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Pet Sitting & Drop In Visits in Winchester, CT

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

Tip: Contact sitters now to confirm availability.
1. Gina

Love, Laughter & Canines

Winsted, CT, 06098

House Sitting, Drop-In Visits, Dog Walking

"Eloise and Gina M. are best friends forever! Gina is a dog whisperer and we love her! (more)"

2. Christi

Trustworthy, responsible dog lover.

Goshen, CT, 06756

House Sitting, Drop-In Visits, Dog Walking

"Outstanding. Treated the dog well and took great photos. Recorded everything on the web site and we got regular updates. Very responsive and responsible.... (more)"

Confirmed availability
4th of July
3. Jenna

Dog trainer & vet assistant

Torrington, CT, 06790

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

"Jenna was great. I have a dear old jack Russell who would not leave her great! She texted me daily and went above and beyond to try and get our nervous Nelli... (more)"

Calendar Recently Updated
4. Noa

Intelligent and loving sitter

New Hartford, CT, 06057

Drop-In Visits, Dog Walking

About: I am and always have been a dog person. I've dog-sat for my neighbors, various family members, both with more than one dog, and for bosses and frie... (more)

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5. Tori

I love to hike & walk with dogs!

Winsted, CT, 06098

Drop-In Visits, Dog Walking

"Tori is great with all dogs; big, small, one, many at a time. You name it she can do it. She grew up with dogs all her life. And would watch my own dog when ... (more)"

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6. Lynsey

My Expertise

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

About: I have been working with service dogs for almost 9 years. I have experience with grooming, training, and basic care. I'm a 2nd year Vet Tech studen... (more)

7. Keyata

Patient, loving and fun pet sitter!

Torrington , CT, 06790

House Sitting, Drop-In Visits, Dog Walking

"I wanted to send a quick message to let you know how pleased I was with Keyata S. She really showed great concern and care for my 2 dogs and was very descr... (more)"

8. Jessikah

We’re making “Fetch” happen!

torrington, CT, 06790

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

"Jessikah is an excellent dog walker. She doesn't just take the dog around the block. She often takes them to various parks and hikes where the dog can enjoy... (more)"

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9. Camila

Your pet will be part of our family

Torrington, CT, 06790

Dog Boarding, Drop-In Visits, Doggy Day Care

"I highly recommend Camila as an animal caretaker. Camila is not only a compassionate animal lover, but also a great person. Camila has personally owned many ... (more)"

10. Krystal

Teacher of children and dogs

torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

"Krystal is responsible, reliable and loves my dog! She takes her out for walks, feeds her, nurtures her when I can’t be there. I’m relieved. (more)"

11. Patrick

Experienced dog sitters

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

"I had Pat take care of my two cats over Thanksgiving. He responded promptly to my request on Rover, showed up on time to meet the cats and get my key and eve... (more)"

12. Donna

Large yard, quiet neighborhood

New Hartford, CT, 06057

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

About: Love dogs of all sizes! I’ve had many dogs over the years. Love to go for long walks, hang out in the yard/deck, play fetch or just sit and pet and... (more)

Confirmed availability
This weekend
13. Madeline

Compassion and play!

New Hartford, CT, 06057

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

"Madeline was so kind and loving to my two dogs! She sent frequent updates and took them for very long walks! I would definitely book her again! (more)"

Confirmed availability
4th of July
14. Kristina

Dogs make my day

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

"I have known Kristina for more than 15 years. She has three concerns. #1, her child, #2, her fur baby Sadie and fianally #3 family, friends and relatives. ... (more)"

15. Melissa

Absolutely LOVES dogs!!

New Hartford, CT, 06057

House Sitting, Drop-In Visits, Dog Walking

"Melissa is a very caring and responsible dog caregiver who loves animals. She has played with my two year old German Shepherd Elsa many times. They love to p... (more)"

Confirmed availability
4th of July
16. Mary

Friends say I am a dog 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)"

17. Nanci

Happy dogs are exercised dogs!

Barkhamsted , CT, 06063

House Sitting, Drop-In Visits, Dog Walking

About: I have been a dog owner all my life. I now have a Rottweiler but have previously had giant breeds to a Jack Russell sharing my home. People have al... (more)

18. Ashley

loving person loving pets

Torrington, CT, 06790

Drop-In Visits, Dog Walking

About: I been a dog trainer for many years. I learned to groom dogs when I worked at Petco. I was a trainer there as well. I worked at a Doggy Daycare unt... (more)

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19. Rachelle

I’m with dogs more than people

Torrington, CT, 06790

House Sitting, Drop-In Visits, Dog Walking

About: I have over two years of experience in training dogs and puppies and I’ve always had pets of my own. I currently work part time in a kennel and lov... (more)

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20. Liv

Your dog will be well cared for.

Winsted, CT, 06098

House Sitting, Drop-In Visits, Dog Walking

"I highly recommend Liv for dog sitting! My pup Pepper now can't walk by Liv's house without begging to go in. Liv is kind, considerate, and caring to all flu... (more)"

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Winchester pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Winchester, CT who meets your — and your pet's — needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet — including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.