House Sitting Winston Terrace
Find a loving house sitter to watch over your pets and your home.
Over 80 pet parents in Winston Terrace have booked house sitting
Winston Terrace, 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.
“Lauren is by far the best pet sitter for my Willow. I must say when she sent me pictures of my baby, I can see she was happy. Lauren you have a permanent client here. Thank you for loving my baby girl while I was away.”
“Craig was wonderful with our dog and cat while we were away, including giving them much-needed meds and rolling with their many quirks. He checked in daily, sent lots of pics, and left the house spotless. We look forward to working with him again!”
“Ayanna is fantastic!!! Our pups and kitty loved her, and were well cared for while we were away!!! She is friendly, professional, and attentive!!! We would hire her again in a heartbeat!!!”
About: I’ve been caring for animals for as long as I can remember! My experience includes dogs, cats, rabbits, guinea pigs, frogs, and plenty of other furry, feathery, and scaly friends. I’m comfortable with animals of all different personalities and love getting to know what makes each pet feel safe, happy, and at home. I’m also an Eagle Scout, where I earned merit badges in Dog Care and other areas that taught me responsibility, preparedness, and how to care for others. I bring that same patience and attention to every pet I look after. Most importantly, I genuinely love animals. I have the patience of an older sibling (lol), the responsibility of a Scout, and the enthusiasm of someone who will absolutely be excited to meet your pet. Whether your animal wants a long walk, a playmate, some quiet company, or just someone to make sure they’re safe and cared for, I’m happy to be that person! I’m currently a full-time student at William & Mary, so my availability is primarily in the mornings, evenings, and late nights, as well as throughout the weekends. I’ll work with you to find a schedule that fits both your pet’s routine and my class schedule, and I’m happy to plan ahead to make sure your pet gets the care and attention they need! Every pet has their own personality, routine, and needs, so I like to follow your lead! Before a stay or visit, I’ll make sure I understand your pet’s feeding schedule, walks, medications, favorite activities, and any house rules. In your home, I’ll keep your pet’s routine as normal as possible while giving them plenty of attention, playtime, and companionship. I’ll also treat your home with the same care and respect I would want for my own. My goal is for your pet to feel safe, comfortable, and loved while you’re away, and for you to have peace of mind knowing they’re in good hands.
“Kelly looked after my two cats for 1.5 weeks while I was gone. Both cats recently developed medical conditions that require medication and monitoring, so I was nervous to leave them. Kelly did an outstanding job with everything and was totally on top of their feeding and medication schedules. It was such a reassurance to have her stay, and she was very responsive with updates and photos. I would absolutely book her again!”
“Nicole is great! She has stayed over to watch our house and cat twice now while we were away. She's prompt and takes good care of everything. We've already hired her again for our next weekend getaway.”
“I have a problem eater 15 year old Yorkie. Matthew worked patiently with my little guy, coaxing him to eat. This was also the first time my Yorkie had been without me in all his life and he was very upset at first. Matthew worked to calm him down and ultimately Laddie was happy to be with his new "brother". He sent lots of pics and videos. He was great; I highly recommend this young man.”
About: I grew up taking care of dogs in my neighborhood as a kid and teenager. I have always had a big love for furr animals! I work a very flexible schedule during the week that allows me to have last minute changes or needs to take care of if need be! My wife is also home with our toddler, so dogs are almost always with company. I live in a quiet apartment complex with not a lot of traffic, but lots of walking trails and a dog park that my dog Koda enjoys!
“Peyton did a great job staying with Mabel and Roxy over the weekend. She sent regular pictures and updates. I was about to enjoy my trip because I knew my dogs were being cared for. 😊”
“Marissa did such a great job house sitting our cat while we were gone for a week. She took excellent care to follow all instructions, and left the house so clean. We are so appreciative! Would definitely recommend Marissa :)”
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 love all animals, and am very patient and energetic and would love to help you with your fur babies when you can't be there for them! I currently work full time weekdays but am available evenings and weekends! Can be a available for weekend house sitting as well. And possibly some morning drop in visits. I can walk your pooches and play with them and would love to help kittu watch as well! Looking to do this with my 12 year old daughter to teach her some responsibility!
About: I have been taking care of animals since I was a little girl. I’ve always had a strong connection with all animals. I’m comfortable with everything from medicine, walks, and even basic training! Pretty flexible to accommodate any of your needs within reason. Please feel to reach out with any questions. I have a flexible schedule and can work pet care into my day easily. I am able to plan my schedule around my clients needs and make sure pets receive constant and reliable care, attention and exercise. Im especially comfortable with drop ins, walks, and overnight care and am happy to accommodate different routines and schedules. I treat every pet and home as if they’re my own. I follow the pets normal routine as closely as possible and ensure your home is just the way you left it! I will also keep you updated daily w messages and photos if you would like!!
The median cost per night for house sitting in Winston Terrace is $45
Pet parents share their Rover experiences - Winston Terrace
Kelly looked after my two cats for 1.5 weeks while I was gone. Both cats recently developed medical conditions that require medication and monitoring, so I was nervous to leave them. Kelly did an outstanding job with everything and was totally on top of their feeding and medication schedules. It was such a reassurance to have her stay, and she was very responsive with updates and photos. I would absolutely book her again!
Derek took wonderful care of our two dogs and our cat while we were on vacation, and we couldn't be happier with the experience. It gave us so much peace of mind knowing our pets were in such caring and capable hands. He was reliable, attentive, and clearly took the time to make sure each of our pets was well cared for and comfortable. We highly recommend Derek to anyone looking for a trustworthy and compassionate pet sitter. We'll definitely be booking with him again!
Alyssa did a great job with my boys. We travelled for 2 weeks and during that time, Alyssa was communicative and did a great job at giving us a great sense of peace that our 2 dogs were well and happy. She followed all instructions well and left the house spotless. We especially appreciated her "days of travel" communication - staying on top of our departures and arrivals with an eye to providing quality care for our boys.
Quinn is a wonderful pet sitter. She gave our Bella good long walks and much attention. We felt very confident throughout our week away as Quinn was very communicative sending us daily pictures from walks and yard play. It was wonderful to be away on vacation knowing all is well with dog and home.
Zoe was wonderful! She was diligent about their care,walks, etc. I was thrilled to receive daily updates on their care and photos. It is so great to know that I can count on someone so dependable and a true dog lover to care for my furbabies when I'm gone. Will most definitely book again.
Once again Joe went above and beyond with taking care of our pets and house. He sent photos and videos multiple times a day so I never had to worry about their care. Our overly needy pup was so relaxed and content when we returned so I know she was well loved! He was also very gracious about staying longer when we had a mix up about our return time. I highly recommend Joe for all your pet care needs.
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.
Meet local sitters who will treat your pets like family
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
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Popular requests for house sitting - Winston Terrace
Select a filter and find qualifying sitters offering house sitting.Sitters in Winston Terrace average 4 repeat house sitting clients
FAQs for House Sitting - Winston Terrace
Frequently asked questions about Rover
The average cost for House Sitting in Winston Terrace on Rover is $38.85 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of August 2026, there are 553 sitters on Rover offering House Sitting across Winston Terrace. 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 Winston Terrace 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 Winston Terrace 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 Winston Terrace 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winston Terrace. On Rover:
- 92% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 100% 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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