House Sitting Winchester Estates
Find a loving house sitter to watch over your pets and your home.
Over 1 pet parents in Winchester Estates have booked house sitting
Winchester Estates, Find top rated house sitting
“Carmel was great! She adapted well to my dog’s needs and was very good at keeping us up to date. She took our dog on great long walks, which she loved! Would definitely book again!”
“Ryan was by far one of the best house sitters Duke and I have seen. He took the time to really get to know Duke and did everything he could to keep Duke’s routine as normal as possible. He sent lots of pictures and videos throughout the stay, and I could tell Duke was having a great time. Will definitely use Ryan for any of Duke’s needs again!”
About: I’ve taken care of dogs my entire life whether that is my own dogs at home or helping out a neighbor or friend! I would love to help your dog as well I’m currently a student at Salisbury university but I am commuting so I only have classes on Tuesday and Thursdays. I am available almost any other time besides then! I will be there for whatever your pet needs may be! I love taking care of dogs of all sizes and know what it takes to make sure they will be ok while you are gone
About: I love playing with dogs and walking them. I've grown up around all types of dogs small and large. I'm very fun and outgoing as well as criminal justice trained ensuring your pets safety. I have taken care of our families dogs as well as watching other family friends pets. I have watched animals with allergies and medication needs. Dogs of all ages are welcome. I will meet any needs of the dog/dogs and ensure to have them back to you safe worn out and happy. I work part time so most of my day is running errands or cleaning the house. If they love car rides they are more than welcome to drive around with me. I will adjust my schedule to meet the needs of the dog or animal. Also absolutely love my kitties. Open to all animal requests just ask! Im a full time optician and part time cook. With plenty of notice I will take off my parttime job to care for your babies. Your pet will be loved as family. Your pet will be able to sleep with me and get full access of my apartment. Toilet bowl lids will always be closed
“Michael was great with our dog and two cats while we were out of town. It was very clear to us that everyone was happy and well cared for. We also loved all the pics and updates. We highly recommend Michael and plan to continue using him to help take care of our crew in the future.”
About: I have taken care of dogs, cats, bearded dragons and snakes for family, friends, and strangers over several years. I am willing to take care of any animal(s), no matter the temperament or how exotic it may be. As long as there are clear instructions and direct communication, I am able to be responsible any animal(s). My primary job is with Maryland Department of Natural Resources and with certain assignments there is no rescheduling. This assignments are generally on weekends from 11:00 AM - 5:00PM. I am still able to arrive early in the morning and in the afternoon on these days, otherwise that I am available most of the week. My calendar will be up to date at the beginning of every month. I can come to your home but I cannot use my own. I am willing to send pictures of your animal(s) every minute if you miss them and need to know how they are doing.
“Patrick was great at taking care of our dogs and home. Our dogs were clearly well taken care of, and a great bonus that he takes better photos than we ever have of our dogs. Our house was cleaner when we got home than when we left it. Very grateful for him.”
About: Hi, I’m Hannah — a responsible, caring pet sitter who treats your home and pets like my own. I know how difficult it can be to leave your furry family member behind, so I’m here to give you peace of mind with loving, attentive in-home care. Whether your dog needs belly rubs, playtime, medications, or a quiet companion on the couch, I adapt to their unique needs and stick to their usual schedule. I’ll also keep your home tidy and safe so you can return to everything just how you left it (or better!). ~Staying overnight at your home ~Feeding, walks, and potty breaks on your schedule ~Playtime, snuggles, and companionship ~Administering medication (if needed) ~Daily updates with photos and notes ~Light home care (mail, plants, trash, etc.) ~Respectful, clean, and professional behavior in your space Hi! I’m Hannah, a very energetic stay-at-home mom. I can’t wait to welcome your pets into my life! I'm home full-time this summer, so your dogs or cats will get constant attention, affection, and supervision while you’re away. I'm a huge animal lover — patient, kind, and great at following routines. Whether your pet needs playtime, snuggles, walks, or quiet companionship, I'll provide a safe, loving environment that feels like home. Our animals are happiest in their environment with their familiar smells, toys, and routines. I help minimize stress and keep them comfortable while you enjoy your time away, worry-free.
About: I have 8 animals of my own, both dogs and cats. I also work part time as a Kennel Technician so I am very familiar with different animal personalities and how I’m expected to care for them! Neighbors, friends, family & clients have relied on me to care for their furry friends and I’ve loved getting to know each one. I am pet CPR & First aid Certified. I work as a nanny from 11-5 as well as dog sitting overnights frequently. I work as a nanny from 11-5 in Southampton. College is online so that won’t be a problem right now. My scheduled days can change but shifts are no longer than 6 hours at a time, Mon-Fri. I live in Sayville. I have plenty of time in the morning & afternoon for long walks and fetch! My weekends are completely free. I will take wonderful care of your pets as if they were my own. My pups love to play outside and get lots of attention so I want to share the love!! It’s always fun getting to know your dogs and cats. I have built a trusted clientele over the last 3 years of being on Rover. I am very responsible and will care for your house just as well as your pets! I know it takes a lot to entrust someone in your home so I won’t let you regret it.
“Donna did a wonderful job staying with our dog Stanley, he was calm and happy when we got back. Knowing he was in good hands made it easy to enjoy our vacation. I highly recommend her, thanks Donna!”
About: Before joining Rover I mainly provided my services through word of mouth. I have experience with providing basic medical care for dogs and cats, and training experience including potty training and easing separation anxiety. I have vast experience and knowledge on various breeds and their specific needs, and really just love being able to have the time and availability to be able to provide these services. They say a dog is a man’s best friend, but in my case, a dog has always been a woman’s best friend! I offer dog sitting, walking, training and boarding at my home as well. I am brand new to the app but I do have plenty of references and want to make all owners feel just as comfortable as I want to ensure their pets will feel with me! I currently work a part-time job from my home, so I have a flexible schedule and able to meet any needs your pet has. I am available everyday, all hours mainly, and can accommodate you and your pets schedule! In my home all pets are welcome. I have plenty of walking trails and a back yard for pets that stay at my home. I typically will customize the walks, food, bathing etc depending on the needs of the pet and what works best for them and the owner.
About: I have always been a big animal lover. I got my first dog when I turned 2 years old and did everything I could to help take care of her. I got another dog a couple of years later who became my best friend. Before I left for college he would come everywhere with me. I am now the happy and proud owner of a 6 and 12 year old cat and want to continue growing my pet family. In addition to growing up taking care of my own pets I had the responsibility of pet sitting for a lot of different families in my neighborhood. I have worked as a client service representative and now as a veterinary assistant at an animal hospital and have been able to gain knowledge and experience about pet healthcare and wellbeing beyond the general scope. I will always do my absolute best to make sure your animals are happy and healthy. I love pets of every kind and would be happy to help you take care of yours if the need ever arises! I am currently a full time employee at an animal hospital. I would be available to do drop ins before and after work and am happy to do overnight visits as long as the owner is aware I will have to leave for around 8 hours to work. Establishing trust with a pet is the most important thing you can do to ensure they are happy and healthy. I will be sure to provide individualized care for your pet depending on their needs and temperament to ensure they are as mentally and physically comfortable as possible.
“This was our first time using Rover and Lydia made it such an easy and wonderful experience for us. We came home to a clean house and very happy pups! We have issued other pet sitting services before but we’ll for sure be using Rover, and hopefully, Lydia again.”
About: I’ve taken care of many animals throughout my teen to adult years. I volunteered at a rescue taking care of mostly the cats. I’ve previously helped rescue kittens and dogs. I’ve always had animals around me. I’m a very big animal lover. I currently have 2 cats and 2 dogs and cat sit a kitten from time to time. I give the cats baths maybe once a month and the dogs weekly and I routinely walk the dogs. I watch the dogs while they’re outside while also giving them extra love. I love taking dogs on walks. I play with cats and even bring along toys that I know my cats love.
About: I’ve always been a lover of animals of any kind. I’ve been the family pet sitter for years and Never was paid for it because I just was doing it for fun. Pet care seamlessly fits into my weekly routine, as I'm able to dedicate flexible hours to ensure your pet's needs are met. I can provide regular walks, playtime, and cuddles, while also accommodating medication schedules and special dietary needs. My schedule allows for regular check-ins and updates, giving you peace of mind while you're away. I provide personalized care for pets in both my home and clients' homes, tailoring my services to meet each pet's unique needs. In my home, pets enjoy the space and environment with comfortable spaces for rest and play. In clients' homes, I respect their space and routines, administering medication, feeding, and providing exercise and playtime as needed. I also keep owners informed with regular updates and photos, ensuring their pet's comfort and happiness.
The median cost per night for house sitting in Winchester Estates is $50
Pet parents share their Rover experiences - Winchester Estates
Carmel did great, she showed up on time, walked them, fed them and kept them company while we were at an event nearby, she also had some flexibility on the end time when I underestimated how long it would take to wrap things up. I Would highly recommend her to anyone looking in her area.
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 - Winchester Estates
Select a filter and find qualifying sitters offering house sitting.Sitters in Winchester Estates average 4 repeat house sitting clients
FAQs for House Sitting - Winchester Estates
Frequently asked questions about Rover
As of November 2026, there are 1,406 sitters on Rover offering House Sitting across Winchester Estates. 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 Winchester Estates 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 Winchester Estates 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 Winchester Estates 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 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 Meet & Greet.
sitters on Rover set their own cancellation policy, 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 Winchester Estates. 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.
Connect anywhere with the Rover app
