House Sitting in Middleway

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Middleway house sitters

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: Heather & Melina I.
Verified Enhanced Background Check
Heather & Melina I.
Star Sitter
from
$55
per night
5.0 out of 5 stars
82 reviews
27 repeat clients
40 years of experience
Martinsburg, WV, 25405

Heather is the absolute best! She took wonderful care of our baby, and we can’t thank her enough. Great communication, and she took the time to send us daily pics to let us know how our pup was doing while we were gone.

Profile image
Jennifer M.
Sitter Profile Image: Aly P.
Verified Enhanced Background Check
Aly P.
Star Sitter
from
$40
per night
5.0 out of 5 stars
31 reviews
12 repeat clients
16 years of experience
Martinsburg, WV, 25405

Aly was kind and communicative. Our dogs seemed to love her, and she sent regular updates throughout the booking. I would definitely recommend!

Profile image
Molly R.
Sitter Profile Image: Jessica M.
Verified Enhanced Background Check
Jessica M.
from
$40
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Winchester, VA, 22601

Was gone for about 3 days. Jessica was able to provide me with a morning and afternoon report on how my pets were doing and sent me plenty of pictures. I was so grateful and was able to enjoy my trip knowing that they were in good hands. My 2 cats and pup were so comfortable with her. Definitely recommend and will rebook again!

Profile image
Jessica N.
Sitter Profile Image: Ava K.
Verified Background Check
Ava K.
from
$28
per night
18 years of experience
Martinsburg, WV, 25405

About: Hi! I'm ava and I've grown up with animals my whole life, i'm used to taking care of senior dogs with disabilities like blindness, deaf dogs/cats or joint problems, I'm also good with puppy's kittens and older cats, with or without disabilities. I now own 2 of my own cats, honey and astra, and 1 dog named milo❤️. I love animals so much, I'll take care of your animal as if they are my own, and make sure they always feel loved! I also am good at tricking dogs and cats to take their medicine if needed!😊 I am available any day and almost anytime! I am currently trying to start my own small business selling art, So I can adjust my schedule very easily! I will have dog or cat treats always with me to: gain trust, teach to sit, and any other circumstances! When walking animals I will keep my eye open for cars and other animals to keep your animal safe at all times!

Sitter Profile Image: Lindsey J.
Verified Background Check
Lindsey J.
Star Sitter
from
$80
per night
5.0 out of 5 stars
53 reviews
13 repeat clients
13 years of experience
Martinsburg, WV, 25404

Lindsey took care of our 2 dogs, a cat and our home. Not only was she wonderful with all the animals she kept my home neat and clean. She even changed the bedsheets. I would definitely recommend her. She is a blessing and made me feel comfortable leaving my family with her.

Profile image
Linda F.
Sitter Profile Image: Joshua D.
Verified Enhanced Background Check
Joshua D.
from
$50
per night
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Martinsburg, WV, 25405

About: I am ready and able to handle anything your dog throws at me (figuratively and literally). I love to hike with my two pups and they have two widely different paces, so I have alot of experience with different styles and activity levels. I am comfortable with any breed and size. From talkative beagles to slobbery Newfoundland's. I have sat and walked for neighbors and friends and this has brought great experience. Cat dad at home 🐈 🐈‍⬛️ Taking care of your pets is my top priority. It is a passion of mine to make sure they are well cared for and loved. I have a deep affection for all dogs and form strong connections quickly. I have a fenced front yard as well as a larger field that is also fenced. I have mowed trails so we can go on little nature walks.

Sitter Profile Image: charlotte g.
Verified Enhanced Background Check
charlotte g.
Star Sitter
from
$40
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
8 years of experience
Winchester, VA, 22601

Our 130# Newfoundland and cat were well taken care of. Communication was great, even using a different app since we were in Europe. Would not hesitate to use Charlotte again, she cared for our animals like they were hers.

Profile image
Giovanna C.
Sitter Profile Image: Lauren H.
Verified Background Check
Lauren H.
Star Sitter
from
$125
per night
5.0 out of 5 stars
110 reviews
50 repeat clients
34 years of experience
WV, 25413

Its hard leaving you fur babies with someone new. This was my first Rover experience and I couldn't be happier. The communication during my absence was great and my twp dogs exceptionally well cared for. 10/10 will use again!

Profile image
Lisa N.
Sitter Profile Image: Linda S.
Verified Background Check
Linda S.
from
$65
per night
4.9 out of 5 stars
103 reviews
53 repeat clients
40 years of experience
Clear Brook, VA, 22624

Linda was a life-saver and took such great care of our pets and house so we could attend to a last minute family emergency. She did a fantastic job and we will definitely use her again in the future.

Profile image
Mae-Beth M.
Sitter Profile Image: David M.
Verified Enhanced Background Check
David M.
from
$69
per night
30 years of experience
Charles Town, WV, 25414

About: I have been around animals my whole life! Anything from a cat, dog, frog, snake, lizard, horse, rats, birds. I love them all! I regularly document my walks and animal care routines and am happy to share examples upon request!🫶 Hello there hows it going? ! I work part time Door Dashing so would like to increase my income and hopefully just do rover full time! I have a large fenced yard that can host quite the dog party. I have 2 dog friendly dogs to give your precious fur babies company too! I also have a car to drive to your home for petcare too of course!

Sitter Profile Image: Charles L.
Verified Enhanced Background Check
Charles L.
from
$55
per night
5.0 out of 5 stars
3 reviews
1 repeat client
11 years of experience
Charles Town, WV, 25414

Charles is awesome. He is sooo generous with meeting me and Woody before my trip. Charles was excellent with giving me an update during his stay at my house with Woody.. Woody loved Charles & they got along fantastic. I would recommend Charles to anyone with a pet! He was extremely respectful of my house, generous with his time & Woody loved him. There is a 💯 % I will ask him to watch Woody again!

Profile image
Paul C.
Sitter Profile Image: Alexia K.
Verified Enhanced Background Check
Alexia K.
Star Sitter
from
$70
per night
4.9 out of 5 stars
20 reviews
5 repeat clients
15 years of experience
Harpers Ferry, WV, 25425

Alexia was absolutely wonderful with our 2 pups and I am so glad we booked with her! She stayed with our pups all day and did an amazing job! Our older golden just had ACL surgery so she was great with taking extra care of him! Our younger golden has a lot of energy and she did great at keeping him entertained and happy. We will definitely be booking again! It was so great to be able to go away for the day and know our pups were happy and very well cared for!

Profile image
Steph D.
Sitter Profile Image: Tess B.
Verified Enhanced Background Check
Tess B.
from
$65
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
10 years of experience
Charles Town, WV, 25414

About: Hi, I’m Tess! I live in Charles Town, WV with my two-year-old Cavalier King Charles Spaniel, Louie, and two cats, Tatiana and Rudy — so your pet is walking into a home that already loves animals. I take a slow, easy approach to dog care. I let dogs sniff, wander, and just be themselves, whether we’re doing a neighborhood walk, a quick potty break, or a longer trail outing. Every walk is just two dogs at most, so your pup gets real time and attention. I always send photo updates along the way so you can see how they’re doing. I welcome dogs of all sizes who are friendly with other dogs, cats, and people. For boarding, I have a large fenced backyard and keep things small and relaxed — more like a home than a kennel. I also offer occasional house sitting for dogs who are happiest in their own space. I’d love to meet your pup! Feel free to reach out to check availability or set up a meet-and-greet. Fridays are my day off, so walks are unhurried and get my full attention. For boarding, I'm home all weekend, so any dog staying with me has someone around rather than sitting alone in an empty house. Dogs staying with me have access to a large fenced backyard and are never left alone outside. Inside, I keep a calm, low-stimulation environment. My Cavalier Louie lives here full time, so any boarding dog will be introduced to him gradually and supervised until I'm confident they're comfortable together. I do a meet and greet with Louie before confirming any boarding stay. For house sitting, I follow the owner's routine as closely as possible so the dog's environment feels as normal as it can while they're away. Photo updates are sent throughout any service.

Sitter Profile Image: Vicki T.
Verified Enhanced Background Check
Vicki T.
from
$50
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
30 years of experience
Harpers Ferry, WV, 25425

Vicki was great, Will most certainly use her again.

Profile image
Dustin K.
Sitter Profile Image: Faith W.
Verified Enhanced Background Check
Faith W.
from
$70
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Charles Town, WV, 25414

Faith took such good care of our dogs! Would highly recommend her to anyone!

Profile image
Carrie F.
Sitter Profile Image: Day B.
Verified Background Check
Day B.
from
$60
per night
4.9 out of 5 stars
67 reviews
25 repeat clients
20 years of experience
Charles Town, WV, 25414

Day was very attentive and thorough. She was able to fit me in last minute, and my dogs loved her. She updated me everyday. I highly recommend her and will definitely book with her again!

Profile image
Lee-Ann F.
Sitter Profile Image: Lauren L.
Verified Enhanced Background Check
Lauren L.
Star Sitter
from
$31
per night
5.0 out of 5 stars
58 reviews
17 repeat clients
6 years of experience
Shepherdstown, WV, 25443

Lauren was friendly and even came a little early! I left for work knowing Diego was a happy pup in good hands. He greeted her with lots of kisses and even took the initiative to find out where cleaning supplies were after I mentioned Diego happy pees and cleaned up after him without needing to be asked. We will definitely be repeat customers! Thanks Lauren :)

Profile image
Jessica T.
Sitter Profile Image: Ariadna O.
Verified Enhanced Background Check
Ariadna O.
from
$40
per night
16 years of experience
Ranson, WV, 25438

About: I had my baby boy, Lui, for 14 years. He is my first and only dog 🐕. I have had my Theo for almost 6 years and our Misha for 2. They are my babies💓 I have been dog and cat sitting as needed for friends, neighbours, and family for a few years now and always love it. I am open to taking care of any pet, just let me know what they require and I will do my absolute best to cater to their needs! 💗 I am currently focusing on online school to be a certified paralegal. I am not working anywhere else, so I have a lot of free time and plan on doing this full time. It's really important to me that I'm making sure I am paying a lot of attention to my kitties so their needs are being met. Not only that, but i like to make sure that they feel seen and heard. Cats can be very clear with their communication if you're willing to pay attention. When it comes to others' babies, I like to make sure I get enough information to be able to care for them the way they are used to and will make them feel the least stressed while you're away.

Sitter Profile Image: Noel W.
Verified Enhanced Background Check
Noel W.
from
$40
per night
4 years of experience
Charles Town, WV, 25414

About: Companion animal care in high school, a member of FFA, have had pets my whole life ranging from dogs-lizards-spiders-etc!! Experience with larger working breeds and senior pets as well. Also have experience with exotics such as snakes lizards frogs and so on I work night shift 4 days a week, and would love to have a new reason to be up and moving during the day. I have more free time than you’d expect, and I’d love to spend it caring for your fur babies I follow instructions thoroughly, and have more than enough extra love to show them, if you have any questions feel free to ask!! I’m willing to answer any and all of them

Sitter Profile Image: Natalie B.
Verified Enhanced Background Check
Natalie B.
from
$55
per night
5 years of experience
Winchester, VA, 22601

About: I work full time at Shenandoah University and am joining Rover to formalize my side hustle, which Ive largely managed through word of mouth thus far. I’ve lived with dogs for about 25 of my 30 years of life - mostly hounds (most recently 2 bassets). And I’ve watched dogs of all sizes, the smallest being a chihuahua mix and the largest a Great Dane. Over the last 5 years or so, I’ve dog sat for friends, family, and connections in the Winchester area. The longest engagement was 6 weeks, but I normally do long weekends or week long jobs. All animals are different and I respect you, their owner, to tell me what’s best for your furry friend. I also will be transparent and over communicate with you so we both can be confident your animals have everything they need. I’m comfortable dispensing medication - including to the really picky ones (I can take a pill/pill pocket and sculpt it pretty much exactly the same shape and size as any mainstream kibble brand). I have experience with puppies and with our senior citizens, who both just need a little extra care and attention. I feel comfortable listening to animals and getting to know their personalities, which are all so different yet equally endearing. If they are trying to say something, though, I feel pretty confident I will notice it - especially after we’ve spent a few hours together. And, if they’re trying to say something and I don’t understand? I’ll reach out just to make sure. I just really, really love animals. I most often watch dogs but have also cared for cats, lizards, bunnies, chickens, and horses (although horses were largely just feeding and brushing/attention). I also have a rescue cat of my own, Luna, who has made me certain I’m equally a dog person AND a cat person. I work 9-5 M-F, and occasionally am tied up on weekends with happenings on campus. I can take an hour lunch (and flex a bit beyond if necessary) to visit the animals for attention and potty breaks. I am single, sober, and genuinely grateful for the work and the company. Animals have so much love to give, and i try to reciprocate that love indiscriminately. Thanks for your consideration and please let me know if I can answer any questions, hop on a zoom call, or speak to any specific needs you find important. No request is too small and I’m grateful for any and all details I can use to keep your animals feeling secure, loved, and cared for in your absence. I work full time at Shenandoah University as an Administrative Assistant in the Office of Global Engagement. My role is in-person on the main campus in Winchester. My routine hours are 9-5 with an hour lunch around 12 or 1. But, there’s a lot of flexibility, especially over the summer when the students are back home. My team is small and I am able to shift my hours when I communicate with them in advance (I.e. I’ll take 2 hours midday but clock in at 8, etc). Outside of work, my schedule largely centers around community and service work. I’m really involved with the recovery community and attend several meetings and events a week, although I can be flexible there too. Most days I’m up no later than 7 am and asleep by 11. But all these things can flex, depending on your and your pets needs. I live alone with a stray-turned-adopted cat named Luna (who I’m preparing to spay, which is part of my need for a more stable second income!). My place has a small fenced area in the back, enough room for a pup to potty but not much more. But I’m also about a half a mile from Jim Barnett Park and I love their walking trails and their dog park. I’d prefer to house sit at your house, but I’m open to certain scenarios if I can ensure your animal is comfortable in my space. Let’s talk about the details!

1 / 1
View more sitters

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

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

  • World-class support

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

Sitters in Middleway average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Middleway on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Middleway house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 417 house sitters in Middleway. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Middleway house sitters respond in under an hour.

House sitters in Middleway have an average of 16 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Middleway.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Middleway house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.