House Sitting in Winchester

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

851 results for House Sitting in Winchester, MA

Sitter Profile Image

Andrew T.

(130)
47 repeat clients
from $84.00
per night

Andrew was a brilliant dog-and-house sitter! Our two large, bouncy dogs LOVED him! He was at our place for six days, and sent daily photos and updates, which were greatly appreciated. I can’t say enough good about Andrew’s attentive, mindful care. We will absolutely ask him back the next time we’re away. Thank you, Andrew — again!

Sitter Profile Image

Zoe G.

(8)
4 repeat clients
from $56.00
per night
Sitter Profile Image

Natalie J.

(144)
52 repeat clients
from $78.00
per night

Natalie is truly the best, she’s incredible with managing all my dog’s needs and is so loving with him. If anything comes up, she’s amazing with communication and flexible if we need to change anything. Thank you so much Natalie!!

Sitter Profile Image

Lauren B.

(21)
2 repeat clients
from $73.00
per night

Traveling can be challenging for us because our senior boxer gets very anxious - he usually goes on a hunger strike and never fully settles when we’re away. Lauren stayed with him for five nights, and it was like we never left. No hunger strikes, and he felt completely comfortable with her. She took amazing care of Booey and was so respectful of our home. We came back to a happy dog and a spotless apartment. We’re truly grateful for her and hope she’s available to care for Booey every time we travel!

Sitter Profile Image

Jupiter B.

(39)
8 repeat clients
from $56.00
per night

Jupiter was great with Hershey. We love the services provided by Jupiter

Sitter Profile Image

Nicole T.

(13)
2 repeat clients
from $67.00
per night

Nicole stayed with our pup Benson for the weekend and he absolutely loved her! She's amazing - a great communicator who sends lots of pics of their time together. He was so happy when we got home so that tells the story. Would book her every time I need a sitter/walk/check in.

Sitter Profile Image

Caroline L.

(6)
1 repeat clients
from $73.00
per night

Caroline was so caring and gentle with Ollie. She was very communicative and kept in touch with me about Ollie’s needs.

Sitter Profile Image

James T.

(69)
27 repeat clients
from $111.00
per night

James stayed with our two dogs and cats and was wonderful. He was responsive and observant. He managed the the quirks that our dogs have on walks. T was clear that he really cares about animals. He is one of the best pet sitters we have used! Highly recommended.

Sitter Profile Image

Abigayle S.

(5)
from $17.00
per night
Sitter Profile Image

Tori R.

(43)
18 repeat clients
from $78.00
per night

Tori was so great with my dog and cat. She sent lots of photos and updates and I felt totally at ease knowing she was taking good care of them and the house while I was away. I’ve already hired her again!

Sitter Profile Image

Jacqueline A.

(21)
9 repeat clients
from $84.00
per night

Jacqueline was amazing! She watched my dogs while I was getting married and made the weekend stress free! Will definitely rebook her in the future :)

Sitter Profile Image

Cheyenne C.

(4)
2 repeat clients
from $56.00
per night

Cheyenne was great, and we came home to happy healthy boys!

Sitter Profile Image

Erin D.

(9)
2 repeat clients
from $56.00
per night
Sitter Profile Image

Jasmin L.

(38)
15 repeat clients
from $73.00
per night

Jasmin was great with our group of fur babies (to very excitable golden retrievers, and two cats). She was professional and very easy to work with.

Sitter Profile Image

Andrea W.

(3)
from $67.00
per night
Sitter Profile Image

Annmarie M.

(17)
6 repeat clients
from $87.00
per night
Sitter Profile Image

Yuzhou D.

(5)
from $67.00
per night
Sitter Profile Image

Christine C.

(8)
from $67.00
per night

I had an amazing experience with Christine! They were absolutely fantastic, super sweet to my dog, and sent tons of adorable pictures throughout the stay. They were incredibly flexible and helpful, and honestly, the best dog sitter I’ve ever had! Highly recommend!

Sitter Profile Image

Olivia M.

(25)
15 repeat clients
from $84.00
per night
Sitter Profile Image

Tanya S.

(11)
2 repeat clients
from $84.00
per night

Tanya clearly was wonderful with Bernie and sent us photos of him playing with her and being his goofy self. Bernie was happy when we got back and the house was immaculate. Tanya was great about letting us posted.


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 851 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.