House Sitting East Winston

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Over 81
pet parents in East Winston have booked house sitting

East Winston, 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.

1 / 1
Sitter Profile Image: Susannah H.
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Susannah H.
from
$40
per night
4.8 out of 5 stars
33 reviews
8 repeat clients
8 years of experience
Winston-Salem, NC, 27104

Susannah was great! Very communicative, responsible, took great care of our dog over a long weekend. Would definitely book her again in the future.

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Lydia H.
Sitter Profile Image: Bonnie C.
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Bonnie C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
106 reviews
37 repeat clients
4 years of experience
Walkertown, NC, 27051

Bonnie stepped in last minute after a cancellation with another sitter. She came by for a meet and greet and my nervous pup warmed up to her almost immediately. She was wonderful with them both and kept me updated with pictures the entire stay. I am very grateful to have had her help! ☺️

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Ashleigh B.
Sitter Profile Image: Hannah S.
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Hannah S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
51 reviews
20 repeat clients
1 year of experience
Winston-Salem, NC, 27105

Hannah is a fantastic pet sitter. She sends me multiple updates throughout the day and always asks questions She is extremely communicative and trustworthy. This is the third time we’ve used her, and I will definitely book her again

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Andrea W.
Sitter Profile Image: Elise S.
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Elise S.
Star Sitter
from
$40
per night
5.0 out of 5 stars
15 reviews
6 repeat clients
8 years of experience
Winston-Salem, NC, 27103

Highly recommend! Elise took care of my pup through days of storms and rain - my dog is terrified of both - and did such a great job! The very regular pictures she sent showed a happy doggo, who seemed very relaxed and very trusting around her. When I came home, doggo was happy, well-fed, clearly well-taken care of. Moreover, Elise graciously took care of the doggo outside of the scheduled hours - both before my (changed) flight out and when my flight back was delayed. Communication with her was super smooth and super friendly. 13/10 recommend!

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Michaela A.
Sitter Profile Image: Lauren & Layla W.
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Lauren & Layla W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
70 reviews
24 repeat clients
15 years of experience
Winston-Salem, NC, 27104

Lauren and Layla are wonderful! Our pup, Bella, was diagnosed with hookworms on the day we were supposed to leave for a family vacation. Lauren and Layla graciously stepped in and watched Bella after our original boarding arrangements fell through. I cannot even begin to express my gratitude and appreciation for them. They made us feel so confident that Bella was in great hands and getting lots of love and attention while taking care of her during her treatment. They kept us updated with lots of messages and pictures. Knowing Bella was safe, comfortable, and well cared for allowed us to enjoy our trip without constantly worrying. Their kindness and professionalism during a stressful, last-minute situation meant so much to our family. We would not hesitate to trust them with Bella again and highly recommend them to anyone looking for exceptional pet care.

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Susan F.
Sitter Profile Image: Hailey P.
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Hailey P.
from
$35
per night
5.0 out of 5 stars
18 reviews
6 repeat clients
11 years of experience
Winston-Salem, NC, 27107

We have now used Hailey repeatedly, and have absolutely loved having her house sit for our boys. Her communication is outstanding, photo updates multiple times daily, and our house is always clean when we return. She loves on our pups like they are her own, and we appreciate her so much!

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Madison N.
Sitter Profile Image: Megan F.
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Megan F.
from
$45
per night
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Kernersville, NC, 27284

About: I’ve been around dogs my whole life and cats for most of it — pet care has just always been part of my world. For the past 5 and a half years, I’ve raised my own dog, a German Shepherd/Belgian Malinois mix, from a puppy to adulthood, including working through his reactivity, so I have real hands-on experience with reactive and high-energy dogs. I know structured exercise, mental stimulation, training, and reading a dog’s cues, and I’m comfortable handling pets that need a more experienced, patient hand. Whether your dog is laid-back or comes with their own quirks, they’ll be in good hands with me. I’m currently work full time, primarily on first shift, so my afternoons and weekends are free! If your pup is ok on their own during the workday I would love to hang out with them in my off time!! Your home and your pet’s safety are always my top priority. I treat every house I stay in with the same care and respect I’d want for my own — securing doors and gates, following your pet’s routine closely, and staying alert to anything out of the ordinary. I’m comfortable, calm, and responsible in someone else’s space, and I communicate regularly so you always know your pet (and your home) are in good hands while you’re away.

Sitter Profile Image: Cameron B.
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Cameron B.
from
$40
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
5 years of experience
Winston-Salem, NC, 27101

Cameron was amazing with our 2 Great Danes and cat! She took them to the dog park and on lots of walks! Lots of pictures were shared and we came back to healthy, happy animals!

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Navid C.
Sitter Profile Image: Valerie S.
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Valerie S.
Star Sitter
from
$48
per night
5.0 out of 5 stars
27 reviews
4 repeat clients
30 years of experience
High Point, NC, 27262

Valerie was great, we got lots of pictures and updates of the pups while traveling, made it feel like they were very much loved while we were gone!

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Joseph M.
Sitter Profile Image: Jacob A.
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Jacob A.
from
$52
per night
5.0 out of 5 stars
8 reviews
4 repeat clients
3 years of experience
Winston-Salem, NC, 27127

Jacob was the perfect sitter for us! He sent daily photo updates of Dino and took him on multiple "outings" daily. Dino is a highly motivated and energetic dog that requires a lot of attention - Jacob had no difficulty fulfilling his needs. He maintained great communication with us throughout our trip so we knew our boy was well taken care of during our trip. When we arrived home, he also had kept our house clean and organized! We will definitely use Jacob again for any future needs :)

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Laura I.
Sitter Profile Image: Alejandra Y.
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Alejandra Y.
from
$70
per night
5.0 out of 5 stars
23 reviews
5 repeat clients
7 years of experience
Walkertown, NC, 27051

Alejandra was amazing, our dogs olly and isla loved her!! She was very patient with them and she cuddled and played with them alot (they’re puppies) + isla really warmed up to her which is rare because she is usually very picky about the people she’s around with. thank you so much alejandra for taking care of our kids! ◡̈ they loved you alot!! til next time!

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Rebecca S.
Sitter Profile Image: Aubrey M.
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Aubrey M.
Star Sitter
from
$80
per night
5.0 out of 5 stars
21 reviews
19 repeat clients
8 years of experience
Winston-Salem, NC, 27103

Aubrey was fantastic!!! She took care of my German Shepard..sofie for 5days. I was so nervous about leaving her because I haven’t left her side for almost 6 years. Aubrey sent me pictures and she kept in touch everyday. She was so professional and loving and there is absolutely no way I would ever have anyone else be with my baby. She is like family now!!!

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Lisa H.
Sitter Profile Image: Kendric & Jana P.
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Kendric & Jana P.
from
$20
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
7 years of experience
Winston-Salem, NC, 27127

About: Hi! We’re Jana and Kendric, a reliable pet care team with a shared love for animals. Having two sitters means your pets receive extra attention, supervision, and care while you’re away. We both have experience caring for dogs and cats of all breeds, sizes, and personalities, from energetic puppies and playful kittens to senior pets who need a calmer, more attentive routine. We’re comfortable with daily walks, feeding schedules, playtime, litter box care, and maintaining your pet’s normal routine so they feel safe and comfortable. We understand that every pet is different, so we take time to learn their habits, preferences, and personality. Whether your dog needs plenty of exercise or your cat prefers quiet companionship, we adapt our care to what makes them happiest. We also have experience following detailed care instructions and can administer oral medications if needed. Safety and communication are very important to us, so we always make sure your pets are supervised, secure, and well cared for at all times. While you’re away, we provide regular updates and photos so you can relax knowing your pets are happy and in good hands. Our goal is to make your pets feel loved and comfortable while giving you complete peace of mind. We treat every pet like they’re part of our own family and look forward to meeting you and your furry friends! 🐾🐶🐱 We (Jana and Kendric) work opposite schedules, which allows us to provide consistent care and supervision for your pets. Because of this, someone is home with your pet most of the time, ensuring they receive plenty of attention, care, and companionship throughout the day. We’re able to accommodate morning, afternoon, and evening routines, including feeding schedules, walks, playtime, and check-ins. Having two caregivers also means greater flexibility if your pet has specific needs or requires extra attention. Our goal is to make sure your pet feels safe, comfortable, and never left alone for long periods, while maintaining the routine they’re used to at home. 🐾🐶🐱 When caring for pets in our home or in a client’s home, we focus on keeping their routine as normal and stress-free as possible. We follow each owner’s instructions closely, including feeding schedules, walks, litter box care, medications, and any special needs their pet may have. For dogs, we provide regular walks, playtime, and plenty of attention to keep them happy and exercised. For cats, we make sure litter boxes are kept clean, feeding routines are maintained, and they receive playtime and affection while still respecting their space. We always prioritize safety, cleanliness, and communication. We keep environments secure, monitor pets closely, and send regular updates and photos so owners know their pets are happy and well cared for while they’re away. Our goal is to make every pet feel comfortable, safe, and loved. 🐾🐶🐱

Sitter Profile Image: Sandra A.
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Sandra A.
Star Sitter
from
$77
per night
5.0 out of 5 stars
23 reviews
10 repeat clients
12 years of experience
Winston-Salem, NC, 27103

Sandra was wonderful. Someone willing to watch the pups in our own home makes everything easier on us and our 2 dogs. They were not stressed at all when we returned, and both seemed very happy to have spent the day with their new best friend Sandra. We will definitely call on her again in the future.

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Randy F.
Sitter Profile Image: Ceili T.
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Ceili T.
from
$40
per night
5.0 out of 5 stars
16 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: Chelsey F.
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Chelsey F.
Star Sitter
from
$125
per night
5.0 out of 5 stars
37 reviews
16 repeat clients
20 years of experience
Kernersville, NC, 27284

Chelsey was fantastic with my three dogs and cat. It was a holiday weekend and I was nervous about leaving my elderly dog for any length of time. Chelsey sent many pictures and regular updates. When we got home the house was perfect and all the babies were relaxed and happy.

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Kimberly P.
Sitter Profile Image: Jan R.
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Jan R.
from
$95
per night
5.0 out of 5 stars
44 reviews
22 repeat clients
15 years of experience

Jan loves our handsome boy! She has house/pet sat for us on numerous occasions and she helps us tremendously. Our bulldog loves to be outside and belly rubs all day. She is great with him. I highly recommend.

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Amanda S.
Sitter Profile Image: Suzanne S.
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Suzanne S.
from
$50
per night
5.0 out of 5 stars
49 reviews
11 repeat clients
30 years of experience
Mt Airy, NC, 27030

Suzanne was a loving, caring and joyful person who took great care of our dog while housesitting. I'd definitely recommend her to anyone in need, and we will certainly be a repeat customer of hers. Thank you, Suzanne!

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DJ B.
Sitter Profile Image: Madilyn F.
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Madilyn F.
from
$45
per night
5.0 out of 5 stars
6 reviews
1 repeat client
12 years of experience
Winston-Salem, NC, 27127

Marilyn took excellent care of our cats and dogs while we were away. She was thoughtful and sent pictures of them enjoying themselves. Thanks so much.

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Shannon R.
Sitter Profile Image: Marci B.
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Marci B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
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.
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The median cost per night for house sitting in East Winston is $45

Pet parents share their Rover experiences - East Winston

1 / 1
5.0 out of 5 stars

I can not say enough about how well Jana did. She took such good care of my babies, even while one was very sick. I feel so lucky to have had her with them during this time!

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Jessica A.
House Sitting
5.0 out of 5 stars

It was so great having Chelsea look after our two English Bulldogs while we were out of town for a long weekend. She stayed at our place and took excellent care of our home and dogs. She even had to give one of our dogs multiple daily medications and did it without a problem! She was communicative, reliable, and we felt at ease knowing they were in great hands. Thanks, Chelsea!

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Kara B.
House Sitting
5.0 out of 5 stars

Brooke was great with our golden retriever! She sent lots of pictures and I know she took great care of her. Definitely will ask her to take care of Bailey again :)

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Kristin A.
House Sitting
5.0 out of 5 stars

Morgan was incredible all around! Communicative, organized, in tune with our dog 100%. She stayed at our home for two nights and everything went perfect. Our pup was super happy to hang out with her and she was the best houseguest. Highly recommend!!!!

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Stefen K.
House Sitting
5.0 out of 5 stars

I am a repeat customer, very happy with Susannah. Multi-day overnight stay, no fuss and a happy dog. Couldn't ask for more.

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Jeffrey V.
House Sitting
5.0 out of 5 stars

Dinira is a fantastic sitter! Very responsive, considerate, and engaging. She was meticulous with the care needed for our fur babies and was above and beyond our expectations. I rate 5 ⭐ and 10/10, I couldn't have been more impressed, and I recommend to anyone with pet needs!

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Benjamin M.
House Sitting
5.0 out of 5 stars

100% give 10 stars. He was very communicative with me. This was the first time I’ve left my elderly dog with anyone besides family. My dog wasn’t lonely and was very well cared for.

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Cindie L.
House Sitting
5.0 out of 5 stars

Eliza took great care of Scout while we went out for the evening! She even checked in with us and sent photos letting us know how he was doing 🥰

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Lauren R.
House Sitting
5.0 out of 5 stars

Elise was kind and friendly, and willing to meet with Kala before her stay to make sure it was a good fit. Kala didn’t even seem to have missed us when we returned.

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Angelia M.
House Sitting
5.0 out of 5 stars

Tara was so great with my kiddos! My boy is not easy at first, and she was very patient with him and by the end, they were snuggling. She also gave my girl some medicated eye drops she needed. She sent lots of updates and pictures and took great care of my house. Thanks so much Tara!

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Jesse O.
House Sitting
5.0 out of 5 stars

Marissa watched our brand new puppy while we went out week 2 of having him and it was such a great piece of mind and she sent the perfect amount of updates!

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Heather & Eric H.
House Sitting
5.0 out of 5 stars

Ceili was wonderful! She sent so many pictures of Wofford every day. Would definitely book with her again & recommend her to anyone!

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Marissa P.
House Sitting
5.0 out of 5 stars

Sandra is the best! We are and will be repeat customers - highly recommend. She takes great care of our sweet little Bill and he just loves her. She’s communicative, trustworthy, and flexible with our crazy schedules!

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Kelly C.
House Sitting
5.0 out of 5 stars

Maggie was a fantastic sitter! She took great care of my dog during the worst of ice/sleet storms in years. My dog is very active and gets antsy when not walked enough, but I came back to a calm, happy furbaby. Not only did Maggie get the doggo's energy out, she also extended her stay when our flights back home got cancelled, twice. I will be forever grateful for the care, and Maggie's flexibility and fast communication in an unstable situation. She also checked in about my dog's comfort, which I appreciated. Recommend 15/10.

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Michaela A.
House Sitting
5.0 out of 5 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 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 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 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
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Popular requests for house sitting - East Winston

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Sitters in East Winston average 4
repeat house sitting clients

FAQs for House Sitting - East Winston

Frequently asked questions about Rover

The average cost for House Sitting in East Winston on Rover is $55.5 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 879 sitters on Rover offering House Sitting across East Winston. 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 East Winston 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 East Winston 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 East Winston 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 East Winston. On Rover:

  • 94% of sitters can help with special care needs
  • 98% can help with giving oral medications or injections
  • 98% 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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