client
14 years of experience
Easton, MD, 21601

She was a wonderful animal sitter. She followed instructions and cuddled with the animals. There was daily updated and pictures send. She really did a great job or making the pets happy.

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Sabrina M.
Sitter Profile Image: Michael P.
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Michael P.
from
$80
per night
5 out of 5.0 stars
65 reviews
33 repeat clients
10 years of experience
Annapolis, MD, 21409

Lolly and Trixie love Michael. My husband and I do too. The dogs love him because he’s gives them lovies and pets and lets them lay all over him. We love him because he’s reliable, on time, follows instructions (especially with medications), sends us pictures, and has a genuine love for his job. All of this is a priceless combination. You’ll never go wrong hiring Michael to take care of your beloveds.

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Teresa C.
Sitter Profile Image: Stacey B.
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Stacey B.
from
$60
per night
5 out of 5.0 stars
10 reviews
1 repeat client
15 years of experience
Chester, MD, 21619

Stacey is trustworthy, kind and caring. I was at ease knowing that Stacey was watching our dog Toby in our home. She sent me updates and photos. She followed the schedule we left for Toby. I would definitely recommend her!

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Janina M.
Sitter Profile Image: Payton W.
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Payton W.
from
$50
per night
5 out of 4.5 stars
3 reviews
1 repeat client
6 years of experience
Stevensville, MD, 21666

About: I have experience taking care of cats and dogs going back to my early teens. I’m just as much a cat lover as I am a dog lover and would love to take care of your fur babies. Whether you have a sweet big dog or a little shy cat, I love them all the same. Most of my family has at-least 2 or more cats or dogs and they often rely on me to take care of them when they go on vacation, have a long work week, or just need a helping hand. I currently work full time, 9-5 Monday through Friday. Most of my availability is on the weekends or late afternoons. But depending on the request I may be able to make an exception. I have experience caring for small dogs, big dogs, shy cats, energetic cats, senior dogs and cats. I’ve cared for almost every type of pet there is. I’ve even cared for reptiles and guinea pigs. Whether your pet would like space and quiet or someone to help them get their energy out I can provide that. I can meet the needs of your pet. Every dog/cat is different and I’m here for it all 😊

Sitter Profile Image: Kat S.
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Kat S.
from
$55
per night
5 out of 4.9 stars
10 reviews
2 repeat clients
20 years of experience
Saint Michael's, MD, 21663

Kat took great care of our two dogs over a long weekend. One is an older Labrador, and Kat seemed to manage all the medications, frequent walks, assists up and down the stairs, etc. with composure and caring! The house looked great, and the dogs had obviously been well taken care of. I recommend Kat highly and without reservation!

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Liz G.
Sitter Profile Image: Kacy W.
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Kacy W.
from
$25
per night
5 out of 5.0 stars
2 reviews
12 years of experience
Cordova, MD, 21625

Kacy was great with taking care of my dog, Luna! Luna is a very high energy, bully mix who can be a little crazy! Kacy handled her very well and Luna warmed up quickly to her, which was great because sometimes Luna can be wary of people. Definitely recommend Kacy!

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Kaileigh T.
Sitter Profile Image: Olivia B.
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Olivia B.
from
$50
per night
2 years of experience
Cordova, MD, 21625

About: I've watched and taken care of dogs for many years, mainly family and near by neighbors. I have grew up on a farm which i've taken care of many other animals as well... mainly farm animals and dogs!! I'm currently in college right now, it's mostly online so that's not really an issue. I'm working part time as well, which I have plenty of time to take care of the dogs!! I'm always free on weekends unless otherwise noted!! I have two golden-doodles, which are crate trained. They are allowed to run freely outside but they know where they are and aren't allowed. I keep them on a schedule, meaning with going outside, playing, and feeding.

Sitter Profile Image: Alicia W.
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Alicia W.
from
$100
per night
5 out of 5.0 stars
4 reviews
15 years of experience
Easton, MD, 21601

About: I volunteer at my local shelter and help train pets there! I also have 3 of my own cats, a lizard, and have had dogs my entire life! I can watch dogs, cats, rabbits, ferrets, reptiles and more! I am a teacher so I have regular hours and during the summer I will be completely free! I can do after school hours during the school year. I would love to walk your pet, play with them, and make sure they feel loved and cared for! I love snuggles with pets and letting them get all their energy out!

Sitter Profile Image: Cristina M.
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Cristina M.
from
$75
per night
5 out of 5.0 stars
5 reviews
25 years of experience
Stevensville, MD, 21666

Kind, loving, responsible, and responsive care for our two pups (one who is a senior and needs extra TLC + daily meds). Highly recommend Cristina!

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Lisa R.
Sitter Profile Image: Leah S.
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Leah S.
from
$60
per night
5 out of 5.0 stars
2 reviews
5 years of experience
Cordova, MD, 21625

I can’t say enough good things about Leah! She saved the day when I needed someone last minute to stay with my three dogs. She responded quickly and made arrangements to come meet the dogs the next day. From the moment she walked in, she was attentive, personable, and showed an obvious love for animals. All three of my dogs took to her right away, which was impressive—especially my little terrier, who is typically quite suspicious of new people. Leah’s calm and caring demeanor put them all at ease. While I was away, Leah kept me updated regularly, sending photos and messages that reassured me everything was going great. When I returned, my home was left in excellent condition, and the dogs were happy and relaxed. Leah went above and beyond, and I will absolutely be booking her again. If you’re looking for someone dependable, caring, and great with pets, Leah is the one to call!

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carrie m.
Sitter Profile Image: Taylor M.
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Taylor M.
Star Sitter
from
$55
per night
5 out of 5.0 stars
5 reviews
3 repeat clients
12 years of experience
Stevensville, MD, 21666

Taylor is fantastic - patient with my grouchy old pup and kept up with my hyper young Aussie. An overnight trip was a stress-free experience for me and the dogs thanks to Taylor!

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Cait B.
Sitter Profile Image: Anna H.
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Anna H.
from
$55
per night
5 out of 5.0 stars
4 reviews
1 year of experience
Chester, MD, 21619

Anna was so amazing with Bentley! Played lots and got so many updates ☺️. Anna is super attentive and handled our bugs like a pro! Bentley is a slightly challenging pup but we had no bumps in the road with Anna. If you’re needing a pet sitter for a larger bread who can be difficult, Anna is your girl. ??

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Carolina H.
Sitter Profile Image: Megan M.
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Megan M.
from
$45
per night
5 out of 5.0 stars
2 reviews
8 years of experience
Easton, MD, 21601

Megan did a great job caring for my pets! The house looked exactly as I left it and the animals were all very happy. She sent updates and pictures. Definitely helped take the worry off of leaving them all for the first time!

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Alex B.
Sitter Profile Image: Sarah N.
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Sarah N.
from
$50
per night
5 out of 4.7 stars
5 reviews
1 repeat client
2 years of experience
Grasonville, MD, 21638

About: I am very affectionate and will show attention to any animal. I have had 4 dogs and 3 cats, but now only have one dog and 2 cats, and love being surrounded by animals, they bring such happiness during my day! My mom has been a dog and animal all of her life and I take after her and show much concern and awareness for all animals. I love laying with animals, taking them outside and throwing them bones or toys, and of course a treat involved after! I am also very responsible at making sure ones anaimal is always stocked up on food and water and treats! I am looking forward into maybe working with animals as my career and this is one step closer!

Sitter Profile Image: Julie K.
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Julie K.
from
$35
per night
5 out of 5.0 stars
4 reviews
1 repeat client
5 years of experience
Chester, MD, 21619

About: I have taken care of many dogs from different families! As well as cats and other animals. I am able to give medication to them and meet all your needs. I will stay at your house and love to meet the animals before hand if you would like. I currently work a full time job at an elementary school, and part time at my church. When I Dogsit I normally stay the night or come over before work to take care of the animals . Then after work I am able to go and take care of them again. I’m very flexible for whatever your dog may need. I’m able to give medicine, walk the dog, create the dog, etc. whatever you need I can do!

Sitter Profile Image: Aliciya M.
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Aliciya M.
from
$50
per night
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: Emily K.
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Emily K.
from
$100
per night
5 out of 5.0 stars
1 review
3 years of experience
Grasonville, MD, 21638

About: I have had a dog for about 3 years now, his name is Fynn! I have been walking and taking care of neighbors dogs for about 3 years now and they would describe me as trustworthy and filled with energy. I love all pets! I would love to meet your fur babies and when they're with me I'll love them as if they're my own! I am available to dog sit and do a drop-in visit anywhere from 6 a.m.-11 a.m. and 3 p.m.-10 p.m. I am currently a student at Towson University and play on the women's soccer team so mid day I have practices. When I care for pets in clients home I stay as respectful and tidy as possible. I always make sure gates are closed, and doors locked, and always leave the home in the same or better conditions than when I arrived.

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Sitter Profile Image: Louise D.
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Sitter Profile Image: Louise D.
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Louise D.

I'm a loving caring animal person
Easton, MD, 21601
9.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 4.9 stars
34 reviews
15 repeat clients
Profile image

Louise left the house tidy and did a great job caring for our pack! We received many photos while away and she was quick to communicate if an issue arose.

Availability updated 2 days ago
Sitter Profile Image: Seth G.
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Sitter Profile Image: Seth G.
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Seth G.

Farmers Paradise
Easton, MD, 21601
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
2 reviews

Seth has been watching my dog for the past eight years, and I couldn’t ask for someone more dependable, attentive, and genuinely caring. He treats my dog like family, always making sure she’s well-cared for, loved, and happy while I’m away. Seth’s own dog, Ziggy, is the sweetest and loves other dogs. My pup always comes home tired from all the fun they have together! It’s such a comfort knowing she’s not just being looked after, but also enjoying herself. It’s hard to find someone you can trust so completely with your pet, and I feel incredibly lucky to have had Seth be such a consistent and caring presence in my dog’s life. I can’t recommend him highly enough to anyone looking for a dedicated and loving pet caregiver

Availability updated 9 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Wendy B.
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Sitter Profile Image: Wendy B.
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Wendy B.

I LOVE Animals and they LOVE me!!!
Queenstown, MD, 21658
6.2 mi. away
House Sitting
from
$60
per night
5 out of 5.0 stars
30 reviews
7 repeat clients
Profile image

Wendy was so great with our two dogs, 8 chickens, and fish! I highly recommend her! She responds quickly and sends lots of updates. This was the best Ive ever felt leaving my animals! Thank you Wendy!

Availability updated 3 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jordan D.
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Sitter Profile Image: Jordan D.
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Jordan D.

Caring, Loving, and Playful
Easton, MD, 21601
7.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
3 reviews
1 repeat client
Profile image

She was a wonderful animal sitter. She followed instructions and cuddled with the animals. There was daily updated and pictures send. She really did a great job or making the pets happy.

Availability updated 4 days ago
Sitter Profile Image: Michael P.
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Sitter Profile Image: Michael P.
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Michael P.
Rover 101

Compassionate, Reliable, Fun Loving
Annapolis, MD, 21409
17.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5 out of 5.0 stars
65 reviews
33 repeat clients
Profile image

Lolly and Trixie love Michael. My husband and I do too. The dogs love him because he’s gives them lovies and pets and lets them lay all over him. We love him because he’s reliable, on time, follows instructions (especially with medications), sends us pictures, and has a genuine love for his job. All of this is a priceless combination. You’ll never go wrong hiring Michael to take care of your beloveds.

Availability updated 4 days ago
Sitter Profile Image: Stacey B.
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Sitter Profile Image: Stacey B.
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Stacey B.

Loving Dog Mom
Chester, MD, 21619
6.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
10 reviews
1 repeat client
Profile image

Stacey is trustworthy, kind and caring. I was at ease knowing that Stacey was watching our dog Toby in our home. She sent me updates and photos. She followed the schedule we left for Toby. I would definitely recommend her!

Availability updated today
Sitter Profile Image: Payton W.
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Sitter Profile Image: Payton W.
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Payton W.

Certified Pet Lover For Life🩷
Stevensville, MD, 21666
9.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.5 stars
3 reviews
1 repeat client

Payton is the best! If you are looking for someone who will go out of their way to make sure your pets needs are met and give you the comfort of great communication, she is your girl! She goes above and beyond putting herself in your shoes. She is easy to work with and very detail oriented, not to mention her great personality. She has taken care of all of my babies (3 cats and my new puppy).

Availability updated 4 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kat S.
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Sitter Profile Image: Kat S.
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Kat S.

Animals make the world go round...
Saint Michael's, MD, 21663
7.2 mi. away
House Sitting, Dog Walking
from
$55
per night
5 out of 4.9 stars
10 reviews
2 repeat clients
Profile image

Kat took great care of our two dogs over a long weekend. One is an older Labrador, and Kat seemed to manage all the medications, frequent walks, assists up and down the stairs, etc. with composure and caring! The house looked great, and the dogs had obviously been well taken care of. I recommend Kat highly and without reservation!

Availability updated 44 days ago
Sitter Profile Image: Kacy W.
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Sitter Profile Image: Kacy W.
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Kacy W.

I'm very passionate about animals
Cordova, MD, 21625
7.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per night
5 out of 5.0 stars
2 reviews
Profile image

Kacy was great with taking care of my dog, Luna! Luna is a very high energy, bully mix who can be a little crazy! Kacy handled her very well and Luna warmed up quickly to her, which was great because sometimes Luna can be wary of people. Definitely recommend Kacy!

Availability updated 12 days ago
Sitter Profile Image: Olivia B.
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Sitter Profile Image: Olivia B.
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Olivia B.

I love animals and caring for them!
Cordova, MD, 21625
13.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
1 review

Olivia always has been a dog lover . She would be very caring and respectful for any pet . She is also a responsible young lady.

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Alicia W.
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Sitter Profile Image: Alicia W.
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Alicia W.

Shelter Volunteer, Teacher, Any Pet
Easton, MD, 21601
12.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$100
per night
5 out of 5.0 stars
4 reviews

About: I volunteer at my local shelter and help train pets there! I also have 3 of my own cats, a lizard, and have had dogs my entire life! I can watch dogs, cats, rabbits, ferrets, reptiles and more! I am a teacher so I have regular hours and during the summer I will be completely free! I can do after school hours during the school year. I would love to walk your pet, play with them, and make sure they feel loved and cared for! I love snuggles with pets and letting them get all their energy out!

Availability updated 4 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Cristina M.
Verified Enhanced Background Check
Sitter Profile Image: Cristina M.
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Cristina M.

Cat & Dog Whisperer for hire!
Stevensville, MD, 21666
8.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
5 reviews
Profile image

Kind, loving, responsible, and responsive care for our two pups (one who is a senior and needs extra TLC + daily meds). Highly recommend Cristina!

Availability updated 3 days ago
Sitter Profile Image: Leah S.
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Sitter Profile Image: Leah S.
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Leah S.

21 year old who adores animals
Cordova, MD, 21625
9.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
2 reviews
Profile image

I can’t say enough good things about Leah! She saved the day when I needed someone last minute to stay with my three dogs. She responded quickly and made arrangements to come meet the dogs the next day. From the moment she walked in, she was attentive, personable, and showed an obvious love for animals. All three of my dogs took to her right away, which was impressive—especially my little terrier, who is typically quite suspicious of new people. Leah’s calm and caring demeanor put them all at ease. While I was away, Leah kept me updated regularly, sending photos and messages that reassured me everything was going great. When I returned, my home was left in excellent condition, and the dogs were happy and relaxed. Leah went above and beyond, and I will absolutely be booking her again. If you’re looking for someone dependable, caring, and great with pets, Leah is the one to call!

Availability updated 9 days ago
Sitter Profile Image: Taylor M.
Verified Enhanced Background Check
Sitter Profile Image: Taylor M.
Verified Enhanced Background Check

Taylor M.
Star Sitter

Stress-Free Companionship
Stevensville, MD, 21666
8.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
5 reviews
3 repeat clients
Profile image

Taylor is fantastic - patient with my grouchy old pup and kept up with my hyper young Aussie. An overnight trip was a stress-free experience for me and the dogs thanks to Taylor!

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Anna H.
Verified Enhanced Background Check
Sitter Profile Image: Anna H.
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Anna H.

Come and be apart of our family!
Chester, MD, 21619
6.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per night
5 out of 5.0 stars
4 reviews
Profile image

Anna was so amazing with Bentley! Played lots and got so many updates ☺️. Anna is super attentive and handled our bugs like a pro! Bentley is a slightly challenging pup but we had no bumps in the road with Anna. If you’re needing a pet sitter for a larger bread who can be difficult, Anna is your girl. ??

Availability updated 2 days ago
Sitter Profile Image: Megan M.
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Sitter Profile Image: Megan M.
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Megan M.

can’t wait to meet your animal
Easton, MD, 21601
11.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
2 reviews
Profile image

Megan did a great job caring for my pets! The house looked exactly as I left it and the animals were all very happy. She sent updates and pictures. Definitely helped take the worry off of leaving them all for the first time!

Availability updated 60 days ago
Sitter Profile Image: Sarah N.
Verified Background Check
Sitter Profile Image: Sarah N.
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Sarah N.

Loving and open arms to any animal!
Grasonville, MD, 21638
3.9 mi. away
House Sitting, Drop-In Visits
from
$50
per night
5 out of 4.7 stars
5 reviews
1 repeat client

Sarah is a dependable, caring & trustworthy pet sitter. You can tell how much she loves all animals, esp cats and dogs. I would recommend her to anyone looking for a great pet sitter or dog walker.

Availability updated 8 months ago
Sitter Profile Image: Julie K.
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Sitter Profile Image: Julie K.
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Julie K.

Trust the best with your pets!
Chester, MD, 21619
6.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 5.0 stars
4 reviews
1 repeat client

Julie does an Amazing job caring for my pets during the day and sometimes overnights. She is so caring for them. Takes them for walks even at the beach. She is on time when it comes to meals. I have used her multiple tiles and will continue to use here.

Availability updated 70 days ago
Sitter Profile Image: Aliciya M.
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Sitter Profile Image: Aliciya M.
Verified Enhanced Background Check

Aliciya M.

15+ Years of Dog & Cat Care
Queenstown, MD, 21658
4.2 mi. away
Boarding, House Sitting, Doggy Day Care, Dog Walking
from
$50
per night
15 years of experience

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.

Availability updated 11 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Emily K.
Verified Enhanced Background Check
Sitter Profile Image: Emily K.
Verified Enhanced Background Check

Emily K.

Hello! Emily here!
Grasonville, MD, 21638
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5 out of 5.0 stars
1 review

About: I have had a dog for about 3 years now, his name is Fynn! I have been walking and taking care of neighbors dogs for about 3 years now and they would describe me as trustworthy and filled with energy. I love all pets! I would love to meet your fur babies and when they're with me I'll love them as if they're my own! I am available to dog sit and do a drop-in visit anywhere from 6 a.m.-11 a.m. and 3 p.m.-10 p.m. I am currently a student at Towson University and play on the women's soccer team so mid day I have practices. When I care for pets in clients home I stay as respectful and tidy as possible. I always make sure gates are closed, and doors locked, and always leave the home in the same or better conditions than when I arrived.

Availability updated yesterday

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The median cost per night for house sitting in Windward Cove is $50

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    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 Windward Cove average 4 repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover