House Sitting in East Winston

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Top rated East Winston house sitters

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

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Sitter Profile Image: Kat M.
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Kat M.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
170 reviews
42 repeat clients
9 years of experience
Winston Salem, NC, 27127

Kat is exceptional!! My husband and I agreed that she’s the best Rover we have ever had. Our dog, Jax, was so well taken care of - she took him for multiple walks a day, played outside with him, and best of all, just gave him so much love and attention. We also really appreciated how many updates and pictures she sent throughout the stay. It was so great!! Can’t recommend Kat enough!

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Emily P.
Sitter Profile Image: Mary Kathryn H.
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Mary Kathryn H.
from
$30
per night
5.0 out of 5.0 stars
3 reviews
5 years of experience
Winston-Salem, NC, 27101

MK did a great job in caring for Stoner and our home. She communicated proactively and exceeded our expectations. Stoner loved her, and had fun playing outside with her! We will reach out again for our next needs. Thank you MK!

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Janice H.
Sitter Profile Image: Maggie W.
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Maggie W.
from
$35
per night
4.8 out of 5.0 stars
19 reviews
7 repeat clients
10 years of experience
Winston-salem, NC, 27127

Maggie was a delightful sitter. She was prompt which is extremely valuable. Very clean, polite and amiable. Sand was comforted by Maggies presence.

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Sue K.
Sitter Profile Image: Dinira S.
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Dinira S.
Star Sitter
from
$40
per night
4.9 out of 5.0 stars
194 reviews
67 repeat clients
12 years of experience
Winston Salem, NC, 27105

We were so happy with Dinira's service. She was very attentive and caring to our dog. To absolute no fault of hers, our dog surprised a skunk and got sprayed. She immediately called me and was very concerned for our dog. Dinira took all measures to clean up our dog and get rid of the smell. I think she may have even cleaned the house as it looked better than it did when we left. I would fully trust Dinira when we need a pet sitter again.

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Sam W.
Sitter Profile Image: Marci B.
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Marci B.
from
$42
per night
5.0 out of 5.0 stars
12 reviews
1 repeat client
6 years of experience
Kernersville, NC, 27284

I recently visited from out-of-town and Marci stayed in my hotel room with my cannot-be-alone French bulldog, Teddy, while I was out at work events. Marci is friendly, responsible, easy to communicate with, and gave Teddy everything he needed (including cuddles). I know he was comfortable with her because he usually refuses to eat while I'm gone but he ate his dinner with her! She made sure he got his energy out and tinkled too. Marci made my life so much easier-- you can tell she "gets" dogs.

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Kara S.
Sitter Profile Image: Marissa P.
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Marissa P.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
18 reviews
6 repeat clients
5 years of experience
Winston Salem, NC, 27103

My dog loved her! I felt comfortable going away as I knew she was in good hands!!

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TAMMY L.
Sitter Profile Image: Ceili T.
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Ceili T.
from
$30
per night
5.0 out of 5.0 stars
14 reviews
5 repeat clients
10 years of experience
winston salem, NC, 27103

Ceili was wonderful. Always felt our dogs were happy and taken care of. We got lots of food photos and videos. She stayed at our home and left it in great shape. Definitely recommend her services and we’ll be reaching out for future needs!

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Carey B.
Sitter Profile Image: Caroline G.
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Caroline G.
from
$40
per night
4 years of experience
Winston-Salem, NC, 27109

About: I frequently pet sit in my hometown, Knoxville, TN, and I’m looking to start doing so in Winston as well! I love going on walks and getting to know the dogs I sit! I am a full time student at Wake Forest. I have no classes on Fridays, and no class on Monday or Wednesday mornings. I have enough time between classes every day except for Thursday to let dogs out during the day! I love to hang out with dogs I sit for! I’ll play fetch, snuggle, and go on walks! I’m happy for the dog(s) to sleep with me if that’s what they’re used to!

Sitter Profile Image: Noelle N.
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Noelle N.
from
$45
per night
5.0 out of 5.0 stars
31 reviews
12 repeat clients
5 years of experience
Winston Salem, NC, 27106

Noelle did an amazing job dropping in to let our two pups out on potty breaks, feeding them and making sure all their needs were met. She was extremely communicative and made sure we got lots of pictures and updates on how they were doing while we were away for a weekend! We will absolutely use her again for any dog sitting needs.🩷

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Tiffany S.
Sitter Profile Image: Heather D.
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Heather D.
from
$40
per night
4.9 out of 5.0 stars
18 reviews
9 repeat clients
45 years of experience
Winston-Salem, NC, 27106

Heather came by prior to the dog sitting night per our request for a 15 minute meet n greet, just so our dog Toby would be a little familiar with her before the actual 'sit' night. When she came tonight to actually sit with Toby at our home, all went well. She sent pics and feedback to us while we were out at a Christmas party. It's important to us to know he is/was doing well as he has separation anxiety and doesn't like to be apart from us. Heather's pictures provided relief to know that he was doing okay and all was well at home. We will use Heather's services again in the future.

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Lorette P.
Sitter Profile Image: Kristin C.
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Kristin C.
from
$40
per night
4.9 out of 5.0 stars
41 reviews
9 repeat clients
20 years of experience
Winston-Salem, NC, 27103

Kristin is wonderful! She took great care of our senior dog and many cats and was communicative throughout with texted updates and photos. Tidied up after herself and did all she promised. This was our first time using Rover and we couldn't be happier. We came home to a house full of relaxed and happy pets 😁 Will definitely re-book with Kristina in the future!

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Frances B.
Sitter Profile Image: Elise V.
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Elise V.
from
$27
per night
15 years of experience
Winston-Salem, NC, 27101

About: I grew up in a home that was always full of all types of animals - dogs, cats, lizards, guinea pigs, hamsters, fish, you name it. Throughout my life, I have been trusted to take care of not only my pets, but neighbors and friends’ as well. My goal is to provide safe and loving care to your pets as if they’re my own I am currently a full-time graduate student at Wake. While my days are busy, being a student allows for a lot of flexibility in my schedule. I am available Monday/Wednesday after 4pm, Thursday all day, and Friday-Sunday scattered availability I provide reliable, attentive and compassionate care in your home, respecting your space, and creating a relaxing and safe environment where you pet feels comfortable while you’re away.

Sitter Profile Image: Samantha P.
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Samantha P.
from
$40
per night
5.0 out of 5.0 stars
9 reviews
2 repeat clients
8 years of experience
Winston Salem, NC, 27104

Samantha was amazing! She was able to watch our animals very last minute, and did everything we asked of her! She was very respectful of our home, and & took photos of everyone! Thanks so much!

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Claire G.
Sitter Profile Image: Bea B.
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Bea B.
from
$30
per night
5.0 out of 5.0 stars
6 reviews
1 repeat client
13 years of experience
Winston-Salem, NC, 27103

Bea did an exceptional job housesitting and taking care of our pups while we were on vacation! She was kind, dependable, and communicative. We felt a sense of relief knowing that our dogs could be comfortable in their normal home environment and well-cared for while we were away.

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Regina H.
Sitter Profile Image: Christina & Jeremy D.
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Christina & Jeremy D.
Star Sitter
from
$82
per night
5.0 out of 5.0 stars
34 reviews
11 repeat clients
10 years of experience
Winston-Salem, NC, 27106

Christina was great! It was kind of a late notice, but she was available and spent alot of time with my girl. Even tho my Shiloh is very shy and timid with strangers, just the thought of knowing someone was there with her gave me peace. We don't travel much, but will definitely have her take care of my babies again when I have a need.

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Jodi H.
Sitter Profile Image: Emily S.
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Emily S.
Star Sitter
from
$60
per night
5.0 out of 5.0 stars
25 reviews
8 repeat clients
10 years of experience
Winston-Salem, NC, 27101

About: I've been around dogs of all sizes and am comfortable with all aspects of care- walks, feeding, playing, snuggles, and will send plenty of pictures for their parents if desired :) Here to provide frequent check-ins and high-quality care. I am starting a job in healthcare this fall! My schedule will be flexible and I hope to spend my off days with some pet therapy! I understand each household is different and am happy to follow each pet's particular schedule and care needs. I cannot have animals in my current apartment but have reliable transportation to come to your home!

Sitter Profile Image: Elena V.
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Elena V.
from
$65
per night
5.0 out of 5.0 stars
65 reviews
16 repeat clients
15 years of experience
Winston Salem, NC, 27103

Elena is a fantastic sitter! We have her booked multiple times and feel great about the service she provides. She sends lots of wonderful updates and takes great care of our dog and house while we are away. We'll be using her lots more and highly recommend her!

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Mallory P.
Sitter Profile Image: Holly B.
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Holly B.
from
$38
per night
5.0 out of 5.0 stars
4 reviews
13 years of experience
Winston Salem, NC, 27107

Holly stayed at my house over the holidays with my two big dogs. I was really anxious to leave them because they are used to traveling with me but Holly put me at ease. She did a great job sending updates and even cleaned my house! Will definitely use Holly again.

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Catie W.
Sitter Profile Image: Isabelle P.
Verified Enhanced Background Check
Isabelle P.
Star Sitter
from
$80
per night
5.0 out of 5.0 stars
66 reviews
37 repeat clients
20 years of experience
Winston-Salem, NC, 27103

Isabelle once again did an outstanding job for us watching all of our pets. She is kind, a great communicator and we are very grateful for her help when our flight got delayed. We highly recommend her!

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Hendree L.
Sitter Profile Image: Maura S.
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Maura S.
from
$70
per night
5.0 out of 5.0 stars
10 reviews
3 repeat clients
10 years of experience
Winston-Salem, NC, 27101

Molly (what she goes by) was fabulous! She got along great with our quirky lil pup. We got regular updates check ins with photos which made us feel very comfortable. Our dog can be a little shy/skittish with new people but they seemed to get along great and we came home to find the house pristine and the dog happy.

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Anna H.
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East Winston pet parents share their Rover experiences

1 / 1
5.0 out of 5.0 stars

As always, Ceili is a godsend to my babies!!! She kept me up to date and sent photos. My pups love her and fight for snuggles with her!

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Laura L.
House Sitting
5.0 out of 5.0 stars

This was our second booking with Kat and it was for a week stay. Our boys were well taken care of and the house was in good order. She communicated consistently with pictures and updates which was comforting.

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Lezlie P.
House Sitting
5.0 out of 5.0 stars

Jniyah was available on short notice over the holidays, and gave us comfort in knowing our pet was well cared for! She sent regular updates & had open communication.

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Gabrielle B.
House Sitting
5.0 out of 5.0 stars

Maggie was easy to work with and great with our dogs. I especially appreciate being able to work with us on our short notice trip. She provided just what we needed!

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Stuart M.
House Sitting
5.0 out of 5.0 stars

Dinira was fantastic she took great care of Zeus and Zena she kept us updated and sent pictures daily. We look forward to using her in the future!

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Don M.
House Sitting
5.0 out of 5.0 stars

Tara was an amazing sitter! She was attentive and kept in touch daily. She sent pics and videos throughout her time with the boys! We will definitely be rebooking Tara!

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Tara T.
House Sitting
5.0 out of 5.0 stars

MK did a great job in caring for Stoner and our home. She communicated proactively and exceeded our expectations. Stoner loved her, and had fun playing outside with her! We will reach out again for our next needs. Thank you MK!

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Janice H.
House Sitting
5.0 out of 5.0 stars

Emily did a great job watching our dog. She was quick to respond to messages and gave us regular updates while we were gone. I particularly liked that she let us know her planned schedule for communicating with us, so we knew when to expect an update each day. Our dog was happy when we returned and our house was just as we left it. We definitely recommend Emily!

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Jenelle C.
House Sitting
5.0 out of 5.0 stars

Ryan was very professional and communicated well throughout the visit. I felt my fur babies were left in good hands and did not worry while we were away. Would not hesitate to book Ryan for future needs.

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Melanie W.
House Sitting
5.0 out of 5.0 stars

Meghan interacted with Fendi beautifully. There was a scheduling conflict due to Meghan's other appointment obligations, causing Meghan to arrive several hours later than expected. A call would have been appreciated; however, she did not want to leave the other dogs unattended as well. After we spoke, Megan came as quickly as she could and took excellent care of Fendi. She sent lots of videos and pictures and gave Fendi lots of love. She was extremely apologetic and even refunded some of the additional cost. Fendi interacted well with Megan and when I returned back home it was evident Fendi was establishing a bond. The house was well taken care of and Meghan adhered to all the specific directions given that Fendi is a service animal. She played with her and gave Fendi the special attention needed to allow us to enjoy our trip with less worry. Meghan is mature and took on this assignment at the last minute, reducing my stress of being worried. This is the first time I have ever left Fendi with (3) different individuals with rotating times since I was going to be away for nearly a week. Meghan came through for us and I appreciate her willingness to make this transition of being away more accommodating. Her interaction with Fendi is why I will certainly call upon her again. She showed love and kindness to Fendi and that is priceless.

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Rita F.
House Sitting
5.0 out of 5.0 stars

She is the best!! Washed my towels and sheets after staying w my pup and left my apartment cleaner than she found it !

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charlie k.
House Sitting
5.0 out of 5.0 stars

Sophia was great withour 3 dogs including a senior. She sent photos and updates. Highly recommend her

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karen g.
House Sitting
5.0 out of 5.0 stars

This was Luci’s second time watching our dog and two cats. She was very responsive and communicative with us. Our pets seemed very happy and she was flexible with us as we had flight delays. Will definitely book again!

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Tory G.
House Sitting
5.0 out of 5.0 stars

I am so happy with Jaclyn! I have a bit of an anxious puppy and I do NOT like leaving him behind, but a work trip made me have to leave my baby this time. Jaclyn was very kind and sent lots of updates. I had a whole list of instructions and she followed all of them. She even gave my beardie some lettuce and water and turned on and off the lights for my reptiles and arachnids. Daisy and Kilo said whenever mom is out of town, Aunt Jaclyn can watch him!

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Laura L.
House Sitting
5.0 out of 5.0 stars

Ed took great care of our dogs (and home)! They were happy and smiley and sad to see Ed go. Would definitely recommend anyone work with Ed, we certainly will (wouldn't hear the end of it from the dogs if we didn't 😅)

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Fabian v.
House Sitting
5.0 out of 5.0 stars

Kayla did amazing with our girl Bella! She did everything that was asked and more, sent pictures and updates, and was easy to schedule with/get ahold of, etc. We will definitely book with her again.

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Jacklyn W.
House Sitting
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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 East Winston is $45

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 East Winston 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 East Winston on Rover as of Jan 2026 was about $45 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 East Winston 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 Jan 2026, there are 795 house sitters in East Winston. 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, 91% of East Winston house sitters respond in under an hour.

House sitters in East Winston have an average of 14 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 East Winston.

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. East Winston 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.