Dog Boarding in Winchester

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
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Sitter Profile Image: Oana & Oliver B.
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Sitter Profile Image: Oana & Oliver B.
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1.

Oana & Oliver B.

Rover 101
For the love of dogs
Woburn, MA, 01801
Boarding, Doggy Day Care
5.0
303 reviews
145 repeat clients
from
$69
per night

Our French Bulldog had a wonderful visit with Oana and Oliver. Our family was traveling and this was the perfect place for our dog to go for the day! Oana and Oliver were extremely flexible with our plans and very knowledgeable about dog behavior. It was very easy to communicate and plan out or drop off and pick up times. We would definitely come back if we are in the area again!

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Sitter Profile Image: Hillary H.
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Sitter Profile Image: Hillary H.
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2.

Hillary H.

Personal bedroom for your cat!
Malden, MA, 02148
Boarding
5.0
27 reviews
8 repeat clients
from
$45
per night

Hillary provides the best setting for our cat, and sent a few photos everyday to keep us in the loop during the stay. We will go back in the future for sure! Thanks again, Hillary.

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Sitter Profile Image: Isabel Q.
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Sitter Profile Image: Isabel Q.
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3.

Isabel Q.

Dog mum of a collie-flower
Somerville, MA, 02144
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
22 reviews
4 repeat clients
from
$70
per night

Isabel is an amazing dog sitter. She is very communicative and sent lots of pictures of Ginger while she was watching her. I felt super comfortable leaving Ginger with her and would definitely call on her again in the future for dog sitting!

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Sitter Profile Image: Kiara H.
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Sitter Profile Image: Kiara H.
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4.

Kiara H.

Bring me all your fur babies!
Medford, MA, 02155
Boarding, Doggy Day Care
5.0
3 reviews
from
$55
per night

Kiara was so great with our dog Barkley, they immediately got along and she also helped us when we ran into a issue with our original sitter at the last minute. We really appreciate her help and Barkley can’t wait to go back!

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Sitter Profile Image: Alissa C.
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Sitter Profile Image: Alissa C.
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5.

Alissa C.

Hustle & Heart
Medford, MA, 02155
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
13 reviews
1 repeat client
from
$120
per night

Alissa took care of our golden retriever Huxley while we were out of town. She is truly a dog person and Huxley felt comfortable with her from the moment we met her. While we were away, Alissa was sending regular updates and pictures of our happy puppy. She made sure he was able to follow his silly bed time rituals (blanket stealing and all) and provided lots of love. He came home a tried and happy. We would not hesitate to leave Huxley with Alissa again. Highly recommend! :)

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Sitter Profile Image: Wendy & Luke X.
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Sitter Profile Image: Wendy & Luke X.
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6.

Wendy & Luke X.

Vet nurse and WFH
Woburn, MA, 01801
Boarding
5.0
27 reviews
6 repeat clients
from
$135
per night

Wendy and Luke were incredibly attentive and thoughtful. Our dog can get quite anxious and they went above and beyond to make sure that she felt safe and cared for. They clearly spent time to acclimate our dog to their space and build trust with her. They also made sure she got plenty of exercise and attention. Their communication was excellent as well and they sent some great pictures. We cannot recommend them enough!

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Sitter Profile Image: Tayna F.
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Sitter Profile Image: Tayna F.
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7.

Tayna F.

Rover 101
Unleashing happiness!
Melrose, MA, 02176
Boarding, Drop-In Visits, Dog Walking
5.0
11 reviews
4 repeat clients
from
$80
per night

Tanya was absolutely amazing with our little guy! She sent updates twice a day and the most amazing pics and videos. She was also very flexible considering I had to meet her at 5am for drop off to make our early flight. I would highly recommend her and definitely be using her again for boarding and dog sitting!

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Sitter Profile Image: Pavan B.
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Sitter Profile Image: Pavan B.
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8.

Pavan B.

The best Friends you can ever find
Woburn, MA, 01801
Boarding, Doggy Day Care, Dog Walking
5.0
11 reviews
3 repeat clients
from
$68
per night

Pavan took great care of Maple while I was away for the weekend. She loved playing with their dog, Yogi, and was exhausted when she got in the car at pick up time. I got multiple daily updates and pictures and I felt at peace knowing she was in good hands.

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Sitter Profile Image: Frederick I.
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Sitter Profile Image: Frederick I.
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9.

Frederick I.

Accept all of life’s treat's
Medford, MA, 02155
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
22 reviews
7 repeat clients
from
$40
per night

Wow, Frederick was the perfect person for and to Bear, our 11 week old cavapoo. Bear loved him, I know because when I picked him up from boarding and Frederick would speak Bear wagged his tail relentlessly and wanted to jump back into his arms. Frederick will be our constant go to for Bear. Frederick is reliable, caring and loves what he does. Thank you, Frederick, for easing my mind on the first time leaving our boy.

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Sitter Profile Image: Joe M.
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Sitter Profile Image: Joe M.
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10.

Joe M.

PhD student + corgi sidekick 🐶
Somerville, MA, 02143
Boarding
5.0
16 reviews
3 repeat clients
from
$75
per night

Joe did a fantastic job taking care of Bunny while I was out of town. He shared photos and updates, and Bunny was healthy and happy upon my return. Thanks Joe!

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Sitter Profile Image: Lucy W.
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Sitter Profile Image: Lucy W.
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11.

Lucy W.

Stay at Home Dog Mom
Somerville, MA, 02143
Boarding, Drop-In Visits, Dog Walking
5.0
47 reviews
15 repeat clients
from
$70
per night

Lucy did a great job caring for my dog. She was very responsive throughout the booking process and was flexible when my plans shifted a bit. Lucy has experience caring for multiple dogs at once and fed my dog and hers in separate spaces to avoid resource conflicts. While I was away, she sent me photos and regular updates. My dog really bonded with Lucy and when we walk by her house now, my dog pulls to try to go in. I wouldn't hesitate to have Lucy care for my dog again.

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Sitter Profile Image: Houda H.
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Sitter Profile Image: Houda H.
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12.

Houda H.

Your pet will be loved like my own
Melrose, MA, 02176
Boarding, Drop-In Visits
5.0
12 reviews
7 repeat clients
from
$65
per night

Houda was a very,very sweet woman, who obviously loves dogs! She treated my Bella as her own.Spent a lot of time everyday, feeding, and playing with Bella.She took her for walks, and groomed her as I would. I was so lucky to find her when my other sitter backed out .I highly recommend Houda❤️?

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Sitter Profile Image: Séamus Ó.
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Sitter Profile Image: Séamus Ó.
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13.

Séamus Ó.

Mature, Responsible, Experienced
Melrose, MA, 02176
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
4 reviews
1 repeat client
from
$45
per night

Seamus is wonderful! Very nice and caring, and was able to make our little dog feel right at home.

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Sitter Profile Image: Isabel S.
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Sitter Profile Image: Isabel S.
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14.

Isabel S.

Work from home dog lover!
Somerville, MA, 02144
Boarding
2 reviews
from
$55
per night

Isabel has been an absolute blessing as our pet sitter for Benny. Not only did she take excellent care of him, but she also made sure he felt right at home. She sent us regular updates and lots of heartwarming pictures that put our minds at ease. Benny was clearly relaxed and content in her company, which made our time away so much more enjoyable. Knowing that our furry family member was in such loving and capable hands gave us the peace of mind we needed. Isabel truly goes above and beyond, and we can’t thank her enough for making Benny’s time away from us feel like a home-away-from-home experience.

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Sitter Profile Image: Erin L.
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Sitter Profile Image: Erin L.
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15.

Erin L.

Rover 101
Fitness goals! Pet More dogs!
Woburn, MA, 01801
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
54 reviews
28 repeat clients
from
$80
per night

Erin is great with Pasha and Hazel! She is always responsive and makes boarding super easy for us and great for my fur babies?

Sitter Profile Image: Paul M.
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Sitter Profile Image: Paul M.
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16.

Paul M.

RoverGO
Puppy Paradise!
Arlington, MA, 02474
Boarding, Drop-In Visits, Doggy Day Care
5.0
80 reviews
30 repeat clients
from
$52
per night

Paul was an excellent host/sitter for my 13 year old Jack Russell. He spent time with me and Benny upon drop off. I instantly sensed his expertise and comfort with her. I was at ease leaving her with him. Paul understood my concerns for my dog while in his care. I liked his confidence and handling Benny during this meet and greet on this first 24 hour stay. Paul sent a couple of texts and a pic of how things were going and I appreciated his matter of fact information sharing. I was totally pleased with this first experience of leaving Benny with an unfamiliar person and home. Couldn’t have gone better for all involved. Definitely will try for Paul for any future needs and I highly recommend Paul to others.

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Sitter Profile Image: Barbara S.
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Sitter Profile Image: Barbara S.
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17.

Barbara S.

Safe, Loving Home Away From Home
Watertown, MA, 02472
Boarding, Doggy Day Care
5.0
22 reviews
12 repeat clients
from
$60
per night

Where do we begin...this was a hard choice when trying to find someone to watch our fur baby for 6 days. He got to know Barb and a visit to her home for a meet and great. Then another visit for half a day. He was in heaven. Barb sent photos throughout the day. He was in a good mood and not anxious at all. Then we left TicTac in her care for 6 days. So many pictures came to us. He definitely has made new friends and was cared for so well. I highly recommend Barb 🌟

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Sitter Profile Image: Rob W.
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Sitter Profile Image: Rob W.
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18.

Rob W.

Responsible long-time friend of dog
MELROSE, MA, 02176
Boarding, Doggy Day Care, Dog Walking
5.0
38 reviews
22 repeat clients
from
$70
per night

This was our second trip which we left our pup with Rob’s family. We got great photos of our dog settling right in again with the family and their dog. Our dog does not do well at kennels, and when we’ve picked her up in the past she was stressed for days afterward. After trips at Rob’s, she’s happy and comfortable. Worth every penny to know our girl is happy while we’re away. Thank you, Rob!

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Sitter Profile Image: Ashley P.
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Sitter Profile Image: Ashley P.
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19.

Ashley P.

Boarding, walking, and play for all
Arlington, MA, 02474
Boarding, Drop-In Visits, Dog Walking
5.0
5 reviews
3 repeat clients
from
$55
per night

Ashley was great with Fred. She sent me pictures every day of his activities. She treated him like he was her own pet. Thanks!

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Sitter Profile Image: Jessica & Amie Q.
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Sitter Profile Image: Jessica & Amie Q.
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20.

Jessica & Amie Q.

A safe vacation home for your pets!
Somerville, MA, 02145
Boarding, Drop-In Visits
5.0
3 reviews
1 repeat client
from
$65
per night

Jess was a wonderful sitter for our dog Reg, and accommodated a very early drop-off time for us on a Saturday morning. We will definitely use her again!

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Winchester Dog Boarding ratings

Overall Rating:

Dog boarders in Winchester are rated on average 5 out of 5 stars based on 134 reviews.


Rover.com is the simple, savvy way to find and book Winchester pet boarding. It's easy to find the perfect dog sitter - many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book dog boarding on Rover, your dog will enjoy a loving staycation in their sitter's home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter in Winchester, MA has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of our dog kennel alternatives. When you book [city name] dog boarding on Rover, your dog gets the loving care they deserve, and you get peace of mind.

The price of dog boarding in Winchester, MA might not be as much as you thought. Whatever your price range, you'll find a dog sitter on Rover for almost any budget. Interested in finding out what the typical Rover dog sitter expects as a dog boarding fee? Visit our average dog boarding rates report to see the general fees before checking out an individual dog sitter's hourly rates.

If you're the sort of person who likes to book services when you're out and about, you'll love the Rover dog boarding app. In minutes, you'll be able to view hundreds of experienced dog sitters no matter where you are, or re-book on-demand with your puppy's favorite dog sitter. You'll get to check in in real-time to see how your dog's day is going, with the photo updates feature from your dog sitter via the Rover dog boarding app. And if you hate carrying cash, or calculating tips, you'll love the Rover app's cashless payment feature which enables fast, secure payment of your dog sitter without money needing to change hands.

Are you a dog lover who wants to know more about how to turn your passion into profit? There's lots of opportunity to earn money with dog boarding in Mauldin, SC. If you're not sure where to start, visit our page about how to become a dog sitter. We're always happy to include new dog sitters in our dog boarding service listings, and the simple application process means you can start your own dog boarding business in no time. We also take the hassle out when it comes to paperwork, because all our Rover dog sitters have access to helpful benefits including premium pet insurance and cashless payment feature, so you don't have to worry about getting paid on time. Why not apply today?

In other words, when you use Rover to find Winchester dog boarding services, your pet is given the best in loving care and hands-on attention, and you don't need to miss out on that just because life got in the way.

Boarding