House Sitting in Winchester

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Michelle C.
Experienced, loving dog trainerWestfield, MA, 01085
House Sitting, Drop-In Visits, Dog Walking

Michelle is awesome! She took great care of our pets (dogs and cats), with daily updates and pictures. The trash was taken out, mail collected, and dishes done!… (more)

from
$40
per night
Calendar Recently Updated
Kathleen M.
Berkshires #1 Trusted Pet Sitter ❤️Becket, MA, 01223
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kathleen is amazing. She is courteous and kind. She instantly formed an attachment to my animals and made sure I was kept up to date on their wellbeing. I highl… (more)

from
$75
per night
Confirmed availability: Memorial day
Angela W.
3.
Certified Dog Trainer Big Pet LoverTorrington, CT, 06790
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Angela is absolutely amazing! She is loving and caring to our new puppy and keeps us updated along the way. We are so happy to have her help us through this new… (more)

from
$50
per night
Confirmed availability: Memorial day
Robin L.
4.
I adore dogs.TOMASTON, CT, 06787
House Sitting, Drop-In Visits, Dog Walking

I was worried about leaving my rescue dog with a sitter for the first time, and this was also my first time using Rover.com. All my fears were unfounded! Not o… (more)

from
$50
per night
Confirmed availability: Memorial day
Courtney S.
Playtime & walks are my specialtiesWest Hartford, CT, 06119
House Sitting, Drop-In Visits, Dog Walking

I felt 100% comfortable leaving my pup with a Courtney! She was very professional, always kept me informed, and took great care of my pup and my house! (more)

from
$50
per night
Confirmed availability: Memorial day
6.
I love dogs and I'm ready to helpBristol, CT, 06010
House Sitting, Drop-In Visits, Dog Walking

Gina has taken care of our pets many times. She is the person we call whenever we go out of town. Our dog Hudson and our cat Sparky absolutely love her. Hudson … (more)

from
$40
per night
7.
Reliable, easy-going animal loverTariffville, CT, 06081
House Sitting, Drop-In Visits, Dog Walking

My boys and I are very happy. Amelia was great, from the minute we met her I could tell my guys would be in good hands. Amelia is excellent at communicating se… (more)

from
$25
per night
Confirmed availability: Memorial day
8.
The kind of care your pets deserveTorrington, CT, 06790
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

It is my pleasure to recommend Jaime to become a dog sitter. I have known Jaime her entire life. She is kind, caring, patient and trustworthy. Jaime is respo… (more)

from
$32
per night
Calendar Recently Updated
9.
Retired, have 3 acres, like hikingBarkhamsted, CT, 06063
Dog Boarding, House Sitting

About: Grew up with dogs,they r always family, my last dog was a rescue froma rescue in newington. Had him for 11 years , he has passed on now. But miss hi… (more)

from
$40
per night
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10.
Heart-centered dog-sittingNew Hartford, CT, 06057
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

I’m writing to highly recommend Marisa M. to be a dog sitter. Marisa loves dogs ( and all animals) and is very knowledgeable about their behaviors, their nu… (more)

from
$40
per night
11.
Dogs are your best friendWeatogue, CT, 06089
House Sitting, Drop-In Visits, Dog Walking

Shadow loved Brad. He was his best bud. He would love his daily walks or swimming days. I could always leave town knowing Shadow was in the best hands, because … (more)

from
$40
per night
Confirmed availability: Memorial day
12.
Let's Walk to Whites!LITCHFIELD/BANTAM, CT, 06759
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Donna is great!! We were so happy to find someone local who we we can trust implicitly to take the best care of our girl. Donna is mature, energetic and a ple… (more)

from
$75
per night
Confirmed availability: Memorial day
13.
I like to be outdoors and walk.Torrington, CT, 06790
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I enjoy the outdoors and taking a walk. Your dog will have lots of play time, as well as fun, treats, food and water. I just like having a dog around… (more)

from
$45
per night
Calendar Recently Updated
14.
Vaccinated gal ready for all petsTorrington, CT, 06790
House Sitting, Drop-In Visits, Dog Walking

Lauren is the nicest, most genuine person I know. She loves all types of animals especially my two dogs and two cats. She’s extremely reliable and I highly reco… (more)

from
$30
per night
Calendar Recently Updated
15.
Experienced and flexible! 🐶✨Torrington, CT, 06790
House Sitting, Drop-In Visits, Dog Walking

My name is Christian R., and Arianna and I are friends from work. She's a very hard working individual with a very patient one as well. She has a heart of gold … (more)

from
$40
per night
Confirmed availability: Memorial day
16.
Welcome to My Dog Pack!Collinsville, CT, 06019
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Richard was the answer I hoped for when I was desperate for an honest, careing, kind preson to take care of my dogs. My dogs are family members and it is very d… (more)

from
$65
per night
Calendar Recently Updated
There for them while you’re awaySalisbury, CT, 06068
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I have watched animals of all shapes, sizes, and species. From dogs and cats to horses and pigs. I am very comfortable around animals and love to spe… (more)

from
$60
per night
18.
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 k… (more)

from
$45
per night
Confirmed availability: Memorial day
19.
Vet tech student who loves animalsTorrington, CT, 06790
House Sitting, Drop-In Visits, Dog Walking

After seeing Sierra around pets for the past 2 years it became very clear that she is very gentile and affectionate towards all animals. Her willingness to prov… (more)

from
$32
per night
Confirmed availability: Memorial day
20.
Patience is keyTorrington, 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 a … (more)

from
$25
per night

Rover also offers House Sitting in:


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.