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

Our dog has stayed with Oana and Oliver several times and we are always completely comfortable dropping her off knowing she will have plenty of attention and exercise while she is there. They send great pictures each day and are very responsive to any questions. We highly recommend Oana and Oliver!

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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 provided great care and continued updates on our pup, which left us reassured that he was in good hands. The videos and pictures she shared showed our pup playing happily, having snacks and bonding with family members. We couldn't have asked for a better place to board our dog. He clearly was in lovely home and taken care of like part of the family.

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Sitter Profile Image: Katerina & Roland C.
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Sitter Profile Image: Katerina & Roland C.
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3. 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

I cannot say enough good things about this family and their care of Sadie. We were in a tough spot and ar 8pm the night before we left on vacation she had an emergency procedure which required extra care, medicine, and monitoring. They stepped up and took care of all of it, sending us pictures daily to show how she was healing, etc. And a lovely family with kids with love dogs. Highly recommend.

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Sitter Profile Image: Paul M.
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Sitter Profile Image: Paul M.
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4. 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 was great, he was very easy to coordinate with (despite our running late to the drop-off). He was very responsive and sent cute photo updates. Thanks, Paul!

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Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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5. 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
28 reviews
10 repeat clients
from
$60
per night

Tmzi was very fortunate to have Julie as their sitter! This was my first experience leaving him with someone other than my family. I had a sense of safety and care throughout the entire two-day period. I have no doubt that he thoroughly enjoyed spending time with Julie. The time my energized son (tMzi) spent with Julie was fantastic! I got a lot of updates that included pictures. Tmzi was surrounded by love and exercise. Boarding with Julie again is something I would do! 🙏🏼😘🐶

Confirmed availability: Memorial Day Weekend
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

Our dog loved staying with Rebecca and her family. He's a very anxious dog but pick up and drop off were very easy. She provided pictures and updates daily. Her kids loved him and were great with him. We would definitely recommend.

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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 had a wonderful experience with Surendra's family for sitting Ruby! They went above and beyond to keep me informed during my time away by sharing regular videos and photos of my furry friend. It was reassuring to see how well my pet was being taken care of. Their attention to detail and communication skills really stood out. I highly recommend Surendra to anyone looking for reliable and caring pet care services.

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Sitter Profile Image: Betsy C.
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Sitter Profile Image: Betsy C.
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9. 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Keunyung P.
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Sitter Profile Image: Keunyung P.
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10. 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: Victoria B.
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Sitter Profile Image: Victoria B.
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11. 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
158 reviews
64 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!!

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Sitter Profile Image: Nana G.
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Sitter Profile Image: Nana G.
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12. Nana G.

Stay at home sitter w/ fenced yard
Medford, MA, 02155
2.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
11 reviews
from
$55
per night

Nana did great with Mac Daddy! I received updates on how he was doing while I was away, and Nana was also certain to ask me important details about taking care of Mac Daddy.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Hannah L.
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Sitter Profile Image: Hannah L.
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13. 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: Rupendra & Lora S.
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Sitter Profile Image: Rupendra & Lora S.
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14. 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
4 repeat clients
from
$55
per night

Peanut had the best time with Rupendra and Lora! They were so accommodating especially when I was running late to pick her up. They sent frequent photos, videos and updates which made me feel so much better knowing she was happy and comfortable with them as it is her first time boarding in quite a while. They administered her medication as directed and kept me up to date on how she was eating. Given her condition I felt extremely comfortable knowing she was taken care of and I would absolutely rebook with them!

Sitter Profile Image: Rob W.
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Sitter Profile Image: Rob W.
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15. 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

I had a really good experience with Rob! He was very easy to work with, and made me feel at ease. It was a great fit for our 9 year old, but still very energetic, Vizsla. Rob made sure that our dog got exercise and affection. I received some pictures, which was very reassuring. I would trust Rob and his family again with our Daisy. Thank you again!!!

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Sitter Profile Image: Sarah S.
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Sitter Profile Image: Sarah S.
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16. 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 is wonderful! She was lovely, responsible, and fabulous with our pup who stayed with her for a whole week, and she was perfect in her communication with me. Our dog can sometimes be a little difficult on leash, and she managed him beautifully. She really helped me feel comfortable while away, in not needing to worry at all about my dog. She was also incredibly flexible as it was better for me to drop him off a day earlier than initially planned. I fully and completely recommend Sarah (though I don't really want to because I know she'll become hard to book!).

Sitter Profile Image: Kimm & Kenn S.
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Sitter Profile Image: Kimm & Kenn S.
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17. 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 Kenn were wonderful with my dog. They took her on great daily walks and made sure she had her daily medication. I felt really good and safe leaving my dog with them. I'm thankful.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Yesika S.
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Sitter Profile Image: Yesika S.
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18. 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 an amazing dog-sitter! She boarded my Luka on short notice during a long weekend. I was assured that he was being taken care of as Yesika was very communicative and sent pictures of Luka throughout. I didn’t worry about him at all and could tell that he loved his time spent with Yesika and her other dog, Grecia. Yesika was very loving towards Luka and took him on plenty of walks to the dog parks nearby her apartment. I can’t recommend her enough, and I know I’ll be using her services again in the future!

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Sitter Profile Image: Siddharth &  Nikita V.
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Sitter Profile Image: Siddharth &  Nikita V.
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19. 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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20. 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
52 reviews
23 repeat clients
from
$60
per night

Philip really took care of our dogs while we were out of town. Updated daily with the pictures and videos. Very nice and kind! Happy to find him!

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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.

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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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