House Sitting East Winston

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

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Over 84
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: Bria G.
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Bria G.
from
$55
per night
5.0 out of 5 stars
2 reviews
20 years of experience
Winston-Salem, NC, 27103

Brianna was amazing!! Very thorough and asked a lot of good questions in order to get to know our dogs and their routines. Very responsive and communicative throughout the day which we appreciate! I highly recommend and will be using Brianna in the future ☺️

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Emily T.
Sitter Profile Image: Emily W.
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Emily W.
from
$40
per night
5.0 out of 5 stars
4 reviews
1 repeat client
3 years of experience
Winston-Salem, NC, 27101

About: I have taken care of a variety of dogs. Last year I got my first pup, who has taught me a lot about dogs with anxiety. I am a science teacher and have my summers off. I am looking forward to spending more time outside with some great dogs on walks! I can crate my dog to accommodate to yours and can have a separate area of the apartment for your pup so they feel like they have their own space.

Sitter Profile Image: Brooke D.
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Brooke D.
from
$55
per night
5.0 out of 5 stars
5 reviews
1 repeat client
7 years of experience
Winston-Salem, NC, 27101

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

Cameron was an absolute delight! She took wonderful care of my boys and gave great updates! The house was tidy upon my return. She really went the extra mile. I highly recommend Cameron and will definitely be using her again.

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Casey R.
Sitter Profile Image: Madilyn F.
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Madilyn F.
from
$45
per night
5.0 out of 5 stars
8 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: Samira P.
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Samira P.
Star Sitter
from
$70
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
5 years of experience
Winston-Salem, NC, 27107

Amazing experience having Samira house and pet sit! My dogs loved her right away and I was able to travel knowing everything was well looked after! Samira sent regular updates and pictures. Communication was great. I could not have asked for a better experience and will hope to have Samira come again next time we need pet sitting!

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Lisa W.
Sitter Profile Image: Hailey P.
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Hailey P.
from
$35
per night
5.0 out of 5 stars
19 reviews
7 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: Alejandra Y.
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Alejandra Y.
from
$70
per night
5.0 out of 5 stars
23 reviews
6 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: Marci B.
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Marci B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
19 reviews
6 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.
Sitter Profile Image: Chelsea R.
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Chelsea R.
from
$50
per night
5.0 out of 5 stars
5 reviews
16 years of experience
Winston salem, NC, 27101

Chelsea was a wonderful house sitter. She took excellent care of Oreo and my home. She sent regular updates and was willing to help with weekly trash pickup when I forgot to put my cans out before leaving. I will absolutely be checking with Chelsea first next time I need a sitter for my sweet senior girl!

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Davis C.
Sitter Profile Image: Kristin C.
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Kristin C.
from
$50
per night
5.0 out of 5 stars
47 reviews
10 repeat clients
20 years of experience
Winston-Salem, NC, 27103

I am so glad that Kristen took care of our dog! She looked so happy, healthy and safe when we came home. Kristen shared some hilarious pictures of her with us during our travels. Kristen was able to understand the many sides of our labradoodle... If you know, you know!! Our home was well taken care of, and we'll entrust Kristen whenever we need someone to look after our fur-baby on future trips.

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R M.
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 took great of my dogs and sent frequent updates with pictures. Things were a little hectic before I left and she adapted well to the changes.

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Kelley W.
Sitter Profile Image: Mary Kathryn H.
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Mary Kathryn H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
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: Haley S.
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Haley S.
from
$30
per night
5.0 out of 5 stars
5 reviews
15 years of experience
Winston-Salem, NC, 27103

Haley was an absolute lifesaver for us!! We were visiting Greensboro for a concert and found ourselves searching at the last minute for someone we could trust with our babies. She responded right away, & even showed up early to get to know Willow and Cricket, before we left. Calm, kind, and instantly tuned into their personalities. She clocked Cricket's love of booty scratches and Willow's princess 👸 energy without much direction. She checked in while we were out, which gave us such peace of mind. Honestly, the worst part about going back to Florida, is we wish we could bring her back with us!! If we lived nearby, she'd be our go-to without question. Thank you, Haley, for turning a stressful situation, into such a relief!! What a Godsend 💛💛

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Heather H.
Sitter Profile Image: Ashley C.
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Ashley C.
from
$20
per night
5.0 out of 5 stars
3 reviews
1 year of experience
Winston-Salem, NC, 27127

Ashley was friendly, responsible and communicative. My two Siberian Huskies were well taken care of and my extremely timid cat would actually come out of hiding, which she never does with strangers. She was a great hire.

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Brenna H.
Sitter Profile Image: Hayley W.
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Hayley W.
from
$40
per night
4.5 out of 5 stars
8 reviews
10 years of experience
Winston-Salem, NC, 27105

Hayley did a great job with our two Bulldogs. They can definitely be high-maintenance, but she handled them very well. Overall, it was a great experience, and we were very happy with her care.

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Steven D.
Sitter Profile Image: Morgan M.
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Morgan M.
from
$50
per night
5.0 out of 5 stars
6 reviews
10 years of experience
Winston Salem, NC, 27103

Morgan was absolutely wonderful! I have a special-needs dog with rear paralysis, so leaving him in someone else’s care can be stressful. Morgan did an exceptional job caring for him and my cat and gave me complete peace of mind while I was away. Her communication was fantastic. She kept me updated, sent pictures, and made sure I knew how my pets were doing throughout my time away. It was such a relief to be able to truly relax and enjoy some time away without worrying about them. I’m so grateful for the patience, compassion, and attention Morgan gave both of my pets. It was a fantastic experience from beginning to end, and I would highly recommend Morgan to anyone looking for a caring, dependable, and trustworthy pet sitter. I will definitely book with her again!

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Renee H.
Sitter Profile Image: Kalyn S.
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Kalyn S.
from
$55
per night
5.0 out of 5 stars
3 reviews
25 years of experience
Winston Salem, NC, 27127

About: I've owned, trained, been around, worked with animals for over 25 years. I would absolutely love to help love on and care for your pet! I work part time from home with a very flexible schedule that I manage myself. I am often found walking the neighborhood with my pup while listening to a podcast! I have a secure fenced in back yard and also have an XL dog kennel as well as a Small size kennel available, if needed.

Sitter Profile Image: Kirsten S.
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Kirsten S.
from
$40
per night
5.0 out of 5 stars
2 reviews
20 years of experience
Winston-Salem, NC, 27103

About: I’ve grown up with dogs. I have experience caring for puppies and elderly dogs. I have an Aussie doodle puppy. I’m available for drop ins, walks, or sittings. I have a flexible schedule and will be available the majority of the day to care of your pets. If I have to leave during boardings, it will be only for short periods of times which will be communicated to you. I live in an apartment with plenty of space and a dog park. There is a nice neighborhood and park nearby for walks. For sittings at your home, I will respect your space and keep it clean. I have a puppy at home, so I am unable to stay at your home overnight. I will update you with as many photos or videos you’d like!

Sitter Profile Image: Jay C.
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Jay C.
from
$50
per night
5.0 out of 5 stars
7 reviews
10 years of experience
Winston-Salem, NC, 27101

Jay house sat for us for six days and did a fantastic job caring for our dogs and cat! He was great with the animals, and it was clear they really enjoyed his company. We came home to happy, relaxed pets and a tidy house. It gave us peace of mind knowing they were in good hands while we were away. Highly recommend Jay to anyone looking for a reliable, caring pet sitter!

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Gregory 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

Brooke was really great with our two girls! She was quick to respond and communicative, and went above and beyond even taking them for walks! They both seemed happy and well cared for when we returned from our 5-night vacation. It’s always hard to leave them but I would definitely feel good about having Brooke watch them again.

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Courtney M.
House Sitting
5.0 out of 5 stars

Morgan was absolutely wonderful! I have a special-needs dog with rear paralysis, so leaving him in someone else’s care can be stressful. Morgan did an exceptional job caring for him and my cat and gave me complete peace of mind while I was away. Her communication was fantastic. She kept me updated, sent pictures, and made sure I knew how my pets were doing throughout my time away. It was such a relief to be able to truly relax and enjoy some time away without worrying about them. I’m so grateful for the patience, compassion, and attention Morgan gave both of my pets. It was a fantastic experience from beginning to end, and I would highly recommend Morgan to anyone looking for a caring, dependable, and trustworthy pet sitter. I will definitely book with her again!

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Renee H.
House Sitting
5.0 out of 5 stars

Ashley was friendly, responsible and communicative. My two Siberian Huskies were well taken care of and my extremely timid cat would actually come out of hiding, which she never does with strangers. She was a great hire.

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Brenna H.
House Sitting
5.0 out of 5 stars

Chelsea was a wonderful house sitter. She took excellent care of Oreo and my home. She sent regular updates and was willing to help with weekly trash pickup when I forgot to put my cans out before leaving. I will absolutely be checking with Chelsea first next time I need a sitter for my sweet senior girl!

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Davis C.
House Sitting
5.0 out of 5 stars

Excellent communication. Cameron send me a lot of updates, puppies were happy when I got home, I can see that they had a good time 🥰. Definitely will let her take care of my furry babies again.

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Yanira C.
House Sitting
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

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
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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 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 880 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
  • 100% 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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