House Sitting Winchester

Find a loving house sitter to watch over your pets and your home.

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Over 2
pet parents in Winchester have booked house sitting

Winchester, Find top rated house sitting

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

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Sitter Profile Image: Ismael J.
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Ismael J.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
4 years of experience
Winsted, CT, 06098

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.

Sitter Profile Image: Katie O.
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Katie O.
Star Sitter
from
$75
per night
5.0 out of 5 stars
22 reviews
3 repeat clients
20 years of experience
Torrington, CT, 06790

Katie is truly the best. She took care of our pit bull and our sphynx, plus our best friend’s older pit who has mobility issues, anxiety, and a pretty involved medication routine. Managing all three could not have been easy, but she handled everything with so much care and attention. We’ve used Katie multiple times and she’s always reliable, communicative, and incredibly trustworthy. She keeps us updated with messages and photos, takes great care of our home, and most importantly makes sure our pets are happy, comfortable, and well cared for. It gives us so much peace of mind knowing they’re in such good hands. This was our third time working with Katie and we wouldn’t hesitate to book her again and highly recommend her to anyone looking for a dependable and compassionate sitter.

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Jamesia B.
Sitter Profile Image: Karina & Jared S.
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Karina & Jared S.
Star Sitter
from
$80
per night
5.0 out of 5 stars
132 reviews
61 repeat clients
23 years of experience
Barkhamsted, CT, 06063

Great communication and frequent updates which was helpful and reassuring since it was our first time with us away. Would definitely use again!

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Erica L.
Sitter Profile Image: Katherine C.
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Katherine C.
from
$100
per night
5.0 out of 5 stars
16 reviews
3 repeat clients
10 years of experience
Torrington, CT, 06790

Katherine did a great job with our Toby! He's a little shy around other people but he warmed up to her fast! We will definitely be asking her to watch Toby again!!

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Izabel R.
Sitter Profile Image: Zoe G.
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Zoe G.
from
$65
per night
5.0 out of 5 stars
1 review
1 repeat client
7 years of experience
Torrington, CT, 06790

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’m currently working part time at a doggie daycare and boarding facility, I absolutely love working with the dogs and am just looking to do some more in my free time. I look forward to hearing from you :) 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

Sitter Profile Image: Angela W.
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Angela W.
from
$75
per night
5.0 out of 5 stars
116 reviews
45 repeat clients
15 years of experience
Torrington, CT, 06790

Angela house-sat and took care of our 10 year old English Bulldog over the Thanksgiving holiday. Angela is reliable, communicative and has genuine affection for our girl. Our dog could not have been in better hands and our house was in perfect shape upon our return. We would highly recommend Angela for any type of pet care, whether it be for walks, daycare or overnight visits. This was the second time that she helped us and we will continue to call upon her services the next time!

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Tony C.
Sitter Profile Image: Stacey G.
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Stacey G.
from
$120
per night
5.0 out of 5 stars
32 reviews
7 repeat clients
15 years of experience
Winsted, CT, 06098

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!

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Emily M.
Sitter Profile Image: charleen m.
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charleen m.
from
$32
per night
2 years of experience
torrington, CT, 06790

About: What sets me apart is my hands-on experience and genuine love for dogs of all ages. I worked at a dog kennel for two years, where I cared for dogs with all kinds of temperaments, ages, and needs. I’m experienced with senior dog care and I’m comfortable with puppies too—whether it’s crate training, potty breaks, or just keeping up with their energy! Your pet’s comfort and safety are always my top priority. Pet care fits easily into my weekly routine since I have a pretty open and flexible schedule. I’m most available Tuesday through Friday between 11:30 AM and 4:30 PM, which works great for midday walks or drop ins. That said, I’m always happy to discuss and make arrangements that work best for you and your pet! Whether I’m caring for pets in my home or yours, their safety and comfort always come first. I take the time to understand each pet’s routine, needs, and personality to make sure they feel secure and loved. I keep a clean, pet-friendly environment and follow any instructions you provide whether that’s feeding schedules or favorite toys. I also provide regular updates so you can feel confident and at ease while you're away.

Sitter Profile Image: Jesse R.
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Jesse R.
from
$150
per night
5.0 out of 5 stars
26 reviews
3 repeat clients
20 years of experience
Torrington, CT, 06790

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!

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Judith C P.
Sitter Profile Image: Sowatey L.
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Sowatey L.
Star Sitter
from
$67
per night
5.0 out of 5 stars
18 reviews
7 repeat clients
16 years of experience
Plymouth, CT, 06786

Sowatey was excellent! He sent several photos and kept me informed the entire time I was away. He is super respectful and truly loves spending time with animals. I highly recommend Sowatey!

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Sara E.
Sitter Profile Image: Alexandrine W.
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Alexandrine W.
from
$45
per night
5.0 out of 5 stars
2 reviews
1 repeat client
18 years of experience
Winchester, CT, 06098

About: I have grown up with pets in my house all my life! Whether it be cats, dogs, chickens, goats, you name it! We rescued all of our fur babies so I have seen and experienced a lot in the animal world. I am currently a full time college student and I work part time. I can drop in before school, before I go to work, and when I am out of work! I can also do other times as long as we stay in communication. As I will be doing drop in and walks I will keep your animals leashed at all times unless specified differently so there are no escapees. I love giving my fur babies treats so if you provide me with the certain kind your babies can have I will gladly give them a treat for being adorable!

Sitter Profile Image: Aaliyah R.
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Aaliyah R.
from
$25
per night
22 years of experience
Canaan, CT, 06018

About: Ive had pets my whole life, from reptiles to birds to our furry friends. Ive done it all! Loving and caring for animals is one of my greatest passions, Ive been taught from a very young age to treat our lovely companions with the greatest kindness and respect. As a college student ill be able to take care of your pets before and after my classes! I of course can discuss details when booking! I am very detail oriented when it comes to our companions, I will adjust to the schedule you have set for them! As a pet owner i understand the importance of keeping your pets comfortable and happy.

Sitter Profile Image: Jemeli N.
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Jemeli N.
from
$45
per night
5.0 out of 5 stars
1 review
20 years of experience
Torrington, CT, 06790

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.

Sitter Profile Image: Tashani H.
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Tashani H.
from
$40
per night
5.0 out of 5 stars
2 reviews
5 years of experience
East Granby, CT, 06026

Tashani was literally the best -- she was super communicative and sent through daily updates about Libby & Cinder! We got back from a week-long trip to a clean house, happy animals, and a flourishing garden. We'll definitely work with Tashani for future trips!!

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Austen W.
Sitter Profile Image: Zachary N.
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Zachary N.
from
$40
per night
3 years of experience
Torrington, CT, 06790

About: I have had dogs my whole life but 2 of my dogs gave birth to 11 puppies in October of 2022 and I helped take care of them all until they were ready to go to their new homes. I kept one of the puppies and have taken care of her since she was a newborn so I am very familiar around all types of dogs. I am currently working part time but am working towards having my own pet business one day. My hope is to meet new people and create lasting relationships that could lead to business opportunities I will make sure your pets are getting enough attention and exercise when you are away and will treat them like they are my own.

Sitter Profile Image: Brad L.
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Brad L.
from
$45
per night
5.0 out of 5 stars
17 reviews
9 repeat clients
6 years of experience
Simsbury, CT, 06089

Brad went above and beyond for Koda! So helpful and great communication. Worked out so well with our big dog. Will absolutely ask Brad to sit again

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Taylor G.
Sitter Profile Image: Aidyn P.
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Aidyn P.
from
$75
per night
10 years of experience
Avon, CT, 06001

About: I have been surrounded by animals since I was little, and not just family pets. While I grew up in a golden retriever family (on golden 4 now), I also currently have a cat, have had fish, guinea pigs, and bunnies. I have worked and volunteered at local farms, and bathed, groomed, fed, and played with all sorts of animals, and am equipped for a variety of animal care services. I also have lots of experience with pets of friends and family, and dog sitting, and get along well with all! I am recently graduated and back home in CT for the foreseeable future. I have a very flexible schedule, so please reach out with any requests and I am sure I can make it work. I am very good at tending to animals needs, but also going beyond. I know how to play with animals and help even the shyest feel comfortable, whether with treats, playtime, cuddles, or even my dog’s personal favorite - classical music! I am good with animals who are fearful as much as I am good with animals bursting with energy. I am able to feed dogs and cats and any pet, make sure they always have water available, give them potty breaks and walks, and playtime and rest time as needed. And of course, I am always happy to just sit and keep animals company - they need it as much as we do!

Sitter Profile Image: Kelly H.
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Kelly H.
from
$125
per night
5.0 out of 5 stars
66 reviews
31 repeat clients
14 years of experience
Otis, MA, 01253

You could not find more thoughtful and caring people to genuinely love your pet than Kelly and Nabil. They prioritized Elmer’s health and happiness to the highest degree and made sure we received videos and photos every day. We feel very lucky to have them in Elmer’s life.

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Joey W.
Sitter Profile Image: Sarah E.
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Sarah E.
from
$63
per night
5.0 out of 5 stars
38 reviews
18 repeat clients
16 years of experience
Windsor, CT, 06095

We have used house and pet sitters for many years because we prefer our pets to stay in the comfort of their own home rather than in a kennel, and this was one of our best experiences. We were away for 10 days and received daily photos and updates, which allowed us to truly relax and enjoy our trip knowing Ali was in good hands. The updates showed a happy, content cat, and it was clear that she spent quality time with Ali and gave her plenty of attention and affection. When we returned home, the house was clean and well cared for, and Ali was relaxed, healthy, and clearly comfortable. In fact, it looked like Ali had become quite fond of her sitter! We are very grateful for the excellent care she provided, both for Ali and for our home. We would not hesitate to book with her again and highly recommend her to anyone looking for a reliable, caring, and trustworthy pet sitter.

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Anya N.
Sitter Profile Image: Kara S.
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Kara S.
from
$50
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
6 years of experience
Farmington, CT, 06085

Kara was amazing with my three rascals! Lots of pictures and even made a pesky, judgmental chihuahua fall in love with her! I will definitely be using Kara again!

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Ashlee H.
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The median cost per night for house sitting in Winchester is $60

Pet parents share their Rover experiences - Winchester

1 / 1
5.0 out of 5 stars

Daniel is wonderful. He cares for our two high energy pups and cat at our house while we’re away and always takes great care of them. He’s extremely trustworthy and a great communicator. Highly recommend booking with him!

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Ashley M.
House Sitting
1 / 1
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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your pets like family

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Popular requests for house sitting - Winchester

Select a filter and find qualifying sitters offering house sitting.

Sitters in Winchester average 3
repeat house sitting clients

FAQs for House Sitting - Winchester

Frequently asked questions about Rover

The average cost for House Sitting in Winchester on Rover is $19.98 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House 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 House Sitting. For more information on service fees, click here .

As of July 2026, there are 974 sitters on Rover offering House Sitting across Winchester. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winchester walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Winchester maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

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 Winchester 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!

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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.

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

  • 99% of sitters can help with special care needs
  • 99% 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.

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