House Sitting In Winsor Hills

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

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Top rated Winsor Hills 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: Kathleen H.
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Kathleen H.
Star Sitter
from
$40
per night
5.0 out of 5 stars
26 reviews
6 repeat clients
8 years of experience
Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21202

Kathleen took great care of our senior cat and our home. She navigated some technical challenges with our alarm system with professionalism and good humor. Highly recommend. Will definitely re-book.

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Karen M.
Sitter Profile Image: SJ J.
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SJ J.
Star Sitter
from
$63
per night
5.0 out of 5 stars
51 reviews
24 repeat clients
15 years of experience
Charles Village, Baltimore, MD, 21218

SJ was a dream dog and house sitter! Very communicative, thoughtful and most importantly, an instant friend to my dog! I would book with them again in a heartbeat. Thanks, SJ!

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Dinah D.
Sitter Profile Image: Naya R.
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Naya R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
38 reviews
10 repeat clients
15 years of experience
Reservoir Hill-Bolton Hill Area, Baltimore, MD, 21201

Naya handled all my dog could throw at someone new - from pooping in his crate to trucking her into extra play time outside, naya handled it all perfectly. When I got home, I literally had to reassure my fiance someone did take care of juicy- she left the house with no trace she was here, she only left behind a happy well loved pup! Will be booking naya again!

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Gem L.
Sitter Profile Image: Bito B.
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Bito B.
Star Sitter
from
$63
per night
5.0 out of 5 stars
27 reviews
10 repeat clients
10 years of experience
Greater Mount Washington, Baltimore, MD, 21209

Came home to happy, well taken care of babies and it’s all I could ask for. There was a mild snag while we were gone and we figured it out together. Wouldn’t ask anyone else to watch my 3 animals (and house).

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Shayna Y.
Sitter Profile Image: Kevin D.
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Kevin D.
from
$65
per night
5.0 out of 5 stars
11 reviews
7 repeat clients
25 years of experience
Greater Rosemont, Baltimore, MD, 21216

I came home to happy and healthy dogs! Although they are normally anxious and nervous about new people, Kevin connected with my two dogs very quickly during our meet and greet, easing my own nerves. He communicated throughout the sit and I was grateful to always get a quick response when needed. Highly recommend and I will be rebooking him for sure!

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Jackie G.
Sitter Profile Image: Preaundrea F.
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Preaundrea F.
Star Sitter
from
$48
per night
5.0 out of 5 stars
50 reviews
9 repeat clients
10 years of experience
Govans, Baltimore, MD, 21218

We loved having Pre stay at our home with our goldendoodle. He was happy and relaxed with her -- he even ate! We can't wait to have her hang out with Eddie again!

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Lisa R.
Sitter Profile Image: Tabitha S.
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Tabitha S.
Star Sitter
from
$32
per night
5.0 out of 5 stars
97 reviews
33 repeat clients
30 years of experience
Halethorpe, MD, 21227

Tabitha is WONDERFUL! My dog is very emotionally needy (has anxiety), and I needed a sitter very last minute. Tabitha came to the rescue and was so attentive with Franny and did such a good job with her! I really trust her and i can’t wait to use her again 🙂

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Christine G.
Sitter Profile Image: Emily S.
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Emily S.
from
$60
per night
5.0 out of 5 stars
31 reviews
12 repeat clients
10 years of experience
West Baltimore, Baltimore, MD, 21223

Emily took such good care of my two senior dogs. Very kind and patient, and also left my house in great condition after house-sitting. I would definitely recommend and will contact for sitting in the future. Thanks, Emily!

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Chloe S.
Sitter Profile Image: Cashae H.
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Cashae H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
2 years of experience
Hunting Ridge, Baltimore, MD, 21229

Cashae was a wonderful sitter for our 2 pups!! She is a Dog Lover for sure! She took great care of our dogs. She was with the dogs 24/7. It meant a lot to me knowing that Cashae was a perfect fit as a dog mom, while we were gone for awhile...I highly recommend Cashae!!?

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Joan B.
Sitter Profile Image: Danielle H.
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Danielle H.
from
$45
per night
10 years of experience
Howard Park, Baltimore, MD, 21207

About: I have taken care of two smaller dogs the past 3 years and have learned the hard work that comes with them. I have also volunteered at BARCS for dog days out. I am comfortable with leash trained dogs and understand feeding schedules, potty breaks, and playtime. Hello! I am currently a college student working a part-time internship and taking a summer class! I am often available on weekends and monday, wednesday, and friday nights. I know how to crate dogs if needed and have reliable transportation to an emergency vet if needed. I have grown up around cats and dogs all my life so I understand the importance of keeping your pet safe.

Sitter Profile Image: Julia P.
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Julia P.
from
$31
per night
2 years of experience
Beechfielf-Irvington Area, Baltimore, MD, 21223

About: I’ve taken care of dogs for a long time as I’ve had many dogs myself throughout my life! I love animals so much!! I work at a school full time from the end of August until the beginning of June. I will be available full time during the summer Monday-Friday all day! I have a fenced yard where your pupper will be able to walk around freely! I will also take them for walks around the neighborhood and to the park! I am willing to travel to you as well! My senior dog recently passed away and would love company!

Sitter Profile Image: Iman K.
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Iman K.
from
$63
per night
5.0 out of 5 stars
5 reviews
9 years of experience
Forest Park, Baltimore, MD, 21207

Iman took such great care of our boys!

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Steve S.
Sitter Profile Image: KB B.
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KB B.
from
$50
per night
30 years of experience
Roland Parl-Homewood-Guilford, Baltimore, MD, 21211

About: I’ve been caring for animals for over 30 years and have experience with pets of all ages, sizes, personalities, and care needs. Animals have always been a huge part of my life, and caring for them comes very naturally to me. Over the years, I’ve looked after everything from energetic dogs who love adventure and playtime to senior pets who need a gentler pace, extra patience, and close attention to routines and comfort. I also previously owned and operated my own pet sitting business for several years, where I built trusted relationships with pet owners and provided dependable in-home care for their pets and houses. I eventually closed the business to help my sister run her company full time, but I never stopped pet sitting. Since then, I’ve continued caring for pets on the side because it’s something I genuinely love and find deeply fulfilling. My experience includes daily walks, feeding schedules, administering medications, overnight care, companionship, litter box maintenance, basic grooming support, and maintaining consistent routines to help pets feel secure while their owners are away. I understand how important communication and trust are, so I always aim to provide thoughtful updates and attentive care that gives owners real peace of mind. Along with pet care, I’m highly respectful of people’s homes and take pride in leaving spaces clean, organized, and well cared for. I’m dependable, communicative, calm under pressure, and genuinely attentive to the little details that make a difference. For me, great pet sitting is about creating a safe, loving, low stress environment where pets can feel comfortable and cared for until their people return. "Until one has loved an animal, a part of one's soul remains unawakened." Anatole France​ I work remotely full-time, which allows me to provide pets with lots of companionship, supervision, and consistency throughout the day. My schedule is flexible, so I’m able to accommodate walks, feeding routines, playtime, medications, and cuddle breaks as needed. I genuinely enjoy spending time with animals, so I naturally build pet care into my daily routine rather than treating it like a task to check off. I have over 30 years of experience caring for animals and previously owned my own pet sitting business, so safety, communication, and trust are extremely important to me. I’m very attentive to routines, behavior changes, medications, and household instructions, and I always aim to create a calm, loving, low-stress environment for pets while their owners are away. I treat every home with respect and care, keep spaces clean and secure, and provide regular updates and photos for peace of mind.

Sitter Profile Image: Janine J.
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Janine J.
Star Sitter
from
$80
per night
4.9 out of 5 stars
456 reviews
227 repeat clients
4 years of experience
Woodlawn, MD, 21207

Janine was a wonderful house sitter and pet sitter! She sent lots of updates and took great care of my pup. I’d highly recommend her!

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Maya S.
Sitter Profile Image: Ana R.
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Ana R.
from
$50
per night
4.8 out of 5 stars
7 reviews
3 repeat clients
4 years of experience
Roland Parl-Homewood-Guilford, Baltimore, MD, 21210

Ana is great! She was always responsive, kind, and reliable, and made sure Ginger stayed safe, comfortable, and happy. She took great care of her and also helped daily medication well! When I got home, Ginger was calm, healthy, and clearly well cared for.

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Vicky J.
Sitter Profile Image: Brittney R.
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Brittney R.
from
$50
per night
4.8 out of 5 stars
45 reviews
24 repeat clients
28 years of experience
West Baltimore, Baltimore, MD, 21223

Brittney was wonderful with our pets and home! Everyone was happy and healthy when we returned. She kept in touch and we were very comfortable having her stay with our pets. We will definitely be back to rebook for long stays! Thank you!

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Sara W.
Sitter Profile Image: Shania H.
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Shania H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
92 reviews
18 repeat clients
10 years of experience
BALTIMORE, MD, 21207

Shania was wonderful! We booked her for a long weekend away and felt very confident in her care of our home and puppy. Our pup seemed to be well cared for and we came home to a clean house! Thank you!

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Carley W.
Sitter Profile Image: Kathleen B.
Verified Enhanced Background Check
Kathleen B.
Star Sitter
from
$63
per night
5.0 out of 5 stars
67 reviews
19 repeat clients
20 years of experience
West Baltimore, Baltimore, MD, 21223

Thank you Kathleen for a great stay with our two pups! We are always a bit uneasy leaving our dogs overnight but there wasn’t a time where we had to feel worried about anything over the past 3 nights! Kathleen sent cute pics and updates of our pups, didn’t mind the occasional behavioral issue and was overall such a great sitter who we’d recommend to anyone!

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Jasmina D.
Sitter Profile Image: Asia N.
Verified Enhanced Background Check
Asia N.
Star Sitter
from
$50
per night
4.9 out of 5 stars
17 reviews
8 repeat clients
7 years of experience
Lower Northwood, Baltimore, MD, 21218

Asia was very communicative and flexible with my schedule, and she did a wonderful job caring for my dogs. They had a lot of cuddles, walks, and photos taken throughout the visit. Will definitely be booking with her again in the future!

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Nikki S.
Sitter Profile Image: Brianna D.
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Brianna D.
Star Sitter
from
$38
per night
5.0 out of 5 stars
24 reviews
8 repeat clients
10 years of experience
Downtown, Baltimore, MD, 21252

Brianna is an amazing Catsitter! Not only did my cats really love her but she was amazing at sending updates and being attentive towards them and their needs! Will definitely be booking her again for my future cat sitting needs!

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Jerson L.
1 / 1
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Over 11
pet parents in Winsor Hills have booked house sitting

Winsor Hills pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Kaitlin was amazing! Will definitely rebook. My animals were so loved and well taken care of. She did a great job at communicating and sending updates. Left my house very clean and I returned to happy pets!

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Alison G.
House Sitting
5.0 out of 5 stars

So meticulous and thorough! Sophie followed every direction I gave her, and took outstanding care of my dogs. Bravo!

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Maria M.
House Sitting
5.0 out of 5 stars

Cashae was a wonderful sitter for our 2 pups!! She is a Dog Lover for sure! She took great care of our dogs. She was with the dogs 24/7. It meant a lot to me knowing that Cashae was a perfect fit as a dog mom, while we were gone for awhile...I highly recommend Cashae!!?

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Joan B.
House Sitting
5.0 out of 5 stars

Eli took very good care of or 2 girls. He communicated throughout weekend and sent updates and was very responsive. I would book him again.

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Lori A.
House Sitting
5.0 out of 5 stars

Emily was great! She was such a champ when we had a leak in our house and then our train got delayed during our stay. We would definitely use her again!

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Alexandra T.
House Sitting
5.0 out of 5 stars

Julion was great! He was very responsive and arrived on time. He provided regular, detailed updates that helped me relax on my trip and not worry about our pets. I'm so happy that he was available for us and hope that we can book him again!

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Jill M.
House Sitting
5.0 out of 5 stars

We're so grateful when Liz and hubby are available to take care of our fur babies. We know that they can handle anything, so we can relax and enjoy our travels!

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Dana S.
House Sitting
5.0 out of 5 stars

Ashley did a great job taking care of my dogs. She’s professional, flexible, and maintained great communication throughout. Would highly recommend.

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Sophie A.
House Sitting
5.0 out of 5 stars

We were happy to have Lyndsay back to take care of our pups! They were happy when we returned and our house was very clean!

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Emily L.
House Sitting
5.0 out of 5 stars

We were very happy with Sean as a pet sitter for Bruno, our American Staffordshire Terrier, who is very anxious with new people. Sean's patience and understanding helped Bruno relax quickly. Sean sent daily updates and photos of Bruno playing in the yard and chilling on the couch. Sean also finished giving Bruno the final doses of medication for an UTI developed just before our vacation. We will definitely use Sean in the future.

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Stacey M.
House Sitting
5.0 out of 5 stars

Trust them completely with our pups and our home. We have a two dog home that includes a senior dog who has mobility issues and medication needs. They’ve never had more exceptional care and are always happy and content when we arrive back home. Same goes for the house. House is clean and always well taken care of. My wife and I even came home to all our mail collected and our recycling put to the curb ❤️

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Anthony F.
House Sitting
5.0 out of 5 stars

Another great week of being able to count on Jhane and EmJay with no worries while we were gone for the week!

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Adam H.
House Sitting
5.0 out of 5 stars

livia was wonderful with our Labrador, Cupcake. She took excellent care of her, making sure she was happy, safe, and well looked after. Olivia also kept the house very clean and tidy while we were away. We truly appreciated her reliability and care, and we are having her watch Cupcake again.

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Dina J.
House Sitting
5.0 out of 5 stars

Carol is a great pet sitter. She related well with my dogs and took great care of them while I was out of town! Thank you Carol!

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Deb S.
House Sitting
5.0 out of 5 stars

Alexis took great care of my cat BD while we were out for almost 3 weeks! She sent me regular updates and pictures which I greatly appreciate, and she also took care of my plants and helped with some issues in my house! I would definitely trust Alexis again to housesit with BD!

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Sophie M.
House Sitting
5.0 out of 5 stars

Robert has a very pleasant personality and easy to get along with. Very conscientious about taking care of my dog and my house while he was house sitting.

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Hannah S.
House Sitting
5.0 out of 5 stars

Erica is amazing! She was wonderful with my cat and dog, and gave us great updates all weekend. Shes the best!

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Jessica P.
House Sitting
5.0 out of 5 stars

Emily was amazing, my boys loved her, and I felt very comfortable leaving them in her care. She was professional and very communicative, the daily photos helped so much. Even when encountering some unexpected issues (on my end) and with Atticus boycotting his meds, she handled them with grace and went above and beyond. I could not recommend Emily enough!

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Cara S.
House Sitting
5.0 out of 5 stars

Johnita was amazing! This was the first time I'd left my cat with a sitter for longer than a few days, and I was nervous, but Johnita gave Lucy lots of love and played with her and sent me daily updates with pictures. She took such fantastic care of Lucy I thought she might not be as happy to see me! I highly recommend Johnita - she's reliable, warm, responsible, and caring; everything you want in the person who will care for your beloved pet!

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Jane Y.
House Sitting
5.0 out of 5 stars

Cecilie was amazing with our high energy German Shepherd. I get a bit nervous asking others to watch my dog because his size and energy level can intimidate people, but Cecilie took such good care of him and made sure he was well exercised. She truly went above and beyond. We couldn’t have been happier with her and I’d definitely request her again!

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Alicia P.
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 Winsor Hills 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 Winsor Hills 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 Winsor Hills on Rover as of Jun 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 Winsor Hills 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 4,865 house sitters in Winsor Hills. 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, 86% of Winsor Hills house sitters respond in under an hour.

House sitters in Winsor Hills have an average of 14 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 Winsor Hills.

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. Winsor Hills 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.