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: James B.
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James B.
from
$35
per night
5.0 out of 5 stars
• 7 reviews
1 repeat client
15 years of experience
Reisterstown, MD, 21136

“⭐️⭐️⭐️⭐️⭐️ James was absolutely amazing with Meiko! From the beginning, he was incredibly attentive and communicative, which gave me so much peace of mind knowing she was in good hands. He kept me updated, was very responsive, and most importantly, Meiko absolutely loved him! He was also extremely respectful of my home and just genuinely so friendly and easy to work with. I really appreciated the care and attention he gave Meiko while I was away. It’s such a relief finding someone you can trust with both your pet and your home. I will absolutely be booking with James again and would highly recommend him to anyone looking for a reliable, communicative, and caring sitter. Thank you so much, James! 🐾💕”

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Cimone B.
Sitter Profile Image: Phoebe K.
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Phoebe K.
from
$75
per night
5.0 out of 5 stars
• 26 reviews
9 repeat clients
6 years of experience
Westminster, MD, 21157

“Phoebe always does an amazing job! She has even won over our shy older pup and keeps our young puppy entertained. Her great communication is always appreciated and she is definitely our go to sitter!”

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Nicole L.
Sitter Profile Image: Lonnie P.
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Lonnie P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 57 reviews
12 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: Anna V.
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Anna V.
from
$80
per night
5.0 out of 5 stars
• 9 reviews
1 repeat client
7 years of experience
Hampstead, MD, 21074

“Anna did a wonderful job taking care of our fur babies! Anna kept us well informed with pictures and any questions she had. We were well please with the care she provided!”

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Susan H.
Sitter Profile Image: Riley K.
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Riley K.
Star Sitter
from
$34
per night
4.9 out of 5 stars
• 17 reviews
10 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: Margaret T.
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Margaret T.
from
$65
per night
5.0 out of 5 stars
• 24 reviews
4 repeat clients
50 years of experience
Reisterstown, MD, 21136

About: I have owned dogs all my life all shapes and sizes. I have been trained and volunteer for MDSPCA and the Baltimore Humane Society. I believe it’s important that all dog’s feel loved and taken care of and are as much a family member as anyone else. I know how important interactive play is and enrichment. Keeping a dog in their own environment is best for their well being. Kennels can be very noisy and stressful to the average dog. I know as a pet owner myself having your dog with a trusted person is critical. I also have a medical background so I would be ready for any emergency., if it should arise. I have no Problem giving medication to your pet if needed I am recently retired and I am looking forward to devoting my time to caring for dogs. My schedule is very flexible and ready to start. I have a fenced in yard and have cared for dogs of all sizes. I make sure they are safe and loved and having fun..

Sitter Profile Image: Sarah M.
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Sarah M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
4 years of experience
Freeland, MD, 21053

“Sarah was absolutely wonderful with my difficult puppy for over a week! She kept me updated, sent me pictures, and made me feel comfortable. I cannot recommend her enough for your pet care needs. Thank you so much Sarah!! Alfie and I appreciate you!!!”

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Alexandra K.
Sitter Profile Image: Quinn B.
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Quinn B.
from
$50
per night
5.0 out of 5 stars
• 20 reviews
4 repeat clients
6 years of experience
Owings Mills, MD, 21117

“Quinn was wonderful with our dogs! She kept us informed and sent pictures, and our dogs just loved her. So happy we found her for our vacation. Highly recommend her!”

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Michelle L.
Sitter Profile Image: Ambrosia H.
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Ambrosia H.
from
$31
per night
10 years of experience
Owing Mills, MD, 21117

About: Hey there! I'm Ambrosia! You can call me Amber. I've been caring for pets for as long as I've been caring for babies. See it goes hand in hand. Every baby that I've nannied usually has a furry frind with them. The fur baby came first then the actually baby. When caring for the baby I often took a liking to the furry friend too. That meant playing and feeding the dog whenever I wasn't taking care of the baby. Often times I would let the dog out to do his buisness. When the child got older and we went on walks the dog of couse came too. As a former athlete and someone who lives an active lifestyle, I love going on walks and runs. So if your dog is a runner that's no problem for me; just let me know. Just like kids, I can understand the fustration when a pet does not listen. Being a nanny helped me to gain a lot of patience, so if your pup isn't a good listener it's ok! Ms. Amber has the time to wait it out. On the other side of that we all love a little reward so don't be shy to let me know if you have a reward system for your pet. I love dogs yound and old! As caregiver I strive to give your pet the best experience while they are in my care. I look forward to meeting and tking care of your furry friend! As I am not working a traditinal job right now, my schedule is pretty flexiable. Pet care can fit into my daily routine around your pets needs. Whether that be for an early morning walk or a a mid day pop in for cuddles and play, I can be the sitter you rely on. When caring for your fur baby in your home, I strive to keep a clean and safe enviorment for your pet and myself. Any mess that might have been made while caring for your pet will be cleaned up. I want your pet to have the best experience with me and whatever malkes them comfortable with me I'll do. I understand that we all need time to warm up to eachother. I keep a calm attitude and love to givethe equal amout of space and cuddles.

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

“Keira is so fantastic! My dog is still a little bit nervous because Keira is new, but she really takes it in stride and seems to magically make my dog more comfortable. Keira is so patient, kind, and gracious, highly recommended if your pup tends to be the nervous kind.”

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Micki D.
Sitter Profile Image: Destiny W.
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Destiny W.
from
$65
per night
4.9 out of 5 stars
• 14 reviews
3 years of experience
Upper Northwood, Baltimore, MD, 21239

“Simply amazing. Went above and beyond in caring for our pets. Photos, videos, updates and all with a dose of love. The top of our list from now on!”

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Ashleigh P.
Sitter Profile Image: Sara W.
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Sara W.
from
$22
per night
5 years of experience
Manchester, MD, 21102

About: I’ve taken care of pets since I was at least 15 years old. Neighbors, friends, and family have relied on me to take care of the furry little creatures. I make sure they’re well taken care of so you never have to worry! I will always make sure your little furry children are well taken care of and full of energy for the next day! I was working home improvement for a few months with a mobile company. My boss currently couldn’t afford to have employees work for him so he let us go. I will be free 100% of the time for your furry children. I will be looking for another job of course.. but currently and for a while I will be available 100% of the time for the week. In the clients home, I will be able to crate the dog if necessary and needed. If they have a fenced in yard the dog will be able to roam freely and have some freedom. If not I will make sure to leash the dog and keep an eye on them 100% of the time. Cats of course if the owner says they do leash them and take them for walks, that will happen. Leashed in the back yard unless told otherwise. Free to roam in the house Obviously whenever!

Sitter Profile Image: Megan D.
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Megan D.
from
$65
per night
15 years of experience
21791

About: I’ve spent years caring for pets and homes for family, friends, and private clients, and I understand that both come with a real responsibility. When someone entrusts me with their home and animals, I take that trust seriously. I’m comfortable caring for dogs of all sizes and personalities, as well as cats, and I’m happy to follow established routines for feeding, walks, treats, medications, playtime, and plenty of attention. I’ve cared for pets who need extra patience and consistency, including a young puppy who was still being potty trained. I also understand that every animal has its own personality and routine, and I make an effort to keep their life as normal and comfortable as possible while their people are away. My house-sitting experience goes well beyond simply being present in the home. I’ve cared for plants and gardens, watered lawns and operated sprinklers, brought in mail and packages, handled basic outdoor chores, and kept an eye on the property. I’ve also handled unexpected responsibilities, including meeting contractors, photographing completed work before authorizing payment, arranging appointments, receiving deliveries, and taking care of errands for homeowners while they were away. Communication is an important part of my approach. I’m happy to provide regular updates, photos, and videos so homeowners can see that their pets and property are doing well. I know how reassuring it can be to see your dog happily lounging on the couch or your garden looking healthy when you're hundreds of miles away. As a freelance writer, I have a very flexible schedule, which allows me to build pet care naturally into my day. I can structure my work around a pet’s routine rather than expecting a pet to fit around a traditional 9-to-5 schedule. Whether a pet needs morning or evening walks, regular meals, medication, playtime, or simply some companionship during the day, I have the flexibility to be there. I’m also able to spend extra time with pets who need more attention or have specific routines. I enjoy the rhythm of pet care and the opportunity to give each animal the consistency, attention, and companionship they’re accustomed to while their owners are away. When caring for pets in a client’s home, I focus on keeping their routine as familiar and comfortable as possible. I follow their normal feeding, walking, playtime, medication, and bedtime routines, while giving them plenty of attention and companionship. Because I’m a freelance writer with a flexible schedule, I can devote time to pets who need more than a quick visit. I’m comfortable caring for multiple pets, following special instructions, and adjusting to each pet’s personality and needs. I also treat your home with the same care and respect I give your pets. I keep things clean and secure, communicate regularly, and provide updates with photos and videos so you know your pets are happy and well cared for while you’re away.

Sitter Profile Image: Julian U.
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Julian U.
from
$70
per night
4.9 out of 5 stars
• 113 reviews
44 repeat clients
10 years of experience
Owings Mills, MD, 21117

“Julian did a great job with both my 100 lb dogs and my 17 year old cat! Julian is very responsive and a good communicator and he has a pleasant upbeat attitude. He was careful about giving medication to two of my pets, asking for clarification when needed. I recommend Julian as an excellent pet sitter.”

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Donna B.
Sitter Profile Image: Lauren M.
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Lauren M.
from
$50
per night
10 years of experience
Westminster, MD, 21158

About: I’ve been around dogs my whole life and currently have two pugs of my own, so I understand how important it is to find someone you truly trust with your pets. I’m patient, dependable, and attentive to each dog’s personality and routine. I’m comfortable with walks, feeding schedules, medications, senior dogs, and giving pets extra attention and affection while their owners are away. I also work in hospice care, so being compassionate, calm, and reliable comes naturally to me. I’ll treat your pets like family and make sure you feel updated and reassured while you’re gone. I work full time during the week from 9am–6:30pm, but pet care fits naturally into my routine since I already care for my two pugs daily. I’m available for evening visits/walks on weekdays and have much more flexibility on weekends for drop-ins, walks, and overnight care. I’m reliable, communicative, and committed to making sure pets feel comfortable, cared for, and loved while their owners are away. Your pet’s safety and comfort are always my priority. I pay close attention during walks and outdoor time, especially in hot weather, and I never leave dogs outside longer than they should be. I make sure pets always have fresh water, a clean environment, and close supervision to keep them safe from anything that could bother or harm them. I’m also very mindful about keeping floors and spaces clear of anything pets could get into or accidentally swallow. I understand how important trust is when someone is caring for your animals, and I’ll always treat your pets with the same care and attention I’d want for my own

Sitter Profile Image: Gervon T.
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Gervon T.
from
$30
per night
3.0 out of 5 stars
• 5 reviews
1 repeat client
5 years of experience
Parkville, MD, 21234

“Gervon in a tremendous Dogsitter. He was communicative, kind, and attentive. He accommodated the medical needs of our pets, too. He even cleaned the sheets before he left! We highly recommend Gervon.”

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Spencer P.
Sitter Profile Image: Trinity W.
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Trinity W.
from
$60
per night
12 years of experience
Westminster, MD, 21157

About: Hi, I'm Trinity! As a dedicated animal lover, my background comes from years of raising and caring for my own pets. I’ve managed everything from a high-energy, young Rotterman (Rottweiler/Doberman mix) to a gentle senior Cockapoo (Cocker Spaniel/Poodle mix), making me comfortable with active leash walking, high-energy play, and patient senior care. I also have hands-on experience with hamsters, fish, kittens, and adult cats. I understand that no two animals are the same, so I focus on personalized care tailored to your pet's exact personality. Above all, I offer strong attention to detail, strictly follow your care instructions down to the letter, and prioritize open communication by asking questions when needed and sending frequent updates so you always know your littles are safe, comfortable, and well cared for. I work remotely which gives me a structured routine. Because I work from home, I am easily available for check-ins, walks, feeding, and spent time ensuring your pets are comfortable and safe throughout the day. I care for every pet strictly based on the agreed-upon instructions provided by their owner. I follow exact feeding schedules, safety guidelines, and care routines down to the letter, maintaining a clean, low-stress environment while asking questions whenever needed to keep your pet safe and comfortable.

Sitter Profile Image: Haylee S.
Verified Enhanced Background Check
Haylee S.
from
$85
per night
9 years of experience
Mt Airy, MD, 21771

About: I’ve always been a huge animal lover and grew up with dogs, so being around them has always been a big part of my life. I’ve dog sat and house sat for friends and family for years, and I’ve also helped friends who foster dogs take care of their puppies. I currently have two dogs of my own that we rescued from Saint Martin in 2023, and I absolutely adore them. They’re a huge part of my life, and I’m so thankful we were able to give them a loving home. I know every dog has their own personality and routine, and I’m happy to adjust to whatever makes yours happiest and most comfortable. Whether that means walks, playing outside, lots of attention and belly rubs, or just hanging out on the couch, I’m there for it! I’ll treat your pets like they’re my own and make sure they feel safe, loved, and cared for while you’re away. I’m currently in between careers, which gives me a pretty flexible schedule and plenty of availability throughout the week. I do have a few other small jobs and am occasionally away on weekends, but my schedule varies and I’m generally pretty open. I’m happy to work with you to find days and times that fit your needs, and I’ll always be upfront about my availability! I will do everything needed to ensure your pets get the care that they deserve and make sure they are as safe, happy and loved as possible!

Sitter Profile Image: Xin H.
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Xin H.
from
$60
per night
4.7 out of 5 stars
• 14 reviews
4 repeat clients
14 years of experience
Ellicott City, MD, 21042

“Xin came on a last minute request and really helped us out! Gave meds to my dogs who were recovering from kennel cough and they really loved her. Thanks again!”

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Erin R.
Sitter Profile Image: Kimberly (Kaye) M.
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Kimberly (Kaye) M.
from
$75
per night
4.8 out of 5 stars
• 52 reviews
18 repeat clients
15 years of experience
Owings Mills, MD, 21117

“Kaye was incredible. She stayed at our place over the Christmas holiday while we were out of the country, and watched over our dog & my mom’s dog as she was also traveling with us. This was an unusual situation because the dogs do not ordinarily live together - Kaye was magnificent at both navigating the little tensions that arose between them, and at keeping us posted about the every-day goings on and how she was handling it. We got updates routinely, and she really went above and beyond in terms of taking care of the house while we were away. Some choice words I would attribute to Kaye: trustworthy, responsive, and thoughtful. Will definitely be hoping Kaye is available the next time we have our-of-town plans!”

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Lilly C.
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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

Maddy stayed with our pups for a long weekend and it went really well. We were able to enjoy our time knowing there was someone staying with our fur-babies.

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Grecia 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.

How to book house sitting

  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 - Winterberry

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Sitters in Winterberry average 4
repeat house sitting clients

FAQs for House Sitting - Winterberry

Frequently asked questions about Rover

As of October 2026, there are 3,074 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.

<b>Tip:</b> 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 , 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 .

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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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

  • 89% of sitters can help with special care needs
  • 93% can help with giving oral medications or injections
  • 95% 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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