House Sitting in Winchester

Find a loving dog sitter to watch your dog overnight in your home.

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1. Kristina Verified Enhanced Background Check

Paws & Relax

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

"Kristina was amazing! She always quickly replied to my texts, asked questions and left the house cleaner than we left it for her. Our dogs absolutely adored... (more)"

2. Gregory Verified Enhanced Background Check

Worry free leaving your dog with me

Bantam, CT, 06750

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Greg was nothing short of amazing! It was so nice to get away for the weekend and not worry about my fur baby. Mack was so relaxed and not stressed out at al... (more)"

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3. Lauren Verified Background Check

Fun, Friendly, Furry😁

Winsted, CT, 06098

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: My name’s Lauren. Passion for animals have been active since i was a little girl. I’ve had dogs, cats, hamsters, and fish my whole life. I have two... (more)

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4. Renee Verified Background Check

Patience is key

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

"Renee has been a good friend of mine for many years now and also happens to be one of the few people I trust to watch my pets when I'm away or find myself in... (more)"

5. Rebecca Verified Background Check

Energetic and Patient Pet Carer

West Simsbury, CT, 06092

House Sitting, Drop-In Visits, Dog Walking

About: I am 18, and will be graduating high school in June 2020. Due to online schooling, I have the flexibility to meet a vast array of needs for your pe... (more)

6. Eliza Verified Background Check

Literate and Loving Pet Provider

Canton, CT, 06019

House Sitting, Drop-In Visits, Dog Walking

"Great experience! Very trustworthy and responsible. Will definitely have her dog sit for us again. (more)"

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7. Marisa Verified Background Check

Heart-centered dog-sitting

New Hartford, CT, 06057

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Hi, I have known Marisa for many years, and she is a true animal lover. She has taken care of both cats and dogs, and is very patient with them. The litt... (more)"

8. Sarah Verified Background Check

Sarah Pop ins Pet Nanny

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

About: Hello pet families My name is Sarah and I absolutely LOVE my job. I have had dogs and cats my entire life. I have three amazing dogs of my own. ... (more)

Active and Accepting Requests (incl. from Essential Workers)
9. Mary Verified Background Check

I am told I am a dog/cat whisperer

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

"Mary had been a dog lover all her life. She is compassionate, kind, and very disciplined when it comes to work. She is always on time and is not only a peopl... (more)"

10. Lynsey Verified Enhanced Background Check

My Expertise

Torrington, CT, 06790

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Lynsey is a dream come true for folks who want to be sure they’ve left their favorite family member in good hands. She’s reliable and sent photos of Sadie th... (more)"

11. Erica Verified Background Check

Loving home for your Furbaby

winsted, CT, 06098

House Sitting, Drop-In Visits, Dog Walking

About: Will feed, walk, and love your animal companion. Will bathe and groom upon request. I treat all animals as my children. I believe that they deserv... (more)

12. Rosie Verified Background Check

Loves dogs–Flexible Schedule

Colebrook, CT, 06021

House Sitting, Drop-In Visits, Dog Walking

About: I grew up on a small farm in Colebrook, CT and have two Pitbulls and two rowdy cats of my own, so I’m up for any pet! Since I generally work in the... (more)

13. Nicole Verified Background Check

Less Talking More Walking!

New Hartford, CT, 06057

House Sitting, Drop-In Visits, Dog Walking

"Nicole was great.. very reliable & attentive. She gave my dog his medication. She regularly brought him to the dog park for exercise & socialization. (more)"

14. Leanna Verified Background Check

Caring and Loyal Pet Sitter

Norfolk, CT, 06058

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: Dog sitting-one of my friends has dropped her puppy off multiple times to stay the night and our favorite things to do when we’re together is go fo... (more)

15. Brian Verified Background Check

Any doggie need you need i'm here

winchester, CT, 06098

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I've grown up all my life with animals. Some cats some dogs and even some bunnies! But i love animals so much. My mission is to save money to go be... (more)

16. Daniel Verified Background Check

Homemade Dog treats and walks!!!!

Winsted, CT, 06098

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I met Dan several months ago while at the park with my 4 dogs. I have a terrier with anxiety who isn't very personable and he loved Dan. No agression what so... (more)"

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17. Sarah Verified Background Check

Pet lover and Caretaker

Litchfield, CT, 06750

House Sitting, Drop-In Visits, Dog Walking

"Sarah is very caring, my male cat loved her and she worked hard to get my shy female cat to open up to her. Unfortunately, my female kitty only just accepted... (more)"

18. Stacey Verified Background Check

Love and care for all puppers

Winsted, CT, 06098

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I grew up with always having dogs around and have had a lifelong passion and love for all animals. I’ve been dog sitting for over 10 years now and... (more)

19. Barbara Verified Background Check

Have Leash Will Travel!

Winsted, CT, 06098

House Sitting, Drop-In Visits, Dog Walking

"Barbara has cared for my fur babies (2 cats and 2 dogs) for years. Her love and affection for animals makes them feel comfortable while I’m away and I neve... (more)"

20. Abbie Verified Background Check

Your Best Friend’s New Best Friend.

Winsted, CT, 06098

House Sitting, Drop-In Visits, Dog Walking

"Abbie is a genuine, good natured, young woman. She has an abundance of patience with animals. She has a very caring and gentle way, a very strong love for al... (more)"


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Winchester house sitting needs. On Rover, it's easy to find a loving dog sitter in Winchester who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Winchester house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Winchester for your dog — people who'll treat him like family.