Dog Boarding in Winchester

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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
Star Sitter
For the love of dogs
Woburn, MA, 01801
2.6 mi. away
Boarding, Doggy Day Care
from
$75
per night
5.0 out of 5 stars
380 reviews
177 repeat clients
Profile image

We had the best experience boarding our dog with Oana and Oliver. They were extremely caring, responsible, and kept us up to date with pictures every day (and the pictures they sent are extremely high quality!). After our meet and greet, we could immediately tell that Oana and Oliver were experts and thorough when it came to boarding. They asked detailed questions including dietary restrictions, how T-Rex prefers to eat/sleep/walk, and how T-Rex interacts with other dogs to make sure that T-Rex would have the best experience at their place. Oana and Oliver's place also has an amazing back yard that T-Rex enjoyed running around. They are also very communicative and we were able to travel with ease knowing that T-Rex was in good hands. We are definitely going to board T-Rex with them again in the future and we'd highly recommend Oana and Oliver to anyone who is looking for someone to trust their dog with.

Availability updated 5 days ago
Sitter Profile Image: Yesika S.
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Sitter Profile Image: Yesika S.
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2. Yesika S.

Star Sitter
Loving, caring and good leader
Medford, MA, 02155
2.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$65
per night
5.0 out of 5 stars
294 reviews
85 repeat clients
Profile image

Yesika was an amazing sitter! She’s very communicative about the pet’s happiness and comfortability and she goes the extra mile to make sure they’re comfortable. She took excellent care of my dog Luke and I would love to book her again in the future.

Availability updated today
Sitter Profile Image: Surendra S.
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Sitter Profile Image: Surendra S.
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3. Surendra S.

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

Our dog always has a great time here! Surendra is so good with communication and sends many photos and videos during the stay. We are SO grateful for her and her family providing a happy place for our pup!

Availability updated yesterday
Sitter Profile Image: Betsy C.
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Sitter Profile Image: Betsy C.
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4. Betsy C.

Star Sitter
WFH dog lover with fenced yard
Arlington, MA, 02474
2.8 mi. away
Boarding, Doggy Day Care
from
$70
per night
5.0 out of 5 stars
25 reviews
12 repeat clients
Profile image

Betsy was a great sitter - very thorough and careful in getting to know my dog’s preferences and letting him see her very nice home and yard! Easy to communicate with and my pup seemed super happy :)

Availability updated yesterday
Sitter Profile Image: Keunyung P.
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Sitter Profile Image: Keunyung P.
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5. Keunyung P.

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

Keunyung and her husband did a fantastic job taking care of my dog Sugar over the holidays. Keunyung is very responsive and meticulous. She takes notes of every time she walks and feeds Sugar and sends me cute photos/videos. She even gave Sugar coconut water when noticing Sugar didn’t drink water. I can easily tell Sugar had a great time there. Would highly recommend Keunyung!

Availability updated 4 days ago
Sitter Profile Image: Carol L.
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Sitter Profile Image: Carol L.
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6. Carol L.

Go to work or vacation guilt free!
Stoneham, MA, 02180
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
Profile image

Wonderful! Carol has boarded my corgi several times now and she's been a pleasure to work with. She always take great care of my dog, she's communicative, flexible, and she's been available whenever I've needed her. Thanks Carol!

Availability updated yesterday
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Paul M.
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Sitter Profile Image: Paul M.
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7. Paul M.

RoverGO
Puppy Paradise!
Arlington, MA, 02474
2.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$56
per night
5.0 out of 5 stars
93 reviews
38 repeat clients
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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!

Availability updated 4 months ago
Sitter Profile Image: Lissette A.
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Sitter Profile Image: Lissette A.
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8. Lissette A.

Star Sitter
Pleasant Pup Inn
Malden, MA, 02148
3.3 mi. away
Boarding
from
$65
per night
5.0 out of 5 stars
374 reviews
172 repeat clients
Profile image

Lissette was awesome! We've never boarded our dog Maggie before, but Lissette was great! We received pictures all week, and we loved that there were a couple other small dogs for Maggie to play with! I know she had a fun week, since she's been tired ever since we picked her up!

Availability updated 5 days ago
Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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9. Julia R.

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

My cat did not want to come home! Cheddar was in such great hands with Julia - she was incredibly accommodating, administered medicine and sent many pictures. Plus her home is spacious and has many places for cats to hang out. Thank you again, Julia!

Availability updated today
Sitter Profile Image: Patrick G.
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Sitter Profile Image: Patrick G.
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10. Patrick G.

Star Sitter
Reliable Pet Sitter :)
Medford, MA, 02155
3.4 mi. away
Boarding
from
$42
per night
5.0 out of 5 stars
16 reviews
2 repeat clients
Profile image

Patrick was great and super responsive, sending me pictures of Albie throughout the day/ night he stayed with him. He also was thorough in making sure he understood Albie’s needs at the start of his visit, which made it even smoother. Would definitely ask him to watch Albie another time!

Availability updated 3 days ago
Sitter Profile Image: Cassie S.
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Sitter Profile Image: Cassie S.
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11. Cassie S.

Rover 101
Star Sitter
One of the pack!
stoneham, MA, 02180
2.9 mi. away
Boarding
from
$50
per night
5.0 out of 5 stars
22 reviews
7 repeat clients
Profile image

Cassie and Alex were wonderful with our dog! She recently had radiation treatment so is on several medications. They had no problem giving her the medications twice a day. They also sent updates and pictures everyday!! We were so nervous to leave but felt instantly at ease with Cassie and Alex. This was the second week they took her. Will definitely be using them for all our future pet sitting needs. Highly recommend!!

Availability updated 5 months ago
Sitter Profile Image: Hannah L.
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Sitter Profile Image: Hannah L.
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12. Hannah L.

Star Sitter
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
from
$65
per night
5.0 out of 5 stars
45 reviews
12 repeat clients
Profile image

Hannah was amazing! She made a huge effort to keep our very active hound exercised and content. We also appreciated the regular communication while we were away. We absolutely recommend Hannah!

Availability updated today
Sitter Profile Image: Andy S.
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Sitter Profile Image: Andy S.
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13. Andy S.

Star Sitter
🐾 Meet Your Pet's New Best Friend!
Arlington, MA, 02474
2.8 mi. away
Boarding, Doggy Day Care
from
$65
per night
5.0 out of 5 stars
19 reviews
5 repeat clients
Profile image

Andy was great and updated us frequently on how Freya was doing while we were away. I’m sure that Freya is looking forward to another stay in the future.

Availability updated 5 days ago
Sitter Profile Image: Arnav J.
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Sitter Profile Image: Arnav J.
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14. Arnav J.

Paws-itively Perfect Dog Sitting
Lexington, MA, 02420
4.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$50
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
Profile image

Arnav is a very responsible and loving young man. He sent often photos of our puppy where we can tell that he was really taken care of and very loved. He and his family were always welcoming and stayed in communication with us. Our dog is part of our family and I would definitely rebook with Arnav, I highly recommend him. He will offer safety love and communication! Thanks Arnav ❤️

Availability updated 3 days ago
Sitter Profile Image: Luciana R.
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Sitter Profile Image: Luciana R.
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15. Luciana R.

Star Sitter
Flexible Full-Time Family Care
Melrose, MA, 02176
4.0 mi. away
Boarding, Doggy Day Care
from
$60
per night
5.0 out of 5 stars
234 reviews
139 repeat clients
Profile image

We left our dog Sheila with Luciana and her mother for 1 night and it was a really good experience. We got regular updates and Sheila looked really happy through out her stay. The house is clean and they keep the dogs also clean throughout the stay.

Availability updated today
Sitter Profile Image: Cheuck L.
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Sitter Profile Image: Cheuck L.
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16. Cheuck L.

Star Sitter
You Leave Em’, We Love Em’ 🐾❤️
Medford, MA, 02155
2.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$73
per night
5.0 out of 5 stars
156 reviews
36 repeat clients
Profile image

Cheuck was great with Melo. Super friendly and great communication! It’s so nice to be able to travel and know that my pup was happy and well cared for.

Availability updated today
Sitter Profile Image: Rupendra & Lora S.
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Sitter Profile Image: Rupendra & Lora S.
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17. Rupendra & Lora S.

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

Rupendra and Lora were AMAZING with our furry family member, Cooper! They sent me updates, including pictures and videos, on a regular basis and they were very flexible! I’m so happy that I no longer need to worry about Cooper while we are away!

Availability updated 14 days ago
Sitter Profile Image: Adriana P.
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Sitter Profile Image: Adriana P.
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18. Adriana P.

Rover 101
Star Sitter
Loving pet sitter, works from home!
Brookline, MA, 02446
7.3 mi. away
Boarding, Doggy Day Care
from
$60
per night
5.0 out of 5 stars
20 reviews
3 repeat clients
Profile image

I felt so comfortable because Adriana is on time and took good care of my dog. She took my dog for walks often and provided everything he needed. I think she’s a really nice sitter.

Availability updated today
Sitter Profile Image: Kristin K.
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Sitter Profile Image: Kristin K.
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19. Kristin K.

Star Sitter
I’ve got love to spare
Winchester, MA, 01890
1.3 mi. away
Boarding, Doggy Day Care
from
$75
per night
5.0 out of 5 stars
28 reviews
5 repeat clients
Profile image

This was Romeo's first stay with Kristin, and I felt so lucky to have found her on Rover to watch him. Kristin gives 100% of herself from start to end of a stay for your dog. When meeting her for the first time she really got to know what Romeo's needs were, and assured me that he would be so loved and cared for through his whole stay. While I was away she asked me how I would like to kept in touch (do I like to get photos all the time to be assured he is having fun, or just from time to time so I could have fun on my vacation. This showed that she was not only thinking about Romeo, but also my needs as the owner). Romeo had a wonderful time with her adorable little babies (Waffles and Lucy). Her dogs are not only the cutest little pups, but so well mannered and calm. Romeo had so much fun whether it was walks around the neighborhood, playing with his new playmates, or snuggling in her bed. I recognize outstanding customer service when I see it, she definitely provided that and more. He was all ready when I said was going to pick him up. I even got a great progress report after. I could not have left my baby in better hands. This is assuring to me, as when I am away on a trip, I will know Romeo is having just as much fun. Thank you Kristin for absolutely everything!

Availability updated 12 days ago
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Ashley P.
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Sitter Profile Image: Ashley P.
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20. Ashley P.

Rover 101
Boarding, walking, and play for all
Arlington, MA, 02474
3.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$65
per night
5.0 out of 5 stars
72 reviews
19 repeat clients
Profile image

Ashley took wonderful care of our dog! She knew he needed exercise and took him on lots of long walks and played ball with him frequently. We would happily use her again.

Availability updated 22 days ago

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