House Sitting Winsome Heights

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Sitter Profile Image: Cheryl B.
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Cheryl B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
26 reviews
12 repeat clients
18 years of experience
Reisterstown, MD, 21136

Cheryl was a great sitter. She stayed at the house and watched our two large dogs. She took good care of them and sent us pictures and updates on them over the weekend. She even took care of a package that was delivered for us. I would use Cheryl again.

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Todd W.
Sitter Profile Image: Riley K.
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Riley K.
Star Sitter
from
$34
per night
4.8 out of 5 stars
13 reviews
7 repeat clients
6 years of experience
Owings Mills, MD, 21117

If you’re looking for a great pet/house sitter, Riley is your person. Riley took great care of my pup and fish, checked in daily with me, sent photos and provided daily walks each day. At the end of the stay, Riley summarized Toby’s week, including highlights and household things she did on a sheet of paper. Riley is very reliable and I’ll definitely book her again in the future.

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Bess B.
Sitter Profile Image: Kerri L.
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Kerri L.
Star Sitter
from
$70
per night
5.0 out of 5 stars
36 reviews
14 repeat clients
8 years of experience
Westminster, MD, 21158

Kerri did an amazing job with our dog who requires daily medication for seizures. She actively communicated with us during our trip with updates and pictures. She left our home in great condition, very neat and tidy. I would highly recommend her for any other family

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Deb H.
Sitter Profile Image: Lora M.
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Lora M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
127 reviews
34 repeat clients
22 years of experience
Finksburg, MD, 21048

Lora is just so wonderful with Sandy. I think Sandy likes her more than us. I never worry about the house or the dog, even with big summer storms. Lora is great!

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Kristi E.
Sitter Profile Image: Amber R.
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Amber R.
from
$50
per night
5.0 out of 5 stars
15 reviews
5 repeat clients
10 years of experience
Westminster, MD, 21158

We had an emergency situation and needed someone right at that moment. On July 4th, she immediately responded and jumped to it to help us out without even meeting our 2 dogs. She has been SO great sending us updates and pictures. I don’t know what we would’ve done without her. Definitely will book again!

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Ashley K.
Sitter Profile Image: Jennifer C.
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Jennifer C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
35 reviews
11 repeat clients
30 years of experience
New Windsor, MD, 21776

Jennifer did a great job pet sitting and letting our 4 dogs out for potty breaks during the day. We came home to happy pups and our home the way we left it. Thank you for caring for our fur babies while we were out of town!

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Stacie W.
Sitter Profile Image: Paris K.
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Paris K.
from
$55
per night
5.0 out of 5 stars
11 reviews
4 repeat clients
5 years of experience
Hampstead, MD, 21074

Murphy and Milo loved having Paris sit for them and everything went perfectly. We love the fact that she sent pictures. We highly recommend her, and Hope to have her sit again in the future

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bart m.
Sitter Profile Image: Kelly E.
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Kelly E.
from
$70
per night
5.0 out of 5 stars
55 reviews
23 repeat clients
7 years of experience
Westminster, MD, 21157

Kelly was FANTASTIC! She checked in regularly, gave our pup so much love, and left our house cleaner than we left it. We will definitely be using her again and I know our dog is happy about that!

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Kelsey C.
Sitter Profile Image: Noah D.
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Noah D.
from
$40
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
8 years of experience
Westminster, MD, 21157

About: Simply put, I truly LOVE animals. I have always enjoyed spending time with, and playing with pets of all kinds. I will put your pets' needs above my own. I'm currently working full time, but I am usually home when not at work. I live 5 minutes away from my job, so I will always be available for your fur babies even while working if I need to be. I care for pets the same way I would care for a baby. Their needs are always more important than mine, and I will always make time for them. They also get plenty of attention and play time! Please note: I will have to crate them while at work. This is the ONLY time they will be crated. I will also be home around 1:30 for lunch to take your pet out for a potty break.

Sitter Profile Image: Ronny G.
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Ronny G.
from
$45
per night
5.0 out of 5 stars
79 reviews
18 repeat clients
16 years of experience
York, PA, 17406

We cannot recommend Ronny highly enough! When another sitter backed out at the last minute, we reached out to Ronny on short notice. He responded promptly and was more than willing to come by for a meet and greet, which immediately put us at ease. From the moment he walked in the door, our cats were comfortable with him which is not always the case. Ronny took his time answering all of our questions and asked thoughtful questions of his own. Even though we admittedly have a very detailed list of instructions, he did an amazing job remembering all the little things and checking in regularly with messages and photos throughout his stay. It was clear that Ronny genuinely cared about making sure our cats were happy, comfortable, and well loved while we were away. He was also incredibly respectful of our home, leaving everything exactly as we left it. He even went above and beyond by offering to clear our driveway after an unexpected snowfall. If you’re looking for someone who truly goes the extra mile and treats your pets like their own, Ronny is absolutely the person to book!

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Sierra L.
Sitter Profile Image: Analise B.
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Analise B.
from
$75
per night
5.0 out of 5 stars
13 reviews
1 repeat client
1 year of experience
Hampstead, MD, 21074

Thank you for taking such good care of Henry and Oliver!

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Steve S.
Sitter Profile Image: Shaelin C.
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Shaelin C.
from
$40
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
6 years of experience
Westminster, MD, 21157

Took great care of our two energetic dogs! Reliable and followed their routines. Happy to have found Shaelin last minute to watch our fur babies. Enjoyed our trip knowing they were in good hands.

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Anne-Marie K.
Sitter Profile Image: Melisha G.
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Melisha G.
from
$60
per night
5.0 out of 5 stars
48 reviews
13 repeat clients
15 years of experience
Littlestown, PA, 17340

Melisha was great! She sent photos of our dog daily and she looked so happy. Coco hates to be alone and we were gone for almost a week, so was glad she was taken care of so well. Thank you!! Will definitely be using you again if needed.

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Kayla S.
Sitter Profile Image: Bronte B.
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Bronte B.
Star Sitter
from
$72
per night
5.0 out of 5 stars
195 reviews
57 repeat clients
15 years of experience
Pikesville, MD, 21208

Bronte did a great job caring for our girl while we were away for a few days. She sent lots of pictures and it looked like Bella really enjoyed her time with Bronte. Would highly recommend.

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Christine P.
Sitter Profile Image: Leilani & Jessie M.
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Leilani & Jessie M.
from
$50
per night
5.0 out of 5 stars
131 reviews
38 repeat clients
20 years of experience
Hanover, PA, 17331

Thank you Leilani for keeping my furbabies company while I was away. I would highly recommend her to anyone. Thanks again. Will be looking for you again when we plan our next vacation.

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Eileen H.
Sitter Profile Image: Ryan H.
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Ryan H.
Star Sitter
from
$70
per night
5.0 out of 5 stars
246 reviews
47 repeat clients
22 years of experience
Owings Mills, MD, 21117

Ryan took great care of our 4 large dogs and 2 cats while we were away on vacation. He sent us lots of photo updates and our animals got lots of snuggle time while we were gone.

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Alexandra D.
Sitter Profile Image: Keira J.
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Keira J.
Star Sitter
from
$55
per night
5.0 out of 5 stars
13 reviews
6 repeat clients
3 years of experience
Woodlawn, MD, 21244

Keira was great with our old pup Toby while we were out of town. She was knowledgeable about care and Toby was in great hands. She gave updates and photos throughout the stay.

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Morgan G.
Sitter Profile Image: Samantha R.
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Samantha R.
Star Sitter
from
$40
per night
5.0 out of 5 stars
29 reviews
11 repeat clients
15 years of experience
Halethorpe, MD, 21227

Samantha stayed in our home with our two girls. She updated me everyday and was a very respectful house guest! Everything was tidy and just where we had left it. The girls were happy and I doubt they missed us at all 😂. I would definitely recommend Sam!

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Jessica D.
Sitter Profile Image: Hailey K.
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Hailey K.
from
$50
per night
4.9 out of 5 stars
22 reviews
7 repeat clients
10 years of experience
Sykesville, MD, 21784

Hailey was so great with our pup! She gave good updates and let us know how he was each day with photo updates. She was also so professional and we loved working with her. Will definitely book again - especially because Kiba loved her!

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Kayla M.
Sitter Profile Image: Lane M.
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Lane M.
from
$25
per night
5.0 out of 5 stars
4 reviews
1 repeat client
8 years of experience
Glenville, PA, 17329

About: I have several years of experience caring for a wide variety of animals. I am currently pursuing my education to become a Small and Large Animal Veterinarian and specialize in Animal Psychology and Internal Medicine/Oncology. Through my experience, I have developed strong knowledge and skills in pet training, dog walking, proper nutrition and feeding, and medication administration. Pet care fits naturally into my daily and weekly routine. I currently work a part-time job on Mondays, Wednesdays, and every other Saturday from 3:00 PM to 8:00 PM, which allows me to maintain a flexible schedule for my pet care clients. I keep my Rover calendar up to date to accurately reflect my availability, though occasional changes may arise. If you don't see the dates or times you need, I encourage you to reach out anyway—I’ll always do my best to accommodate your schedule and provide exceptional care for your furry family member! I do not offer in-home boarding, but I am happy to provide care in your home. I strive to maintain your pet’s normal routine to keep them comfortable and stress-free. When possible, I am available for extended stays, which can provide added consistency for your pet’s care and fit well with my schedule. I also recommend that clients leave detailed care instructions, as every pet has unique needs, routines, and preferences.

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The median cost per night for house sitting in Winsome Heights is $50

Pet parents share their Rover experiences - Winsome Heights

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5.0 out of 5 stars

Alayna is fantastic, she communicates well and sends lots of pictures while we're out of town. She's our go to care giver. Thank you Alayna!

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Cate E.
House Sitting
5.0 out of 5 stars

Camryn is the best! We’ve used her multiple times and she takes the best care of our two fur babies and our home.

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mikelle r.
House Sitting
5.0 out of 5 stars

Jamie & Kasey took great care of our dog. They both sent multiple pictures throughout each day they were there. Giving updates on how she was doing. We had an unexpected snow storm while away and came home to shoveled and salted sidewalk. Our girl was loved and cared for like she was their own pet❤️

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Vicki G.
House Sitting
5.0 out of 5 stars

Carly was absolutely amazing. She took such good care of our babies. I was very worried about leaving them for over two weeks but she did an excellent job at varying their walks and making them feel loved. I will definitely be using her again!

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Amelia F.
House Sitting
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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

    It doesn’t happen often, but if your 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

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Popular requests for house sitting - Winsome Heights

Select a filter and find qualifying sitters offering house sitting.

Sitters in Winsome Heights average 4
repeat house sitting clients

FAQs for House Sitting - Winsome Heights

Frequently asked questions about Rover

As of August 2026, there are 3,078 sitters on Rover offering House Sitting across Winsome Heights. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winsome Heights walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Winsome Heights maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winsome Heights choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

Yes, you can find sitters who have experience with handling special pet needs in Winsome Heights. On Rover:

  • 92% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 93% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

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