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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Amanda B.
1.
I'll run with your dog and play!Brattleboro, VT, 05301
House Sitting, Drop-In Visits, Dog Walking

Amanda was great! (more)

from
$35
per night
Calendar Recently Updated
Emily M.
2.
Experienced Pet CaretakerPutney, VT, 05346
House Sitting, Drop-In Visits, Dog Walking

About: I have had 4+ years of experience in taking care of multiple dogs at one time in the same household. I have personal pet care experience with cats an… (more)

from
$40
per night
Calendar Recently Updated
Palma T.
3.
I love all dogsBRATTLEBORO, VT, 05301
Dog Boarding, House Sitting

Palma was a wonderful sitter for our Scottie, Pepper! Pepper immediately befriended Palma when she came to meet us, and we could tell Palma was enjoying playing… (more)

from
$40
per night
Confirmed availability: Memorial day
Carol D.
4.
Pet Care in the Pioneer ValleySunderland, MA, MA, 01375
House Sitting, Drop-In Visits, Dog Walking

Caring, considerate, reliable. Will definitely be asking Carol to care for our pups again. (more)

from
$28
per night
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Kathy W.
5.
Quality care while you're not thereSwanzey, NH, 03446
House Sitting, Drop-In Visits, Dog Walking

Kathy is amazing!!! She is knowledgeable about dogs from her years of experience working with them in various settings. We knew she was the one for our dogs fro… (more)

from
$25
per night
Calendar Recently Updated
6.
Ready to love on your pups!Brattleboro, VT, 05301
House Sitting, Drop-In Visits, Dog Walking

Megan is excellent! She not only takes great care of your pet but she also sends pictures of your beloved pet while you are away so that you know your furball i… (more)

from
$35
per night
Confirmed availability: Memorial day
I am your Fairy Dog Mother 🧚‍♀️Ashburnham, MA, 01430
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I keep a lovely woodland home where I welcome your friendly beast to play whilst you're away. I am highly sensitive to the emotional needs of animals… (more)

from
$50
per night
Confirmed availability: Memorial day
Pet lover of all breeds!Winchendon, MA, 01475
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I have owned pets my whole life from little rodents to cats and dogs. I do not discriminate size or breed or even temperament. I love them all I live… (more)

from
$50
per night
Calendar Recently Updated
9.
Experienced Animal Enthusiast!!!S Deerfield, MA, 01373
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We have an elderly and blind jack russel terrior who has a bit of an attitude and can be reluctant to get out and about but needs it. After meeting Bree I felt… (more)

from
$45
per night
Confirmed availability: Memorial day
10.
Caring & ConsiderateBrattleboro, VT, 05301
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Violet, was born to work with animals. She owns a large breed Mastiff that was a previous rescue who had behavior issues. Her and her family did obedience class… (more)

from
$25
per night
Confirmed availability: Memorial day
11.
Lifelong Animal Lover and Pet OwnerGreenfield, MA, 01301
House Sitting, Drop-In Visits, Dog Walking

Arie has many years of experience taking care of cats, dogs, horses and even lizards. She's very responsible when it comes to how each needs to be cared for. … (more)

from
$25
per night
Energetic Animal LoverGreenfield, MA, 01301
House Sitting, Drop-In Visits, Dog Walking

Dannie is such a great person. She has such a big heart and absolutely loves animals. She'll be a great candidate with dog sitting for anyone! (more)

from
$30
per night
Confirmed availability: Memorial day
13.
I’m that animal girlAthol, MA, 01331
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hello, my names Evie! I have trained and handled many dogs , teaching new tricks and diminishing bad behavior. I’ve also worked with many other anima… (more)

from
$25
per night
14.
Love working with animals!keene, NH, 03431
House Sitting, Drop-In Visits, Dog Walking

About: Since I was a little kid I’ve always wanted to work with dogs and for the past three years I have been and it has been the greatest three years ever.… (more)

from
$25
per night
Calendar Recently Updated
15.
Pro. Who Has Been Kissed by WolvesGuilford, VT, 05301
House Sitting, Drop-In Visits, Dog Walking

I would like to highly recommend Kendra for any of your dog care needs. Kendra's love for dogs and ALL animals shines through in the care she gives them. Seve… (more)

from
$25
per night
Hello, I’m Danie.Westmoreland, NH, 03467
House Sitting, Drop-In Visits, Dog Walking

Wonderful experience with Dani! My animals were at ease and well cared for in our home. She updated with pics, and took great care of home and pets! Will def … (more)

from
$25
per night
17.
Avid dog lover!Northfield, MA, 01360
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Kelsey is very reliable, friendly & responsible. My dog, Molly, is always as happy to see Kelsey as Kelsey is to see her. It's comforting to know Molly is in t… (more)

from
$30
per night
18.
College Grad who loves dogsWest Chesterfield, NH, 03466
House Sitting, Drop-In Visits, Dog Walking

About: I pet the dogs and really care for them. I do not make a mess and really am not a fuss in someone house. I do not make a mess and when I do I clean i… (more)

from
$32
per night
19.
Experienced pet caregiverSwanzey, NH, 03431
House Sitting, Drop-In Visits, Dog Walking

About: Hi! I love dogs and everything about caring for them. Prior to moving to New Hampshire, I worked as a lead volunteer with a local dog rescue in my Ca… (more)

from
$25
per night
Confirmed availability: Memorial day
20.
Your dogs next hiking hero! 🐶Keene, NH, 03431
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Scarlet was great! Bailey is usually very anxious when boarded. We were so lucky to have found Scarlet on Rover. When we picked Bailey up other than a little ac… (more)

from
$25
per night

Rover also offers House Sitting in:


Never beg a friend to watch your dog again. With Rover, you can find your the perfect Winchester house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Winchester who can provide the care your dog needs, when they need it.