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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What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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

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: Memorial Day Weekend
Sitter Profile Image: Jess L.
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Sitter Profile Image: Jess L.
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2. 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
32 reviews
7 repeat clients
from
$30
per day

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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Cheyenne F.
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Sitter Profile Image: Cheyenne F.
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3. 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

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: Memorial Day Weekend
Sitter Profile Image: Teresa D.
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Sitter Profile Image: Teresa D.
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4. 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
12 reviews
2 repeat clients
from
$28
per day

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!

Confirmed availability: Memorial Day Weekend
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
118 reviews
34 repeat clients
from
$45
per day

Kathleen was an absolute gift with our Panucho! He fell in love with her so quickly and did not want to leave when I came to pick him up. This is saying a lot because he is a major mama's boy :) She sent photos and updates and was incredibly kind and gentle with him. He also loved playing with her other dogs and seemed to be very comfortable in her space. We can't wait for him to play there again.

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Sitter Profile Image: Mary & Todd H.
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Sitter Profile Image: Mary & Todd H.
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6. 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

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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Gulsanat S.
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Sitter Profile Image: Gulsanat S.
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7. Gulsanat S.

Loving Pet Sitter, Works from Home
Ancramdale, NY, 12503
20.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
3 reviews
1 repeat client
from
$40
per day

About: Hello, my name is Gulsanat. I am a dog owner looking to care for other dogs at my home. I work remotely and a proud owner of my sweet little dog named Simba. I often care for pets belonging to family and friends. I’m working at home remotely and I have a plenty of time take care of your dog. I’m available any days, weekends and weekdays, I’m looking forward ! I will take care your dog at my place. Your dog and my dog will become friends. Dog will feel like at home and play.

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Sitter Profile Image: Peter K.
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Sitter Profile Image: Peter K.
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8. 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
17 reviews
7 repeat clients
from
$40
per day

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: Memorial Day Weekend
Sitter Profile Image: Adrienne H.
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Sitter Profile Image: Adrienne H.
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9. 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
46 reviews
17 repeat clients
from
$28
per day

Adrienne aka Sissy was amazing. You can tell right away that she and her husband were dog lovers. They took our puppy out for a hike and when we came to pick her up she seemed very content. We plan on using her again. I highly recommend her.

Sitter Profile Image: Heather M.
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Sitter Profile Image: Heather M.
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10. 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

I have a 6 month old goldendoodle, Orion. He was a skittish little thing that needed training and interaction, and lot of patience. Heather worked so well with him, she took her time to gain his trust, it was wonderful to watch him blossom with her! She can pet him now and he even gave her kisses! She used German commands as well as English because we are teaching him both as well as hand signals. When he had his first groom and was very scared, she came to his rescue. We are looking forward to more training with Heather as Orion grows!!! I know with her training I will have a well mannered dog, who will behave with others.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Bella B.
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Sitter Profile Image: Bella B.
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11. Bella B.

Lakeside Sitter, Works from Home.
Stockbridge, MA, 01262
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$60
per day

Bella is my daughter so, of course, I am biased. But she has taken care of my dogs since she was little. I absolutely trust her with my animals' well-being. Also--again, I'm biased--but most people find her really fun to deal with and be around. I totally recommend her to take care of your dog.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tiffany A.
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Sitter Profile Image: Tiffany A.
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12. 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tetiana M.
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Sitter Profile Image: Tetiana M.
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13. 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

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: Teresa M.
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Sitter Profile Image: Teresa M.
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14. 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: Sandra W.
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Sitter Profile Image: Sandra W.
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15. 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

I highly recommend my friend Sandra as a pet caregiver. She is responsible, caring, and loving towards animals. Sandra's dedication to providing a safe and nurturing environment for pets is unmatched. Her genuine love for animals shines through in her interactions with them. I have full confidence in Sandra's ability to provide excellent care for any pet entrusted to her.

Sitter Profile Image: Emily P.
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Sitter Profile Image: Emily P.
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16. 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 is an amazing dog sitter! She fully understands the details that come with caring for a pet, and you can just tell that she adores animals. She was kind and compassionate with my dog and very flexible with scheduling, and my dog loved her. She even sent pictures periodically. Would highly recommend Emily!

Sitter Profile Image: Michael V.
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Sitter Profile Image: Michael V.
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17. 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

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.

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 has taken care of my dog for all my long vacations over the last six years. My dog can be a little anxious, but Melanie went out of her way to make sure she was comfortable and had her "safe space". My dog loves playing with her very welcoming and friendly two pups, and I can always enjoy my time away knowing that my pup has plenty of play time, socialization, and cuddle time.

Sitter Profile Image: Jessica P.
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Sitter Profile Image: Jessica P.
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19. 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

Jessica has taken care of my pup Willy a for a few weekends that I was away on travel. She is very responsive and takes caring for my dog to the next level. Willy always follows her out the door when I come back home begging her to stay and I can tell she gives him much love and play while I am gone. 10/10 would recommend.

Sitter Profile Image: Olivia N.
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Sitter Profile Image: Olivia N.
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20. 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

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

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