House Sitting in Winchester

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

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Top rated Winchester house sitters

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: Della B.
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Della B.
Star Sitter
from
$50
per night
4.9 out of 5 stars
77 reviews
23 repeat clients
10 years of experience
Winchester, TN, 37398

Della was available on short notice and took good care of my fur baby.

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Linda W.
Sitter Profile Image: Hannah D.
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Hannah D.
from
$55
per night
5.0 out of 5 stars
5 reviews
1 repeat client
17 years of experience
Cowan, TN, 37318

About: I've been a pet groomer for 17 years, with 10 years under ownership of a veterinarian clinic. I've been doing pet sitting in client's homes for several years. I love all animals, but have a special love for the elderly and ailing. I'm experienced in giving medications, injections, grooming, etc. Feel free to reach out by message or email for extra details or for services outside my specified range. I work 8-4 Tuesday through Friday, and 8-2 on Saturdays. I do sitting overnight, mornings before work, and afternoon/evenings after work. In some cases, if I am overnight sitting, I may also be able to bring a dog to work for daycare as well. Requirements for that include proof of rabies vaccination, spay/neuter after 6 months, and an understanding of general temperament. I have several years experience dog sitting in client's homes. I'm able to walk, play, administrator medications, feed, and do daily maintenance for coat and skin.

Sitter Profile Image: Mike M.
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Mike M.
from
$65
per night
4.9 out of 5 stars
44 reviews
10 repeat clients
35 years of experience
Manchester, TN, 37355

Mike was great! We just moved into a new home so our baby girl was in a more protective state than normal. Mike took the time to come out not once, but twice! to make sure she was comfortable with him before we confirmed our booking. By the end of his stay, she was giving him hugs so she loved him so much. Our baby boy is still such a pup and Mike was patient with him. He left our home as he found it and sent us pictures while we were gone so we could see our babies having fun. It was so nice to not have to worry about them knowing that they were being well cared for while we were gone. We definitely would like to book Mike for any future trips we take.

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Molly F.
Sitter Profile Image: Kristine G.
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Kristine G.
from
$50
per night
4.4 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Tullahoma, TN, 37388

About: For the past year, I have spent every Wednesday night volunteering at my local dog rescue. I feed, clean, administer medication, and play with the rescued dogs. We have two senior dogs that need extra care, and we also take care of dogs that have been injured or are sick. I have almost two years of experience volunteering at the local cat rescue as well, and I'm known to be an animal whisperer. I have three cats of my own, and know that pets truly are family members. Normally I go in the evenings to the dog rescue around 5 o'clock to feed the animals before going home. It has become a weekly ritual for me outside of taking care of my own cats. I won't be able to keep client's pets at my own house, since my cats are very possessive. I am available for check ins or overnight stays.

Sitter Profile Image: Kristen T.
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Kristen T.
from
$65
per night
5.0 out of 5 stars
21 reviews
8 repeat clients
20 years of experience
Tullahoma, TN, 37388

Thank you so much for your service. You’re very trusting. And reliable person to take care of my animals.

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Ilona M.
Sitter Profile Image: Abigail P.
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Abigail P.
from
$40
per night
5.0 out of 5 stars
2 reviews
4 years of experience
Estill Springs, TN, 37330

About: With two years at a dog shop, I've mastered boarding, grooming basics, and playtime. Growing up with dogs, now owning a Frenchton and Shih Tzu, I offer hands-on, loving care beyond the basics! I’m currently working part time at another job! So I’ll have plenty of time in the afternoons and weekends for all your fur babies needs! In my home and clients homes, I ensure pets have been feed, fresh water, and exercise. I maintain a clean environment, provide companionship, and follow specific care instructions from their owners.

Sitter Profile Image: Hannah C.
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Hannah C.
Star Sitter
from
$35
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
15 years of experience
Murfreesboro, TN, 37129

Hannah, aka Mikki, was awesome!!! Super personable, great communication, & took great care of both my critters. I would absolutely use her again—thanks Mikki!!

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Sam J.
Sitter Profile Image: Gabby G.
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Gabby G.
from
$45
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
3 years of experience
Tullahoma, TN, 37388

Gabby was very good with Chester, responsive to messages, and very respectful of the house. Will book again.

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Autumn A.
Sitter Profile Image: Lucius G.
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Lucius G.
from
$30
per night
12 years of experience
Hillsboro, TN, 37342

About: My name is Luke, I am a CATCH Canine Trainer Academy certified dog trainer. I use positive reinforcement to encourage and maintain behaviors. I have always had a passion for working with dogs but after losing one of my rescues to cancer only 2 months after saving her my passion grew. This had inspired me to help owners and their dogs learn and grow together. I am a Co owner of a food truck which we are only operating part time. On the opposite days I have open availability to help support you and your current fur baby. I am unable to offer boarding for animals at this time. I am certified in pet cpr and first aid through ProPetHero by Pro Trainings

Sitter Profile Image: Brianna B.
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Brianna B.
Star Sitter
from
$85
per night
5.0 out of 5 stars
5 reviews
4 repeat clients
10 years of experience
Scottsboro, AL, 35767

Bri did a wonderful job looking after our cats and dog and hen. Came home to everyone calm and relaxed like we had never left. Absolutely no reservations about having her house sit again.

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justin g.
Sitter Profile Image: Josue M.
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Josue M.
from
$30
per night
5.0 out of 5 stars
3 reviews
1 repeat client
11 years of experience
Sewanee, TN, 37375

Hey was amazing with our 3 dogs! Sent great pictures and even printed them out and left them for us. He comforted all our dogs during storms and even cleaned before leaving! Absolutely great!

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Erin A.
Sitter Profile Image: Alydia M.
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Alydia M.
from
$60
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
16 years of experience
Christiana, TN, 37037

Our giant doofus of a dog loved her. She took care of not only the dog and cat but also two dramatic pigs and two stubborn goats. When we had last-minute scheduling hiccups she was flexible and understanding. We're grateful we found her!

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Rachel B.
Sitter Profile Image: Kaitlyn P.
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Kaitlyn P.
from
$75
per night
5.0 out of 5 stars
3 reviews
10 years of experience
Tullahoma, TN, 37388

About: I have been a veterinary technician for 3 years, and have experience working with and caring for dogs, cats, birds, fish, and rodents of all ages (a few days old-senior ages) for 10+ years. I currently work full-time at a veterinary clinic, but normally have 2-3 days off and often have scheduled half days where I am able to tend to my own pets as well as other people’s pets. I have a large yard and love walking, so your baby will get plenty of exercise. I also have cats and a dog, all of which are very friendly and well socialized, to keep your babies entertained and keep them company.

Sitter Profile Image: Anita M.
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Anita M.
from
$50
per night
15 years of experience
WINCHESTER, TN, 37398

About: Our home has always been filled with dogs and cats. The strays find me and know they will always have a spacial place to call their own. I own a small consulting business and have flexibility with my schedule. I am easing into early retirement and looking to share my love of animals. I am an experienced professional who is phasing into early retirement. I have spent years traveling and have an empathy for pet parents who have to leave their fur babies while away from home.

Sitter Profile Image: Peyton T.
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Peyton T.
from
$26
per night
3 years of experience
Cowan, TN, 37318

About: I am friends and families go to dog sitter for when there is vacations, or someone is busy. I have been doing this for family and friends for a couple of years now im currently college student and would love to watch over your fur babies! with me being in school and work i’m normally pretty flexible with my schedule as all my classes are early in the morning! I have a huge fence around my yard and two adorable fur babies if yours are needing some company. I will be able to watch over your dog at all times if needed.

Sitter Profile Image: Christabell E.
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Christabell E.
from
$55
per night
26 years of experience
Shelbyville, TN, 37160

About: I have many years of caring for pets and ran my own kennel in Florida for about 13 years and was a Vet technician for 8years I’m available weekends and can also be on call if needed. I can also be available on some Wednesday’s and holidays I’m open to any times I will care for your pet as if they are my own fur baby and will provide what is needed to take the best care of your pet

Sitter Profile Image: Jenn G.
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Jenn G.
from
$79
per night
5 years of experience
Manchester, TN, 37355

About: I’ve taken care of pets from rabbits to dogs for several years. I understand that you know your pet best so I look forward to taking on the various tasks that your pet needs to continue to feel like you are the one taking care of them! My husband and I are run a commercial real estate company remotely. This puts us in the position to be flexible while pet and home sitting. We are active walkers and will gladly take your pet/s on a walk. I am attentive to their needs and I am able to follow special instructions. I love to take the customized approach since you know your pet best!

Sitter Profile Image: Shelby Sadler
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Shelby Sadler
from
$50
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
4 years of experience
Tullahoma, TN, 37388

About: My name is Shelby. I’m 23 and I have 2 dogs, a cat, a Bunny, Hamster and Two Turtles as my pets. I’m a Pet Groomer. I am full time work working with clients and taking care their pets while they are out of town dogs sitting and pet grooming/bath to make their furbabies them pretty. I love and respect animals. I am looking to gain more experience in pet care and I want to build by client base. I listen, take notes, and follow instructions. I will give your pet 100% of my attention while I am with them. I am excited to take on these new challenges in my life and look forward to taking care of your pet’s needs. Thank you and look forward to meeting you. Premium Bath Only! Bath, Blow dry, brush out, Scented spray , Nail trim, Ear cleaning, Fresh Breath treatment Small Dogs (Up to 15 Ibs) $30 Medium Dogs (16-40 Ibs) $34 Large Dogs (41-80 Ibs) $38 X-Large Dogs (81Ibs and Up) $42 Wash And Go Spa baths Bath & Towel dry Small Dogs (Up to 15 Ibs) $15 Medium Dogs (16-40 Ibs) $20 Large Dogs (41-80 Ibs) $25 X-Large Dogs (81Ibs and Up) $35 De-shedding Treatment Bath ,Blow dry, brush out, Scented spray , Nail trim, Ear cleaning. the prices are Small Dogs (Up to 15 Ibs) $20 Medium Dogs (16-40 Ibs) $30 Large Dogs (41-80 Ibs) $40 X-Large Dogs (81Ibs and Up) $50 Others spa services Ads ons Nail trim $12 Nail file $12 Nail trim & Nail file $18 Fresh breath treatment $12 Ear Cleaning $10 Paw Balm $8 Hypoallergenic Shampoo Upgraded $15 Flea and Tick Shampoo & Flea/Tick pet spray $18 Oatmeal Shampoo & conditioner Updated $11 Tea Tree & Aloe Shampoo & conditioner Updated $11 Nature's Miracle Skunk Odor Control Shampoo & Conditioner Lavender Scent Updated $11 Nail Polish $12 Hair color $20 add Glitter power $10 Pet Grooming service •Tidy up Bath & Trim Bath, Blow Dry, Brush out, Scented Spray, Nail Trim, Ear Cleaning, Basic Feet, Face and Sanitary Trim NO Body Take off!! Small Dogs (Up to 15lbs) $35 Medium Dogs (16-40 lbs) $55 Large Dogs (41-80 Ibs) $70 X-Large Dogs (81lbs and up) $90 • Full Groom Bath, Blow dry, Brush out, Scented Spray, Nail Trim, Ear Cleaning, Bandana, Bowtie or Hair Ties. Small Dogs (up to 15 lbs) $50 Medium Dogs (16- 40lbs) $60 Large Dogs (41-80 lbs) $75 X-Large (81lbs and up) $95 I will not be available those day on my calendar.My only day off is Saturday and Sunday. let me know when it is best for your dog or cat to need a drop-in visit, dog walking, playtime and grooming. I have a private fence in yard, I also have crates if needed. I love spending time with dogs and cats as well as caring for them like family.

Sitter Profile Image: Milly G.
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Milly G.
from
$55
per night
15 years of experience
Bridgeport, AL, 35740

About: I’ve taken care of my pets for as long as I can remember. That moved onto actual sitting when I was in middle school. I have cared for elderly dogs, special needs animals, and puppies. I am reliable to take your overactive dog on the walk it needs and am comfortable with a multiple dog or mixed animal household. I am working part time in a pharmacy currently while I apply to pharmacy school. I have pretty flexible hours and am off most weekends! I have a small yard at my home and can easily crate your dog if needed. I live in a small safe neighborhood with many neighbors who also own pets.

Sitter Profile Image: Kyra C.
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Kyra C.
from
$80
per night
2 years of experience
Scottsboro, AL, 35768

About: I have lifelong experience caring for pets, having grown up in a household with animals and being responsible for their daily care. I’ve also provided pet sitting services for friends, including feeding, walking, basic care, and ensuring pets stay comfortable and happy in their familiar environment. I am dependable, attentive, and committed to treating every pet as if they were my own I have a very flexible schedule and am available full-time for pet care. I currently do Walmart Spark deliveries, which allows me to create my own schedule and easily work around pet sitting, walks, drop-in visits, and other pet care needs. This flexibility helps me provide dependable care and plenty of attention for your pets I care for pets in their own home, where they feel most comfortable and secure. I follow your pet’s usual routine, including feeding schedules, walks, playtime, and any special instructions you provide. I also make sure they get plenty of love, attention, and companionship while you’re away. For dogs that enjoy getting out and about, I can take them on walks or trips to the park for exercise and fun. I treat every pet as if they were my own and strive to make their time away from you as stress-free as possible.

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Over 14
pet parents in Winchester have booked house sitting

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The median cost per night for house sitting in Winchester is $43

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

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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 Winchester on Rover as of Jun 2026 was about $43 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 Winchester 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 36 house sitters in Winchester. 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, 90% of Winchester house sitters respond in under an hour.

Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Winchester.

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. Winchester 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.