Doggy Day Care in Winchester

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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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
Star Sitter
For the love of dogs
Woburn, MA, 01801
2.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
335 reviews
164 repeat clients
from
$55
per day

Oana and Oliver are wonderful dog sitters!! They are kind, easy going, and always send the best pictures! We had an extenuating circumstance with our trip and they were completely accommodating and understanding. I highly recommend them for all doggy daycare and sitting needs!!

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Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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2. 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
5.0 out of 5 stars
31 reviews
10 repeat clients
from
$54
per day

Julia provided exceptional care for my furry friend while I was away. Her attention to detail, genuine love for animals, and regular updates put my mind at ease. I highly recommend her services to anyone in need of a reliable and compassionate dog sitter.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Keunyung P.
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Sitter Profile Image: Keunyung P.
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3. 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
5.0 out of 5 stars
42 reviews
13 repeat clients
from
$48
per day

Keunyung (Grace) has been amazing and our dog loved staying with her! Our dog is a little anxious and has difficulty getting to know new people, she was very attentive, caring and gentle with him, which helped him adjust to the new environment. He was tired and happy when I picked him up. Grace was also very responsive and friendly, and sent us photos of him having a good time. We can highly recommend her!

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Sitter Profile Image: Andy S.
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Sitter Profile Image: Andy S.
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4. Andy S.

🐾 Meet Your Pet's New Best Friend!
Arlington, MA, 02474
2.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$45
per day

Andy watched our dog for the day. He was accommodating with our early drop off and was also quick to respond to any messages. Our dog looked in good shape and happy when we picked him up.

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Sitter Profile Image: Philip T.
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Sitter Profile Image: Philip T.
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5. Philip T.

Star Sitter
Loving and responsible caretaker
Somerville, MA, 02145
4.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
54 reviews
24 repeat clients
from
$47
per day

Philip is the absolute best! Very communicative and very caring! He has watched our Pomsky for the day (who is probably the craziest dog you'll meet) and they did wonderful together. Milo went on plenty of walks with Philip and got plenty of playtime. When I got Milo at the end of the day he went straight to sleep! (something you never see LOL)!

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Sitter Profile Image: Yesika S.
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Sitter Profile Image: Yesika S.
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6. Yesika S.

Star Sitter
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
172 reviews
56 repeat clients
from
$63
per day

Yesika is a great dog sitter. It was my first time on Rover and I was really worried about leaving my 5 moths old puppy with a stranger, but after meeting Yesika and her partner I immediately felt at ease because you can see how much the love and care for the dogs in their care. Loki had a wonderful time at Yesika's place: I could tell not only from the pics, but from the fact that when I went to pick him up he was staying close to Yesika while we were chitchatting about Loki's stay, and we were ready to leave he wanted to go back in the building with her. Loki also had a couple of pee accidents at home the first day he was in Yesika's care (he was not used to the new house, despite being putty trained in our home) and Yesika handled this with a lot of compassion and understanding. She also gave me a few useful tips about games that she played with Loki to entertain his brain in a positive way and some advice on chewing toys that I had gotten for Loki which could be potentially harmful. Overall I was incredibly happy trusting Loki to Yesika's care and I will do that again in the future. Highly recommend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Mana C.
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Sitter Profile Image: Mana C.
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7. Mana C.

Star Sitter
Tail-Wagging Dog Bliss 🐾
Melrose, MA, 02176
3.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
9 reviews
6 repeat clients
from
$40
per day

Mama was very responsive, kept us updated, and provided great care for our dog! He came home a happy and tired guy- had the best time with Brian :) looking forward to booking again

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kim H.
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Sitter Profile Image: Kim H.
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8. Kim H.

Star Sitter
Simply treat pets as same as human
North Cambridge, Cambridge, MA, 02140
4.0 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
36 reviews
9 repeat clients
from
$40
per day

Jason was fantastic taking care of our pup, Doug. Jason is extremely communicative, fast to respond, and provides pictures and descriptive updates of how our pup is doing. Jason was fast to adapt and very accommodating to our pup, by the 2nd day of our day care, Doug was wagging his tail when he first saw Jason in the morning I'd highly recommend Jason to anyone in need of providing a place and loving attention for their dog.

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Sitter Profile Image: Alana B.
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Sitter Profile Image: Alana B.
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9. Alana B.

I’ll love them like they’re my own
Medford, MA, 02155
3.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
9 reviews
3 repeat clients
from
$45
per day

Alana is a fantastic dog sitter! She took care of Pudding for the day, and I couldn't be happier with the experience. Alana's love and attention to detail were evident from the moment we met. Pudding had a wonderful time with her, and I felt completely at ease knowing that my furry friend was in such capable hands. I highly recommend Alana to anyone in need of a caring and responsible dog sitter. She's simply the best!

Sitter Profile Image: Andrew K.
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Sitter Profile Image: Andrew K.
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10. Andrew K.

Star Sitter
Camberville dog owner for 10+ years
North Cambridge, Somerville, MA, 02144
3.7 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
14 reviews
3 repeat clients
from
$50
per day

Once more, Jerry had a BLAST with Andrew. Truly so grateful for Andrew. He’s beyond competent and kind. Our puppy left happy and we can tell that our puppy was loved while with Andrew. Highest rating!

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

Rover 101
Star Sitter
Comfort of home for your pet
Burlington, MA, 01803
3.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
102 reviews
16 repeat clients
from
$50
per day

Biscuit spent a great day with Surendra and family. There is a big back yard to roam and their dog was a good playmate. Lots of pictures and videos came my way throughout the day which was appreciated. Will utilize this homes services when needed. It is obvious they are animal lovers. ??

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Emily C.
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Sitter Profile Image: Emily C.
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12. 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
23 reviews
7 repeat clients
from
$48
per day

Emily was wonderful! Our dog clearly had a blast. Will be using her again :)

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
23 reviews
7 repeat clients
from
$40
per day

Hannah was great! We are new pup parents and this was the first time we left our puppy with a sitter. I really appreciated how Hannah kept us updated throughout the day with pictures, videos, and messages. I booked last minute and she was responsive and answered all my questions beforehand. I will definitely look to rebook with Hannah 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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14. 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
6 reviews
1 repeat client
from
$55
per day

Nikita and Siddharth were great - they are very professional, extremely responsive and they clearly love dogs! They sent a lot of pictures and videos of coco and always responded to my messages within minutes. This was coco’s first day care experience and she loved it! We also loved their community with the cleanest dog park. We would absolutely book with them again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Charlene C.
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Sitter Profile Image: Charlene C.
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15. Charlene C.

Hangin with my dawgs!
Arlington, MA, 02474
2.5 mi. away
Boarding, Doggy Day Care
2 reviews
from
$33
per day

Charlene is a caring and loving person who has cared for and loved dogs her whole life. She will provide a warm and safe environment along with fun and exercise. Highly recommend.

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Sitter Profile Image: Louisa S.
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Sitter Profile Image: Louisa S.
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16. Louisa S.

Unleash Reliable & Loving Pet Care!
Medford, MA, 02155
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
24 reviews
8 repeat clients
from
$40
per day

Louisa took great care of my dog. I could tell that my dog was happy and relaxed during her time there. Louisa was quick to respond and seems very reliable. I'll be sure to use her in the future!

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Sitter Profile Image: Jade L.
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Sitter Profile Image: Jade L.
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17. Jade L.

Safe, Fun, and Well-Researched!
Medford, MA, 02155
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
2 repeat clients
from
$55
per day

Jade was fantastic with Lena again. Lena always seems really happy when we pick her up! Thanks Jade!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kristin K.
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Sitter Profile Image: Kristin K.
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18. Kristin K.

I’ve got love to spare
Winchester, MA, 01890
1.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
10 reviews
from
$50
per day

Highly recommend Kristen! She did such an amazing job at making my dog George comfortable (he has really bad separation anxiety). Throughout the day I got picture and video updates of George, and it looked like he was having a blast! I had never seen him so happy with a babysitter before. She was very professional; great with communication and even offered a meet and greet prior to our appointment. I would absolutely have Kristen watch George again in the future.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jacqueline S.
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Sitter Profile Image: Jacqueline S.
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19. Jacqueline S.

Let me love on your pup!!
Woburn, MA, 01801
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
3 repeat clients
from
$38
per day

About: Hi! I have a 2 year old medium to large sized dog of my own. I have experience with both small and large dogs. When I was living in Texas I volunteered regularly at our local dog shelter and I have fostered and found forever homes for 8 incredible dogs. I unfortunately work in the office, but your pup (and mine) would be left alone for 7 hours max. I use the positive reinforcement method of training. Everyone makes mistakes and dogs are no different! My foster dogs all had basic manners and understood basic commands before moving into their forever homes. Dogs get destructive when bored, so I like to take them on multiple walks a day and keep them both physically and mentally stimulated. I wake up at 6am, let the pups out for the bathroom, go inside for feeding, then back out for 20-30 minutes of exercise. I leave for work around 8:30 and I typically have a friend who comes by midday to let my pup out to potty and play. My roommate is home by 5:30 and would resume care until I’m home around 6. I have a high energy pup so I then exercise him for about an hour in the evening and then we go to bed around 10 or 11! I have a fenced backyard with plenty of room for the pups to run around and play. Inside the dogs have free roam, but my own pup sleeps in a crate at night. Whatever works best for your dog is what we’ll do!

Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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20. Michael D.

Star Sitter
A loving experience for your pet!
Winchester, MA, 01890
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
24 reviews
11 repeat clients
from
$55
per day

Our puppy seemed to have a great time based on the pictures Michael sent us and also the way the pup didn't seem to want to leave. We'd cheerfully use Michael again.

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Winchester Doggy Day Care ratings

Overall Rating:
4.8 out of 5 stars

Doggy Day Care sitters in Winchester are rated on average 4.8 out of 5 stars based on 19 reviews.

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