Doggy Day Care in Stockbridge

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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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Juneteenth
Sitter Profile Image: Diana H.
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Sitter Profile Image: Diana H.
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1. Diana H.

Walk. Run. Sit. Stay
Athens, NY, 12015
24.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
7 repeat clients
from
$55
per day
Profile image

Diana and her family provided day care to my puppy Jolene and I cannot say enough good things. She is a wonderful and attentive sitter and provided great care. I would definitely recommend her.

Confirmed availability: Juneteenth
Sitter Profile Image: Teresa D.
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Sitter Profile Image: Teresa D.
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2. Teresa D.

Dog Mom w/Rich Fostering Background
New Marlborough, MA, 01230
9.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
15 reviews
2 repeat clients
from
$28
per day
Profile image

Ahsoka is a high energy pup and is properly tuckered out and allowed us to sleep in this morning! Mission accomplished for play date while we were out. Theresa was flexible with drop off and pick up, which was a huge help. Thank you!

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Sitter Profile Image: Peter K.
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Sitter Profile Image: Peter K.
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3. Peter K.

Dogs speak to those who listen.
South Egremont, MA, 01258
10.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
18 reviews
7 repeat clients
from
$40
per day
Profile image

Peter was great with my very energetic pup! He called a day before the appointment to make sure all my preferences are met. Very flexible with the times I requested. Most importantly, I was confident that my puppy was safe and enjoying himself. Peter’s home is dog friendly and he was kind enough to send me a picture of my beloved pup. Would definitely recommend!!

Confirmed availability: Juneteenth
Sitter Profile Image: Cheyenne F.
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Sitter Profile Image: Cheyenne F.
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4. Cheyenne F.

Animal Lover - Work from Home
Kinderhook, NY, 12106
21.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
6 reviews
1 repeat client
from
$45
per day
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Cheyenne was amazing! We had a very last minute trip and Cheyenne was able to watch our pup the very next day. She was communicative and would recommend!

Confirmed availability: Juneteenth
Sitter Profile Image: Kathleen M.
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Sitter Profile Image: Kathleen M.
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5. Kathleen M.

Rover 101
Berkshires #1 Trusted Pet Sitter ❤️
Becket, MA, 01223
14.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
120 reviews
34 repeat clients
from
$45
per day
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I can’t say enough good things about Kathleen. Panuchi had another wonderful day with her and her pups. He comes home tired and satisfied and is always excited to see her again. Can’t wait till next time.

Confirmed availability: Juneteenth
Sitter Profile Image: Jess L.
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Sitter Profile Image: Jess L.
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6. Jess L.

I care for the care of your pets
Pittsfield, MA, 01201
12.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
39 reviews
9 repeat clients
from
$33
per day
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Jess took great care of my pup and sent me lots of pics and updates throughout the day! She has a sweet dog, and her dog and mine played together all day. Uva came home fed, healthy and tired! Thank you Jess!

Sitter Profile Image: Mary & Todd H.
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Sitter Profile Image: Mary & Todd H.
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7. Mary & Todd H.

Weekend getaway with active people
Chatham, NY, 12037
13.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
35 reviews
10 repeat clients
from
$35
per day
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Toby was in great hands with Mary and Todd! We were in communication throughout the day — Mary sent updates as well as photos. And Todd went above and beyond by riveting together Toby’s leash after it snapped in two.

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Sitter Profile Image: Adrienne H.
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Sitter Profile Image: Adrienne H.
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8. Adrienne H.

Love dogs!
Pittsfield, MA, 01021
11.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
48 reviews
18 repeat clients
from
$28
per day
Profile image

Minnie loved her recent stay with Adrienne: she walked, played fetch, had space to explore inside their dog-friendly home and did not want to leave when it was time to go home. We hope to have her stay with Adrienne again when we're in the area.

Sitter Profile Image: Heather M.
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Sitter Profile Image: Heather M.
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9. Heather M.

Your pets new best friend
Lanesboro, MA, 01237
16.6 mi. away
Boarding, Doggy Day Care, Dog Walking
5 reviews
from
$40
per day

Heather is great! She is very approachable with concerns and always has a trick up her sleeve to better work with dogs. She is very well versed in dog language and always has their safety and well-being at the forefront.

Sitter Profile Image: Sandra W.
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Sitter Profile Image: Sandra W.
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10. Sandra W.

Dog Enthusiast
Pittsfield, MA, 01201
10.3 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
from
$60
per day

Sandi is a lover of pets!! She can’t walk past any dog without stopping to ask permission from their owner if she can love on their dog. Sandi has cared for my pets on a number of occasions and makes the experience for both me and my pet the absolute best. I would entrust her at all levels to care for my pets, knowing they are well cared for, safe, and having loads of fun :)

Confirmed availability: Juneteenth
Sitter Profile Image: Tiffany A.
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Sitter Profile Image: Tiffany A.
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11. Tiffany A.

A walk a day will keep the vet away
Pittsfield, MA, 01201
11.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$28
per day

Tiffany is an excellent dog walker/boarder. She is professional, friendly, reliable, and organized. Your fur babies will be in great hands with her, I know mine love her! Working with Tiffany has always been a pleasant experience and I highly recommend booking her.

Sitter Profile Image: Teresa M.
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Sitter Profile Image: Teresa M.
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12. Teresa M.

Caring, loving, compassion .
Great Barrington, MA, 01230
7.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
3 reviews
from
$95
per day

About: I’ve taken care of dogs of every kind since 2009 working with Neighbors, friends and family help them with bathing, feeding, hair cut, nail trim. I’m concurrently don’t have a full time job, I have a lot time available to help you with your doggie with walking, car ride, park. I have a big yard to play, run, jumping, very responsible, have a finish basement with open room to play . I can cook a low diet food .

Sitter Profile Image: Bella G.
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Sitter Profile Image: Bella G.
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13. Bella G.

Rover 101
Huge animal lover 🩵
lanesborough, MA, 01237
16.7 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
from
$28
per day

Bella is great friend, and really care for animals. I’ve seen so first hand with her dog and mine. I would say one person I would trust the most with my animals if I was every way or something would be Bella. She just a all around good person and knows how to brighten the day. I’ve also never seen anyone else take care of a animal like she does. Great person with great personality and caring.

Sitter Profile Image: Emily P.
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Sitter Profile Image: Emily P.
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14. Emily P.

I’m here for pets, kisses and wags!
Pittsfield, MA, 01201
11.4 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$40
per day

Emily would certainly make a wonderful addition to your service. She is a loving, warm and caring individual! She has had pets,dogs and cats, most of her life. She takes very good care of them and considers them part her family. Do not hesitate to hire her as she would be a very responsible employee!

Sitter Profile Image: Michael V.
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Sitter Profile Image: Michael V.
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15. Michael V.

7 acre remotely located ranch!
Pittsfield, MA, 01201
13.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
4 reviews
1 repeat client
from
$28
per day
Profile image

Minnie had a safe, fun, comfortable stay at Michael's, was relaxed and happy when we picked her up. Michael responded quickly and stayed in touch. We appreciated his flexibility and care and definitely want to return.

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Sitter Profile Image: Emma B.
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Sitter Profile Image: Emma B.
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16. Emma B.

I’ll keep your pet safe and loved
Dalton, MA, 01201
14.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$40
per day
Profile image

Emma was fantastic! We immediately felt at ease when we dropped our dog off with her as it was clear that Emma is great with dogs. She took our girl out for an amazing hike and shared awesome photos and videos. Thanks so much for giving Bailey such a fun afternoon, Emma!

Sitter Profile Image: Olivia N.
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Sitter Profile Image: Olivia N.
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17. Olivia N.

animal lover is an understatement.
New Marlborough, MA, 01230
9.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
2 reviews
2 repeat clients
from
$40
per day
Profile image

Olivia was very helpful and friendly. Koo seemed to enjoy time with Olivia and Popcone. Highly recommended!

Sitter Profile Image: Melanie & Sean H.
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Sitter Profile Image: Melanie & Sean H.
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18. Melanie & Sean H.

Dog-loving home with large dog run!
Richmond, MA, 01254
7.4 mi. away
Boarding, Doggy Day Care, Dog Walking
5 reviews
from
$55
per day

Melanie and Sean took care of our dog Maisy for six days while we were visiting family out west. They were extremely responsive to our initial inquiry, and we quickly arranged for a meet-and-greet to ensure Maisy would be comfortable boarding there (and she was). She had a great stay there and became very friendly with one of their dogs - we have never seen Maisy be so attached to another dog! Melanie posted pictures and videos regularly and gave us updates. Now that we are home, I think Maisy misses her new dog buddies, as well as Melanie and Sean. We are planning to bring her back for a play date in the near future. I'd highly recommend Melanie and Sean to anyone who needs pet care in the Berkshires!

Confirmed availability: Juneteenth
Sitter Profile Image: Tetiana M.
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Sitter Profile Image: Tetiana M.
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19. Tetiana M.

I care for the dogs
Lenox, MA, 01240
7.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$60
per day
Profile image

I’m so thankful I found Tetiana. I left my 5-month puppy for the first time with her and I could not be happier. She took care of her with love and so much warmth. I received many pictures thought the day. Thank you Tetiana!!!

Sitter Profile Image: Jessica P.
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Sitter Profile Image: Jessica P.
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20. Jessica P.

Fun and caring dog sitter
Canaan, NY, 12029
9.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
14 reviews
1 repeat client
from
$50
per day

We had Jessica watch our cat Lucy and turtle Rio for two weeks and it was the best pet sitting experience we have had! Jessica sent updates and images each visit. Lucy was played with every visit and when we returned we could tell she had a good time. I would highly recommend Jessica and look forward to having her pet sit again!

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Rover also offers Doggy Day Care in:

Rover also offers other services in Stockbridge:


Don't let your 9-to-5 stop you from being a great pet parent. When you're heading to work, drop off your beloved pet with a loving dog sitter near you. Your dog will get the love and care they're used to at home, and you'll get photo updates and the peace of mind that comes from finding great care for your pet. We're proud to offer a wide range of pet care, including puppy day care and pet day care for all kinds of pets. We know you love your pets, but you can't always be there, which is where our loving sitters come in. Forget kennels, find a loving neighbor who will give your dog the one-on-one attention they deserve. That way, when you head to work, you know your dog's in good hands.

Doggy Day Care