House Sitting in Winchester

Your pet stays in your home as a reliable pet sitter drops in feed and play with them

83 results for House Sitting in Winchester, CT

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Katie O.

(19)
3 repeat clients
from $75.00
per night

Katie took great care of my pets! She checked in and let me know of any changes to the planned schedule. Everyone was happy and healthy while I was away. She even let me know they were paving the roads and adjusted the walking route for Oscar!

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Karina & Jared S.

(123)
55 repeat clients
from $80.00
per night

Jared & Karina happily took on my last-minute request for a week of house sitting with my 2 dogs, after another sitter fell through. They made fast friends with my babies and took great care of them. Knowing my dogs were happy and well cared for made my time away so much easier, and the daily pictures Jared & Karina sent brightened my days.

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Ismael J.

(2)
from $40.00
per night
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Theresa C.

(81)
29 repeat clients
from $120.00
per night

We came back to happy dogs, who seemed very well taken care of. Theresa communicated clearly as to when she arrived and departed and sent pictures to allow us to see happy playful puppies. Our house was left in the same condition we left it as if she wasn’t here 😀. We are looking forward to having Theresa spend time with our dogs again.

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Stacey G.

(30)
6 repeat clients
from $120.00
per night
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Jemeli N.

(1)
from $45.00
per night
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Jesse R.

(25)
3 repeat clients
from $150.00
per night

Jesse was simply wonderful. He connected with our dog Woogie immediately, and you could tell that he truly cares about animals. I was in a somewhat urgent need to find a dog sitter who can stay overnight, and Jesse took the time to meet us - and Woogie - beforehand. Woogie loved him right away, and when I got back home, I could tell that he treated Woogie very well, like his own family. He even let her sleep with him in the guest bed (which was likely not too comfortable), but he wanted to do everything to keep Woogie happy. Jesse sent regular updates and photos and left the house like he found it. I cannot say enough good things about him! I highly recommend Jesse - and Woogie does too.

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Zoe G.

(1)
1 repeat clients
from $80.00
per night
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Carol K.

(119)
37 repeat clients
from $95.00
per night

Carol is amazing! She stayed at our house for four nights to care for our dog (who recently had TPLO surgery) and our two cats. When we returned home from our trip the pets were so happy and the house was spotless. Carol sent daily pictures and detailed updates while we were gone. She really got to know the personalities of our pets and worked hard to keep them entertained. All of our pets loved her!

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Megan M.

(3)
1 repeat clients
from $25.00
per night
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Katherine C.

(15)
3 repeat clients
from $100.00
per night

Katherine was great! Her and our dog got along awesome and she was more than willing to take him on hikes due to his high energy. He was a shelter dog and we were very worried about his PTSD issues, but Katherine made it easy for him. Thank you for being awesome!

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Angela W.

(116)
45 repeat clients
from $75.00
per night

Very attentive and comfortable with my dogs. They responded very well to her. Always very prompt with communications. Very pleasant to deal with. Will definitely use her services in the future!

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Katherine N.

from $32.00
per night
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Kevin D.

(3)
1 repeat clients
from $55.00
per night
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Elizabeth S.

(10)
3 repeat clients
from $65.00
per night
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Jennifer H.

(1)
from $32.00
per night
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Amy H.

(4)
1 repeat clients
from $32.00
per night
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Kelly H.

(65)
31 repeat clients
from $125.00
per night

Wow— I can’t say enough great things about Kelly! We are so grateful to her and her husband — we had to leave on short notice due to a family emergency and Kelly really was such a huge help to us. She cared for Jack and Nash for about 10 days, which is awhile to be away from the dogs and I felt so at ease knowing Kelly was with them. She is a true dog lover — very attentive to their needs and sent us updates the whole time. We feel very lucky we found Kelly! I highly recommend booking her and her husband to care for your doggies!! Thanks for everything — Jack and Nash can’t wait to see you again!

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Meaghan G.

(17)
7 repeat clients
from $90.00
per night
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Annie D.

(85)
24 repeat clients
from $60.00
per night

Annie was excellent with our Lilly. She sent photos & updates routinely. It was a comfort to know our sweet Lilly was in good hands. Would definitely hire Annie again.


Find House Sitting in Winchester

Trusted and local house sitters

Are you looking for house sitting in Winchester to take care of your beloved pet? You are in the right place! We currently have 83 experienced, loving and background-checked house sitters in Winchester. Our sitters offer a variety of pet services such as home dog boarding, dog walking and doggy daycare. Make an informed decision based on reviews, response rates and contact at least 3 approved house sitting professionals. Your dog will be delighted to be looked after by our loving house sitters.