Dog Boarding in Winchester

Your dog stays overnight at a reliable dog sitter's home whilst you're away

1859 results for Dog Boarding in Winchester, MA

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Belinda B.

(11)
6 repeat clients
from $78.00
per night

We're so grateful to have had Belinda watch our dog Mocha while we were away! She shared videos with us each day, which was great. Communication was always quick and easy. We loved that Mocha had Belinda's dog Sloan as a playmate, and they played great together. Belinda is friendly, easygoing, and has a lot of dog experience. She provided a crate and tons of toys; her house is the perfect setup for pups. Mocha loved the fenced yard and doggie door too. Thanks so much Belinda! Looking forward to having Mocha stay with you again.

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Oana & Oliver B.

(447)
196 repeat clients
from $93.00
per night

Oana and Oliver are amazing hosts. Our 1.5-year-old goldendoodle stayed with them for eight days over the holidays and he had the best time ever. They were incredibly professional, shared photo updates every single day, and really welcomed our boy into their family. Their yard is a dog heaven! It felt reassuring for us to see everyday how he was feeling so comfortable and happy. We will 100% choose them again next time we are away. Thank you, Oana and Oliver!

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Yang S.

(16)
5 repeat clients
from $67.00
per night

Yang and Pat were amazing with Romeo. I got many wonderful photos throughout my trip. The best was him going to school with her son❤️. Romeo was in such great hands. He was quite tired from all his wonderful walks everyday. He can't wait to see this lovely family again.😊

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Betsy C.

(76)
39 repeat clients
from $78.00
per night

Betsy was incredibly responsible and compassionate with our dog. My dog was in the process of healing from a paw injury and needed to wear a cone. Betsy and her sweet family gave our dog all the TLC she needed.

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March A.

(12)
2 repeat clients
from $67.00
per night

March is an excellent dog sitter! We feel so comfortable traveling knowing that he’s taking care of our girl. He sends daily pictures and has a yard and nearby trails, so my dog always comes home well exercised and happy. We couldn’t recommend him more highly!

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Ann & Jim N.

(16)
2 repeat clients
from $54.00
per night

Ann and Jim were so caring and made Stella feel right at home. Ann sent several photos and updates each day that made us feel at peace. Stella played a ton and got lots of love. Would highly recommend Ann and Jim and would love to have them watch Stella again!

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Guillermo M.

(12)
1 repeat clients
from $56.00
per night

Guillermo was fabulous…the best. He was very flexible when our flight was delayed and was able to keep Blue an extra day. He communicated regularly and kept us posted on Blue with lots of pictures. We definitely recommend Guillermo…he is top of the list next time we need someone to watch Blue!

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Samantha L.

(11)
2 repeat clients
from $78.00
per night

Samantha took excellent care of Stella. all of my instructions were followed and I received many updates with pics of my girl. I am very grateful for the care she gave my dog.

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Paul M.

(121)
48 repeat clients
from $63.00
per night

Argos my greyhound is a somewhat anxious old man in general, and can be skittish in new situations. Paul won him over, which allowed me to enjoy my long weekend away without worries. if I need to board Argos again I will be hoping the dates show be available on Paul's calendar.

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Janette L.

(9)
1 repeat clients
from $67.00
per night
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marilyn g.

(6)
6 repeat clients
from $56.00
per night

Real nice lady, took great care of our elderly pup!

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Elizabeth K.

(3)
2 repeat clients
from $58.00
per night
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Luci P.

(21)
12 repeat clients
from $100.00
per night

Luci and family took wonderful care of our rescue dog who can be nervous in new situations. They provided frequent updates with photos and videos, which were so helpful to receive. Our dog got to play with the other dogs and seemed to really enjoy herself. We are so appreciative!

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Yesika S.

(532)
157 repeat clients
from $78.00
per night

From beginning to end, Yesika did an outstanding job taking care of my corgi, Echo. Yesika has top-notch communication. She kept me updated the whole time and sent pictures that honestly made being away so much easier. It was clear Echo was happy, comfortable, and truly being cared for, which gave me so much peace of mind. You can tell Yesika genuinely loves what she does. Her warmth and authenticity really show in how she treats the dogs she watches. When she dropped Echo off, he was relaxed, content, and clearly had a great time. He didn’t even want to come back home. I would trust her again without hesitation and highly recommend her to anyone looking for someone caring and dependable to watch their pet. I’m so happy and satisfied with her care that I’ll be requesting her services again in April and July. Knowing Echo is in such good hands makes all the difference.

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Aurora C.

(354)
79 repeat clients
from $78.00
per night

I’ve used Aurora to dog sit my dog twice and she has been amazing. My dog was so excited for his second visit which speaks volumes and made me so happy! She is very responsive and diligent in sending updates. I have no issue recommending her.

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Carol L.

(86)
47 repeat clients
from $84.00
per night

Carol was so sweet with JB and while not necessary, sent very much appreciated updates everyday. Her home was ideal for our old lady, one story and fenced in yard. JB would love to go back soon!

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Linda K.

(45)
12 repeat clients
from $62.00
per night

I was very happy with Linda! She had my 13 year old Maltese for 7 nights. She was sending me pics with updates. Gave Lola her meds in the morning and night. I chose Linda because of her fenced in backyard and because she does not have kids or other pets. We loved her and will use her again!

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Patrick G.

(70)
19 repeat clients
from $64.00
per night

Patrick was great watching Maverick, he sent daily updates, pictures and videos. He answered all our questions and was very fast at responding!

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Elizabeth & Rodrigo S.

(43)
14 repeat clients
from $64.00
per night

I couldn't be happier! Elizabeth & Rodrigo were amazing with Timber. They Sent updates and pictures regularly. Our boy has some real aniexiety from being displaced after a house fire and they took him On and cared for him. I will definitely be calling them again. You can tell they love caring for your fur babies. Again I can't recommend them enough. Thank you soooo much!

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Carlotta A.

(28)
7 repeat clients
from $67.00
per night

I was very hesitant about leaving my puppy with someone new, but from the very first interaction, Carlotta completely put my mind at ease. She was incredibly loving with Kiko and took the time to ask me many thoughtful questions to make sure the entire process was smooth and comfortable for both of us. Throughout the stay, she was extremely communicative. Every day she sent me multiple pictures and updates, and she frequently checked in and asked questions just to make sure everything was being done exactly the way Kiko needed. That level of care truly made a difference. I could tell that Kiko was not only well taken care of, but genuinely happy and loved. 100% I would leave Kiko with Carlotta again — not only did I find an amazing sitter, but Kiko found a great friend.


Find Dog Boarding in Winchester

The alternative to dog boarding kennels

Are you looking for Dog Boarding in Winchester to take care of your beloved dog? You are in the right place! We currently have 1859 experienced, loving and background-checked dog care specialists 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 Dog Boarding professionals. Your dog will be delighted to be looked after by our loving dog sitters.