House Sitting Winfield Woods

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

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Over 3
pet parents in Winfield Woods have booked house sitting

Winfield Woods, 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: Sarah L.
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Sarah L.
from
$38
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
5 years of experience
Eldersburg, MD, 21784

“Sarah was easy to work with to set up our booking. She communicated clearly and was quick to respond. Our 2 dogs were well taken care of and we came home to a clean house. I would absolutely book with Sarah again.”

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Leilani R.
Sitter Profile Image: Maxwell N.
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Maxwell N.
from
$40
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
7 years of experience
Westminster, MD, 21157

“Max saved us after multiple other sitters ghosted or even stood me up for a meet and greet! He did fantastic with our dog. He was immediate comfortable with him. He left our house spotless and is overall a great communicator. Highly recommend!”

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Judith J.
Sitter Profile Image: Casey G.
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Casey G.
from
$35
per night
5.0 out of 5 stars
• 2 reviews
6 years of experience
Eldersburg, MD, 21157

“Casey did a great job taking care of our pups! She sent pics and they were very well taken care of and happy. We have her booked again for next month, so I’m sure our girls are looking forward to her staying with them again.”

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Michelle H.
Sitter Profile Image: Sofia A.
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Sofia A.
from
$65
per night
4.5 out of 5 stars
• 8 reviews
1 repeat client
8 years of experience
mount airy, MD, 21771

“Sofia was wonderful! She took great care of our dog!”

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Beth L.
Sitter Profile Image: Hannah W.
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Hannah W.
from
$50
per night
5.0 out of 5 stars
• 6 reviews
1 repeat client
7 years of experience
Gaithersburg, MD, 20882

“Hannah was amazing! We’ve had issues with sitters in the past so she went above and beyond to put us at ease while away! Came home to a clean house with happy pups!”

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Kaylin S.
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: 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: Leah U.
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Leah U.
from
$20
per night
3 years of experience
New Windsor, MD, 21776

About: I have been pet sitting for 3 years and love all animals! I have a perfect setup for animal care, including a walking trail behind my house. I’m home during the week-I have 2 middle school aged boys that are in school and my husband works long hours. I am able to get up early for morning walks or feedings. I have a fenced in yard, with stairs leading to a deck, walk out basement with kitchenette for food storage, play area, and a resting bedroom.

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 N.
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Sarah N.
from
$31
per night
35 years of experience
Sykesville, MD, 21784

About: Hi! I’m a lifelong animal lover with hands-on experience caring for both cats and dogs of all sizes, including my two cats and my 80 lb English yellow lab. Animals have always been a huge part of my life, and I genuinely love getting to know each pet’s unique personality, needs, and routines. I’m patient, attentive, and dependable, and I like to think I have a special connection with animals and an instinct for understanding what makes them feel comfortable, safe, and happy. Whether your pet loves playtime, long walks, cuddles, or simply calm companionship, I’ll make sure they feel cared for and loved while you’re away. I’m available for dog walks and drop-in visits for cats and dogs, and I treat every pet like family! Lastly, I am also comfortable giving pets medications as my dog Gigi has allergies and takes some medication and supplements. Also I have had to give medicines for multiple cats over the years including inhaler treatments. Currently my elderly cat Mrs. Norris is 17 and living with cancer. She is taking a few medicines to keep her comfortable before it’s time. We have lots of snuggles on her heated blanket, look out the window and bask in the sun. I understand the extra care and love your older animal needs. I look forward to getting know your fur babies!! You could say: Pet care fits naturally into my daily routine because I am currently home while my children are out of school. I genuinely enjoy caring for animals and have the time and flexibility to provide consistent attention, exercise, feeding, companionship, and general care throughout the day. Caring for pets complements my lifestyle and is something I find both rewarding and fulfilling. I care for pets by following their regular routine, including feeding, providing fresh water, exercise, potty breaks, playtime, and lots of attention. I make sure pets feel safe, comfortable, and loved while in my care. When caring for pets in a client’s home, I follow all instructions provided, keep the home tidy, and provide updates so owners know their pets are doing well. I am dependable, attentive, and genuinely enjoy spending time with animals.

Sitter Profile Image: Cassidy B.
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Cassidy B.
from
$100
per night
5.0 out of 5 stars
• 12 reviews
4 repeat clients
10 years of experience
Sykesville, MD, 21784

About: I’ve had hands on experience caring for pets for many years and currently help take care of my 15 year old senior dog, Charlie. Being an online college student gives me a very flexible schedule, so I’m able to spend plenty of quality time with the pets I care for. I’m especially comfortable with senior dogs and understand the patience and extra attention they may need, but I also enjoy caring for younger, more energetic dogs. I always treat pets like they’re my own and make sure they feel safe, comfortable, and loved while you’re away! 🐾💕 I’m an online college student, so my schedule is super flexible. I’m home a lot and love structuring my days around the pets I’m caring for, whether that’s walks, playtime, feeding, or just hanging out and giving them attention. Making pets feel comfortable, happy, and cared for is something I really enjoy! 💗 I love caring for pets right in their own homes where they feel safe and comfy. I treat every pet like family, giving them lots of love, attention, and gentle care. Keeping your pet happy and relaxed is my top priority!

Sitter Profile Image: Stephanie D.
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Stephanie D.
from
$60
per night
40 years of experience
Woodbine, MD, 21797

About: Hi there! I’ve had cats throughout childhood and through most of my adult life, so caring for animals has always been something I've loved. I’ve also helped out friends and neighbors by pet sitting for their cats and dogs. I've given medication and supplements to my own cats. I’m active and love being outdoors — walking, running, or hiking with a dog sounds like the perfect day to me! Several years ago, I actually had a Rover sitter care for my cat Baby when she was sick. She was very reliable — she kept me updated, showed so much compassion, and gave me total peace of mind. That experience really stuck with me and I aspire to be that same trusted, reliable sitter for others. My own fur babies have since crossed the rainbow bridge, so I don’t currently have pets at home — which means my schedule is flexible and I can give your fur babies my full attention. I’d love to meet your furry family members and make sure they feel safe, loved, and cared for while you’re away. ❤️ I ran my own business for 10 years and am taking some time off right now, so my schedule is flexible. I focus on overnight pet sitting, which means I can stay with your fur babies to keep them company, follow their normal routine, and make sure they feel safe and cared for while you’re away. Keeping your fur babies safe is my top priority. I like to have a list of care instructions so I know exactly what they need, and I always ask for your vet’s contact info just in case. I’ll keep you updated and reach out right away if anything comes up. Since I do overnight stays in your home, I make sure to keep things comfortable and familiar for your fur babies so they feel safe and relaxed while you’re away. Overnight Care Guidelines To ensure a comfortable and successful stay for everyone: • Companion animals sleep in their own beds (I don’t share my bed). • Indoor cameras are turned off during my stay. • Homes are reasonably clean & tidy, and free of strong odors. • Clean linens are provided for my use. • A meet-and-greet is required prior to confirming a booking.

Sitter Profile Image: Kemberlei S.
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Kemberlei S.
from
$100
per night
5.0 out of 5 stars
• 5 reviews
20 years of experience
Mt. Airy, MD, 21771

About: I have a strong passion for animal care, with experience working with a wide variety of pets, including puppies, senior dogs, and animals with special needs. What sets me apart from other sitters is my ability to customize care based on the unique needs of each pet. I’m skilled in basic puppy training, such as potty training and socialization, and have a keen understanding of how to support senior pets with mobility issues, dietary restrictions, and more. I also provide extra attention to pets that may be nervous or have anxiety, ensuring they feel comfortable and safe in my care. I take pride in treating each pet like family, ensuring they receive both the mental stimulation and physical care they need. I am currently working part time so I have plenty of time to care for pets of all kinds. I also have 2 children that love animals. In providing pet care, whether in my own home or a client’s, safety is always a top priority. I ensure pets are in secure environments by pet-proofing spaces, using non-toxic products, and closely supervising their activities to prevent accidents. Trust is fundamental in my relationship with both the pets and their owners; I take the time to understand the specific needs of each pet, maintain open communication, and follow through with the agreed-upon care routine. Creating a comfortable environment is equally important — I ensure pets feel at ease by maintaining familiar routines, providing cozy spaces, and offering plenty of stimulation and love. By focusing on safety, trust, and a pet-friendly environment, I ensure each pet receives the best care possible, tailored to their unique needs.

Sitter Profile Image: Yeji S.
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Yeji S.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 23 reviews
10 repeat clients
18 years of experience
Catonsville, MD, 21228

“Watched my cat Lucy and she was well-cared for. Also, this was a bit of a last-minute booking, so I’m grateful for the quick response and good care on short notice”

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Hillary H.
Sitter Profile Image: Laurel G.
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Laurel G.
from
$32
per night
5.0 out of 5 stars
• 2 reviews
1 repeat client
25 years of experience
Westminster, MD, 21157

About: With over 25 years of experience raising my own dogs and providing trusted house-and-pet sitting for friends and family, I offer a lifetime of dedicated care. I am a passionate advocate for the human-animal bond; my own dog is a certified therapy dog, and together we volunteer at hospitals, nursing homes, hospice facilities, and schools. I treat every dog I watch with the same compassion and attention I give my own. Because I work during the day, I am primarily available for evening and weekend care, making me an ideal fit for owners who need a reliable presence while they are away or working late. Your pets will receive expert care in a loving, safe environment. Because I work during the day, I am primarily available for evening and weekend care, making me an ideal fit for owners who need a reliable presence while they are away or working late. I will treat your pets and your home with respect and care. Your animals and your home are safe with me! I am considerate and very responsible.

Sitter Profile Image: Nicole L.
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Nicole L.
from
$70
per night
5.0 out of 5 stars
• 127 reviews
36 repeat clients
14 years of experience
Damascus, MD, 20872

“Another great house sitting for our pets by Nicole. Whenever we leave them with her, we know they will be well taken cared of. She also went the extra mile by shoveling our walkway and driveway during the winter storm. You won’t regret choosing Nicole for your pet sitting needs.”

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Janelle S.
Sitter Profile Image: Rachel W.
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Rachel W.
from
$50
per night
40 years of experience
Mount Airy, MD, 21771

About: I was an obedience instructor in high school, and took my Sheltie, Mistie, to earn our CD at dog shows. I’ve had dogs my entire life, and feel like I trust them more than people. I’ve never met a dog I was afraid of - bring on your “terrifying” pittie, we’ll be besties within an hour. I’m also great with the teeny, tiny dogs - I’m calm and soothing which puts them at ease. I work part time in Baltimore, so I am available most of the time! I love going on walks and exploring. I also love cuddles on the couch, as well as a fast-paced game of fetch! I will obsessively keep your baby in a leash when we are outside, and well as keep him/her away from other dogs, while out-and-about.

Sitter Profile Image: Camila M.
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Camila M.
from
$48
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
3 years of experience
Reisterstown, MD, 21136

“Camila is excellent! She is punctual, professional and took such great care of our dogs Nala and Kota. I HIGHLY recommend. We will definitely be using her in the future.”

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Wendy J.
Sitter Profile Image: Christina B.
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Christina B.
from
$65
per night
5.0 out of 5 stars
• 3 reviews
4 years of experience
Reisterstown, MD, 21136

About: Hello, I’ve worked closely with dogs during my time in the Military. From big to small, there’s nothing I can’t handle. I can assure you, you’re furry friend is in great hands with me. I also look after cats and some reptiles I am available 7 days a week, if there are any requests I can make accommodations as well. I’m available 24hrs for all questions or concerns I have crates available in my home for boarding and am awesome dog park available for your fur baby to run and play in as well

Sitter Profile Image: Nadia L.
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Nadia L.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
1 repeat client
12 years of experience
Mount Airy, MD, 21771

“Nadia stayed at our house with our dogs and was great! Super easy to communicate with and our dogs loved her. Would highly recommend using her for pet sitting!”

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Lauren A.
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The median cost per night for house sitting in Winfield Woods is $50

Pet parents share their Rover experiences - Winfield Woods

1 / 1
5.0 out of 5 stars

We recently had Hailey stay with our 2 older labs (one is blind and requires insulin), 2 cats and a gecko while we were away on vacation for a week. Hailey was wonderful! She kept us updated along with photos of our pups and handled medications and feedings schedules with ease. This was honestly the first time we didn’t worry while on vacation. When we arrived home, our pups and cats were happy and the house was as clean and tidy as it was when we left. I highly recommend Hailey. She is professional, honest, respectful, reliable and very sweet. Thank you Hailey!

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Jennifer G.
House Sitting
5.0 out of 5 stars

Navetta was wonderful taking care of our for babies! She was easygoing and very communicative. We got daily updates, pictures, and videos.

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Jennifer W.
House Sitting
5.0 out of 5 stars

Hailey recently watched our three dogs and two cats while we were out of town. She took such good care of them and was in constant contact with us, going above and beyond to care for our physically disabled cat. I truly felt like she cared for our animals as if they were her own. Knowing that she could handle everything, we were able to relax completely on our vacation. We always felt connected and knew our pets were safe and happy. If you are looking for a pet sitter who is reliable, responsible, and genuinely compassionate—especially if you have a multi-pet household or pets with special needs—I cannot recommend Hailey highly enough!

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Judy W.
House Sitting
5.0 out of 5 stars

I was very pleased with Haley taking care of Hershey. When I got home, he didn’t seem to be stressed out at all. I will definitely use her again.

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Tom E.
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?

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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.

How to book house sitting

  1. 1. Search

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  2. 2. Meet In Person

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Popular requests for house sitting - Winfield Woods

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Sitters in Winfield Woods average 4
repeat house sitting clients

FAQs for House Sitting - Winfield Woods

Frequently asked questions about Rover

As of October 2026, there are 7,457 sitters on Rover offering House Sitting across Winfield Woods. 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 Winfield Woods 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 Winfield Woods 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 Winfield Woods 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 Winfield Woods. On Rover:

  • 86% of sitters can help with special care needs
  • 91% can help with giving oral medications or injections
  • 94% 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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