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Top rated Winchester house sitters
“Natalie house sat my 2 dogs and 3 birds for a long weekend. Natalie is responsible and easy to reach. She responded promptly to any messages. One of my dogs requires special care as a senior and Natalie cared for him well. I would book Natalie again!”
“Jupiter did a great job. The house was clean and orderly when we returned, and the dogs were content.”
“It being our first time using a sitter for our two catahoulas we were understandably nervous. Rachael made the whole process easy, stress-free and an overall great experience. The dogs had a great time and really got along well. Highly recommend!”
“Andrew went above and beyond taking care of Wagner who was very sick a few days before we left . He gave him all his meds and had to deal with reintroducing his food . Kept us up to date twice a day at least . Thank you Andrew !!!!”
About: Hello my name is Jocelyn. I am a huge dog lover and I am unable to currently own any because I live in an apartment. I grew up with dogs and cats. In my pictures ( blonde husky/labs and Weimaraner) are my family pets at parents home. I have experience walking large breeds or handling smaller breeds. Also, I can work with a younger pup and teach it commands. I have volunteered at the Humane Society dog walking.I love dogs and kitties will give my full attention on your fur baby. Making sure your dog stays busy and happy while you are away. Please consider me as your dog walker or dog sitter so your pup stays happy while your away! I love forward to meeting your fur babies!! :) I would be available M-F, mornings earliest 9am, lunch hour flexible, afternoons and evenings. Available occasionally on weekends so please ask if needed those days. Keeping full attention on the pet to make sure they are safe and being cared. Always making sure doors and gates are shut. My parents have a part husky and he likes to be an escape artist.
“Caleigh took amazing care of my pup Rylo He is a rescue that I’ve had for about 3 months and she was great with him, giving him space and he took to her quickly I loved getting the photos and updates each day I feel very lucky finding Caleigh!”
“Jasmin took care of our two dogs at our house for a weekend and did a wonderful job. She was communicative and attentive to details. She took excellent care of our two dogs, including paying close attention to our care instructions and following up with questions when needed. She was easy to reach and quick to respond. Our pups loved her and she left the house spotless. We would book her to take care of our pups again anytime in the future.”
“Ashley is the absolute best!! She has an easy going and wonderful personality and quickly established a great rapport with our 10 month old mini-Aussie. Ashley has stayed at our house to take care of our puppy several times and she has been so open to the dog's needs in terms of walks, feeding, playing. We've loved having Ashley as a puppy care taker and would highly recommend her!”
“Fahad was wonderful with our two fur babies. He stayed in our home so they would be more comfortable. Fahad clearly has a love for animals and is a very kind person. I would highly recommend him and plan to have him stay with our dogs in the future.”
“Aaron did a great job dogsitting our pup, Henry, during the workday. Great communication throughout!”
“Carly stayed with my dog for the weekend and did a fabulous job! She sent frequent photos of their adventures and was excellent with communication. I highly recommend her!”
“Ayat did a great job with my 2 year old black lab Roni over a long weekend. She sent two updates a day with photos and videos, and it sounded like she kept my energetic lab very busy! I'll definitely book with her again.”
“From first contact Rhianna was an A+. She's caring, communicative, and so easy to coordinate with. This was my first experience using Rover and she patiently helped with every step of the logistics when I had trouble with the app. She is responsive, asks great questions, and is extremely kind and capable. Our dog injured her leg just before we went away and Rhianna didn't hesitate to step up with extra care to make sure she stayed safe and happy. The photos she sent us tell the story so clearly: Henry and Lulah were in great hands and can't wait for Rhianna - their new favorite person - to come back soon!”
“We cannot recommend Tricia highly enough! From the moment we met, we knew our home and pets were in great hands. She was incredibly reliable, responsible, and attentive to every detail. Our pets adored her, and it was clear they received lots of love and care while we were away. We came home to a spotless house and happy pets, we made our return so much easier. If you are looking for someone trustworthy and compassionate, look no further than Patricia. We will definitely be booking her again!”
“Buddy was very well taken care off! I would definitely ask Mattthew to watch Buddy again. He provided me with updates and pictures of Buddy every day”
“Christine was lovely with Bonnie. She spoiled her and I felt very comfortable leaving Bonnie in her care. She has a natural gift with dogs and just loves to be around them. Absolutely happy with Christine”
“Martin was very professional and respectful of my pets and home. He is overall the best pet sitter and we will be using him again. Thanks again Martin.”
About: I am a former member of Tufts' "Animal Aid" club, a program that connects Tufts University students with local Medford/Somerville dog owners for free dog walking. Throughout this program, I have walked (and dog-sat for) seven dogs of various breeds, sizes, and temperaments. Even though I've graduated, I still want to continue caring for pets in my neighborhood! You can have peace of mind knowing that your pets will receive high quality care from an experienced, passionate, and attentive caregiver. I am currently a full-time intern in Beverly. Thus, on weekdays, I am available for evening walks after 4pm. On weekends, I am available at any time for walks, check-ins, or extended stays! I am more than happy to discuss your furry friend's specific needs and find a care plan that works best for both you and your pet!
About: I have grown up with dogs all my life, from large Pitts and Rottweilers to Jack Russel Terriers and chihuahuas. I love them all. I am also okay with dogs with some behavioral issues. My current family dog, Milo, has some leash aggression and we have been able to work through it the past 4 years we have had him. I am a fast learner and can follow directions very well. I would love to get to know your furry friend and help you out along the way! I get summer Fridays off from work so it leaves me with plenty of time to be able to house sit on weekend, or even do quick potty break, or walk throughout the day. I also get one work from home day a week (typically Mondays) that gives me additional flexibility. I am a true dog lover an will care for your pet(s) as if it were my own. I understand how important and loved your dog is along with your home. I will be very respectful of both and follow any instructions you give me.
“Danielle was awesome!! Our first booking with her already booked again. She sent lots of pictures of Jackson who always looked happy, the house was spotless, Thank you again!!”
Loving house sitters in your neighborhood
Search Results
Natalie J.Star Sitter
“Natalie house sat my 2 dogs and 3 birds for a long weekend. Natalie is responsible and easy to reach. She responded promptly to any messages. One of my dogs requires special care as a senior and Natalie cared for him well. I would book Natalie again!”
Jupiter B.Star Sitter
“Jupiter did a great job. The house was clean and orderly when we returned, and the dogs were content.”
Rachael B.Star Sitter
“It being our first time using a sitter for our two catahoulas we were understandably nervous. Rachael made the whole process easy, stress-free and an overall great experience. The dogs had a great time and really got along well. Highly recommend!”
Andrew T.Star Sitter
“Andrew went above and beyond taking care of Wagner who was very sick a few days before we left . He gave him all his meds and had to deal with reintroducing his food . Kept us up to date twice a day at least . Thank you Andrew !!!!”
Jocelyn C.
“I highly recommend Jocelyn! She loves all animals but has a deep love and connection with dogs. She is a very attentive, trustworthy, caring and compassionate dogsitter. She looks forward to her dog walks. If you want a true dog Lover then you want Jocelyn!”
Caleigh I.
“Caleigh took amazing care of my pup Rylo He is a rescue that I’ve had for about 3 months and she was great with him, giving him space and he took to her quickly I loved getting the photos and updates each day I feel very lucky finding Caleigh!”
Jasmin L.Star Sitter
“Jasmin took care of our two dogs at our house for a weekend and did a wonderful job. She was communicative and attentive to details. She took excellent care of our two dogs, including paying close attention to our care instructions and following up with questions when needed. She was easy to reach and quick to respond. Our pups loved her and she left the house spotless. We would book her to take care of our pups again anytime in the future.”
Ashley F.Star Sitter
“Ashley is the absolute best!! She has an easy going and wonderful personality and quickly established a great rapport with our 10 month old mini-Aussie. Ashley has stayed at our house to take care of our puppy several times and she has been so open to the dog's needs in terms of walks, feeding, playing. We've loved having Ashley as a puppy care taker and would highly recommend her!”
Fahad S.Star Sitter
“Fahad was wonderful with our two fur babies. He stayed in our home so they would be more comfortable. Fahad clearly has a love for animals and is a very kind person. I would highly recommend him and plan to have him stay with our dogs in the future.”
Aaron G.Star Sitter
“Aaron did a great job dogsitting our pup, Henry, during the workday. Great communication throughout!”
Carly D.
“Carly stayed with my dog for the weekend and did a fabulous job! She sent frequent photos of their adventures and was excellent with communication. I highly recommend her!”
Ayat W.
“Ayat did a great job with my 2 year old black lab Roni over a long weekend. She sent two updates a day with photos and videos, and it sounded like she kept my energetic lab very busy! I'll definitely book with her again.”
Rhianna S.
“From first contact Rhianna was an A+. She's caring, communicative, and so easy to coordinate with. This was my first experience using Rover and she patiently helped with every step of the logistics when I had trouble with the app. She is responsive, asks great questions, and is extremely kind and capable. Our dog injured her leg just before we went away and Rhianna didn't hesitate to step up with extra care to make sure she stayed safe and happy. The photos she sent us tell the story so clearly: Henry and Lulah were in great hands and can't wait for Rhianna - their new favorite person - to come back soon!”
Patricia & Mark G.
“We cannot recommend Tricia highly enough! From the moment we met, we knew our home and pets were in great hands. She was incredibly reliable, responsible, and attentive to every detail. Our pets adored her, and it was clear they received lots of love and care while we were away. We came home to a spotless house and happy pets, we made our return so much easier. If you are looking for someone trustworthy and compassionate, look no further than Patricia. We will definitely be booking her again!”
Mattthew M.
“Buddy was very well taken care off! I would definitely ask Mattthew to watch Buddy again. He provided me with updates and pictures of Buddy every day”
Christine C.
“Christine was lovely with Bonnie. She spoiled her and I felt very comfortable leaving Bonnie in her care. She has a natural gift with dogs and just loves to be around them. Absolutely happy with Christine”
Martin D.
“Martin was very professional and respectful of my pets and home. He is overall the best pet sitter and we will be using him again. Thanks again Martin.”
Jolene G.
“Jolene walked and dog-sat my dog Juniper in-home for two years, and I am devastated that I moved so she can't watch her anymore! She is attentive, responsible, caring, and always reliable. She dealt with Juniper's reactivity really well, and I was always confident leaving Juniper in Jolene's care. I would highly, highly recommend Jolene to anyone.”
Maria J.
About: I have grown up with dogs all my life, from large Pitts and Rottweilers to Jack Russel Terriers and chihuahuas. I love them all. I am also okay with dogs with some behavioral issues. My current family dog, Milo, has some leash aggression and we have been able to work through it the past 4 years we have had him. I am a fast learner and can follow directions very well. I would love to get to know your furry friend and help you out along the way! I get summer Fridays off from work so it leaves me with plenty of time to be able to house sit on weekend, or even do quick potty break, or walk throughout the day. I also get one work from home day a week (typically Mondays) that gives me additional flexibility. I am a true dog lover an will care for your pet(s) as if it were my own. I understand how important and loved your dog is along with your home. I will be very respectful of both and follow any instructions you give me.
Danielle B.
“Danielle was awesome!! Our first booking with her already booked again. She sent lots of pictures of Jackson who always looked happy, the house was spotless, Thank you again!!”
Over 115 pet parents in Winchester have booked house sitting
Winchester pet parents share their Rover experiences
Stacy did a wonderful job with Maple and Cocoa; the pictures she sent were super reassuring, and we came home to two dogs that were happy and clearly well cared for while we were away!
We wholeheartedly recommend Carly as a house sitter. She took wonderful care of our three dogs, keeping us updated with plenty of fun photos and messages. Even our highly sensitive and reactive pup warmed up to her quickly — a true testament to her gentle and caring nature.
Natalie took great care of our pets (cat and dog) and our home! She met with us in person prior to the sit, and provided several updates with photos everyday throughout the sit. We appreciate the care she took to ensure we would feel comfortable and confident during our time away from our pets and home. We would definitely welcome here again and highly recommend her for future pet care :)
Lindy was wonderful with our super energetic pup! She left our house in great condition and was a good communicator. When she ran into an issue with Riley, she let us know it and how it was resolved. Would definitely have her watch Riley again.
Maria did so great with Mouse! Unfortunately, Mouse got into some of her allergy medicine while Maria was sitting her (not Maria's fault at all!). Maria was quick to communicate with us and coordinated with us to make sure we could get Mouse to a nearby vet. Mouse is doing great and we really appreciated Maria's responsiveness and communication.
This is Kristen’s second time watching Muller at our house, and she does a fabulous job! He is happy the whole time!
Rhianna took great care of my Dog Zoey while we were away. She was very communicative and sent lots of pictures!
Alix was terrific. Super responsive, the house was left in terrific shape, and (most importantly) the pets had a great time.
Allyson was a fantastic house sitter! I have three dogs (one of them reactive and one elderly), and two cats, and she was very communicative and did a great job managing all of them. She was very attentive of the instructions I left and sent lots of great pictures as well!
Lindsay took great care of our dog and our chicks while we were away for a few days. She left the house just as it was when she arrived and we received updates throughout the stay!
Catherine was amazing to work with - she is warm and friendly to both people and pets and communicated well. The house was just as we left it and the dog was clearly happy and well cared for upon our return. We would not hesitate to book with Catherine again, and would recommend her without reservation.
Paulina is an amazing sitter, great to come home to a happy pup. Extra attentive to the needs of our somewhat anxious, blind, senior dog!
Ryan was one of, if not the best, dog sitter we’ve ever had! He was responsive when I had a question or request, communicative with check-in dog pictures and updates, and extremely kind and caring towards us and our pups. One of our dogs, Comet, can be reactive, and not only was Ryan knowledgeable and aware with how to interact with our pup, he was patient and sweet towards him. We’ve felt anxious with previous dog sitters, but with Ryan, we truly had no worries, because we knew our dogs were in great hands. We are looking forward to having Ryan watch our dogs, Comet and Alfie, again in the near future!
My experience with Kailee was exceptional. She is a strong communicator and I left for my trip feeling confident the pups were in good hands. She did a great job taking care of them and my home. I would not hesitate to book her in the future.
Louisa house/cat sit for me and was great! They responded quickly to messages, sent a lot of great pics during the stay, and followed all instructions. My cat was happy and healthy when I got back, and my apartment in good condition. Would highly recommend!
Camryn was absolutely fantastic with Moose! She provided great updates and he was so happy hanging out and going on walks while I was away. I'm so greatful I could relax on my trip knowing she was caring for him :)
We cannot say enough wonderful things about Sara and Ari! As first-time Rover users, we weren’t quite sure what to expect. From the very first message through the meet and greet to the actual sitting, they went above and beyond to explain how everything works and to make sure we felt completely comfortable, not just with them but with the whole process. They treated our beloved cats like cherished members of their own family, and their attentiveness, warmth, and genuine love for animals shone through in every interaction. Throughout our vacation, they kept us updated with thoughtful messages, adorable photos, and sweet videos, all without us even needing to ask. But what meant the most was the incredible peace of mind they gave us. For the first time ever, we were able to truly relax on vacation without feeling the constant need to check in or rush home. Our fur babies were clearly happy, relaxed, and so well cared for! They also left our home absolutely immaculate, if not in better condition than when we left it. Their respect for our space and attention to detail made coming home a joy. We’re already looking forward to our next trip knowing our cats will be in the best hands! Sara and Ari are absolute gems, and we feel so lucky to have found them. Future bookings can’t come soon enough!
Helen is a lovely human being. Takes good care of our pets. I know, because they were not as eager to see us. I think they miss her. Highly recommend. Very responsible.
Mackenzie was able to accommodate our request with only a week's schedule, even rearranging her schedule to ensure she could spend more time with our dog. Bella, who is usually an anxious dog, seemed really comfortable with her right from the start. She kept us updated during the day with cute photos. Would recommend!
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 $60
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 Jul 2025 was about $60 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 2025, there are 5,950 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, 83% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 14 years of experience. 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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