House Sitting in Winston Terrace

Find a loving house sitter to watch over your pets and your home.

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Winston Terrace house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Candice F.
Verified Enhanced Background Check
Candice F.
from
$45
per night
5.0 out of 5 stars
3 reviews
1 repeat client
10 years of experience
Williamsburg, VA, 23188

Candice was great! Came home to a happy pup :)

Profile image
Sally M.
Sitter Profile Image: Christina S.
Verified Enhanced Background Check
Christina S.
Star Sitter
from
$65
per night
5.0 out of 5 stars
238 reviews
110 repeat clients
15 years of experience
Williamsburg, VA, 23188

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!

Profile image
Jennifer N.
Sitter Profile Image: Lauren W.
Verified Background Check
Lauren W.
from
$72
per night
5.0 out of 5 stars
20 reviews
3 repeat clients
25 years of experience
Williamsburg, VA, 23188

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!

Profile image
Mark A.
Sitter Profile Image: Craig S.
Verified Enhanced Background Check
Craig S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
53 reviews
20 repeat clients
20 years of experience
Williamsburg, VA, 23185

Craig was such a godsend to us. He handled our two rambunctious lab puppies with ease and sent photos and videos frequently to show us that they were having a good time. He is our go to Dogsitter after our first experience with him. He will also come over and do an intro session with the dogs and walk through their routine with you to get familiar. Hard-working, prompt, devoted - what else could you ask for?

Profile image
Stephanie B.
Sitter Profile Image: Alexa S.
Verified Enhanced Background Check
Alexa S.
from
$26
per night
5.0 out of 5 stars
1 review
2 years of experience
Williamsburg, VA, 23188

Alexa was amazing. So great with our senior dogs, sending photos too. Highly recommend!

Profile image
Jenn M.
Sitter Profile Image: Rhianna M.
Verified Enhanced Background Check
Rhianna M.
from
$26
per night
5.0 out of 5 stars
7 reviews
5 years of experience
Williamsburg, VA, 23185

Rhianna took very good care of our senior kitty and our house. Would definitely recommend her if you are looking for a cat whisperer!

Profile image
Elizabeth M.
Sitter Profile Image: Jenny D.
Verified Enhanced Background Check
Jenny D.
from
$50
per night
5.0 out of 5 stars
5 reviews
30 years of experience
Williamsburg, VA, 23185

Jenny was wonderful!!! My two pups normally take a bit to warmup to new people but at the meet and greet they both clearly showed a liking to her. Jenny watched my pups in my home and messaged me several times a day and sent pics to let me know how things were going. This was very comforting for someone like me, with having anxiety with leaving them. My house was as clean as I left it, and I was very grateful that she brought in my packages as they were delivered. I would recommend Jenny, we will definitely be asking her to watch our pups again!!! Thank you so much Jenny, for easing my mind with my sweet babies and taking such great care of them😊!!!

Profile image
Jennie N.
Sitter Profile Image: Payton E.
Verified Enhanced Background Check
Payton E.
from
$50
per night
5.0 out of 5 stars
4 reviews
1 repeat client
8 years of experience
Williamsburg, VA, 23188

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. 😊

Profile image
Kelli F.
Sitter Profile Image: Julie R.
Verified Enhanced Background Check
Julie R.
from
$65
per night
5.0 out of 5 stars
9 reviews
1 repeat client
30 years of experience
Williamsburg, VA, 23185

Julie did a great job with my pup! She had no problem administering his medication and was sure to send me updates. I will definitely be booking her again for future travel.

Profile image
Karen C.
Sitter Profile Image: Jared L.
Verified Enhanced Background Check
Jared L.
Star Sitter
from
$65
per night
5.0 out of 5 stars
50 reviews
16 repeat clients
25 years of experience
Williamsburg, VA, 23188

Highly recommend!!! Jared was so accommodating, responsive, and truly loves dogs.

Profile image
Missy K.
Sitter Profile Image: Nicole M.
Verified Enhanced Background Check
Nicole M.
from
$42
per night
5.0 out of 5 stars
40 reviews
19 repeat clients
20 years of experience
williamsburg, VA, 23185

I am always worried when I leave my pets to go on vacation but Nicole kept us updated with pictures on a daily basis and everyone was healthy and happy to see us when we got home. The house was also neat and clean. Thanks, Nicole! I will definitely contact you for future trips!

Profile image
Catherine T.
Sitter Profile Image: Patricia D.
Verified Enhanced Background Check
Patricia D.
from
$25
per night
50 years of experience
Williamsburg, VA, 23185

About: I have taken care of pets since I was young girl. I also have worked as a Veterinary Technician on Langley Air Force Base. I enjoy pet sitting all kinds of animals, especially dogs and cats. I am retired and involved in some weekly activities, so pet sitting fits perfectly with my schedule. I enjoy the freedom and flexibility of pet sitting, not to mention the joy of being around pets. I am attentive, detail oriented and versatile. I believe in leaving things the way I found them, or better. I always strife to do my best at whatever I do, and I am a very trustworthy person.

Sitter Profile Image: Marissa S.
Verified Enhanced Background Check
Marissa S.
from
$50
per night
4.7 out of 5 stars
23 reviews
13 repeat clients
10 years of experience
Williamsburg, VA, 23185

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 :)

Profile image
Hannah T.
Sitter Profile Image: paula c.
Verified Enhanced Background Check
paula c.
from
$60
per night
6 years of experience
Williamsburg, VA, 23185

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.

Sitter Profile Image: Maggie K.
Verified Enhanced Background Check
Maggie K.
from
$49
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
12 years of experience
Newport News, VA, 23608

Maggie was great! Very responsive and my dogs loved her. She kept my house in great condition to return to and was super flexible, will use her again!

Profile image
Travis W.
Sitter Profile Image: Kelly S.
Verified Enhanced Background Check
Kelly S.
from
$30
per night
28 years of experience
Williamsburg, VA, 23188

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.

Sitter Profile Image: Quinn G.
Verified Enhanced Background Check
Quinn G.
from
$87
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
3 years of experience
Williamsburg, VA, 23188

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.

Profile image
Laurie A.
Sitter Profile Image: Lauren K.
Verified Enhanced Background Check
Lauren K.
from
$34
per night
4.8 out of 5 stars
18 reviews
9 repeat clients
17 years of experience
Williamsburg, VA, 23188

Lauren was great with our black lab. She didn’t shy away from walking her, even though she’s 70 lbs. She texted when she had questions (appropriately, not overdone) and we will definitely ask her to take care of our beast again.

Profile image
Sarah K.
Sitter Profile Image: Lucas C.
Verified Enhanced Background Check
Lucas C.
from
$50
per night
5.0 out of 5 stars
2 reviews
12 years of experience
Williamsburg, VA, 23188

Lucas was absolutely amazing. He was so accommodating and watched our doggo last minute. He was so great about staying on top of her medication and sending us pictures! 10/10 recommend

Profile image
Madisyn Q.
Sitter Profile Image: Michele K.
Verified Enhanced Background Check
Michele K.
from
$48
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
1 year of experience
Williamsburg, VA, 23188

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!

1 / 1
View more sitters

Over 90
pet parents in Winston Terrace have booked house sitting

Winston Terrace pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

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.

Profile image
Diane S.
House Sitting
5.0 out of 5 stars

Alexa did a wonderful job watching our fur baby. She was very responsive, punctual, and attentive to Rocky. We willing definitely be requesting her again!!

Profile image
Thomas H.
House Sitting
5.0 out of 5 stars

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.

Profile image
Laura G.
House Sitting
5.0 out of 5 stars

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!!

Profile image
Rick D.
House Sitting
5.0 out of 5 stars

Julie did a great job with my pup! She had no problem administering his medication and was sure to send me updates. I will definitely be booking her again for future travel.

Profile image
Karen C.
House Sitting
5.0 out of 5 stars

We’ve booked Caitlin multiple times and highly recommend! The dogs love her, the apartment looks just as we left it, and she was nice enough to put away the groceries we had delivered. Will definitely book with her again!

Profile image
Madeline T.
House Sitting
5.0 out of 5 stars

Meaghan was amazing! Our travel dates shifted at last minute and she was extremely flexible. Highly recommend for sitting and any other services on rover.

Profile image
christian o.
House Sitting
5.0 out of 5 stars

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.

Profile image
Danay E.
House Sitting
5.0 out of 5 stars

Wilhelmina was fantastic! My two dogs seemed so relaxed and happy when I returned from my trip. She treated our home with respect and sent regular updates and photos of the dogs. Each photo they looked so happy! Will certainly be using her again.

Profile image
Cailla D.
House Sitting
5.0 out of 5 stars

Skylar's our go-to for taking care of our dog, two cats, and house! She is a great communicator and is very reliable. The pets are always happy and relaxed when we return home and the house is in good shape.

Profile image
Emily G.
House Sitting
5.0 out of 5 stars

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.

Profile image
Rachel K.
House Sitting
5.0 out of 5 stars

Hope was lovely and took such good care of my puppy. She was respectful of my home and the needs of my pup and was extremely communicative.

Profile image
Micayla W.
House Sitting
5.0 out of 5 stars

Caroline is wonderful! She keeps me well informed with pictures and is always willing to be flexible with my schedule. She gets my high st recommendation.

Profile image
Cathy D.
House Sitting
5.0 out of 5 stars

Allie was fantastic. We did our meet and greet and I was very impressed with her qualifications. She kept us up daily with our pets and their activities as well as pictures of them. We can’t wait to have her back.

Profile image
Larraine S.
House Sitting
5.0 out of 5 stars

Wonderful! She was very responsive and took care of everything as asked. She always asked questions to make sure all my pets were getting the care they needed.

Profile image
Alexander B.
House Sitting
5.0 out of 5 stars

Emily was great. She was very communicative, and I felt comfortable leaving my blind and mostly deaf buddy with her.

Profile image
Valerie S.
House Sitting
5.0 out of 5 stars

Wonderful service. She took care of of our three dogs and two rabbits for ten days, and one of them was ill. She did a fantastic job. Kept in contact with us with daily updates. House looked great on our return. I highly recommended Erin!

Profile image
Patrick C.
House Sitting
5.0 out of 5 stars

Second time going with Nina and no issues! She’s super nice and the house and pups were just the way we left them 👌🏼

Profile image
Christopher S.
House Sitting
5.0 out of 5 stars

Lucas was absolutely amazing. He was so accommodating and watched our doggo last minute. He was so great about staying on top of her medication and sending us pictures! 10/10 recommend

Profile image
Madisyn Q.
House Sitting
5.0 out of 5 stars

If I could give Haley 100 stars I would. We were looking for a responsible, caring person to stay at our home and watch our two German Shepherds and chickens while we went on vacation and Haley exceeded our expectations in every way. As soon as she came over for the meet and greet we felt at ease with her, she was punctual, kind, friendly and most importantly our dogs loved her. She sent us daily pictures and updates of the dogs-which I greatly appreciated! I didn’t have to worry one bit about the care our dogs were getting and I can’t tell you how wonderful that feels, we were able to enjoy our vacation knowing our babies were in good hands. We will for sure use her again and we can’t recommend her enough.

Profile image
Cassi L.
House Sitting
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Winston Terrace is $42

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 house 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.

Sitters in Winston Terrace average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winston Terrace on Rover as of Jun 2026 was about $42 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Winston Terrace house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 552 house sitters in Winston Terrace. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 89% of Winston Terrace house sitters respond in under an hour.

House sitters in Winston Terrace have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winston Terrace.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winston Terrace house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.