Doggy Day Care in Winchester

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

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Top rated Winchester doggy day care sitters

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Sitter Profile Image: Jaylese H.
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Jaylese H.
Star Sitter
from
$35
per day
5 out of 5.0 stars
21 reviews
7 repeat clients
6 years of experience
Terryville, CT, 06786

Ziggy had a great time spending the day with Jaylese for doggy daycare! They went on a nice walk and Ziggy came back happy and sleepy. She accepted my request last minute and was a breeze to work with - highly reccomend!

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Gabriella I.
Sitter Profile Image: Amber B.
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Amber B.
from
$60
per day
5 out of 5.0 stars
10 reviews
1 repeat client
30 years of experience
Bethlehem, CT, 06751

Amber was great with Ollie while I had to do something during the day. Took photos and kept a good eye on Ollie while I was gone. She was flexible and communicative. Highly recommend and would use again if in the are

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Taylor P.
Sitter Profile Image: Fiona O.
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Fiona O.
Star Sitter
from
$40
per day
5 out of 5.0 stars
23 reviews
7 repeat clients
24 years of experience
Terryville, CT, 06786

Excellent service, was sent great pictures of Sadie and she was happy. Very accommodating. We Will use Fiona again for sure.

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Lynn D.
Sitter Profile Image: Mary Ann P.
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Mary Ann P.
Star Sitter
from
$55
per day
5 out of 5.0 stars
15 reviews
5 repeat clients
14 years of experience
Cornwall, CT, 06753

About: Grew up on a farm caring for animals since my youth. now enjoy the company of visiting dogs, just like I had with my own. I currently work part-time and many situations able to bring a boarding dog with me; as I work with mostly older folks who would love the sweetness of a dog visit; considered therapy. I have a side fenced yard, safe from the road, and only do private walks in a comfortable grass field near my home, leashed and one at a time for individual attention.

Sitter Profile Image: Eric L.
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Eric L.
Star Sitter
from
$29
per day
5 out of 5.0 stars
16 reviews
4 repeat clients
55 years of experience
Weatogue, CT, 06089

This was the first time that I used Eric. Eric and his wife were wonderful with Milo. Eric let me know that Milo was doing well and also sent a picture. Milo came home happy and tired. I will definitely use Eric again.

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Nancy W.
Sitter Profile Image: Katie L.
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Katie L.
Star Sitter
from
$30
per day
5 out of 4.9 stars
111 reviews
53 repeat clients
35 years of experience
Simsbury, CT, 06070

Katie was so awesome with our puppy. She was incredibly flexible. Will definitely use her services again.

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Michael D.
Sitter Profile Image: Angela & Tommy P.
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Angela & Tommy P.
from
$38
per day
5 out of 5.0 stars
68 reviews
30 repeat clients
9 years of experience
Avon, CT, 06001

Rockie had a wonderful time playing chase with her new doggie friends in the back yard and came home a tired and happy pup after a wonderful day with Khanh and Tommie, She will stay with them again!

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Kitty C.
Sitter Profile Image: MJ M.
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MJ M.
Star Sitter
from
$45
per day
5 out of 4.9 stars
110 reviews
55 repeat clients
20 years of experience
Simsbury, CT, 06070

Our first time having MJ take care of our puppy. She loves dogs and gave our dog some quality time while we were away. We will call on her again.

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Joel H.
Sitter Profile Image: Cruz Maria D.
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Cruz Maria D.
Star Sitter
from
$35
per day
5 out of 4.9 stars
381 reviews
238 repeat clients
30 years of experience
Simsbury/Avon/Canton/Hartford County, CT, 06070

Our dog Rocky loves to go to Maria’s house. Everyday Rocky runs up the steps and can’t wait to go inside. He has a great time playing with other dogs. Maria is flexible and accommodating. There were nights that we couldn’t pick up Rocky until late and she was always accommodating and flexible. I can tell that she really love dogs! We had a great experience with her and very thankful of her watching Rocky.

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Yang L.
Sitter Profile Image: Karina S.
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Karina S.
Star Sitter
from
$50
per day
5 out of 5.0 stars
89 reviews
40 repeat clients
23 years of experience
Barkhamsted, CT, 06063

Karina was WONDERFUL! Our dog hasn’t been boarded a lot in her life, and has been nervous when she has, but she was comfortable as soon as we walked into the yard and so calm and happy when we picked her up! Karina was so communicative before and during her stay, and I appreciate how through she was with what to bring and making sure all the dogs in her care are up to date on vaccinations. We are so happy with our stay and will definitely bring our dog back!

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Caitlin D.
Sitter Profile Image: Gail S.
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Gail S.
from
$45
per day
5 out of 5.0 stars
8 reviews
1 repeat client
10 years of experience
Granby, CT, 06035

Gail is a dream! She kept my girl active and engaged and shared pictures as well. I had total peace of mind leaving my pup with her. She is also a great communicator. Highly recommend.

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Sarah L.
Sitter Profile Image: Kimberlly C.
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Kimberlly C.
from
$60
per day
5 out of 5.0 stars
38 reviews
9 repeat clients
18 years of experience
Harwinton, CT, 06791

Super easy drop off and pick up for my two cats, and they had a nice little time. She sent photos and kept me updated and made everything easy ????.

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Noah M.
Sitter Profile Image: Katrini L.
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Katrini L.
Star Sitter
from
$30
per day
5 out of 5.0 stars
62 reviews
31 repeat clients
25 years of experience
Simsbury, CT, 06002

Katrini and Potter have been an incredible addition to our puppy’s day! He is so excited to go to day care every single time we drop him off. Potter has an incredible temperament and is an excellent play partner while Katrini is an amazing communicator and always goes the extra mile. Leaving your puppy with someone is always hard but Katrini and Potter make it so easy. I couldn’t recommend them enough!

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McKaylah D.
Sitter Profile Image: Briana  V.
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Briana V.
from
$35
per day
5 out of 5.0 stars
12 reviews
6 repeat clients
3 years of experience
Granby, CT, 06035

Briana was very kind and available for my puppy. I believe Molly was very happy in her care and was given enough attention. I will definitely use Briana again in the future as needed.

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Amy B.
Sitter Profile Image: Ashley D.
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Ashley D.
from
$25
per day
30 years of experience
Southfield, MA, 01259

About: Hi there! I'm Ashley, a lifelong dog lover and work-from-home mom ready to give your pup the care and comfort they deserve. I have a special place in my heart for senior dogs, especially after caring for my fur daughter, my sweet long-haired Chihuahua who was by my side for 17 wonderful years. I understand the slower pace and extra TLC that older pups need, and I’m here to provide just that. We’ve also had two German Shepherd mixes in the past, so I’m no stranger to larger breeds. While I typically prefer small to medium-sized dogs for our home setup, I’m open to exceptions for well-mannered larger dogs — especially seniors. Because I work from home and my kids are at daycare during the day, it’s just me and your pup…which means plenty of calm, one-on-one attention and companionship in a quiet environment. I know how stressful it can be to find care you trust…especially when options in our area are limited. That’s why I treat every dog like family, with love, routine, and lots of affection. I’ll care for your furry loved one as if they were my own and will happily share updates and photos as often as you'd like to give you peace of mind while you're away. I provide attentive, loving care while fitting seamlessly into my daily routine. Because I work from home with a lot of flexibility, I can offer daily daycare with plenty of walks, playtime, and cuddles. I’m also happy to provide overnight boarding for dogs who need a home-away-from-home. Throughout, I’ll keep you updated as much as you’d like, so you always feel comfortable and connected. I care for dogs in a safe, comfortable home environment where your dog will be treated like a valued family member. While I don’t have a fenced backyard, your dog will always be supervised and safe. They’re always free to explore and relax throughout the home. Because pets are part of the family, we often allow them on the couch and beds to snuggle and feel at home, but I’m always happy to follow your preferences to make sure your fur baby feels comfortable and loved.

Sitter Profile Image: Nell S.
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Nell S.
Star Sitter
from
$25
per day
5 out of 4.9 stars
41 reviews
20 repeat clients
52 years of experience
Harwinton, CT, 06791

Nell is wonderful. Super flexible with arranging time to drop off and pick up. Dizzy loves staying here. He would run down the steps to the front door! I would definitely recommend her for any pet care needs !

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alex f.
Sitter Profile Image: Angela W.
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Angela W.
from
$45
per day
5 out of 5.0 stars
112 reviews
43 repeat clients
15 years of experience
Torrington, CT, 06790

Angela was great! Phoebe is always a little sad and anxious away from home and Angeka really helped her settle in. She has a wonderful kindness that the animals really connect with..Phoebe really liked her from the very first. Will definitely use her again for our next weekend away

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Keelia P.
Sitter Profile Image: Matt T.
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Matt T.
from
$50
per day
1 repeat client
15 years of experience
Torrington, CT, 06790

About: As someone who has taken care of animals for almost two decades, I've seen it all. From aggressive pets, to escapists, to pets with serious health problems. But even with those hardships I've managed to get through for those dogs and their owners. I've met some very amazing animals throughout my years, and everytime they can't get enough of me, I'm basically the Pet Whisper. And I'm always able to complete the checklist, feed, walk, take them to their appointments, and so on. My clients have been able to trust me, I'm a hard worker who doesn't give up, who goes above and beyond to make my clients proud and their pets happy. I'm currently employed as a Sales Associate at Ocean State. My hours vary quite a bit, but normally I work up to 3 weekdays and both weekends, sometimes only one of them. My hours can be from 7-1 to 11 or 1-7:30 Currently I have a dog and cat. My cat stays in my room while my dog is allowed in our stairway, hallway, living room, dining room and kitchen. My cat gets along with all cats, but is very finicky around other dogs, even my own. They are both separated by a gate, so there's no fear of them ever interacting as my dog loves trying to chase her if he ever gets the chance. My dog gets along with most dogs regardless of size but, he'll always be egging them on to play haha. My house isn't entirely large but it's enough for your pet to move around, play, and relax. My complex is very large and a great walking area for your pet. There's also a dog park right around the street that's a wonderful place for your dog to socialize. And, next to that park is a large trail that's perfect for walking. If your dog likes the beach, there's plenty of them in my vicinity.

Sitter Profile Image: Richard W.
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Richard W.
from
$50
per day
5 out of 5.0 stars
10 reviews
1 repeat client
15 years of experience
Collinsville, CT, 06019

Our young pup Hank spent the day with Rich and his three dogs. Hank had an amazing day running around Rich’s awesome backyard. Rich was so attentive, made sure to work on the commands we’ve been training, sent lots of updates, and really went above and beyond taking care of him. We can’t wait for Hank to keep going back :)

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Sarah P.
Sitter Profile Image: Rebecca P.
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Rebecca P.
from
$55
per day
5 out of 5.0 stars
4 reviews
1 repeat client
8 years of experience
Torrington, CT, 06790

Sam had the best day ever with Rebecca and we felt comfortable knowing he was with her. She was great at communicating with us throughout the day and sending pictures. He will definitely be back for more fun.

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Molly H.
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Loving doggy day care in your neighborhood

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Sitter Profile Image: Jaylese H.
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Sitter Profile Image: Jaylese H.
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Jaylese H.
Star Sitter

Pet Pal: Play, Cuddle, Repeat!
Terryville, CT, 06786
18.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
21 reviews
7 repeat clients
Profile image

Ziggy had a great time spending the day with Jaylese for doggy daycare! They went on a nice walk and Ziggy came back happy and sleepy. She accepted my request last minute and was a breeze to work with - highly reccomend!

Availability updated today
Sitter Profile Image: Amber B.
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Sitter Profile Image: Amber B.
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Amber B.

Loving Pet Care
Bethlehem, CT, 06751
21.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per day
5 out of 5.0 stars
10 reviews
1 repeat client
Profile image

Amber was great with Ollie while I had to do something during the day. Took photos and kept a good eye on Ollie while I was gone. She was flexible and communicative. Highly recommend and would use again if in the are

Availability updated 11 days ago
Sitter Profile Image: Fiona O.
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Sitter Profile Image: Fiona O.
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Fiona O.
Star Sitter

Happy to watch your furbaby
Terryville, CT, 06786
20.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
23 reviews
7 repeat clients
Profile image

Excellent service, was sent great pictures of Sadie and she was happy. Very accommodating. We Will use Fiona again for sure.

Availability updated 2 days ago
Sitter Profile Image: Mary Ann P.
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Sitter Profile Image: Mary Ann P.
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Mary Ann P.
Star Sitter

Country, calm home with one adult
Cornwall, CT, 06753
13.1 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$55
per day
5 out of 5.0 stars
15 reviews
5 repeat clients

Mary Ann has had dogs all her life. She has a loving and caring personality that comes across in all her interactions with others. I'm a two year ROVER sitter and she is very familiar with how it works. I assure everyone she would be a great hostess for your loved pets.

Availability updated yesterday
Sitter Profile Image: Eric L.
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Sitter Profile Image: Eric L.
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Eric L.
Star Sitter

No pet too big or small
Weatogue, CT, 06089
16.4 mi. away
Boarding, House Sitting, Doggy Day Care
from
$29
per day
5 out of 5.0 stars
16 reviews
4 repeat clients
Profile image

This was the first time that I used Eric. Eric and his wife were wonderful with Milo. Eric let me know that Milo was doing well and also sent a picture. Milo came home happy and tired. I will definitely use Eric again.

Availability updated yesterday
Sitter Profile Image: Katie L.
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Sitter Profile Image: Katie L.
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Katie L.
Star Sitter

Mom to 3 cats, 1 dog (and 2 humans)
Simsbury, CT, 06070
15.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$30
per day
5 out of 4.9 stars
111 reviews
53 repeat clients
Profile image

Katie was so awesome with our puppy. She was incredibly flexible. Will definitely use her services again.

Availability updated 31 days ago
Sitter Profile Image: Angela & Tommy P.
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Sitter Profile Image: Angela & Tommy P.
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Angela & Tommy P.

Pawsome Boarding: Love & Care
Avon, CT, 06001
16.1 mi. away
Boarding, Doggy Day Care
from
$38
per day
5 out of 5.0 stars
68 reviews
30 repeat clients
Profile image

Rockie had a wonderful time playing chase with her new doggie friends in the back yard and came home a tired and happy pup after a wonderful day with Khanh and Tommie, She will stay with them again!

Availability updated yesterday
Sitter Profile Image: MJ M.
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Sitter Profile Image: MJ M.
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MJ M.
Star Sitter

Your pup’s new best friend
Simsbury, CT, 06070
15.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 4.9 stars
110 reviews
55 repeat clients
Profile image

Our first time having MJ take care of our puppy. She loves dogs and gave our dog some quality time while we were away. We will call on her again.

Availability updated 4 days ago
Sitter Profile Image: Cruz Maria D.
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Sitter Profile Image: Cruz Maria D.
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Cruz Maria D.
Star Sitter

PICK ME, HAPPY TAILS, HAPPY CHERUBS
Simsbury/Avon/Canton/Hartford County, CT, 06070
15.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
from
$35
per day
5 out of 4.9 stars
381 reviews
238 repeat clients
Profile image

Our dog Rocky loves to go to Maria’s house. Everyday Rocky runs up the steps and can’t wait to go inside. He has a great time playing with other dogs. Maria is flexible and accommodating. There were nights that we couldn’t pick up Rocky until late and she was always accommodating and flexible. I can tell that she really love dogs! We had a great experience with her and very thankful of her watching Rocky.

Availability updated 3 days ago
Sitter Profile Image: Karina S.
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Sitter Profile Image: Karina S.
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Karina S.
Rover 101
Star Sitter

TLC provider for furry friends;).
Barkhamsted, CT, 06063
10.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per day
5 out of 5.0 stars
89 reviews
40 repeat clients
Profile image

Karina was WONDERFUL! Our dog hasn’t been boarded a lot in her life, and has been nervous when she has, but she was comfortable as soon as we walked into the yard and so calm and happy when we picked her up! Karina was so communicative before and during her stay, and I appreciate how through she was with what to bring and making sure all the dogs in her care are up to date on vaccinations. We are so happy with our stay and will definitely bring our dog back!

Availability updated 6 days ago
Sitter Profile Image: Gail S.
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Sitter Profile Image: Gail S.
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Gail S.

Retired and love dogs
Granby, CT, 06035
16.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
8 reviews
1 repeat client
Profile image

Gail is a dream! She kept my girl active and engaged and shared pictures as well. I had total peace of mind leaving my pup with her. She is also a great communicator. Highly recommend.

Availability updated 7 days ago
Sitter Profile Image: Kimberlly C.
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Sitter Profile Image: Kimberlly C.
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Kimberlly C.

Loving &Caring for your furbabies❤️
Harwinton, CT, 06791
11.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$60
per day
5 out of 5.0 stars
38 reviews
9 repeat clients
Profile image

Super easy drop off and pick up for my two cats, and they had a nice little time. She sent photos and kept me updated and made everything easy ????.

Availability updated 35 days ago
Sitter Profile Image: Katrini L.
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Sitter Profile Image: Katrini L.
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Katrini L.
Star Sitter

Experienced pet care.
Simsbury, CT, 06002
15.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$30
per day
5 out of 5.0 stars
62 reviews
31 repeat clients
Profile image

Katrini and Potter have been an incredible addition to our puppy’s day! He is so excited to go to day care every single time we drop him off. Potter has an incredible temperament and is an excellent play partner while Katrini is an amazing communicator and always goes the extra mile. Leaving your puppy with someone is always hard but Katrini and Potter make it so easy. I couldn’t recommend them enough!

Availability updated 2 days ago
Sitter Profile Image: Briana  V.
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Sitter Profile Image: Briana  V.
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Briana V.

Animal Lover, Home Full-time!
Granby, CT, 06035
16.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$35
per day
5 out of 5.0 stars
12 reviews
6 repeat clients
Profile image

Briana was very kind and available for my puppy. I believe Molly was very happy in her care and was given enough attention. I will definitely use Briana again in the future as needed.

Availability updated yesterday
Sitter Profile Image: Ashley D.
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Sitter Profile Image: Ashley D.
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Ashley D.

Your dogs home away from home!!
Southfield, MA, 01259
10.2 mi. away
Boarding, Doggy Day Care
from
$25
per day
1 review

Ashley is the definition of a true dog lover. I have known her for 15 years and would highly recommend her as a pet sitter. She is caring, responsible and your pet would be in good hands with her!

Availability updated 8 days ago
Sitter Profile Image: Nell S.
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Sitter Profile Image: Nell S.
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Nell S.
Star Sitter

I’ll soothe even the savage beast
Harwinton, CT, 06791
9.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per day
5 out of 4.9 stars
41 reviews
20 repeat clients
Profile image

Nell is wonderful. Super flexible with arranging time to drop off and pick up. Dizzy loves staying here. He would run down the steps to the front door! I would definitely recommend her for any pet care needs !

Availability updated yesterday
Sitter Profile Image: Angela W.
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Sitter Profile Image: Angela W.
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Angela W.

Certified Dog Trainer Big Pet Lover
Torrington, CT, 06790
8.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
112 reviews
43 repeat clients
Profile image

Angela was great! Phoebe is always a little sad and anxious away from home and Angeka really helped her settle in. She has a wonderful kindness that the animals really connect with..Phoebe really liked her from the very first. Will definitely use her again for our next weekend away

Availability updated 3 days ago
Sitter Profile Image: Matt T.
Verified Enhanced Background Check
Sitter Profile Image: Matt T.
Verified Enhanced Background Check

Matt T.

Whatever the pet,youre in my hands!
Torrington, CT, 06790
9.2 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per day
2 reviews
1 repeat client

He will be there to take care of that pats every need and make sure he can be trusted to do said job. He’s a very trustworthy person and he’s so reliable if I could hire anyone to take care of pets it would be him.

Availability updated over 1 year ago
Sitter Profile Image: Richard W.
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Sitter Profile Image: Richard W.
Verified Background Check

Richard W.

Welcome to My Dog Pack!
Collinsville, CT, 06019
11.1 mi. away
Boarding, Doggy Day Care
from
$50
per day
5 out of 5.0 stars
10 reviews
1 repeat client
Profile image

Our young pup Hank spent the day with Rich and his three dogs. Hank had an amazing day running around Rich’s awesome backyard. Rich was so attentive, made sure to work on the commands we’ve been training, sent lots of updates, and really went above and beyond taking care of him. We can’t wait for Hank to keep going back :)

Availability updated 61 days ago
Sitter Profile Image: Rebecca P.
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Sitter Profile Image: Rebecca P.
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Rebecca P.

Loving caring & fun home for pets!
Torrington, CT, 06790
8.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per day
5 out of 5.0 stars
4 reviews
1 repeat client
Profile image

Sam had the best day ever with Rebecca and we felt comfortable knowing he was with her. She was great at communicating with us throughout the day and sending pictures. He will definitely be back for more fun.

Availability updated over 1 year ago

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The median cost per day for doggy day care in Winchester is $40

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Sitters in Winchester average 5 repeat doggy day care clients

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