House Sitting Winstead Crossroads

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Winstead Crossroads, 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.

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Sitter Profile Image: Cheryl M.
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Cheryl M.
from
$35
per night
5.0 out of 5 stars
336 reviews
89 repeat clients
25 years of experience
Nashville, NC, 27886

I have nothing but awsome things to say about Cheryl. This the second time booking her services and have already booked again. She is always on time and sends lots of pictures daily of our furbabies. I would recommend her to anyone looking a care taker for their furbabies.

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Crystal T.
Sitter Profile Image: Janine D.
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Janine D.
Star Sitter
from
$40
per night
5.0 out of 5 stars
160 reviews
63 repeat clients
20 years of experience
Bailey, NC, 27807

I was very impressed with Janine and how she took care of our animals. Two huge dogs and a cat, she even went above and beyond to solve an unforeseen problem. I would definitely recommend her to anyone needing pet sitting and I would definitely use her again.

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J D.
Sitter Profile Image: Jeffrey C.
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Jeffrey C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
24 reviews
8 repeat clients
8 years of experience
Wilson, NC, 27896

Jeffrey was wonderful with our pets, and very attentive to them! He took and shared so many great pictures, and our dog especially had so much fun with him. He was responsive and helpful throughout our time away from home. We will definitely be hiring him again!

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Karly M.
Sitter Profile Image: Kelly M.
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Kelly M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
59 reviews
16 repeat clients
40 years of experience
Rocky Mount, NC, 27803

They got along very well together. He stayed on schedule and was in a happy mood when we returned. This was her third visit and she thought he was fun with his big boy 12 pounds personality.

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Brenda J.
Sitter Profile Image: Carley R.
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Carley R.
from
$25
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Wilson, NC, 27896

About: I have a blue heeler that loves to play with other dogs. I am a very out going person I take my dogs with me to let them run and have fun When I do go run earns that are pet friendly I carry the dogs with me or I will take them on day trips to a nature park and go hiking. I will also wash, groom, cut nails and give medicine if needed. I’ve worked with and lived with dogs and horses my entire life. I work at a vets office. I have always loved caring for animals. I've watched many family friends dogs including their farm animals for weeks at the time. I will also watch over farm animals as well I treat every animal like it is my own. I work at a veterinary hospital. I would still be able to care for any pets that you have. I would be able to do up to 4 times a day check ins for those who want to do drop ins I always check the area the dogs play to make sure there is nothing harmful and check each pet for anything new or unusual after coming back inside I will send pictures of them having fun

Sitter Profile Image: Jessica C.
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Jessica C.
from
$35
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
Wilson, NC, 27893

About: I have always loved caring for animals and treat every pet like a member of the family. While I don’t currently have any pets of my own, that allows me to provide your dog with my full attention and a calm, comfortable environment during their stay. My home features a secure fenced-in patio with pet-friendly turf for outdoor time, and I’m fortunate to have a large dog park directly across the street as well as another dog-friendly area within my neighborhood. Whether your pup enjoys playtime, walks, cuddles, or simply relaxing, I can tailor their care to their individual needs. I have experience caring for dogs of different sizes, ages, and personalities, and I have also volunteered with animal shelters, giving me a strong understanding of dog safety and behavior. My goal is to make sure your pet feels safe, loved, and comfortable while you’re away. I understand how important it is to trust someone with your furry family member, and I would be honored to provide reliable, attentive care for your dog. I look forward to meeting you and your pup! I am currently a nursing student and stay at home mom. This allows me to give your fur babies my full attention and lots of love and interactive play! I believe every pet is happiest when their normal routine is maintained as closely as possible. Before each booking, I take time to learn about your pet’s feeding schedule, exercise needs, favorite activities, medications, and any special instructions. In my home, pets receive plenty of supervision, attention, playtime, potty breaks, and a clean, safe environment. Dogs have access to a fenced-in patio with pet turf and can enjoy walks or trips to the nearby dog park if approved by their owner. Cats are provided with a quiet, comfortable space, fresh water, clean litter boxes, and enrichment activities tailored to their personality. When caring for pets in a client’s home, I respect both the pet’s routine and the owner’s home. I follow all care instructions carefully, provide regular updates and photos, maintain feeding and medication schedules, clean up after pets, and make sure they receive plenty of attention and affection while their family is away. My priority is always making pets feel safe, comfortable, and loved while giving owners peace of mind.

Sitter Profile Image: Ileana L.
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Ileana L.
from
$45
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
15 years of experience
Rocky Mount, NC, 27804

Ileana did a great job taking care of our fur babies. They instantly loved her! She provided us with regular updates and some adorable pictures while she was pet sitting. We will definitely be reaching out to Ileana for future pet sitting.

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Heather J.
Sitter Profile Image: John N.
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John N.
Star Sitter
from
$70
per night
5.0 out of 5 stars
83 reviews
24 repeat clients
18 years of experience
Zebulon, NC, 27597

John was FANTASTIC! He was diligent with sending plenty of photos and videos of our three dogs. He even took them on plenty of walks and gave them treats that they loved. This made our out of state travel easier to know how well taken care of they were! He was so responsive and genuinely seemed to enjoy being around our pups. Thank you so much for taking great care of our pets and of our home!! 10/10 recommend for all your pet care needs.

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Kennedie S.
Sitter Profile Image: Kennedy S.
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Kennedy S.
from
$36
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Rocky Mount, NC, 27804

Kennedy is a fantastic sitter! Just got back from my first trip away from my pup, and Kennedy helped me feel totally comfortable with it all. She sent lots of pictures and updates while I was gone, and my pup is very happy! Not only did she take good care of my dog, she also took great care of my home and left it looking better than she found it. Would definitely HIGHLY recommend her. So happy to have a good, reliable sitter for future adventures! Thanks Kennedy!

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Erin C.
Sitter Profile Image: Jessica J.
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Jessica J.
from
$40
per night
5.0 out of 5 stars
31 reviews
8 repeat clients
20 years of experience
Zebulon, NC, 27597

Jessica was great! She stayed at my apartment with my mina for a couple of days while I went out of town. Mina got a few walks and Jessica even cuddled with her and administered her medicine (which is no easy feat). They had a great time and Jessica sent many photos throughout her stay. She left my apartment in great order. I will definitely be booking her again!

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Migs M.
Sitter Profile Image: Kelly W.
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Kelly W.
from
$65
per night
5.0 out of 5 stars
44 reviews
18 repeat clients
15 years of experience
Middlesex, NC, 27557

This was a last minute booking. We had to leave for NJ when my father died and Kelly stepped up for us. She did a wonderful job taking care of our three dogs. One has diabetes and needs insulin shots twice a day and is also blind. Kelly had no problems with the shots or with bonding with our babies. She kept us updated, which was wonderful. Kelly even did some unexpected cleaning during her down time, which was unexpected, but so appreciated. I would not hesitate to recommend Kelly and would definitely use her again in the future.

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Jeanmarie B.
Sitter Profile Image: Michelle L.
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Michelle L.
from
$75
per night
5.0 out of 5 stars
58 reviews
10 repeat clients
40 years of experience
Selma, NC, 27576

Michelle was fantastic and our dogs loved her so much! They had a fantastic vacation while we were on vacation too! Definitely will have her back!

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Jessica C.
Sitter Profile Image: Sarah S.
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Sarah S.
from
$50
per night
5.0 out of 5 stars
4 reviews
5 years of experience
Red Oak, NC, 27809

Booked Sarah for an in house sitting for my three dogs for a 7 day family trip. The house looked exactly as I left. She provided amazing care to our 3 dogs and was attentive the whole stay. We received multiple updates through out the stay along with pics and videos.

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Shaun W.
Sitter Profile Image: Hannah A.
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Hannah A.
from
$20
per night
5.0 out of 5 stars
1 review
1 year of experience
Rocky Mount, NC, 27803

About: ! I’m a lifelong animal lover who has grown up in a home with five Labrador Retrievers and a cat, so caring for pets has always been a part of my everyday life. Being around so many animals has taught me the importance of patience, consistency, and giving every pet the individual attention they deserve. I recently graduated from college, where I was a collegiate athlete, and I’m currently earning my MBA. Balancing athletics, academics, and work has made me dependable, organized, and responsible, these are qualities I bring to every pet I care for. Pet care is a part of my everyday life. My family has five Labrador Retrievers, so I have daily experience feeding, walking, exercising, and caring for dogs of all ages and energy levels. I’m currently earning my MBA through an online program while working part-time, which gives me a flexible schedule to provide reliable pet care throughout the week. I enjoy being active, so walks and playtime are something I genuinely look forward to. I always make it a priority to give every pet the attention, exercise, and care they need while keeping them comfortable and following their normal routine. I know every pet is different, so my goal is to make them feel as comfortable as possible while you’re away. I’ll follow their normal routine, whether that’s feeding, walks, playtime, giving medication, or just spending time with them so they don’t feel lonely. I’m very respectful of other people’s homes and will treat your space the same way I’d want someone to treat mine. Your pet’s safety is my biggest priority, so I’ll always make sure doors, gates, and leashes are secure and pay close attention during walks and outdoor time. I’ll also send plenty of updates and photos because I know how reassuring it is to know your pet is happy and doing well while you’re away. I genuinely love being around animals, and I’ll care for your pet like they’re one of my own.

Sitter Profile Image: Kalyn N.
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Kalyn N.
from
$70
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
5 years of experience
Wake Forest, NC, 27587

Kalyn was AWESOME, sent lots of photos and spent lots of quality time with my dogs, would gladly have her house sit again.

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casey h.
Sitter Profile Image: Kristin K.
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Kristin K.
from
$50
per night
5.0 out of 5 stars
39 reviews
5 repeat clients
20 years of experience
Southeast, Raleigh, NC, 27610

Our 3 doggies were very relaxed and happy during their week with Kristin! She made sure to understand and follow all of the instructions and she communicated and sent us photos every day. The house was spotless when we got back. Highly recommend Kristin!

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Christen B.
Sitter Profile Image: Brian M.
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Brian M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
16 reviews
6 repeat clients
40 years of experience
Nashville, NC, 27856

About: Summary: Hi! I’m an experienced caregiver with a passion for animals. I have a fenced yard and all the supplies your pet needs to feel at home. Just bring their food, & any meds. I’ll provide love & a safe environment—your pet will be in great hands we me! Details : All pet water is filtered. I'm great with all animals of all sizes. I've had dogs, cats, and fish, and I get along with them all. I'm sure that your fur, feathered, scaled, or finned family and I - will be great friends. I mostly board and sit with some walks and drop-ins. Mostly depending on the timing. Reach out for special needs and requests. While not trained professionally - I can also help with some behavioral issues. I'd love to meet your pet family. Work from home professional. Single father. I have my daughter every other week and I have a dog that can be kept completely separate if needed. I also have plenty of dog toys that are okay to be beaten up. Gates in-house to control pet location. Allowed to get on furniture and bed. We have a big comfy dog bed as well. Two litter boxes are available. Just ask that you bring food, any special toy, litter for cats, and any medicines. I have two tie-out leads for dogs and a shady backyard that is fenced in. Our neighborhood is quiet and great for walks. I usually board at my home in Nashville (Near Rocky Mount and Spring Hope) but I also have a location in Raleigh that is also a big home with a large backyard and two separate floors. For sitting, I would likely stay with the pet most of the day as I work remotely.I do require high-speed internet access and preferably a decent work desk area. I will work on any behavioral issues that I see in the time that I have. Let me know if you have a question! I work from home and typically do boarding in either Raleigh or Nashville, NC. I have my daughter every other week but she is great with animals also. Takes after her dad. Prefer a little notice but will always try to accommodate last minute requests. I have the ability to keep multiple pets. I have a large fenced in back yard at both locations. Both are single family homes with lots of space. Gates and seperate areas if pets need to be separated. We can also accommodate requests for no other animals be present, however I am great at acclimating animals with each other. Even ones that do not tend to play nice with others. Always up to you in the end. I have muzzels and a Kennel at both homes (if needed) , cat litter boxes at both locations as well. Leases safety collars , and for a small added fee , daily health tracking during the stay with a special collar monitor tracking device that I have. All pets are treated like family with love care and respect. Will work with all breeds ages and sizes.

Sitter Profile Image: Kansas B.
Verified Enhanced Background Check
Kansas B.
from
$30
per night
5 years of experience
Wilson, NC, 27896

About: I have had various experiences with dogs and cats. I grew up around animals. I have dog sit and cat sit for friends and families for multiple years now and am very reliable. I have let sit for large dogs that are in older age and needs special care. I have also pet sit for multiple pets at once. It was a small dog and 2 cats. We went in walks, had cuddles, and played games. We even got to play with some toys. I am currently on summer break from teaching and am completely free. As I am not teaching right now I am able to be flexible to your needs of your pets. Whether that is going for a walk or going outside to play. I have my own apartment and it is animal friendly. Due to this the environment is very safe and inviting. In my home it is very calm and clean. This is important just in case your pet has allergies. Since I don’t have any pets myself I am able to give lots of care and attention to your pets.

Sitter Profile Image: Caroline & Gavin C.
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Caroline & Gavin C.
from
$159
per night
4.9 out of 5 stars
28 reviews
12 repeat clients
11 years of experience
Raleigh, NC, 27613

Caroline and Gavin took such good care of our fur babies while we were away. We appreciate their communication with us and we could tell from pictures our dogs were happy and cared for. Thank you both!!

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Emily B.
Sitter Profile Image: Lucie G.
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Lucie G.
from
$60
per night
11 years of experience
rocky mount, NC, 27804

About: For as long as I could remember I’ve been my family’s go-to pet sitter. Anytime my Grandmother had a doctors appointment or my Aunt and Uncle left town, I would be their first choice. I love animals and caring for them, making them comfortable when their families are gone is not an easy task but easing their anxiety and keeping them comfortable is a very rewarding job. I’ve worked with rover in the past when I was in high school and it was a great experience. I am currently working part time but my schedule is relatively flexible. As far as boarding goes there is and will always be someone at the house caring for the dogs 24/7. I have a large plot of land adjacent to my house for the puppies to play in. I currently have three very friendly small dogs who love to play and make friends.

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The median cost per night for house sitting in Winstead Crossroads is $50

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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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Popular requests for house sitting - Winstead Crossroads

Select a filter and find qualifying sitters offering house sitting.

Sitters in Winstead Crossroads average 4
repeat house sitting clients

FAQs for House Sitting - Winstead Crossroads

Frequently asked questions about Rover

As of August 2026, there are 738 sitters on Rover offering House Sitting across Winstead Crossroads. 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 Winstead Crossroads 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 Winstead Crossroads 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 Winstead Crossroads 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 Winstead Crossroads. On Rover:

  • 91% of sitters can help with special care needs
  • 94% can help with giving oral medications or injections
  • 92% 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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