Dog Boarding in Winchester

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Confirmed availability: Memorial Day Weekend
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
2.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
331 reviews
159 repeat clients
from
$69
per night

This was the second time for Bub and third time for Kennedy. I received lots of great pics of both of them. Kennedy had a blast running around and playing with the other dogs. Bub is not great at being left with others, but the pics showed her with her tail curled up - always a very positive sign for a pug! Thank you once again for taking such great care of them.

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Sitter Profile Image: Emily C.
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Sitter Profile Image: Emily C.
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2. Emily C.

My kids are amazing with your pups
Stoneham, MA, 02180
3.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
6 repeat clients
from
$53
per night

Emily was incredible. Truly went above and beyond for my pup, who I knew was in excellent care. Emily is super communicative and sent tons of pictures and videos. She truly treated Ellie as if she were her own pet, and I cannot recommend her highly enough.

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Sitter Profile Image: Paul M.
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Sitter Profile Image: Paul M.
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3. Paul M.

RoverGO
Puppy Paradise!
Arlington, MA, 02474
2.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
83 reviews
34 repeat clients
from
$52
per night

Paul did a fantastic job looking after our old gal, Nami. She has significant mobility issues, but Paul made sure she was comfortable, happy, and engaged through her stay. Paul was excellent at communication, providing photo and text updates while we were away.

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Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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4. Julia R.

Rover 101
Safe & happy place for your pets 😻
Malden, MA, 02148
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
29 reviews
10 repeat clients
from
$65
per night

Julia was wonderful! She was extremely understanding of my dog’s needs and demonstrated excellent attention to care. She was also very clear and responsive with her communication!

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Sitter Profile Image: Betsy C.
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Sitter Profile Image: Betsy C.
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5. Betsy C.

WFH dog lover with fenced yard
Arlington, MA, 02474
2.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
4 repeat clients
from
$65
per night

Betsy and her family were wonderful hosts for our pup. Betsy sent pics and videos, and Ronja seemed to have a fantastic time. Great communication, we felt safe leaving our dog in Betsy's care.

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Sitter Profile Image: Rebecca P.
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Sitter Profile Image: Rebecca P.
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6. Rebecca P.

Fun for your pup
Arlington, MA, 02474
3.4 mi. away
Boarding
5.0 out of 5 stars
18 reviews
5 repeat clients
from
$59
per night

I am so grateful for Rebecca caring for Stella. She did an excellent job with my dog. I will definitely book her again and highly recommend her for all pet sitting services.

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Sitter Profile Image: Andy S.
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Sitter Profile Image: Andy S.
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7. Andy S.

🐾 Meet Your Pet's New Best Friend!
Arlington, MA, 02474
2.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$50
per night

First time, and hopefully not the last, working with Andy. Kind and flexible with drop off and pick up. Very helpful in caring for our dogs, daily pics and updates. Highly recommend, thank you Andy!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Surendra S.
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Sitter Profile Image: Surendra S.
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8. Surendra S.

Rover 101
Comfort of home for your pet
Burlington, MA, 01803
3.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
98 reviews
16 repeat clients
from
$55
per night

I was worried leaving Biscuit being it was my first time away. There was no need. She was one happy pup, had playmates every day and a large fenced in yard They provided excellent care and daily photos and video just put my mind at ease. I highly recommend this family and will definitely book again. Thank you for everything 🐶🐾

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Sitter Profile Image: Victoria B.
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Sitter Profile Image: Victoria B.
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9. Victoria B.

Rover 101
Full time WFH doggy lover 🐾
Chelsea, MA, 02150
6.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
159 reviews
65 repeat clients
from
$65
per night

I highly recommend Victoria. She is very reliable, flexible and trustworthy. Callie enjoyed her stay and is looking forward to her next visit!!

Sitter Profile Image: Rob W.
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Sitter Profile Image: Rob W.
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10. Rob W.

Responsible long-time friend of dog
MELROSE, MA, 02176
3.4 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
55 reviews
33 repeat clients
from
$70
per night

Rob is excellent with our older dog. We always feel comfortable leaving her with Rob even though she's on lots of meds because we know she's well cared for with him and his family.

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Sitter Profile Image: Rupendra & Lora S.
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Sitter Profile Image: Rupendra & Lora S.
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11. Rupendra & Lora S.

Meet your pet’s new best friend!
Burlington, MA, 01803
4.2 mi. away
Boarding
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$55
per night

They are dependable, and conscientious with our Beagle mix, Scout. When we pulled up on our second visit, Scout could not wait to greet Rupen as we approached the house. Highly recommend.

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Sitter Profile Image: Kimm & Kenn S.
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Sitter Profile Image: Kimm & Kenn S.
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12. Kimm & Kenn S.

Love dogs, love to walk!
Woburn, MA, 01801
2.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
172 reviews
94 repeat clients
from
$70
per night

Kimm and her husband took great care of our nearly 2yr old golden doodle. He was comfortable with them and she updated me each day with a photo. This was our first stay through Rover and it went well. We’d use Kimm again for sure.

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Sitter Profile Image: Sarah S.
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Sitter Profile Image: Sarah S.
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13. Sarah S.

WFH with training experience!
Somerville, MA, 02143
4.9 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
5 reviews
1 repeat client
from
$60
per night

Sarah was incredible. A total professional with a clear natural way with dogs - Zazu absolutely loved her. I had so much confidence that Zazu was treated like a little prince and so, so well taken care of. Amazing communication over the time I was away too, I'd recommend her to anyone. I'll most certainly be requesting Sarah's services again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Yesika S.
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Sitter Profile Image: Yesika S.
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14. Yesika S.

Loving, caring and good leader
North Cambridge, Cambridge, MA, 02140
4.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
168 reviews
54 repeat clients
from
$70
per night

Yesika was very nice and kind with my Sammy. She always respond promptly and send photos and videos every day. She is the best. I really recommend her. 🥰

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Sitter Profile Image: Keunyung P.
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Sitter Profile Image: Keunyung P.
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15. Keunyung P.

Love all furry friends :-)
North Cambridge, Cambridge, MA, 02140
4.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
41 reviews
13 repeat clients
from
$60
per night

Keunyung took such good care of Noah while I was away for a weekend! She provided regular updates with tons of pictures and videos, and I appreciated the daily journal of his walks and meals. She really helped me feel at ease while I was away. Thank you for giving Noah the best weekend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Hannah L.
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Sitter Profile Image: Hannah L.
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16. Hannah L.

Care and fun walks for your dog!
Stoneham, MA, 02180
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
5 repeat clients
from
$65
per night

Hannah was absolutely amazing with our strong-willed, yet anxious pup. She was incredibly communicative and did a great job keeping us posted regarding any developments (she also made sure to send us cute photos and videos at regular intervals). We will definitely look to book with her again when the need arises!

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Sitter Profile Image: Siddharth &  Nikita V.
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Sitter Profile Image: Siddharth &  Nikita V.
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17. Siddharth & Nikita V.

Always here for the fur babies! 🐶
Stoneham, MA, 02180
1.9 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
5 reviews
1 repeat client
from
$65
per night

It was such a great experience with Siddharth and Nikita! Luna had a great time playing with their dog and they gave her lots of love and care! They also sent me plenty of pictures and video of Luna for updates which I really appreciate! Highly recommended!

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Sitter Profile Image: Philip T.
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Sitter Profile Image: Philip T.
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18. Philip T.

Loving and responsible caretaker
Somerville, MA, 02145
4.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
53 reviews
23 repeat clients
from
$60
per night

Philip was very responsive to my communications leading up to Chloe's stay and during the stay. He sent multiple updates with photos every day which allowed me to relax while I was away. She got plenty of attention and walks! from him and his son. (Chloe slept in son's bed. 😃). I can recommend Philip to take good care of your dog! Thank you Philip!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sarah B.
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Sitter Profile Image: Sarah B.
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19. Sarah B.

Your pup’s safe space ❤️
Somerille, MA, 02144
4.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
7 repeat clients
from
$60
per night

My dog had such a great time and was clearly well taken care of! My dog was so excited when I dropped her off! Sarah reached out consistently with photo updates and asked about my dogs needs and boundaries I’m trying to instill.

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Sitter Profile Image: Katerina & Roland C.
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Sitter Profile Image: Katerina & Roland C.
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20. Katerina & Roland C.

Rover 101
Pet-less family to love your pet
Arlington, MA, 02476
3.7 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
28 reviews
9 repeat clients
from
$60
per night

Katerina and Roland took excellent care of our dog for us for a weekend trip. They sent us photos and videos of Lucy having a great time and were easy to communicate with. Highly recommend.

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  1. 1. Search

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Winchester Dog Boarding ratings

Overall Rating:
5.0 out of 5 stars

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.

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