House Sitting in Winchester
Find a loving house sitter to watch over your pets and your home.
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Loving house sitters in your neighborhood
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1. JaNiya P.
“JaNiya is a phenomenal housesitter, especially if you have shy animals (but *any* animal would love her!). We have two skittish greyhounds and a very shy adopted cat. Within one day, our cat was sitting in JaNiya’s lap, and our dogs were relaxed and happy. I couldn’t believe it! She has such a calm, tender presence, and you can tell she adores animals. She’s even studying to be a veterinarian! Do not pass her up! She’s the only housesitter we’ll use from now on!”
2. Mike M.
“What a great sitter!! This was our first time using Rover and generally have relied on family/friends to watch our 3 boys! Since moving to new state we dont know many and based upon reviews we gave Rover a shot! Mike was welcoming and we instantly knew our boys would be fine. Very personable and easy going, Mike took to our 3 boys like they were his own. Would highly recommend him!! In fact we have already booked him for more future dog sitting.”
3. Susan F.
“Susan was wonderful. Archie had a great time with her. Susan took Archie on some wonderful walks and gave the attention that Archie needed while I was away. Susan was also flexible with my schedule. There was a time that I was coming back to my house then leaving, then coming back. She was very gracious and professional when these unforeseen events happen. I would definitely use her again when I am traveling.”
4. Ren M.
“Ren stayed at our house and watched our two dogs for the weekend. She sent photos and was easy to communicate with. Returned to a clean home and happy pups! Will definitely book again.”
5. makaylah s.
“She is absolutely amazing with animals and currently has some of her own! She takes great care of the dogs she has and even does amazing with my dog! Anytime she’s at the house, she is very loving and playful with her. She’s even had experience working a doggie day care! I know she would be a wonderful, reliable, and loving person to watch over your dog!”
6. Katelynn C.
“Katelynn would be an exceptional caregiver for any type of pets. Her compassion and love of animals gives her a special connection with animals that she meets. My 2 cats are very shy of anyone that come over and will hide until they leave. They will come out within minutes of her arrival and go to check her out. I strongly recommend Katelynn to be a caregiver of anyone’s pets.”
7. Chelsea S.
“We had used Rover a couple of times before, but this was our first time with Chelsea and she was great! She stayed with our dogs for a week and took really good care of them, which is saying a lot because they are still very high energy for 6 year olds. She sent us pics and updates and was very responsive whenever I reached out. We highly recommend her.”
8. Hannah B.
About: I’ve taken care of dogs since I was around the age 10-11. I love to be around and take care of dogs of all types! I’m currently working 38 hours a week at Dunkin! I am able to take of fur babies after 9 on some nights and mid day on other days! I can only take care of pets at my clients houses! I have 3 dogs of my own so I rather take care of the fur babies at their own house!
9. Alydia M.
“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!”
10. Brittany D.
“Brittany was absolutely phenomenal with my kiddos! I would recommend her to anyone & everyone! Her prices are extremely reasonable! And she is hands down one of the best sitters, we've ever had! I have two high energy pups whom are a little over a year old; Miah Hale (Siberian Husky/Alaskan Malamute) & Artemis Skye (Australian Cattle Dog). I was a little nervous about leaving Artemis, even if only for an couple hours since he tends to be a little picky about whom he likes & doesn't like. But, Brittany came over to them prior to watching them... and Artemis took to her like a bee to honey. My fiancè was quite impressed, to say the least. And we knew right then & there, that she would be the best fit to watch them. She was definitely a delight to work with, and we look forward to having her watch our kiddos again in the future!”
11. Amanda B.
“Amanda was awesome to my little geriatric dogs. They are spoiled rotten and have several quirks to their care. She stayed a week in my home and very attentive to everything asked of her. Highly recommend!”
12. Daniel B.
“Daniel was awesome! Great communication and provided photos. This was our first time using Rover and we were nervous leaving our boy. Cash loved him and we got to enjoy our getaway a little less worried. We came home to a clean house and a happy boy. We will definitely use Daniel again.”
13. Jayda K.
“Jayda is a lifelong, passionate dog owner, and it shows. Their love for animals and their ability to bond with them and care for them is exceptional. I can easily trust them with my pets, both the dogs and the cat. I can always count on my companions being safe and happy with Jayda, who clearly loves them almost as much as I do.”
14. Josh & Thomas C.
“Josh chadd is a very kind hearted person. He loves his dogs like a mother loves her children. I honestly trust him with my dogs 100%. I highly recommend him to take care of anyone's fur babies. You can't go wrong when hiring Josh to treat your pets as his treats his own.”
15. Kaitlyn P.
“I hired Kaitlyn to care for my elderly dog for a week while I had a family emergency out of state. Kaitlyn took Excellent care of Jazzy and always sent me a daily update/picture to ease my worries about being away from him. She was very responsible, she is dedicated and has a great passion for animals. Kaitlyn is friendly and dependable and I would hire her again in the future, if needed.”
16. Laila R.
About: As a Rover Dog Caregiver, I am committed to providing exceptional care for your beloved pets. With a background in veterinary technology and a passion for animals, I ensure that your furry companions receive the attention, exercise, and affection they deserve. Whether it's daily walks, playtime, or overnight stays, I tailor my services to meet the unique needs of each dog, creating a safe and comfortable environment for them to thrive in. With me, you can rest assured that your dogs are in loving and capable hands. I often volunteer at dog sanctuaries with disabled and senior dogs. And I have one puppy and one adult (both female) of my very own!! I also have a female cat I adopted 5 years ago!! I’ve cared for various small animals and reptiles also. I am an upcoming freshman in a Veterinary Technology program. I’m currently working part-time and there is never “not enough time” to care for pets!! Everyday I take time out of my day from my dogs to enjoy my company. There is no excuse for neglect! Although I do not have a fenced home I have a LOT of yard space and my neighborhood is perfect for dog walks. I also live 5 minutes away from a trusted dog park. Just tell me what I can do to best care for YOUR animal since not all dogs/cats are the same.
17. Aubree T.
“She took good care of our pup and kitty!”
18. Sarah S.
“My husband was in a traumatic motorcycle accident and has been in the hospital/rehabilitation hospital for several months now. Sarah has been keeping our fur baby, Ziggy, while we are away. She’s been absolutely wonderful and sends us updates along with pictures/vidoes all the time. I have never once worried about Ziggy’s care with Sarah which has been a blessing when we have many other things to worry about at this time. I would 100% recommend Sarah to take care of your fur baby. She treats our Ziggy just like her own!! She’s amazing!!”
19. Michelle H.
“Best house/dog sitter. Very communicative, patient with a rescue dog and a very needy dog. I knew my dogs and home were in great hands! I would use her again and again! A must book.”
20. Kayla A.
“We usually come to Huntsville for Christmas to see family since I grew up there & we travel with our Cavalier King Charles Spaniel. I had a bad experience once with a couple who came to sit for us so I was a bit skittish. Kayla was wonderful though! She is down to earth & accommodating & my little munchkin loved her!”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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 Jul 2024 was about $40 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.
As of Jul 2024, there are 23 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, 94% of Winchester house sitters respond in under an hour.
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 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.