House Sitting in Windyhill

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Top rated Windyhill 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: Carolina P.
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Carolina P.
from
$60
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
7 years of experience
Trappe, MD, 21673

About: I’ve owned different breed’s throughout my life and have had puppies grow up to live long, healthy lives! I’ve also had the pleasure of taking care of small and large dogs with hip displacia, blindness, cancer and other special needs. I’m also a huge health nut, so I’m always researching nutrition topics and things that may benefit the doggies I get to meet! I have an early job in the morning so I’ll be available for very early visits and I’ll be out of work at 1:30pm so I can spend the rest of the of the day and weekends taking care of my fur friends. I’ll keep and eye on them, make sure there is nothing around or anything they can get into to get hurt. On outside walks they always be on a leash and we will avoid big highways.

Sitter Profile Image: Grace F.
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Grace F.
from
$60
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
22 years of experience
Easton, MD, 21601

I had Grace housesit/petsit for 3 days. She was excellent! I'm a helicopter cat mom and it's not easy leaving your home and baby with someone you don't know, Grace made the experience worry-free, my shy cat loved her and she sent frequent pics/updates. My house looked great when I got back, she even watered my plants. I'm definitely booking her again, and you should too, she's trustworthy, reliable and was just a nice, easy person to work with.

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Marta F.
Sitter Profile Image: Lily K.
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Lily K.
from
$65
per night
5.0 out of 5 stars
14 reviews
4 repeat clients
11 years of experience
Oxford, MD, 21654

Lily was great all the way thru our trip and before. She came to meet the dogs twice before our trip. Sent updates and pictures throughout and left our house in the same condition as when she arrived. My mom's dog is nervous and had never been left with a sitter before and Lily was patient and sensitive to her needs. We will definitely be calling her the next time we need a sitter!

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Hallie P.
Sitter Profile Image: Marijah B.
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Marijah B.
from
$60
per night
10 years of experience
Easton, MD, 21601

About: Ive been caring for dogs and cats since I was about 8 years old. I’ve always had multiple dogs in the house at a time. I’ve cared for dogs ranging from big to small, Seniors to puppies. I provide daily photos throughout your pets daily routine and tons of love I’m currently working part time so I will have plenty of enough time to care for your fur baby. I believe all animals should be treated like they are you own even if they are temporary I live in a quiet cozy apartment with a big yard in the back. There is plenty of room for playtime and resting. Pets are welcome on all furniture

Sitter Profile Image: Stephanie R.
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Stephanie R.
from
$75
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Oxford, MD, 21654

Stephanie took great care of my dog Sammy. I am thankful I found her. She was wonderful.

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Mary O.
Sitter Profile Image: Imani W.
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Imani W.
from
$31
per night
5.0 out of 5 stars
1 review
20 years of experience
Easton, MD, 21601

About: I’ve taken care of dogs since I was 8 my family and friends always ask me to take care of walking ,feeding , and administrating medicine . I work at the Easton Elementary i usually get off anywhere between 3:55-4pm so I can do check ins and or walks Monday through Friday after I get off from work on the weekends I have a very flexible schedule so I can do anytime I had 2 dogs they passed away this year due to older age couple of months ago but I have a backyard with a closed off fence top to bottom so your pets will be very safe and have a good yard to run around and stretch

Sitter Profile Image: Wendy B.
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Wendy B.
from
$63
per night
5.0 out of 5 stars
35 reviews
8 repeat clients
54 years of experience
Queenstown, MD, 21658

My first experience using Rover and I really lucked out with Wendy. She was communicative and kept my mind at ease while we were gone for 6 nights and 7 days. She’s not kidding when she says your dogs won’t care when you come home. One of mine is a crazy English bulldog that loses her mind and acts like she hasn’t seen us for days, even if we are gone for 15 minutes. She could care less that we were back. This tells me she was well loved and got plenty of play time. 100% recommend Wendy!

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Kristi O.
Sitter Profile Image: Maura M.
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Maura M.
from
$60
per night
5.0 out of 5 stars
4 reviews
1 repeat client
7 years of experience
Easton, MD, 21620

Bagel was in the most caring hands with Maura.

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Marina G.
Sitter Profile Image: Emily T.
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Emily T.
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
13 years of experience
Trappe, MD, 21673

About: Current Veterinary Technician (2 yr) Previous Veterinary Assistant (1 yr) Recent University of Maryland graduation with a Bachelors of Animal Science degree - Pre Veterinary track Current veterinary school applicant Current animal care assistant of University of Maryland Avian Behavioral Neuroscience Laboratory Pending Masters of Animal Health and Industry program Life long pet experience - various species, breeds, sizes, and demeanors I value the importance of not only caring for pets on visits, but also in spending time engaging in enriching and quality time - it is just as important as potty breaks and feeding times! I am confident in my ability to accommodate each client and pets personal needs and routine! I do work during the week (Mon-Fri). Depending on the pet and owners permission I have the ability to bring my pets to the work with me in the veterinary hospital. Otherwise, I am able to be around weekends and drop in morning and evening (noon if in Easton, MD), and overnights if arranged I follow deeply to clients request, I encourage leaving a note/list of needs, directions, requests! It’s very handy and personable to my care for you and your pet!

Sitter Profile Image: Johanna T.
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Johanna T.
from
$40
per night
5.0 out of 5 stars
4 reviews
3 repeat clients
15 years of experience
Cambridge, MD, 21613

About: My dog passed and I miss her company! So I love having visitors to keep me company and play with while working from home :) Work from home, I'm free to walk the dogs first thing the the morning, around noon and anytime in the evening and spend the whole day with them if needed :) Quiet home, no children, no smoking, no other dogs or cats - just fish n two birds, half way fenced Yard, but very safe. We can walk around the neighborhood, there is a park down the street as well and the back yard.

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

About: What sets me apart is my attention to detail, reliability, and healthcare background as a registered nurse. I understand the importance of following routines, monitoring for changes in behavior, and providing safe, compassionate care. I am comfortable caring for pets of all ages, including kittens and senior cats, and can administer medications if needed. I treat every pet as if they were my own and provide regular updates and photos so owners can feel confident their pets are in good hands As a registered nurse, I have a flexible schedule that allows me to provide dependable pet care throughout the week. Caring for animals has always been a part of my daily routine, and I enjoy spending time feeding, playing with, and checking in on pets. I make it a priority to ensure each pet receives attentive, loving care and maintains their normal routine while their owners are away. 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: Sydney W.
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Sydney W.
from
$75
per night
5.0 out of 5 stars
4 reviews
10 years of experience
St Michaels, MD, 21663

Sydney is professional, attentive and was very good watching our labradoodle, Stash.

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Lynn V.
Sitter Profile Image: Mya H.
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Mya H.
from
$50
per night
10 years of experience
Easton, MD, 21601

About: I've taken care of dogs since I was 10. Whether it was my personal dog or family and friends, each dog was cared for as my own. I can provide a safe and interactive environment for your animal while you are away. If your animal has any unique needs, I would be happy to support with training while you are away. I will care for your pets as you do, ensuring that they get all the playtime and tummy rubs they could ever want. I have the flexibility to work from home, so your pet will be monitored and walked consistently. This also makes it easy for me to adhere to any normal routines that you may have already set. My neighborhood has many walkable areas, trails, and parks for your dog to enjoy. I appreciate any opportunity to be outdoors and I would be happy to bring your dog along!

Sitter Profile Image: Brante D.
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Brante D.
from
$150
per night
5.0 out of 5 stars
2 reviews
2 repeat clients
25 years of experience
Trappe, MD, 21673

About: I have taken care of dogs and cats since childhood . My father breed Dobermans for many of my pre teen years and I was apart of caring for the pups .My friends and family find it amazing how much care and love I provide for my pets and theirs too. Animal are Gods children too, and I do my best to care for them with that in mind. I own a 15 year old Datsun that has been with me since he was 8 weeks old! He is well mannered with the lots of personality and brings me much joy ! I look forward to helping to care for your pet with integrity and kindness, just as I would want someone to care for mine. I am currently working full time and have sometime to share with your letting before winding down for the evening. Taking them for a walk will only add to my evening wind down . Ensuring they are safe and fed while you are away is important , and as a pet owner I understand this totally! When coming to care for your pet for feeding , walking , or drop in I will ensure that communication is provide on the status of your pet while respecting your home while there to care for your pet.

Sitter Profile Image: Sabrina B.
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Sabrina B.
from
$27
per night
4.9 out of 5 stars
27 reviews
4 repeat clients
15 years of experience
GREENWOOD, DE, 19950

Took excellent care of all of our fur babies while we were on vacation! Very communicative and sent regular updates/photos of how everyone was doing. Thank you S for the wonderful care!!! 💓

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Maren H.
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: Chloe T.
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Chloe T.
from
$95
per night
4.9 out of 5 stars
8 reviews
1 repeat client
17 years of experience
Easton, MD, 21601

About: Hi! I’m Chloe, a reliable and caring pet sitter with a genuine love for animals of all kinds. Whether your pet needs daily walks, playtime, or just some extra affection while you’re away, I’m here to make sure they feel safe, comfortable, and loved. I’m attentive, patient, and experienced with pets who have special routines or unique personalities. Your furry family member will be in good hands! Im a Healthcare worker, beach lover and enjoy cruising in my Jeep. Doggy Daycare is $25 a hour for all day, min 8 hours. $32 an hour for less then 8 hours. Available Fridays,Saturdays and Sundays some mondays. I do work Tuesday Wednesday Thursday 12 hour shifts but I wouldn't mind stopping over before work or after work. I will treat pets like they are my own. I will feed them,play with them and make sure they are comfortable and happy before I leave.

Sitter Profile Image: Christie R.
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Christie R.
from
$40
per night
4.9 out of 5 stars
30 reviews
16 repeat clients
10 years of experience
Church creek, MD, 21622

Christie was very professional. She did a meet and greet with our babies a month in advance. We ended up adopting a stray and she didn't hesitate to watch over our pups. She left the house the way she found it and sent updates throughout her visit. I highly recommend her!

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Heather S.
Sitter Profile Image: Busara C.
Verified Enhanced Background Check
Busara C.
Star Sitter
from
$65
per night
5.0 out of 5 stars
84 reviews
11 repeat clients
5 years of experience
Dover, DE, 19904

Busara was a delight! She gave a lot of feedback on her time with Jasper. Jasper seemed to enjoy having her here. I’d definitely ask her to come another time!

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Lois D.
Sitter Profile Image: Summer B.
Verified Enhanced Background Check
Summer B.
from
$50
per night
20 years of experience
Cambridge, MD, 21613

About: ✨ Schedule & Availability I currently maintain a full-time position but please do not hesitate to reach out and we can talk about options to accommodate your pets needs. Open Availability : Monday / Tuesday Limited Availability : Wed - Sun ✨My Experience I have experience caring for both dogs and cats with a wide range of personalities, energy levels, and care needs. From energetic puppies who need extra patience and consistency to independent cats who prefer a quieter approach, I believe every pet deserves individualized attention and care. In addition to caring for my own pets over the years, I have volunteered with animal rescue and shelter organizations, giving me experience working with animals of different temperaments and backgrounds. ✨Drop-in visits / Dog walking / Cat care visits / Puppy visits / senior pet care ✨Meet & Greet I strongly encourage a meet-and-greet before any first-time booking. Meet-and-greets can be conducted either in person or through a video call, depending on your preference and schedule. This gives us an opportunity to: • Make sure we’re a good fit • Allow your pet to become familiar with me • Review feeding schedules and daily routines • Discuss medications or special care requirements • Review behavior preferences and household expectations • Answer any questions before services begin I currently work full-time, but I still maintain availability outside of my work schedule for pet care, drop-ins, walks, feedings, and quality time with your pets. I’m reliable with routines and make sure pets receive the attention, consistency, and care they need while their owners are away. I understand how important trust is when someone is caring for your pets and entering your home. I treat every animal with patience, respect, and attention to their individual comfort level and routine. I’m experienced with shy pets, senior animals, anxious pets, and pets that may need a calmer approach or extra time to adjust. I always prioritize safety, clean environments, secure doors/leashes, and careful attention to instructions so owners can feel confident their pets are being cared for like family.

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Windyhill pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Kelly as per usual was amazing! She truly loves our dogs and sends us constant pictures throughout our time away. She is trustworthy and super friendly. We appreciate you Kelly!

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Stephen W.
House Sitting
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  1. 1. Search

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  2. 2. Meet & Greet

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  3. 3. Book & Pay

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The median cost per night for house sitting in Windyhill is $55

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  • 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.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Windyhill average 3
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 Windyhill on Rover as of Jun 2026 was about $55 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 Windyhill 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 Jun 2026, there are 248 house sitters in Windyhill. 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, 84% of Windyhill house sitters respond in under an hour.

House sitters in Windyhill have an average of 18 years of experience. House sitters with repeat customers have an average of 3 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 Windyhill.

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. Windyhill 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.