House Sitting Winterberry

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

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pet parents in Winterberry have booked house sitting

Winterberry, Find top rated house sitting

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: 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 absolutely wonderful with Chance. She took such great care of him, kept us at ease, and clearly loves what she does. We came home to a happy pup and couldn’t be more grateful. Highly recommend!

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Rachel D.
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

Absolutely loved Kerri! She did an amazing job with our two pups. Showed so much love. And always made sure she sent pics! She took amazing care of our pups and home. Def consider her part of our family! Thanks again!

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

Amber is a true miracle worker and our dog sitting unicorn 🦄 She’s patient, kind, and so understanding with our FOUR older, adoptive, stubborn angels and is the sole reason we are able to take much needed weekends away!

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Jessica B.
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
10 repeat clients
30 years of experience
New Windsor, MD, 21776

Jenny was kind, caring, punctual and a great communicator. She took wonderful care of our sweet puppy while we were away. Jenny also took great care of our home, even getting the mail I forgot to put on hold. Her communication by text both before and during our time away was speedy and she even included photos of our pup having fun. We look forward to Jenny caring for our pup the next time we are away.

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Karen M.
Sitter Profile Image: Analise B.
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Analise B.
from
$75
per night
5.0 out of 5 stars
11 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: Riley K.
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Riley K.
Star Sitter
from
$34
per night
4.8 out of 5 stars
13 reviews
6 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: Tracie L.
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Tracie L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
4 reviews
5 repeat clients
13 years of experience
Reisterstown, MD, 21136

About: I’ve taken care of dogs for 13 years and have 2 dogs of my own. I’ve rescued stray dogs off the street before and put them in a safe environment. I was once very active in helping animal shelter. A close friend of mine is a Veterinarian and had asked me to dog sit for her when she traveled, it was a pleasure to handle 5 dogs at a time at her house. I enjoy taking walks in nature with dogs. I can also take care of chickens, horse, rabbits, hamsters, and fish when you are away. I have plenty of time to play with your dog and take them on walks. My schedule is open daily and weekly routine as well once established. I love to give dog treats and play ball with them. Taking them on long walks. I can also give them a lot of petting for attention. I will take pictures for updates on their activity.

Sitter Profile Image: Alexander S.
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Alexander S.
from
$50
per night
19 years of experience
Reisterstown, MD, 21136

About: I’ve been caring for animals since I was 11 years old, and I’m comfortable with cats and dogs of all sizes, personalities, and energy levels. People have called me a “pet whisperer” because I have a calm, patient way of connecting with animals and earning their trust. I’m also physically strong and confident handling large, powerful, and energetic dogs, including dogs who need firm leash control, longer walks, structure, and plenty of activity. Safety, patience, and clear communication are always my priorities. In addition to the Rover Guarantee, I carry my own premium Pet Care/Liability Insurance for your peace of mind. I’m available 7 days a week and have a flexible schedule throughout the day. I can help with morning, afternoon, evening, and late-night care depending on your pet’s needs. Whether you need regular visits, last-minute help, walks, drop-ins, or extended care, I’m happy to work with your schedule whenever possible. I follow each client’s instructions closely and do my best to keep every pet’s routine consistent. I know every animal has their own personality and comfort level, so I take a patient, respectful approach to care. If your pet wants playtime, attention, or companionship, I’m happy to give that. If they are shy, anxious, independent, or simply prefer space, I’m just as comfortable keeping them company from a calm and safe distance. My goal is always to help your pet feel secure, respected, and well cared for.

Sitter Profile Image: Kaitlin G.
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Kaitlin G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
17 reviews
7 repeat clients
25 years of experience
Baltimore, MD, 21215

My dogs loved Kaitlin! She did a great job with them. She was easy to work with and very responsive. She sent pics every day. I would use her again.

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Maureen 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: 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: Lonnie P.
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Lonnie P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
51 reviews
11 repeat clients
50 years of experience
Finksburg, MD, 21048

Lonnie handled my high energy big dogs wonderfully. He clearly cared about their health and well being, which means a lot to my husband and me when we put our babies in someone else's care. Thanks Lonnie, we'll see you next time!

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Miriam F.
Sitter Profile Image: Andrea M.
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Andrea M.
from
$27
per night
5 years of experience
Hanover, PA, 17331

About: I have been passionate about dogs ever since I was a child but because experienced working with dogs and cats (and some bunnies) while working for the Humane Society of Memphis and Shelby County. I was a veterinarian assistant for one year and then became an adoptions Manager for three years. This was the most fulfilling experience of my adult life, being able to help animals and the community daily. I recently lost my closest companion, Xander, about a month ago. He was 13 years old and I had him since he walked into the humane society at two months old. Through him I gained even more experience with aging dogs, medical care and many behavioral changes as he aged. While using positive reinforcement training we navigated 6 military moves, life adaptions to aging and the introduction of two kittens. I will take all this experience and use it to provide the same amount of love an attention for you furry family members as I did for Xander. I am currently unemployed and have most days free as well as can stay over night or board animals in my home. I have a very flexible schedule and am happy to work with any clients schedule as needed. I currently only have two cats in my home, so I’m able to provide boarding for cat friendly animals. I have a fenced in back yard and am usually not gone from the house for more than four hours. I also am available for staying over nights at clients houses for a more comfortable experience for everyone in the family.

Sitter Profile Image: Maxwell N.
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Maxwell N.
from
$29
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
7 years of experience
Westminster, MD, 21157

About: I have experience with and am comfortable with all sizes, breeds, ages and personalities of any dog! I am reliable, friendly, and have good communication skills! I have two cats I take care of day in and day out! I also regularly dog sit one larger dog roughly once a month on weekends! I treat every animal I meet and or sit as if they were my own. As previously stated, I am an animal lover that believes every animal is unique and needs their own personalized care!

Sitter Profile Image: Nicole O.
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Nicole O.
from
$50
per night
28 years of experience
Westminster, MD, 21157

About: I’ve been a dog owner for nearly 30 years and genuinely enjoy spending time with animals. Whether your dog loves long walks, hiking adventures, or simply exploring the neighborhood, I’m happy to match their energy and routine. I also enjoy playing with both dogs and cats, making sure they get plenty of exercise, enrichment, and attention while you’re away. I understand that every pet has a unique personality and needs. My goal is to provide reliable, compassionate care so your pets feel safe, comfortable, and loved, and you can have peace of mind knowing they’re in good hands. I have a flexible routine throughout the school year with a lot of extra availability in the summer time. I can work the needs of your pets to make sure they get the care and time they need! I understand that each cat and dog has unique needs. I will work with you to best meet the needs of your pet in their own space. I love spending time outside and look forward to incorporating your dog(s) into my routine!

Sitter Profile Image: Nicole S.
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Nicole S.
from
$50
per night
5.0 out of 5 stars
7 reviews
20 years of experience
upperco, MD, 21155

Nikki was very easy to work with for our needs. She was very communicative with questions and updates. We will definitely use her again!

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Carol F.
Sitter Profile Image: Camryn F.
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Camryn F.
from
$55
per night
5.0 out of 5 stars
14 reviews
5 repeat clients
5 years of experience
Westminster, MD, 21157

Camryn was great with our two golden retrievers! She sent lots of updates and great pictures while we were gone. We really appreciated having her and will definitely be booking with her again!!

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mikelle r.
Sitter Profile Image: Jaime T.
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Jaime T.
from
$60
per night
5.0 out of 5 stars
46 reviews
12 repeat clients
30 years of experience
Upperco, MD, 21155

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

Hailey took very good care of our cat for almost a week house sitting, We were happy to see our home and cat very happy once we returned! She was very responsive, we would have loved more updates but were very happy with the service she provided. We could see our cat got along with her very well

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Anirudh B.
Sitter Profile Image: Katharine D.
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Katharine D.
from
$50
per night
13 years of experience
Sykesville, MD, 21784

About: I’ve been caring for pets since I was 5 years old and have grown up with both bunnies, cats and dogs of all sizes, giving me over 13 years of hands on experience. Throughout the years, I’ve helped with feeding, walking, playtime, grooming, cleaning up after pets, and making sure they feel safe, happy, and comfortable. I understand that every pet has its own personality and routine, so I’m committed to following your instructions and providing patient, dependable, and loving care. Whether it’s going for walks, sticking to a feeding schedule, or simply giving your pet companionship while you’re away, I’ll treat them with the same love, attention, and respect that I give my own pets. I am currently working part time so I am available early morning and afternoons up until 3/4/5pm during the weekdays and weekends. Pet care has been a part of my daily life since I was a child. I currently care for my own cats every day by feeding them, cleaning their litter boxes, playing with them, and making sure they’re happy and comfortable. I also have experience caring for dogs, including walks, exercise, feeding, and companionship. I work part-time in the evenings, which leaves my mornings and afternoons available for pet care. When house sitting, I’ll make sure your pet’s routine is followed closely and that they receive plenty of attention, exercise, and affection while you’re away. I believe every pet deserves to feel safe, comfortable, and loved while their owner is away. I take the time to learn each pet’s routine and follow all care instructions closely, including feeding schedules, walks, medications (if needed and instructed), playtime, and any special requests. I prioritize your pet’s safety by keeping a close eye on them during walks and outdoor time, making sure doors, gates, and leashes are secure. I also understand the importance of respecting your home, keeping it clean, and providing regular updates with photos and messages so you can have peace of mind while you’re away. My goal is to make your pet feel happy and cared for in the environment they’re most comfortable in their own home.

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

Pet parents share their Rover experiences - Winterberry

1 / 1
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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  • 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?

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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.

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    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
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Popular requests for house sitting - Winterberry

Select a filter and find qualifying sitters offering house sitting.

Sitters in Winterberry average 4
repeat house sitting clients

FAQs for House Sitting - Winterberry

Frequently asked questions about Rover

As of July 2026, there are 3,223 sitters on Rover offering House Sitting across Winterberry. 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 Winterberry 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 Winterberry 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 Winterberry 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 Winterberry. On Rover:

  • 91% 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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