House Sitting Windsor
Find a loving house sitter to watch over your pets and your home.
Windsor, 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.
“Kelly was great! Maggie loved her right away. She was punctual and friendly. She followed my instructions for feeding times, etc. Sent pictures of Maggie during the day, which we appreciated. I will use her again if she is available.”
“Robert spent a weekend caring for our fur babies. We had a meet and greet prior to his stay and he did a thorough assessment of our animals needs to make sure he provided top notch care. Over the weekend he sent pictures and updates. I knew my fur babies were well-taken care of.”
About: I have always lived with cats and dogs. The longest I have house sat for someone was 30 days when I watched their 2 large dogs and 1 small dog, which included me living at the home, letting them out multiple times a day, feeding breakfast and dinner, playtime, and snuggle time. I helped my grandma’s dog lose 10 lbs by jogging/walking and playing. I also have experience with rabbits, reptiles, fish, and birds. I’m open to working with senior pets who may need special treatment and care. I have a special place in my heart for animals who need extra attention. I am working full time 9 am - 5 pm Mon - Fri in Hampton, VA. I live in Smithfield. I have my own transportation. At the moment, I am offering to feed breakfast and dinner with potty breaks. If you need more frequent trips, house watching, or overnight stay, please message me and we can discuss it.
About: I have taken care and grown up with animals my whole entire life. I love and appreciate all animals, I have taken care of almost every single animal of all ages shapes, and sizes! I am currently available at all times and I do look forward to playing and exercising experiences with all of your furry friends. Plus taking care of all personal wants and needs, accommodations and everything else in between! I have a fenced in yard and I can also crate if need be but prefer to keep ur precious pup very active and entertained at all times!
“I would be so hesitant to leave our dogs with anyone but Kelsey. This is the third time we've booked him for in home sitting and each time we come home, the pups are healthy and happy. This trip especially was important to us because it was our wedding and honeymoon. We wouldn't have been able to enjoy either without someone we trusted and appreciated as much as him.”
“Kim has been amazing throughout my time away from my dogs. Kept them on their schedule, made adjustments when my travel plans unfortunately got changed. I will definitely be rebooking with her in the future.”
“Sara was a great house and dog sitter. She took special care and interest of each dog and was happy to follow all of our requests. She communicated well and I could tell she genuinely enjoyed spending time with our boys.”
“Ginny did a great job!!! My dogs were well loved and had excellent care. Ginny administered medicine for my pet's while she took care of them. She spent two full days with them. She even emptied my dishwasher. Ginny truly loves animals and my pets were so happy to see her. She played with them in the yard. Ginny sent me a text each day to let me know how they were doing. We were very satisfied with Ginny. She will be the first person we call when we need a sitter again.”
About: Hello! I’ve owned 3 dogs, one small and two medium, my last border collie was the only one I trained since the other two behaved so well, I taught him a lot of “patience” tricks for him to be comfortable not being around me since he had separation anxiety, I also taught him different tricks and did different exercises from day to day since well he is a border collie haha. Other than that I’ll follow your list of demands and pet needs while you’re away, don’t worry your baby is in good hands!! I am currently in the military, so my schedule is not flexible. I’ll be completely off on the weekends but on weekdays I’ll be free after 4pm some days possible 3pm. I cannot do Thursdays unfortunately that’s my busiest day of the week. If you need overnight pet sitting I don’t mind at all just let me know! I cannot take any pets “home” because i currently live in the barracks and I won’t be able to give the needed support for your furry friend.
“We had a wonderful experience with Elasa and Stephen! They took excellent care of both our dogs and cats, including administering medications without any issues. We really appreciated the daily updates, which gave us peace of mind while we were away. We were delayed coming home and they came back to check on the dogs. We came home to a clean house and, most importantly, very happy and well-cared-for pets. Highly recommend!”
About: My family has tradition of owning pugs and now I own my own pet. I've always been around animals from in my own home to looking after my friends pets. I have taken care of labs, poodles and collies to name a few breeds I have dog sat for. I have the patience, friendliness and responsibility to take care of any breed, age, gender and size. I look forward to making new canine friends and believe it will be mutual.
About: I’ve been caring for pets for over 10 years and have plenty of hands-on experience with dogs and cats. I have a dog of my own and also regularly help care for cats, so I’m comfortable with different personalities and routines. I have experience with feeding, walking, playtime, basic grooming, litter box care, and giving pets lots of love and attention. I’m patient, attentive, dependable, and always follow any special instructions you provide. As a healthcare professional, I’m also very detail-oriented and take safety and routines seriously. I’ll treat your pets with the same love and care I give my own! Pet care fits well into my weekly routine, and I’m happy to make time for walks, drop-ins, playtime, feeding, and companionship. My availability varies depending on my work schedule, but I keep my Rover calendar updated so pet parents always know when I’m available. I take your pet’s safety and comfort seriously and will always follow the routine and instructions you provide. I’m attentive to feeding schedules, walks, medications or special care instructions, and keeping pets secure in their environment. I also make sure they get plenty of attention, affection, and playtime while you’re away. I’ll keep you updated so you can feel comfortable knowing your pet is being well cared for.
About: My name is Alannah and I am 20 years old. I love animals, I have experience pet sitting, I worked in a kennel and have helped deliver several litters of labs, I have had animals in my household since I was born, and I would love to help you keep your pets happy and cared for whenever you might need the extra help. I am in the military but work a shortened schedule, and I cannot have an animal of my own since I could go on deployments last minute. I love animals, dogs the most, and I would love so much to come take care of any pets and just lend some help. I currently work part time hours so I have plenty of time to care for animals. My average hours are 8-12 am. I have volunteered at some shelters to care for some cats and dogs, and I am actually considering fostering. I just love pets but am not in a stable enough environment to keep one with being in the military and I could have to leave for months on end with no notice. I am very respectful, will follow any and all restrictions / directions, and I have great decision making. I will know what to do to keep your pet safe and happy. Any sort of extra care I have no issue providing I am very attentive and very respectful of not only your wishes but also your space if you invite me to your home. I am eager and excited to help as needed.
About: I’ve had dogs my entire life and genuinely love caring for them. To me, every dog deserves patience, kindness, and plenty of attention. Whether your pup loves long walks, playtime, or simply relaxing with good company, I’ll make sure they feel safe, comfortable, and loved while you’re away. I understand that every dog has a unique personality and routine, so I’ll follow your care instructions carefully—from feeding schedules and medications to favorite toys and walking habits. My goal is to treat your dog like a member of my own family, giving you peace of mind knowing they’re in caring, reliable hands. Please note, we board on family at a time, we do not cage the dogs. Pet care fits seamlessly into my daily routine because I work from home, and my wife is home full-time. This means your pet will receive plenty of attention, companionship, and supervision throughout the day rather than being left alone for long periods. We have a clean, safe, and pet-friendly home where dogs can feel comfortable and relaxed. Whether it’s regular walks, playtime, feeding, or simply providing affection and companionship, we’re committed to making every pet feel like part of the family while they’re in our care. I care for every pet as if they were my own. I follow each owner’s instructions carefully, including feeding schedules, exercise routines, medications, and any special needs or preferences. I make sure pets receive plenty of attention, affection, playtime, and regular potty breaks while maintaining their normal routine as much as possible. In my home, pets stay in a clean, safe, and comfortable environment where they are supervised throughout the day. Since I work from home and my wife is home full-time, your pet will have lots of companionship and won’t be left alone for extended periods. When caring for pets in a client’s home, I respect both the pet’s routine and the owner’s home. I provide reliable, attentive care, keep the space tidy, and send regular updates and photos so you can have peace of mind while you’re away.
About: I’ve dog sat for family, friends, and clients that resided in Philadelphia, New Jersey, and Virginia. My clients have relied on me to check on, walk, and feed their little family members. I have a little bundle of joy named Mochi. Taking care of him is my favorite thing to do. He makes me realize that I have what it takes to care for pets of all different backgrounds. :) I’m currently working transitioning into a new job and looking to use all my free time to take care of your little family member!❤️🐱🐶 🏡 Trust, Safety & A Comfortable Environment 🐾 Your pet’s safety and comfort are my top priorities! Whether your pet stays in my home or I come to yours, I’ll provide a clean, calm, and caring environment where they can feel comfortable and secure. I’ll follow your instructions closely, respect your home and routines, and make sure your pet receives plenty of attention, supervision, and care. You can have peace of mind knowing your furry family member is in a safe and loving environment while you’re away. ❤️🐶🐱
About: I am a dog lover and I’m comfortable with all breeds. I had multiple pets including a dog and cat that I took care of growing up. I currently have no pets but have recently taken care of friends’ dogs. This has included overnight and daytime boarding at my house while taking care of all walking, playing, and feeding needs. I’m currently working PRN (part time) as a physical therapist and I have a lot of flexibility and freedom in my schedule. I’m looking to fill some of this free time with something that I’ve always enjoyed, taking care of pets. I am trustworthy, clean, and respectful of others homes when entering to care for their pets. I am happy to walk your dog wherever they normally like to go around your home.
The median cost per night for house sitting in Windsor is $45
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 - Windsor
Select a filter and find qualifying sitters offering house sitting.Sitters in Windsor average 4 repeat house sitting clients
FAQs for House Sitting - Windsor
Frequently asked questions about Rover
As of November 2026, there are 1,290 sitters on Rover offering House Sitting across Windsor. 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 Windsor 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 Windsor 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 Windsor 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 Windsor. On Rover:
- 88% of sitters can help with special care needs
- 94% 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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