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Top rated Winchester house sitters
“Sarah is so accommodating she not only came for the initial meet n greet but made herself available for an additional visit before my scheduled trip. She took such good care of my 2 boys that they didn't have time to miss me! She followed all directions I left for her but there were a few curve balls that came up and she improvised perfectly!”
“Pamela was wonderful with our three dogs! She was very responsive and friendly and they enjoyed their time with her. Pam was also flexible enough to accommodate a last minute booking change due to illness. We enjoyed meeting her and will be booking her again!”
“We were so happy to find Hannah to watch our fur baby! He is fearful of new people and staying away from home and Hannah took great care of him. We don’t like to leave him for extended periods alone at home and she was more than willing to accommodate our request. She was also patient with us and our check ins.”
“did a great job looking after my two dogs, even my needy problem child 😅 house was spotless after the stay over, and communication was great. will book again when the time comes 😁”
“Shawnda watched our dogs for an overnight getaway, They both loved her and we felt very comfortable having her stay in our home. It was great to get lots of photos showing our happy fur babies while we were gone.”
“Alainnah always does a wonderful job with my pets! I’m lucky to have her as a sitter, I never have to worry, and I know she will send me great photos of the fun times they are having!”
“We were so happy Brittany was able to stay and care for Freja, who can be a challenge. We so appreciate the care and consideration she gave to Freja, and made sure Freja felt safe and happy. Would book her again, thanks.”
About: I can care for a wide variety of animals. Care will include lots of physical and mental stimulation, as well as anything else you’d like! Let me know if your animal(s) needs any additional care such as medication administration or needs to be kept separate from other animals, and I will be more than happy to accommodate your animal’s needs. My dogs will need to come with me for overnight housesitting. There will also be an opportunity to become a private client to avoid the insane Rover fees, so you can save money and I get the full amount that you pay! (Currently, Rover takes 20% of my pay AND charges you even extra!) Just let me know what time works for you and I will do my best to accommodate time you need. I will do my best to be flexible and use effective communication with all my clients. I have 2 dogs, an almost 4 year old cattle dog and a 2 year old golden retriever. I also have 2 cats at home. Let me know in advance if your animal(s) are reactive or aggressive to people or dogs. All dogs will have plenty of training, physical and mental exercise, love, and anything else that they need during the day. They will be treated as if they’re my own whether I’m house sitting at your house or just doing a drop in visit.
About: I have been an animal lover since I was born! I grew up on a farm that included all farm animals; mainly horses, dogs, and cats. I’ve had many years of experience with training, and proper pet care! I currently work from home and I have plenty of time throughout the day for pet sitting! I’m available 24/7 I enjoy walks, and nature so I spend a lot of time outside. I have a large fenced yard, fit for animals. We have a loving friendly 7 year old hound dog named Copper. We live in a safe quiet neighborhood close to trails and parks.
“Hannah took wonderful care of my chihuahua and cat! My chihuahua is very particular about people and he absolutely adores her! She is my go to sitter. Thank you for making my fur babies feel loved and at home while we were away. 😊”
About: I’ve had dogs in my life since I was 5. I’ve had my own dog since I was 16 and currently live in a household with 5 dogs. I even have and do pet sit for friends and family. Proper animal care is like second nature to me. I’m currently unemployed so my availability is very open (especially after June). Taking care of dogs is basically my whole life, we have 5 of them in our household. I also live with a dog trainer so I have a little bit of knowledge on that as well. Proper pet care is my top priority. I take care of clients animals just like they’re my own. making sure they’re fed and watered and have their enrichment time. If your dog gets along with others I will bring mine for a playmate
About: Hi, my name is Nadia! I’m currently trying to save money for college! I’ve been surrounded by dogs my whole life, raising litters of puppies, caring for my own pets, and dog sitting for friends and family. I even took a veterinary science course and was on track to graduate as a vet tech, so I know how to give pets the love they deserve while keeping them safe and healthy. Whether it’s playtime, snuggles, or walks, I treat every dog like my own. I’m available anytime between now and September 15. I leave for college the 20th. I have free weeks and weekends so anytime I’m needed I’m available! I have a fenced yard and 2 dogs myself. One is older and more cranky so I would prefer to sit in the clients home but If not we can figure something out! I have 3 cats at my house as-well.
“Aliyah is top notch. Our pups were cared for as if they were her own. She went above and beyond to make sure our dogs and house was well taken care of while away visiting family. Thanks Aliyah!”
“Breezy was just fabulous took care of my dogs like a they were hers. Was very comfortable that my dogs were in good hands.kept me in touch daily with pictures. Will definitely book breezy again. Thanks breezy for taking care of my dogs.”
“Our dogs enjoyed their time with Christopher! He has a calm and relaxing presence with our anxious pup. Great communication allowed us to relax and enjoy our time away. Will be requesting Christopher again!”
“Jonathan is the best pet sitter I have ever had. He is so loving and caring my fur babies were on vacation being with him. They get so lonely when I’m gone but not with Jonathan ! He even let my pups sleep with him . I can’t thank you enough for the great job.”
About: I have owned a dog and 2 cats for a year now. I have always been around animals growing up. I love taking dogs on walks and playing with furry friends. I’m currently working part time so I have some time to spare. Due to this, my work schedule isn’t always the same each month. But I would love to make some time to help take care of some cute doggies and cats! I have taken care of different kinds of dogs. I rescued a dog from the shelter so I have experience with taking care of animals that can be a bit more difficult. I am willing to clean up messes. I am very patient with animals and I will give them lots of love:)
Loving house sitters in your neighborhood
Search Results
Sarah J.
“Sarah is so accommodating she not only came for the initial meet n greet but made herself available for an additional visit before my scheduled trip. She took such good care of my 2 boys that they didn't have time to miss me! She followed all directions I left for her but there were a few curve balls that came up and she improvised perfectly!”
Jenny K.Star Sitter
“Jenny is fabulous! We’re so grateful we found someone so caring and trustworthy to look after our boys while we’re away. Highly recommend her!”
Pamela M.Star Sitter
“Pamela was wonderful with our three dogs! She was very responsive and friendly and they enjoyed their time with her. Pam was also flexible enough to accommodate a last minute booking change due to illness. We enjoyed meeting her and will be booking her again!”
Hannah C.
“We were so happy to find Hannah to watch our fur baby! He is fearful of new people and staying away from home and Hannah took great care of him. We don’t like to leave him for extended periods alone at home and she was more than willing to accommodate our request. She was also patient with us and our check ins.”
rashell w.Star Sitter
“did a great job looking after my two dogs, even my needy problem child 😅 house was spotless after the stay over, and communication was great. will book again when the time comes 😁”
Shawnda W.
“Shawnda watched our dogs for an overnight getaway, They both loved her and we felt very comfortable having her stay in our home. It was great to get lots of photos showing our happy fur babies while we were gone.”
Alainnah K.
“Alainnah always does a wonderful job with my pets! I’m lucky to have her as a sitter, I never have to worry, and I know she will send me great photos of the fun times they are having!”
Remi R.
“We were so happy Brittany was able to stay and care for Freja, who can be a challenge. We so appreciate the care and consideration she gave to Freja, and made sure Freja felt safe and happy. Would book her again, thanks.”
Cherakea R.
About: I can care for a wide variety of animals. Care will include lots of physical and mental stimulation, as well as anything else you’d like! Let me know if your animal(s) needs any additional care such as medication administration or needs to be kept separate from other animals, and I will be more than happy to accommodate your animal’s needs. My dogs will need to come with me for overnight housesitting. There will also be an opportunity to become a private client to avoid the insane Rover fees, so you can save money and I get the full amount that you pay! (Currently, Rover takes 20% of my pay AND charges you even extra!) Just let me know what time works for you and I will do my best to accommodate time you need. I will do my best to be flexible and use effective communication with all my clients. I have 2 dogs, an almost 4 year old cattle dog and a 2 year old golden retriever. I also have 2 cats at home. Let me know in advance if your animal(s) are reactive or aggressive to people or dogs. All dogs will have plenty of training, physical and mental exercise, love, and anything else that they need during the day. They will be treated as if they’re my own whether I’m house sitting at your house or just doing a drop in visit.
Natalie M.
“Natalie did a terrific job on such short notice providing house and pet sitting needs for us . She was a lifesaver and will definitely use her services again”
Danielle H.
“I am so glad I found Danielle. She takes such good care of my fur babies and is always prompt and attentive to our needs. When I leave my fur babies with her, I know I don't have anything to worry about. Highly recommend.”
Hannah H.Star Sitter
“Hannah took wonderful care of my chihuahua and cat! My chihuahua is very particular about people and he absolutely adores her! She is my go to sitter. Thank you for making my fur babies feel loved and at home while we were away. 😊”
Dot F.
“Dot has a love and passion toward animals and pets. She would be a great caregiver as a dog sitter or walker. You can’t go wrong with Dot!”
Nadia B.
About: Hi, my name is Nadia! I’m currently trying to save money for college! I’ve been surrounded by dogs my whole life, raising litters of puppies, caring for my own pets, and dog sitting for friends and family. I even took a veterinary science course and was on track to graduate as a vet tech, so I know how to give pets the love they deserve while keeping them safe and healthy. Whether it’s playtime, snuggles, or walks, I treat every dog like my own. I’m available anytime between now and September 15. I leave for college the 20th. I have free weeks and weekends so anytime I’m needed I’m available! I have a fenced yard and 2 dogs myself. One is older and more cranky so I would prefer to sit in the clients home but If not we can figure something out! I have 3 cats at my house as-well.
Aliyah F.
“Aliyah is top notch. Our pups were cared for as if they were her own. She went above and beyond to make sure our dogs and house was well taken care of while away visiting family. Thanks Aliyah!”
Breezy K.
“Breezy was just fabulous took care of my dogs like a they were hers. Was very comfortable that my dogs were in good hands.kept me in touch daily with pictures. Will definitely book breezy again. Thanks breezy for taking care of my dogs.”
Christopher C.
“Our dogs enjoyed their time with Christopher! He has a calm and relaxing presence with our anxious pup. Great communication allowed us to relax and enjoy our time away. Will be requesting Christopher again!”
Jonathan V.
“Jonathan is the best pet sitter I have ever had. He is so loving and caring my fur babies were on vacation being with him. They get so lonely when I’m gone but not with Jonathan ! He even let my pups sleep with him . I can’t thank you enough for the great job.”
Elizabet S.
“Elizabeth has been over to watch our 2 dogs many times and they absolutely love her, including our grouchy Beagle who doesn’t get alone with most people. She has shown great compassion for all animals that I’ve seen her with and has a dog of her own that she treats like family. She is patient and understanding to our dogs even when they are not at their best behavior. I recommend Elizabeth to anyone who is wanting their dogs or cats taken good care of. She is also capable of walking with them with no issues.”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
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. 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 Winchester is $45
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 Winchester average 3 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 Winchester on Rover as of Aug 2025 was about $45 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 Aug 2025, there are 32 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, 86% of Winchester house sitters respond in under an hour.
House sitters with repeat customers have an average of 3 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.
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