House Sitting Winston Terrace
Find a loving house sitter to watch over your pets and your home.
Over 90 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.
“Christina took great care of our two dogs and cats while we were traveling. This was our first time using a pet sitter and she helped us be at ease! We got lots of pics and updates which were so welcomed!”
“Lauren was great - arranging the visit was super easy (although the app isn’t all that great) Lauren’s service was!! She spent the entire day with our three dachshunds while we were at Busch Gardens. She sent a few updates and pics through out the day and we didn’t have to worry about them at all. Peace of mind allowed us to relax and enjoy our time together. Thank you Lauren. We will definitely call on you again our next visit!!”
“We just got back from a 2 week trip from Italy. Our home and our pets were very well taken care of. We have used Craig several times and have always been 100% happy with the care he provides.”
“I can't believe I neglected to write this review for so long! Likely because I returned home and was so comfortable and knew the dogs were safe and sound thanks to Deborah's”
About: I have been looking after my neighbors' animals and my own for years, so I have a lot of experience when it comes to pets. I love dogs of any shape and size, and having bigger dogs myself has taught me how to handle them. I have a pretty good grasp on dogs and their behavior due to having an interest in them since I was little. I am happy to do just about anything, whether that be feeding, walking, playing with, or just hanging out with your dog. I am quick to learn how to do things as well, so if they have special requirements, I am happy to learn! I work part-time and am looking for something to supplement my time over the summer, as hours are hard to come by right now. My schedule is very flexible, as I don't get up to much. I can be there as early or as late as you need, though I am more of an afternoon-night person. I am happy to do whatever is necessary to keep your pet safe and comfortable. If they need to be put in a crate or kept in a specific room of the house, I can handle that! I also have experience with keeping pets from darting out the door on my way in and out, so no worries about escapees!
“Lauren sent pictures and kept us posted on our pets well being. They all seemed very happy. She was flexible as we returned early but we made sure she was compensated for the entire booking.”
“Julie was great! She came over twice to see Lola before her stay,and was very flexible about Lola’s schedule. Additionally, her home is great and the huge backyard is totally fenced. Our home was kept clean and we got photos of Lola showing how comfortable she was! Since she is a Great Dane, finding someone who is open to staying at our house or having Lola at hers is great 😊”
“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. 😊”
About: I have cared for many pets and homes over the years, the vast majority being repeat clients. I prefer to stay in-home with the pets to reduce their anxiety, provide a sense of normalcy, and retain stability in their owners’ absence. I have booked by word of mouth for over 25 years; this will be my first Rover experience. I am available for your pets the majority of the day, and will be able to work around their set schedules as needed. Very flexible! I strive to provide the care you seek for your four-legged loved ones. Feeding schedules, walking schedules, playtime, and care for your home are all vital factors taken into consideration when considering if this is a mutual match.
About: Ever sense I was a kid I've loved taking care of any animal under the sun, and I still do. When I got my first dog I was so excited and loved him no matter what. I am currently not working so I have all the time in the world for your pets. I am avaliable on weekdays at anytime and will give your pets the attention they want. I can give all of my attention to your pets and make them feel happy and excited or the opposite where both of us can relax and enjoy eachothers company.
“We will request Quinn again. She was very loving to our dog and thoughtful in her communications and care of our home. She even shoveled and salted our driveway for our return home during a snow storm - going way beyond our expectations. Our anxious dog is happy and secure after Quinn’s 14 days of care.”
About: I’ve taken care of all kinds of animals since I was 12. I’ve worked on a farm caring for horses since I was a child. I’ve watched dogs, cats, rabbits, and fish for friends and neighbors. No animal is too small or large for me to love! I rescued my own dog three years ago and now have experience in R+ (positive reinforcement) training. I’d love to practice loose leash walking with your dog. I love taking my dog for long walks and hikes, if your dog likes company I’d love to take them together! I’m experienced in administering medicines, caring for puppies, and senior dogs. I work full time so I’m mostly available on weekends and weekday evenings. I have a car and can get myself anywhere in the Williamsburg area pretty easily. I’ll always do my best to make sure your pet is well taken care of. I understand dog’s body language, and am meticulous in making sure your pets needs are met.
“Carissa is awesome with my girl, Nyla!! She took such good care of her while I was gone. I was so worried about Nyla but Carissa reassured me that she was in good hands! Carissa also took such good care of my house like it was her own, which gave me such piece of mind while I was gone! I would highly recommend Carissa for anyone who is looking for a responsible, caring person to watch their house and/or dog while they’re gone!”
“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 both cats and dogs of all ages and really love spending time with animals. As someone who has frequently had walkers for my own dog I understand how important it is to know your pet is being watched by someone who can give them ample exercise and show them lots of love when owners are away. I'd love to be the one to give it to them! I'm good with dogs of any level of energy and size and love to play! I'm a hiker and would be happy to take your pet along with me if they need extra exercise! I have an energetic 7 year old pup who gets along with every dog he meets! I can't wait to get to take care of you pet!
About: I have experience rescuing cats and dogs and administering medication. I’ve also done house sitting and pet sitting for several homes. I enjoy running and playing with dogs to keep them active and happy, and I can also help them stay calm when needed. I offer walks up to 1 hour and can safely handle up to 3 dogs at a time. I’m comfortable cleaning up after pets, changing diapers if needed, and giving medication. I work Mondays and Wednesday–Friday from 7 to 3, and Saturdays from 3 to 11pm. I’m free all day on Tuesdays and Sundays 😊 I adapt to each home and follow the owner’s preferences and routine for their pets. I make sure they feel comfortable, safe, and cared for, whether that includes walks, playtime, feeding, medication, or keeping their space clean. I always adjust to each pet’s personality and needs.
“Jenny was just great! She left the house spotless, which I appreciate. But even more, I appreciate how much I know Chico enjoyed having her company and watchful eye. I'd highly recommend Jenny to anyone looking for a pet sitter or pet/house sitter.”
The median cost per night for house sitting in Winston Terrace is $45
Pet parents share their Rover experiences - Winston Terrace
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.
Lauren was great - arranging the visit was super easy (although the app isn’t all that great) Lauren’s service was!! She spent the entire day with our three dachshunds while we were at Busch Gardens. She sent a few updates and pics through out the day and we didn’t have to worry about them at all. Peace of mind allowed us to relax and enjoy our time together. Thank you Lauren. We will definitely call on you again our next visit!!
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
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winston Terrace sitters!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 July 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 July 2026, there are 558 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:
- 93% of sitters can help with special care needs
- 98% 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.
Connect anywhere with the Rover app
