Dog Sitting Winsted

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Over 16
pet parents in Winsted have booked dog sitting

Winsted, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Kevin D.
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Kevin D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Burlington, CT, 06013

About: When I was 10 I joined a dog training program through my school, that’s where my training experience began. I provide a premium, low-volume dog care experience for owners who want their dog to have more one-on-one attention in a calm home environment. Your dog won’t be just one of many in a crowded space. I keep my care more personal so each dog gets plenty of attention, supervision, and outdoor time. I have a big yard for dogs to enjoy, but my indoor space is smaller, so I am very intentional about keeping the number of dogs low. That means I can focus on your dog’s comfort, safety, and overall experience much more closely. This is a great fit for dogs who do better with a quieter setting and for owners who value quality of care over high-volume boarding or daycare. I generally only take one to a few dogs at a time unless they are from the same household. I have a lot of experience with senior dogs. I took care of my childhood dog for 17 years of her long, beautiful life. I have experience working with small senior dogs specifically and I know all the little things that they appreciate. I also have experience with large dogs and can handle very big strong dogs. I also love hiking with dogs so if you have an energetic dog you need to burn off energy I am your guy. I have an acre yard with a fenced in front yard in a nice area. Any dog that boards with me would be treated like my own dog and let out very frequently to go to the bathroom and play outside. I would always remain home with your dog. Thank you for considering me and I hope to meet your pet soon! I’m currently a fully remote student so I am fully available. If I board a pet I will be with them full time to make sure they receive the care they deserve. I have a fenced in front yard, and a good amount of unfenced land in the back. My dog is very friendly and would keep your pet great company. He loves dogs and cats. I can easily crate your dog if needed, but would love to give your dog the pet experience and treat them like my own. I live in a nice are and have great access to the woods nearby as well.

Sitter Profile Image: Katie O.
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Katie O.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
22 reviews
3 repeat clients
20 years of experience
Torrington, CT, 06790

About: I have been around dogs my whole life, I took animal science in High school and worked in dog related jobs for about 5 years. I currently have five of my own fur babies. 3 pups and 2 cats I currently am out of work for the summer and I have open availability. Late August I will return to work as a preschool teacher and will be available evenings and weekends. I will take care of your dog as if they were my own, following all the requirements that you set up before hand. Giving your dog all my attention and love.

Sitter Profile Image: Ashley E.
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Ashley E.
from
$30
per visit
5.0 out of 5 stars
50 reviews
10 repeat clients
28 years of experience
Torrington, CT, 06790

This is the first time I’ve used Rover and I couldn’t be more pleased with Ashley E., who recently cared for our 2 male doggies, while we threw a wedding for our daughter. We have a 6 yr old Belgian Shepherd and a 13 yr old Westie. Ashley was wonderful with each of them giving equal love and attention according to their energy and needs level and all the while keeping me calm by sending texts and photos each time she visited. When she came to meet our dogs, our Belgian actually kissed her, which he rarely does with us! Our Westie requires much medication which she made sure to clearly understand and administer, that was one of my biggest worries about hiring a pet sitter and she did it with ease. Most impressive to me was the morning of the wedding my husband was alone to get ready and needed help with his bowtie, cufflinks and button covers of his shirt. Ashley rescued all of us by helping him, THANK YOU!!! That was above and beyond the call of duty, ha ha. I will definitely be using Rover again and definitely Ashley E!

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Karen K.
Sitter Profile Image: Paige B.
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Paige B.
from
$30
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
18 years of experience
Avon, CT, 06001

Paige has watched Izzie overnight several times and done a drop-in visit too. Izzie is always happy to see her, and we can tell she doesn’t miss us when Paige is around!

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Lindsey C.
Sitter Profile Image: Laina W.
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Laina W.
from
$25
per visit
4.7 out of 5 stars
11 reviews
1 repeat client
18 years of experience
Central East Denver, Harwinton, CT, 06791

She was awesome taking care of our cats! She’s very good at giving oral medication so I felt comfortable with her giving meds to our boy. Thank you so much!!

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Felicity F.
Sitter Profile Image: Alexis G.
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Alexis G.
from
$57
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
36 years of experience
Avon, CT, 06001

About: Taken care of different breeds, small and big dogs, cats and small critters. Trained dogs used for disabilities. I walk small dogs with a harness only, and don’t allow them to jump from high places, due to their tiny bones. I make sure they are secured before opening any door where they might run off. I have an Instagram page where I upload dogs I meet , dogs I take care of or watch , dogs that were placed in safe homes. I will take photos to give updates. Can change day to day but if notified ahead of time , can usually work around my schedule. I do check my texts and email if something changes. My dogs are sociable, always keeping an eye out, they are like little kids. There is currently a Japanese Chin, Shitzu, Pekingese, Saint Bernard, a cat, a bird and 3 guinea pigs, in the home.

Sitter Profile Image: Mae J.
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Mae J.
from
$25
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
3 years of experience
Canton, CT, 06019

Mae has been great with my cat, Moon! I can tell she is definitely less anxious when I return from a weekend away. Good communication as well👍🏻👍🏻

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Liam C.
Sitter Profile Image: Lynsey M.
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Lynsey M.
from
$30
per visit
5.0 out of 5 stars
27 reviews
11 repeat clients
8 years of experience
Torrington, CT, 06790

Lynsey is absolutely phenomenal! She took fabulous care of our wonderful cat, Inga, who is often shy with new people. Lynsey made Inga feel comfortable immediately and this continued for the entire time we were away. Lynsey was reliable, communicative, and it was a true privilege to work with her. We'd give her ten stars if we could, and cannot.say enough good things about her.

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Christina B.
Sitter Profile Image: Melanie D.
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Melanie D.
from
$20
per visit
5.0 out of 5 stars
12 reviews
5 repeat clients
14 years of experience
Southwick, MA, 01077

This is the second time we had Melanie take care of our four cats - she gets a 16 (out of 16) paws up from the 4 cats! We came home to very clean food bowls and litter boxes. Food was also left organized! She had great communication. She even accommodated a special diet and feeding cats in two locations. Will use again! Top ratings for Melanie!

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Simone B.
Sitter Profile Image: Trista S.
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Trista S.
from
$25
per visit
5.0 out of 5 stars
21 reviews
9 repeat clients
30 years of experience
Pittsfield, MA, 01201

Trista was wonderful! She sent great pictures of all the pets. They all look so happy and well cared for. Great communication and followed all instructions. You can tell she really cares for your pets. We would highly recommend! 😊

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Alana L.
Sitter Profile Image: Michelle R.
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Michelle R.
from
$45
per visit
5.0 out of 5 stars
1 review
1 repeat client
28 years of experience
Winstead, CT, 06098

About: I’ve worked at animal hospitals for 28 yrs I’m reliable and good with peoples pets I can give meds if needed insulin as well I get lots of waging tails my way I prefer come to your home so your pet is more comfortable and has there familiar surroundings and all the things they’re used to toys their bowls, etc. I can stay the night if needed I like staying with pets at there home this helps also with stomach upsets and stress of being somewhere new and unfamiliar I like the pets to be able to keep there routine

Sitter Profile Image: April H.
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April H.
from
$25
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
10 years of experience
Burlington, CT, 06013

April was terrific to work with. She sent me a daily update and pictures and I knew my kitties were safe with her. Excellent communication also. I highly recommend April to care for your pets.

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Susan S.
Sitter Profile Image: Thomas B.
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Thomas B.
from
$16
per visit
4.7 out of 5 stars
7 reviews
3 repeat clients
6 years of experience
Avon, CT, 06001

Thomas was very responsive and helpful. Was able to provide quick updates and great care for Bella. I recommend his services!

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Don B.
Sitter Profile Image: Maren P.
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Maren P.
from
$14
per visit
5.0 out of 5 stars
1 review
1 year of experience
Simsbury, CT, 06089

We needed someone to check in on our pups last minute and Maren came to our rescue! Will definitely hire her again!

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Miranda D.
Sitter Profile Image: Debbie S.
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Debbie S.
from
$32
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
30 years of experience
Avon, CT, 06001

About: Hello! I have 30 years of experience caring for pets. I own an 80lb lover-girl named Lobster and a 10lb rascal-cat named Trinity (from The Matrix!) My schedule is very flexible and I'm available for couch snuggles, energetic playdates, and walkies. My furry companions have other members of the family to care for them at home if I'm pet-sitting overnight. I can drop-in your place, go for walks, stay overnight, give your cat snuggles, or (with your approval) bring your pup(s) to my large fenced-in backyard!

Sitter Profile Image: Jamilat A.
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Jamilat A.
from
$14
per visit
12 years of experience
Torrington, CT, 06790

About: I’ve loved and cared for dogs of all kinds since middle school, walking and pet sitting for family, friends, and neighbors alike. I believe every dog deserves the same level of affection, patience, and care as my own, while also giving each one the individual attention they need to feel comfortable and happy. I work full-time during the week, typically until 4 p.m. Monday through Wednesday and until 5 p.m. on Thursdays and Fridays. I’m available for evening walks on weekdays, as well as full availability on weekends and holidays. I love spending my free time with animals, so pet care naturally fits into my routine and is something I genuinely look forward to. When caring for pets in their own home, I always ensure they feel safe and comfortable in their familiar environment. I follow their owners instructions closely for feeding, routines, and any special needs. I take time to build trust with pets through gentle communication and positive attention while remaining focused on keeping them happy and active.

Sitter Profile Image: Yvonne D.
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Yvonne D.
from
$19
per visit
5.0 out of 5 stars
2 reviews
20 years of experience
southbury, CT, 06488

Yvonne was fantastic! Highly recommend!

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Sharon C.
Sitter Profile Image: Alina M.
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Alina M.
from
$25
per visit
1 year of experience
Winsted, CT, 06098

About: I have hands-on experience caring for and walking dogs, including my own Golden Retrievers, who I personally trained and walk regularly. I also care for two other dogs, so I’m very comfortable with different personalities and needs. I’m patient, reliable, and understand how important it is to keep your dog safe, happy, and well-exercised. You can trust that I will treat your pet with the same love and care as my own I’m currently working on part time and go to school, but I have morning availability, so I can make sure your dogs are taken care of early, giving you one less thing to worry about. I provide a safe, loving, and clean environment for all pets in my care. I make sure they are well fed, exercised, and supervised at all times. I follow your pet’s routine closely and ensure they feel comfortable and stress free. I also provide updates and will contact you immediately if there are any concerns or emergencies. Your pet’s safety and happiness are my top priorities.

Sitter Profile Image: Katrin L.
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Katrin L.
from
$25
per visit
5.0 out of 5 stars
27 reviews
12 repeat clients
5 years of experience
Glastonbury, CT, 06033

About: Combining my love for animals and the outdoors with photography. I live in a very green peaceful area close to downtown Glastonbury with lots of space for sniffs and walks, in close proximity to many trails we can explore. My schedule is flexible, currently am a full time student and M off for the summer which allows more time for structure with feeding, walking, hiking, and playtime. Will make sure your dog receives all the love , care , and attention they deserve when you are not available to them . 🐶

Sitter Profile Image: Matthew V.
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Matthew V.
from
$15
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
3 years of experience
Bristol, CT, 06010

About: Not only have I cared for other people's animals, but I have a furry friend of my own. I know what it takes to love and care for our little family members, and I know what an owner would expect from a caregiver. I take time out of every day to ensure my dog has the best possible care I can provide, and I'll give the same effort to your pet. I have always felt a special bond to animals. At a young age I started caring for animals and slowly gaining more responsibility over their care. I have left food out and changed litter boxes for cats while owners are away, and stayed over for multiple days to care for rescue dogs who needed the company and support while their owner's were away. I work 100% from home, so my schedule is very flexible. I am a professional and already use my break times to get outside and take walks / go to parks, so getting your pet exercise is not an issue. I defer to the requests and comfortability of each client. Every pet is unique, and I want to give the best possible care for each furry friend.

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The median cost per visit for dog sitting in Winsted is $22

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Popular requests for dog sitting - Winsted

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Sitters in Winsted average 5
repeat dog sitting clients

FAQs for Drop-In Visits - Winsted

Frequently asked questions about Rover

The average cost for Dog Sitting in Winsted on Rover is $27.75 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 1,753 sitters on Rover offering Dog Sitting across Winsted. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winsted stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winsted choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Winsted with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Winsted. On Rover:

  • 97% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 99% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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