House Sitting Winfield Woods
Find a loving house sitter to watch over your pets and your home.
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.
“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.”
“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!”
“Absolutely fantastic experience with Katharine! She took great care of my dogs and handled giving medicine expertly, and was perfectly comfortable taking care of a giant breed dog. She also sent us pictures periodically of the dogs while she was caring for them which was so nice! Would recommend to everyone!”
“Hannah is WONDERFUL! It is quite obvious that Atticus was loved and well cared for. The house was immaculate upon our return. We will definitely ask for her again the next time we need a dog sitter!”
“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.”
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.
“Kayla is amazing! She took such good care of Bealey! She was flexible and worked with me too since I had a change in travel plans! I appreciate her so much and will definitely ask for her in the future!”
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.
“Ember was absolutely fantastic with our Husky. She played with him, went out of her way to make him frozen Kings, and even BRUSHED him which is a whole chore for husky owners? She made us feel at ease while we were away and helped around the house while we were gone - took out the trash on trash day, gathered/sorted our mail, and went above and beyond washing towels and sheets. We were very appreciative of Ember and will book again!”
“Angela was the perfect sitter for our dog, Kima! Angela took the time to get to know Kima prior to our trip. Our dog is anxious in meeting new people but Angela’s easy, gentle manner won her over. Throughout our trip, Angela sent photos and videos of her and Kima getting along and having fun! I highly recommend Angela as a pet sitter. We will definitely have her take care of Kima again!”
“I cannot say enough great things about Bronte! When my cat got sick at the start of her stay, Bronte went above and beyond to care for her and ease my anxiety. She was highly responsive and sent daily updates, giving me total peace of mind. My cat can be wary of strangers, but she was quickly enamored with Bronte—purring and cuddling in bed in no time. Bronte is truly fantastic at what she does!”
“Nicole was amazing with our pets again! We haven’t traveled in some time, so one of our nervous/anxious dogs “forgot” her, but Nicole was very patient and took her time re-introducing herself to our dog. It wasn’t long before our dog remembered and trusted her again. Overall great experience once again!”
“Camryn was so wonderful to work with and took excellent care of our dog. She was an excellent communicator, sent lots of pics and left our home in tip top shape. I've already recommended her to friends and will definitely use her again!”
“Christa is very easy to work with and helped us feel reassured about the dog and house being looked after. Her son, Elias, clearly became a preferred playmate of our dog & will be missed (!). Thank you to both Christa & Elias. We will hope she is available yo use her again”
About: I've taken care of many different dogs, I am comfortable with all breeds and ages. Ive had experience with every energetic puppies, as well as low energy older dogs, small dogs that are all over the place and loud ones. I've lived in a household with pets basically my while life, aside from dogs I have experience with cats, lizards, small animals (specifically rats and hamsters), and parrots. I am very passionate with them all, love spending time with them. My house and neighborhood is great and safe for walking pets, not many cars come through and there are not that many dogs around, so accidents would not happen. And my house is large with a lot of large empty spaces so the dog wouldnt have a chance to be destructive. Most of the time I would be available, I spend most of my time at home, and I do college online. Occasionally I might leave for a day, and in October I'm going on a trip 5-17. My house is very pet friendly, I currently have rats but they have their own room to which I usually keep the door closed. A large part of the house has a lot of empty spaces and the main living room currently doesn't have much furniture, but still a lot of space to run around. It does have stairs. Our neighborhood is a great place to walk around, not that many cars or people walk around, so there would be no accidents. Unfortunately my back/front yard is not fenced, so the dog would need to stay on a leash. I will also listen and follow all the instructions provided by you in your home, I respect other people's spaces and privacy.
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.
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
The median cost per night for house sitting in Winfield Woods is $50
Pet parents share their Rover experiences - Winfield Woods
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!
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!
Book with peace of mind
- 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
Book and pay through Rover’s secured platform—no cash or checks required.
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. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for house sitting - Winfield Woods
Select a filter and find qualifying sitters offering house sitting.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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