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Top rated Winsted house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Katie was absolutely lovely, and the pets got on with her really well. She sent through updates and photos, and made sure we felt comfortable (all on a holiday, too!) -- thank you Katie!”

“Jared stayed over night with our dog Moose. He was very communicative, sent constant picture updates and was also very flexible on timing. He made sure Moose was well taken care of. We will definitely use Jared for any future needs for Moose.”

“Theresa was great with my tiny puppy (14 weeks)! I came home to a very happy and calm pup who had clearly had a wonderful afternoon. Theresa is a real pro - I’m new to this, and she was extremely helpful explaining potty training and leash weights.”

“Carol is simply the best sitter I’ve ever used! She is so caring, kind and accommodating and provides sweet updates for my girl. I know that Harper is in excellent hands with her and will be so well taken care of. She loves the dogs like her own and will be SO missed after her move!!! Thank you 🥰”

“Zachary was so kind and conscientious of my older dog. Stayed a couple of nights and took great care of my home. Also, I came home to a calm dog and a clean home. He also gave me some great advice on end of life for my 17-year-old boy.”

About: I’ve been pet sitting for over three years. I’ve had various experiences with dogs and cats. As someone who has a dog of their own, I’ve been able to observe behaviors that’s helped when taking care of other dogs, to understand their needs and wants. I currently work remotely however, it doesn’t take time away when it comes to the fur babies! In fact, it allows me to be present and give them the much needed attention. I understand the environment the pets are settled in. I give daily updates to the home owner, making sure that any anxiety of leaving their pets behind is relieved. I bring my own food and care.
“Wish we could give ten stars! Marisa was so attentive to our dog with special needs and looked after everything at the house. This was the first time in three years we were able to go away without worrying. Such a blessing!”

“Where do I begin, Midori exceeded my expectations in every way! She is gentle and loving toward our pets, flexible and trustworthy. She kept me updated with pictures and daily activities. At the last minute my daughter dropped her cat over too and Midori took care of both animals with TLC!!! I will hire Midori again and again…she is wonderful and accommodating and I was so relaxed on vacation because of her care!!!”


“Elizabeth did a great job watching our two labs (one is a puppy!) at our home. She was very easy going and easy to work with. When we got home the dogs were happy and quite tired! I would definitely use Elizabeth again!”

“Jesse is THE BEST. After requesting the booking, he came out to meet us and our two boys, taking his own personal time to make sure it was a good fit. During his stay, he kept us informed with pictures and notes on the pups. He left our house just as he found it and, most important, we came home to 2 happy, sleepy dogs, tired after a vacation of their own! Jesse is reliable and incredibly knowledgeable and hardworking. Can’t wait to have him back!”

“Hunter was really accommodating when we got sick while trying to schedule our meet & greet for a last minute trip. She did great with the dogs & allowed us a stress free weekend away!”

“Stacey was wonderful! She was so easy to communicate with ahead of watching our dog and was also super self sufficient around our house. There was a bad storm when she was scheduled to watch our dog and we live in a pretty remote area and she had zero complaints. She was fantastic all around!”
About: I have raised dogs, cats, a turtle, and parakeets since I was the size of a puppy, and I’ve treasured every minute of the experience. I’m always looking for ways to improve the lives of all animals I share a space with, from brushing teeth and giving baths to hiking and basic training - plus plenty of scratches and love. I'm currently working part-time, with a ton of availability for you and your pet family! Nights, weekends, even potentially some holidays are all on the table. I am an attentive and caring pet owner, and an animal lover in general, and am happy to suit your loved one’s needs and tempo. I’ve been around many different animal personalities in my life, and am well adjusted to frequent walks and attention, as well as capable of handling minor first aid should the need arise.

About: Animals have always been a big part of my life. I have experience working at a dog daycare and providing pet-sitting services for friends, family, and clients. I am comfortable caring for dogs of all sizes and personalities, including feeding, walking, playtime, and following specific care instructions. I am dependable, attentive, and committed to making sure every dog feels safe, comfortable, and loved while their owner is away. My goal is to provide peace of mind and quality care for both pets and their families. 🐾 Pet care fits naturally into my daily routine because caring for animals is something I genuinely enjoy. I have a flexible schedule and make it a priority to provide reliable, consistent care. Whether your pet needs walks, feeding, playtime, drop-in visits, or overnight care, I will make sure they receive the attention, exercise, and companionship they need Your pet’s safety and comfort are my top priorities. I carefully follow all care instructions, including feeding schedules, medications, exercise routines, and any special needs. I take the time to build trust with each pet and ensure they feel comfortable while you’re away. I will treat your home with respect and provide regular updates so you can have peace of mind knowing your pet is in caring and responsible hands. 🐾
About: I’ve taken care of dogs on and off for years and I’ve had a couple of my own. Would be happy to host your pet for a day or a few days, whatever your need is. I am fully retired at this time and will have plenty of time to play with and care for your pet. I am available weekdays and nights as well as some weekends. I am also available to watch them at your house as well if you’d prefer. I am happy to follow your feeding schedule and to take your pet for a daily walk. There are no young children or anyone else living in the house except me.

About: I’ve always been comfortable with dogs of all types. I grew up with dogs and have spent my whole life around animals, so caring for them feels natural to me. I’m calm, confident, and make sure to adjust to each dog’s individual needs so they feel safe, understood, and well cared for. I work full‑time during the day, but I’m available in the early mornings and evenings to take care of your pet. That gives me plenty of time for feeding, walks, playtime, or whatever they need before and after work. Mondays are my completely open day, so I’m available all day then for longer visits or extra care. My goal is to ensure your pet feels genuinely cared for. I pay close attention to their routine and what they need, and I make sure they stay comfortable, happy, and relaxed the whole time they’re with me.
“Angela took great care of our three dogs while we were away for 10 days. They were all comfortable and relaxed with her. She’s gentle and patient and she even taught our littlest wild one some better manners. She sent regular updates and photos. We highly recommend her!”

About: I absolutely love dogs all shapes and sizes, when you book with me your dog will be in a safe and loving environment with me. it’s important to me that any dog i’m with at the time will have a fun and enriching environment with me and the time we’re spending together. I have experience training puppies and pet sitting puppies. I’ve done extended petting sitting stays and have done petting sitting with multiple animals, i’ve done week long stays with 6+ animals, so I can handle a big crew if you have it. I have experience with farm animals and horses as well if that’s ever needed as well! I currently am not working and would love to add some furry friends to my day! I am quite flexible with my timing right now and offer free meet and greets for the safety and benefits of all of us. If you use me for pet sitting you can expect your dog to be fully safe! I will follow your directions and expectations to the tea because I know what it’s like to have to leave your dog with someone and not wanting to have to worry about your loved one
Over 17 pet parents in Winsted have booked house sitting
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 Winsted 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 Winsted 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 Winsted on Rover as of Jun 2026 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 Jun 2026, there are 565 house sitters in Winsted. 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, 88% of Winsted house sitters respond in under an hour.
House sitters in Winsted have an average of 17 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 Winsted.
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. Winsted 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.


