House Sitting Winston Terrace
Find a loving house sitter to watch over your pets and your home.
Over 87 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.
“Another excellent experience with Christina! The fact that we chose Christina again speaks volumes about the confidence we have in her care. Having a pet sitter who is dependable and genuinely cares for your pet is priceless. Prada was happy and comfortable, and I appreciated the updates while we were away. We will definitely continue booking with her. ❤️🐾🐾”
“I wanted a mature and responsible sitter, especially since one of my dogs is just a baby, and Lauren was the perfect choice. She was attentive and affectionate to the doggos....and even stayed an extra hour because I messed up on the return time. Thanks so much, Lauren!”
“Craig is the BEST! He took great care of Peluche and the house as well. There was a traveling SNAFU on our end on the way home which also resulted in our inability to communicate and he was very concerned about leaving our boy. Can't say enough about how trustworthy he is.”
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.
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.
“Ayanna took great care of our two large dogs. I especially appreciated that she was available at the last minute, flexible, and communicative. Would definitely book again!”
About: I just graduated college and am now looking for ways to make cash and also have some fun! I have lived with my parents' dogs for over 10 years and cared for them, but sadly my new apartment won't allow me to get a dog of my own. I'm very active, eager to care for animals in the best way possible, and especially friendly. Dogs never cease to bring me joy, so looking after animals and walking them is a dream job. I'm willing to learn and/or follow directions and care for any special needs as best as I can. Mornings are my best time for visits but up for negotiation depending on my work schedule. In case you're wondering, that last picture I posted is a selfie with a feral pony I met on a hike, if that tells you anything about my animal interaction skills.
“Meaghan was awesome to work with. She took excellent care of my dog while I was away, from taking him to new trails to bathing him, she even bought him some treats when I didn’t have any. She kept me updated throughout each day with pictures and letting me know what they did and how he was doing. Highly recommended!”
About: Hi! I’m Jake, a second-year law student at William & Mary Law School and an avid animal lover. I grew up in a home that always had at least three dogs, along with cats, so caring for animals has been a part of my life for as long as I can remember. Being around pets has always brought me so much joy, and I truly miss having them around every day. Since my roommates aren’t looking to have pets right now, Rover is the perfect way for me to spend time with amazing dogs and cats while helping owners feel confident that their pets are in great hands. As a law student, responsibility, reliability, and attention to detail are part of my daily life. I’ll care for your pet as if they were my own—whether that means long walks, playtime, cuddles, or simply making sure they feel safe, comfortable, and loved while you’re away. I know how important it is to trust someone with your furry family member, and I take that responsibility seriously. I look forward to meeting you and your pets! I keep a structured schedule that makes it easy to plan pet care into my day. I enjoy taking breaks from studying to get outside for walks, exercise, and fresh air, so dog walks fit naturally into my routine. Whether it’s a quick potty break, a long walk, or spending time playing with your pet, I’m happy to provide them with the attention and care they deserve. I also have flexibility during mornings, evenings, and weekends, allowing me to accommodate a variety of schedules. Caring for animals is something I genuinely enjoy, and spending time with pets is one of my favorite ways to unwind from school while giving them plenty of love, exercise, and companionship. When caring for pets in a client’s home, my priority is making sure they feel safe, comfortable, and stick to their normal routine. I carefully follow all care instructions, including feeding schedules, medications (if needed), exercise, and any specific preferences or routines your pet is used to. I make sure every visit includes plenty of attention, playtime, affection, and exercise based on your pet’s personality and energy level. Whether your dog loves long walks or your cat prefers quiet companionship, I’ll tailor my care to their individual needs. I also treat every home with the utmost respect, keeping it clean, secure, and exactly as I found it. Communication is important to me, so I’ll send regular updates and photos so you can relax knowing your pet is happy and well cared for while you’re away.
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.
“Arianna was great with my puppies 😊. She walked the puppies every day and was very patient with my senior dog. She communicated with me often and responded quickly when I reached out to her. I’m very happy with her service and will definitely book her again ☺️.”
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!
“Genevieve took wonderful care of our cat Brody at our house. He was his usual fat happy self when we got home. She also daily updated us how he was doing and sent pics. She was very respectful of our house during her stay. If you’re looking for a reliable and caring pet and house sitter, we highly recommend her.”
“Nicole took wonderful care of my pup. She stayed in communication with me throughout my trip and sent me tons of pictures. I highly recommend her and will book her for all my future dog sitting needs.”
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!
“To say Linda was phenomenal is an understatement. This was the first time I left my fur-sister for more than a few hours. Nervous at first we were relieved when Linda came for the first meet and greet. Kia instantly loved her and welcomed her into her world. From the minute we left until the minute we got home Linda kept in touch with us. With pictures, texts and updates. She even started teaching Kia French!!! To think we have a bilingual dog now!! I cannot say enough about how happy we are with Linda and now feel even happier that we found Kia’s furever sitter!!!!”
The median cost per night for house sitting in Winston Terrace is $45
Pet parents share their Rover experiences - Winston Terrace
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
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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 September 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 September 2026, there are 563 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.
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