House Sitting Windward Trail

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Over 74
pet parents in Windward Trail have booked house sitting

Windward Trail, 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: Kimberly O.
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Kimberly O.
from
$35
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
20 years of experience
Belton, SC, 29627

Kim did a wonderful job with our babies. She was great with communication and sent lots of pics :) loved hearing from her. All our babies were happy and the house was in perfect condition join our return. Would definitely recommend and book Kim again! ♥️

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Jennifer H.
Sitter Profile Image: Julie D.
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Julie D.
from
$50
per night
5.0 out of 5 stars
18 reviews
8 repeat clients
25 years of experience
Anderson, SC, 29621

Julie was wonderful! She came prior to our getaway to meet us and our animals. She kept us updated on how they were doing while we were gone and with pictures! My dogs seemed very comfortable with her! Grateful to have found her and look forward to more getaways now that we have a sitter!

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Jill H.
Sitter Profile Image: Madison H.
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Madison H.
from
$50
per night
5.0 out of 5 stars
3 reviews
7 years of experience
Anderson, SC, 29621

About: Growing up, my family always had at least two dogs at all times. Although I don’t have a dog of my own, I love taking care of and spending time with other people’s dogs. 🩷 I am a teacher by day (Aug-end of May) and dog sitter on the side! I love kids but dogs truly have my heart. The bigger, the better! I am a teacher, so I will be gone from 6:30am-3:30pm. I have watched dogs while I’ve been at school who are used to be alone for an extended amount of time but but I will walk them prior to leaving for work and then spend the evening with them once I get home. :) ***If your dog isn’t used to being alone while I would be at work, I do have someone who can check on your pet and also take them out midday while I’m at work! :) Although I do not have a fenced in yard, my neighborhood community has a fenced in dog park area to give your dog(s) the space and freedom to roam as needed. :)

Sitter Profile Image: Nadia R.
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Nadia R.
Star Sitter
from
$27
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Anderson, SC, 29621

Nadia was wonderful! She watched our pets while we were out of the country for two weeks and kept in regular communication and always sent fun photos. We recently moved to the area so I feel such a relief in finding someone who I can trust and that my pets enjoying being with.

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Hollye C.
Sitter Profile Image: Paige C.
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Paige C.
Star Sitter
from
$50
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
15 years of experience
Pelzer, SC, 29669

Paige was a wonderful pet sitter for Gemma! She is the sweetest and kept me in the loop with photos and updates. Would highly recommend 😊

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Emily C.
Sitter Profile Image: Emily B.
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Emily B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
19 reviews
3 repeat clients
12 years of experience
Anderson, SC, 29625

About: I’ve been caring for dogs for most of my life. At 13, I started a neighborhood dog-walking business for owners who were “too pooped to walk their dogs,” which quickly grew into in-home and overnight dog sitting. I got my first dog at age ten and trained her myself, and I’ve since attended multiple dog training classes because I genuinely enjoy working with dogs. Over the years, I’ve cared for labs, golden doodles, pit bulls, and more for families that I have worked with through high school and college. Now that I have my own home (next to a park) I’m excited to start again with plenty of space, structure, and love for every pup. Pet care fits naturally into my weekly routine. I’m an emergency nurse and work every Monday and Tuesday and every other weekend, which gives me most weekdays free and flexible for walks, drop-ins, and sitting. On my off days, I enjoy staying active with walking, running, and hiking, and I love including dogs in those activities for both exercise and enrichment. I plan my schedule carefully to ensure every pet receives consistent attention, timely care, and plenty of love. Safety and trust are my top priorities. As an emergency nurse, I have strong medical training and stay calm and attentive in all situations, including emergencies. I closely follow pet parents’ instructions and routines in both my home and theirs, ensuring a low-stress, loving environment. I provide supervised play, secure walks, and plenty of mental and physical stimulation. Living next to a park gives dogs safe space to explore, exercise, and enjoy structured outdoor time while always being carefully monitored.

Sitter Profile Image: Sketcher M.
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Sketcher M.
from
$40
per night
5.0 out of 5 stars
7 reviews
15 years of experience
Clemson, SC, 29631

Sketcher did great housesitting our anxious 2 yr old dog and 11 yr old indoor cat. She was good at communicating promptly during booking and during the stay. We came home to happy pets and everything was as expected.

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Erin and Ted
Sitter Profile Image: Alicia S.
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Alicia S.
from
$60
per night
5.0 out of 5 stars
21 reviews
8 repeat clients
5 years of experience
Anderson, SC, 29621

Alicia was wonderful with our pups. We have used her twice and could tell that our dogs enjoyed their time with her in our home. We will be calling on her again for sure!

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Amy Z.
Sitter Profile Image: Jayda K.
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Jayda K.
Star Sitter
from
$63
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
2 years of experience
ANDERSON, SC, 29625

Jayda was awesome, we have a dog who stresses out a lot and can’t go anywhere. So it was important to have someone come to the house and stay. We highly recommend her and will use her again.

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Kenny S.
Sitter Profile Image: Kortney W.
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Kortney W.
Star Sitter
from
$63
per night
5.0 out of 5 stars
24 reviews
9 repeat clients
6 years of experience
pendleton, SC, 29670

About: I have been on Rover for over a year now and have fallen in love with pet sitting! I have several repeat clients who I love. I have always had dogs in my house and I am currently raising my puppy Roy! I feel as though pets have more feelings than humans so I make sure to give them special attention! I am a full time student at Clemson University and work a part time job so when i’m away from those i always make sure to spend time playing with my dog and taking care of him. I love to be around and let him hangout with me anytime I can since he’s so sweet and funny! I typically find myself watching a few pets every month! I typically work a few days out of the week and 4-6 hour shifts! These 4-6 hour shifts are either 10am-3pm or 3pm-9pm! I always give pets as much attention as they will let me. I feel as though feedings schedules and daily walks and attention are necessary for animals. I also like to make sure they have clean food and water and plenty of it! I also make sure to pay special attention to their body language and can change my routines or anything they may need to make them more comfortable.

Sitter Profile Image: Jennifer A.
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Jennifer A.
from
$35
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Anderson, SC, 29621

Jenn was so helpful and communicative and really made it easier for me to leave the pups at home. She provided updates and pictures and helped me feel at ease! Absolutely would recommend!

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Molly P.
Sitter Profile Image: Nia C.
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Nia C.
from
$50
per night
10 years of experience
Anderson, SC, 29621

About: I’ve had both dogs and cats my whole life! My current pet, Gus, is a pomeranian-bichon. Im experienced in dog sitting and training. Fun fact, i’ve also had fancy mice before! I’d love to ease your mind and give your babies the care they need when you’re unable to. I am working Part-Time, so on days that I work, i can be available before 10, and after 7:30. On days when I’m off, I can do anytime! I have a fenced in yard that accommodates my 3 dogs here at home. We also take care of several strays in the neighborhood that have a little sanctuary on the front porch.

Sitter Profile Image: Isabella Q.
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Isabella Q.
from
$50
per night
12 years of experience
Clemson, SC, 29631

About: I have always grown up with pets: 3 dogs, 1 cat, and a beared dragon. I have helped train a puppy, cared for a dying senior dog, and everything in between. I have experience with pets who have high energy, anxiety, dietary needs, and physical disabilities. Family, friends, and neighbors have trusted me to pet sit, drop in, provide over night care, and walk their dogs. I have worked at a dog groomer for over 2 years, which has given me experience with a wide variety of animals and their temperaments. I’m a full time student at Clemson University who has most afternoons/ evenings and weekend free to care for your pets! I am studying wildlife conservation so spending time with animals is one of my favorite things to do! Following instructions, I can care for your pet however you direct me to. I am comfortable taking your dog for walks/ hikes, playing indoors and outdoors, dosing medications, keeping up with training, and providing all the love and comfort your pet will need while you are away!

Sitter Profile Image: Nicole K.
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Nicole K.
from
$25
per night
4.7 out of 5 stars
26 reviews
12 repeat clients
4 years of experience
Anderson, SC, 29625

About: Pets have so much fun here, they try to come back in during pickup time! My family and friends also help play with dogs and assist with drop off. Look for the yellow sign at 1210. For boarding schedule between 7am and 745pm, only bring dog food. All pickups and drop offs must be before 8pm. No bowls, no beds, no leashes, there are plenty of extras here. Several dogs here play together everyday like a big dog park so I can only take healthy active dogs that do not have any infectious or contagious illnesses. The best fit is a playful friendly dog that wants to run and have fun (not a dog that needs to be alone or the only pet). I cannot take senior dogs that need multiple medications or dogs with mange, or bordatella or heart worms. I provide several services including boarding, training, walking, daycare and more! My boarding schedule is usually 7am to 730pm for pet drop off and pet pickup. However, I take a day off or two and friends or family will substitute for me. I do have some family time at dinner so its best to schedule drop off and pick ups before 5pm or after 7pm to accommodate the time it takes for new arrivals. All pets get to play with other dogs. Every dog gets free time outside daily I ensure all dogs are safe and create a calming environment for them! Puppies and small dogs are welcome and do great here with the friendly group of little dogs.

Sitter Profile Image: Meghan H.
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Meghan H.
from
$75
per night
4.8 out of 5 stars
13 reviews
1 repeat client
4 years of experience
Anderson, SC, 29625

Meghan was absolutely amazing! She sent photos every day and had great communication throughout the week. Our dogs loved her and we’ll definitely use her again in the future!

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Paige H.
Sitter Profile Image: Aubrey L.
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Aubrey L.
from
$40
per night
5.0 out of 5 stars
7 reviews
5 years of experience
Anderson, SC, 29621

Aubrey was great! She came and did a meet and greet with both boys to make sure we all felt comfortable prior to the booking. The pups loved her and she did great with them. We have one who can be a little more hyper and she handled him well! She communicated well and sent pictures. We booked her over the holidays and she spent a great deal of time taking care of our boys and juggling family time. Will definitely use Aubrey again.

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Mandee T.
Sitter Profile Image: Amber A.
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Amber A.
from
$75
per night
5.0 out of 5 stars
47 reviews
10 repeat clients
10 years of experience
Pelzer, SC, 29669

My dogs love Amber! When I return from a trip, they are calm and relaxed. Well...except for a little attitude from Zoe....but that is short lived. Amber will continue to take care of my dogs in the future, when she is available. I suggest booking as soon as your plans are set.

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Ann K.
Sitter Profile Image: Vanja M.
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Vanja M.
from
$65
per night
5.0 out of 5 stars
4 reviews
5 years of experience
Anderson, SC, 29625

Vanja was great. Very communicative and responsible. I had no worries leaving my dogs with her. They were very happy when I got home.

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Susan L.
Sitter Profile Image: Zoie S.
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Zoie S.
from
$35
per night
10 years of experience
Piedmont, SC, 29673

About: I lived on a farm growing up, taking care of all types of animals. I have a genuine love & care for them. Assuring your pets will get the best care. Also, I worked in a K-9 unit for 2 years. I am reliable & respectful of you & your pet needs. I am currently taking a break from work at the moment & pursuing my bachelors degree online. I can fit pet care in at anytime on any day. Everyone cares for their pets differently, that’s no surprise. My job is to listen to what you want for your pets. If I’m not already outside play or walking pets, I like to take them out every hour. I treat them like royalty & I will treat your pets the same.

Sitter Profile Image: Colleen H.
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Colleen H.
from
$60
per night
5.0 out of 5 stars
2 reviews
25 years of experience
Anderson, SC, 29621

Colleen was absolutely amazing! She was available on short notice and took such wonderful care of our German Shepherd. She was so sweet and attentive with him, and she kept us updated throughout her visits, which gave us so much peace of mind. It was clear that she genuinely cared about him and treated him like her own. We couldn’t have asked for a better dog sitter! I would recommend Colleen 10 out of 10 times and will definitely be using her again! 🐾❤️

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Jolanta D.
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The median cost per night for house sitting in Windward Trail is $50

Pet parents share their Rover experiences - Windward Trail

1 / 1
5.0 out of 5 stars

Pella is such a great sitter! She took the best care of our dog who is recovering from a CCL injury. Super responsive and responsible, and I know my dog Laila will be so excited to see her again soon!!

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Mary D.
House Sitting
5.0 out of 5 stars

Aubrey took such good care of our two pups! She was professional and made sure to give us updates and pictures! We are excited to use her again for our next vacation!

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Mackenzie J.
House Sitting
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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
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
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Popular requests for house sitting - Windward Trail

Select a filter and find qualifying sitters offering house sitting.

Sitters in Windward Trail average 3
repeat house sitting clients

FAQs for House Sitting - Windward Trail

Frequently asked questions about Rover

The average cost for House Sitting in Windward Trail on Rover is $38.85 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 844 sitters on Rover offering House Sitting across Windward Trail. 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 Windward Trail 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 Windward Trail 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 Windward Trail 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 Windward Trail. On Rover:

  • 95% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 95% 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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