Doggy Day Care in Chesterfield

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 Chesterfield doggy day care sitters

1 / 1
Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter
from
$40
per day
5 out of 5.0 stars
31 reviews
11 repeat clients
25 years of experience
Greenfield, MA, 01301

Nicole was amazing! My pup had a blast at her place, and she came back very happy and tired after the fun playtime. Nicole provided photos and updates along the way. Thank you!!

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Laura R.
Sitter Profile Image: John M.
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John M.
Star Sitter
from
$35
per day
5 out of 5.0 stars
107 reviews
37 repeat clients
15 years of experience
Turners Falls, MA, 01376

Thanks for taking care of Jaxi, John. We could tell she was in good hands and will definitely have her stay with you again if we are in the area.

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Mary Beth B.
Sitter Profile Image: Yenifer V.
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Yenifer V.
from
$60
per day
5 out of 5.0 stars
14 reviews
2 repeat clients
3 years of experience
Pittsfield, MA, 01201

We had such a great experience with Yenifer! Our dog, Rocky, absolutely enjoyed his stay—he came home happy and relaxed. Yenifer was incredibly kind and responsive, and even accommodated us on very short notice, which we really appreciated.

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Liliya K.
Sitter Profile Image: Kathleen M.
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Kathleen M.
Star Sitter
from
$50
per day
5 out of 5.0 stars
141 reviews
38 repeat clients
12 years of experience
Becket, MA, 01223

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.

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Janell H.
Sitter Profile Image: Jessica C.
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Jessica C.
Star Sitter
from
$28
per day
5 out of 5.0 stars
44 reviews
15 repeat clients
35 years of experience
Sunderland, MA, 01375

Jessica and her daughter were fabulous hosts!! First off where they live is phenomenal!! It is so green and surrounded with wilderness. Loads of beautiful hiking areas and a nice big house!! They both come across as really gentle giving kind hearted people who are great with animals!! Bruno had a great time with them and was ready to go to sleep when we got home last night!! I would definitely recommend them and plan to use them again in the future!!

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Amy A.
Sitter Profile Image: Emma G.
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Emma G.
Star Sitter
from
$55
per day
5 out of 5.0 stars
33 reviews
7 repeat clients
15 years of experience
Northampton, MA, 01060

Emma was great!! She took my two puppies, one being only 3 months old and they look like they had the best time. She kept me updated throughout the day with pictures and videos and how they were doing. 10/10 would recommend!

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Megan M.
Sitter Profile Image: Jessica C.
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Jessica C.
from
$35
per day
5 out of 5.0 stars
8 reviews
1 repeat client
10 years of experience
South Hadley, MA, 01075

Jessica went above and beyond to make sure my dog was comfortable, happy, and well cared for while I was away. She provided updates, including photos, which gave me peace of mind, and I loved seeing how quickly my pets warmed up to her and her dogs. I highly recommend Jessica to anyone looking for a reliable, kind, and attentive pet sitter.

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Laura S.
Sitter Profile Image: Shawna B.
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Shawna B.
from
$62
per day
5 out of 5.0 stars
8 reviews
3 repeat clients
15 years of experience
Westhampton, MA, 01027

Shawna was a great sitter. My dogs are never tired. But they were worn out when I picked them up so I know they got plenty of exercise and attention. I highly recommend Shawna!!

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Amanda G.
Sitter Profile Image: Janice A.
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Janice A.
from
$40
per day
5 out of 5.0 stars
18 reviews
8 repeat clients
30 years of experience
Amherst, MA, 01002

About: I took care of dogs growing up, and now dogs are part of my family. My children have also grown up with dogs, helping with training, feeding, brushing, bathing, and playing with our dog. I am a middle school teacher who is home with my family during the summer. My 10 year old son and I are available to welcome your dog into our family life during the summer weeks and on weekends during the school year. We have a large yard with a stream and conservation land behind our house. We enjoy walks in the woods, running around and playing catch in the yard with dogs who stay with us. Inside dogs are allowed on the couch. We are home all day during the summer. We are excited to meet your dog and welcome them into our family life.

Sitter Profile Image: Sarah F.
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Sarah F.
from
$45
per day
20 years of experience
Florence, MA, 01062

About: I’m a responsible, animal-loving mom with a flexible work-from-home schedule and a big fenced-in yard for your pet to play in. I have had pets (cats and dogs at different times) for my whole adult life, but said goodbye to my sweet elderly dog last year and am now enjoying the adventure of pet-sitting for others. My wife and I have an adorable 1-year-old child (she is in daycare most weekdays but she LOVES animals) and I have a peaceful home and routine that allows me to give lots of attention, love, and care to your pet. I offer a calm, predictable environment and we treat every pet like part of the family, with lots of love, attention, play, walks, and belly rubs. Your pet will enjoy a secure, spacious outdoor play area, comfy indoor areas to relax, a walkable neighborhood with forest trails, and (with your permission) lots of treats. I’m around all day for walks, feedings, and companionship, and I love sending you pictures of your pet having a blast on their vacation. My Schedule: I work full time from home (with some flexibility) on weekdays while my child is in daycare, and am happy to watch your pet on a daily basis or board them overnight. The environment : I have a large fenced in yard and a comfortable, climate controlled home, and have experience caring for dogs and cats, including elderly animals. I host one pet at a time (unless the pets are from the same family) and will lavish your fur baby with attention, play, and plenty of time outdoors. Because I have a young child, I can currently only care for pets 25lbs or under who are comfortable with babies/toddlers.

Sitter Profile Image: R. Anuhea S.
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R. Anuhea S.
from
$50
per day
5 out of 5.0 stars
5 reviews
13 years of experience
Hadley, MA, 01035

About: I have fostered dogs and cared for them my whole life. I know how to train and positively reinforce the training you have already set in place. I have worked with dogs ranging from puppies to senior hospice. I love walking and caring for dogs in the winter time. Nothing better than seeing a dog get the zoomies in the snow. Excited to meet your dog! I have worked with all types of dogs while fostering and use positive reinforcement modalities and trauma informed training techniques. I prefer longer walks or frequent shorter walks

Sitter Profile Image: Saige G.
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Saige G.
from
$30
per day
5 out of 5.0 stars
17 reviews
6 repeat clients
11 years of experience
Easthampton, MA, 01027

Benny had a great day playing with Mylo at Saige’s!

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Jesse G.
Sitter Profile Image: Erin B.
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Erin B.
from
$35
per day
5 out of 4.5 stars
70 reviews
12 repeat clients
15 years of experience
Easthampton, MA, 01027

Erin is great! Took excellent care of my dog, and sent cute updates throughout the day. Very friendly, helpful, and communicative. Highly recommend!

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Cayley W.
Sitter Profile Image: Amad E.
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Amad E.
from
$45
per day
5 out of 5.0 stars
25 reviews
8 repeat clients
15 years of experience
Northampton, MA, 01060

Amad was amazing!! Would definitely recommend him to take care of your pup. Marley was well taken care of and came back tired from all the walks they went on🙌🏼 10/10

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Jessica Z.
Sitter Profile Image: Isabella M.
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Isabella M.
from
$38
per day
5 out of 5.0 stars
3 reviews
1 repeat client
18 years of experience
Easthampton, MA, 01027

About: I’ve taken care of dogs and cats in my house since I was born and I’ve always been a part of walking, feeding, bathing, playing with, and giving meds to them. I have taken care of my dog who is elderly, has worn diapers and has experienced surgery and anesthetics. I really enjoy being around animals of all kinds! I only work about 1-3 hourly per day! I’m always around to hang out and play with pets. I always will have someone around the pets so they’ll never be alone. I know a lot of the behavioral signs of discomfort in animals, I always want the pets I’m working with to enjoy their time. I will always make sure a pet is in a safe and fitting environment for their needs. I have worked with pets who are sick, directly after surgery, and who need medication administered

Sitter Profile Image: Evan A.
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Evan A.
from
$75
per day
5 out of 5.0 stars
5 reviews
10 years of experience
Florence, MA, 01062

Evan was great with my dogs - they loved being with him and he took super care of them, tired them out on nice long walks and sent videos of snuggling them. Cannot recommend him strongly enough!

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Jim Q.
Sitter Profile Image: Gail H.
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Gail H.
from
$45
per day
5 out of 5.0 stars
7 reviews
1 repeat client
50 years of experience
Haydenville, MA, 01039

About: I am a lifelong dog person with a large fenced yard and miles of trails out my back dog. A tired dog is a happy dog. Unless I am traveling myself I am extremely flexible and available. I will let you know if I will need to spend more than a few hours away from your pet before booking a stay. I think it’s important for pets to keep to their normal routine while their people are away. A little extra attention and affection also helps ease the stress of separation. I have a pretty mellow disposition and enjoy cuddling with a furry friend while reading or watching a show.

Sitter Profile Image: Leah B.
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Leah B.
from
$30
per day
5 out of 5.0 stars
5 reviews
40 years of experience
Westhampton, MA, 01027

About: I can't remember a time that I didn't have at least one dog. I often had several at a time and they all lived a long and happy life with tons of love and affection! I will care for your dog(s) as if they were my own and provide the affectionate, loving care they deserve. I have raised 3 great kids who are now all grown so I would love the opportunity to share my life with as many pets as possible. I have a flexible schedule. I believe in keeping your dog in a fenced-in area (supervised) or on a leash at all times while outside. I also believe in crate training puppies for potty training and safety only.

Sitter Profile Image: Susan R.
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Susan R.
from
$30
per day
5 out of 5.0 stars
39 reviews
13 repeat clients
40 years of experience
Florence, MA, 01062

Sophie was well taken care of during her evening stay with Susan - and Susan was able to take the reservation even last minute. So appreciated!

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Karen W.
Sitter Profile Image: Kristin B.
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Kristin B.
from
$45
per day
5 out of 5.0 stars
15 reviews
4 repeat clients
20 years of experience
Goshen, MA, 01032

I was passing through the area and Kristin was very accommodating about fitting my dog into her home for the few hours in the afternoon and evening that I needed. Thanks to her dog Maggie and her family my dog Sadie felt welcomed and gave her the love and attention she craves. Thanks Kristin!

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Juliette M.
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Sitter Profile Image: Nicole S.
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Sitter Profile Image: Nicole S.
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Nicole S.
Star Sitter

Animal loving person!
Greenfield, MA, 01301
21.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
31 reviews
11 repeat clients
Profile image

Nicole was amazing! My pup had a blast at her place, and she came back very happy and tired after the fun playtime. Nicole provided photos and updates along the way. Thank you!!

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: John M.
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Sitter Profile Image: John M.
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John M.
Star Sitter

I will treat your pets like my own.
Turners Falls, MA, 01376
20.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
107 reviews
37 repeat clients
Profile image

Thanks for taking care of Jaxi, John. We could tell she was in good hands and will definitely have her stay with you again if we are in the area.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Yenifer V.
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Sitter Profile Image: Yenifer V.
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Yenifer V.

EXCLUSIVE PETSITTER 💕☘️✨
Pittsfield, MA, 01201
21.7 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$60
per day
5 out of 5.0 stars
14 reviews
2 repeat clients
Profile image

We had such a great experience with Yenifer! Our dog, Rocky, absolutely enjoyed his stay—he came home happy and relaxed. Yenifer was incredibly kind and responsive, and even accommodated us on very short notice, which we really appreciated.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kathleen M.
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Sitter Profile Image: Kathleen M.
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Kathleen M.
Rover 101
Star Sitter

Berkshires #1 Trusted Pet Sitter ❤️
Becket, MA, 01223
12.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per day
5 out of 5.0 stars
141 reviews
38 repeat clients
Profile image

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.

Availability updated 6 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jessica C.
Verified Enhanced Background Check
Sitter Profile Image: Jessica C.
Verified Enhanced Background Check

Jessica C.
Star Sitter

Animal-loving family
Sunderland, MA, 01375
14.7 mi. away
Boarding, Doggy Day Care
from
$28
per day
5 out of 5.0 stars
44 reviews
15 repeat clients
Profile image

Jessica and her daughter were fabulous hosts!! First off where they live is phenomenal!! It is so green and surrounded with wilderness. Loads of beautiful hiking areas and a nice big house!! They both come across as really gentle giving kind hearted people who are great with animals!! Bruno had a great time with them and was ready to go to sleep when we got home last night!! I would definitely recommend them and plan to use them again in the future!!

Availability updated 24 days ago
Sitter Profile Image: Emma G.
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Sitter Profile Image: Emma G.
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Emma G.
Star Sitter

Lifetime dog lover w/ genuine care
Northampton, MA, 01060
11.8 mi. away
Boarding, House Sitting, Doggy Day Care
from
$55
per day
5 out of 5.0 stars
33 reviews
7 repeat clients
Profile image

Emma was great!! She took my two puppies, one being only 3 months old and they look like they had the best time. She kept me updated throughout the day with pictures and videos and how they were doing. 10/10 would recommend!

Availability updated 4 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jessica C.
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Sitter Profile Image: Jessica C.
Verified Enhanced Background Check

Jessica C.

Animal lover
South Hadley, MA, 01075
16.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
8 reviews
1 repeat client
Profile image

Jessica went above and beyond to make sure my dog was comfortable, happy, and well cared for while I was away. She provided updates, including photos, which gave me peace of mind, and I loved seeing how quickly my pets warmed up to her and her dogs. I highly recommend Jessica to anyone looking for a reliable, kind, and attentive pet sitter.

Availability updated yesterday
Sitter Profile Image: Shawna B.
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Sitter Profile Image: Shawna B.
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Shawna B.

Responsible Reliable Pet Care
Westhampton, MA, 01027
4.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$62
per day
5 out of 5.0 stars
8 reviews
3 repeat clients
Profile image

Shawna was a great sitter. My dogs are never tired. But they were worn out when I picked them up so I know they got plenty of exercise and attention. I highly recommend Shawna!!

Availability updated 2 days ago
Sitter Profile Image: Janice A.
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Sitter Profile Image: Janice A.
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Janice A.

We love dogs!
Amherst, MA, 01002
16.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
18 reviews
8 repeat clients

Janice took such great care of my dog Laila. She sent me lots of photos and updates and it was clear how happy Laila was there. I highly recommend Janice and will book with her again next time I need a dog sitter.

Availability updated 3 days ago
Sitter Profile Image: Sarah F.
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Sitter Profile Image: Sarah F.
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Sarah F.

Loving care for your sweet pet
Florence, MA, 01062
9.3 mi. away
Boarding, Doggy Day Care
from
$45
per day
2 reviews

Sarah has a way with animals. She’s the best - super friendly, reliable, and a very attentive pet caregiver. She has watched my cats and dog and they love her. I always know I can count on Sarah, and I have peace of mind knowing that my babies are in good hands.

Availability updated yesterday
Sitter Profile Image: R. Anuhea S.
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Sitter Profile Image: R. Anuhea S.
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R. Anuhea S.

I will love your dog
Hadley, MA, 01035
13.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per day
5 out of 5.0 stars
5 reviews

R. Anuhea is not only a best friend to dogs of all breeds and sizes. They truly seem to enjoy spending the time giving their clients "dogs " a loving safe environment to play and exercise. I've watched the reactions that dogs have to R.Anuhea and they say a picture says a thousand words we'll let me tell you it looks like a wonderful friendship/love affair anytime I've been witness to the interactions. I highly recommend R. Anuhea for your fur babies plus the bonus is you get to know a very genuine authentic person in them too ⭐️

Availability updated 3 days ago
Sitter Profile Image: Saige G.
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Sitter Profile Image: Saige G.
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Saige G.

Lover Of All Living Things
Easthampton, MA, 01027
14.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 5.0 stars
17 reviews
6 repeat clients
Profile image

Benny had a great day playing with Mylo at Saige’s!

Availability updated 13 days ago
Sitter Profile Image: Erin B.
Verified Enhanced Background Check
Sitter Profile Image: Erin B.
Verified Enhanced Background Check

Erin B.

Canines'( and felines) best friend
Easthampton, MA, 01027
12.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 4.5 stars
70 reviews
12 repeat clients
Profile image

Erin is great! Took excellent care of my dog, and sent cute updates throughout the day. Very friendly, helpful, and communicative. Highly recommend!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Amad E.
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Sitter Profile Image: Amad E.
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Amad E.

I treat the pets as my own
Northampton, MA, 01060
12.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
25 reviews
8 repeat clients
Profile image

Amad was amazing!! Would definitely recommend him to take care of your pup. Marley was well taken care of and came back tired from all the walks they went on🙌🏼 10/10

Availability updated 4 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Isabella M.
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Sitter Profile Image: Isabella M.
Verified Enhanced Background Check

Isabella M.

I really enjoy working with animals
Easthampton, MA, 01027
12.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$38
per day
5 out of 5.0 stars
3 reviews
1 repeat client

About: I’ve taken care of dogs and cats in my house since I was born and I’ve always been a part of walking, feeding, bathing, playing with, and giving meds to them. I have taken care of my dog who is elderly, has worn diapers and has experienced surgery and anesthetics. I really enjoy being around animals of all kinds! I only work about 1-3 hourly per day! I’m always around to hang out and play with pets. I always will have someone around the pets so they’ll never be alone. I know a lot of the behavioral signs of discomfort in animals, I always want the pets I’m working with to enjoy their time. I will always make sure a pet is in a safe and fitting environment for their needs. I have worked with pets who are sick, directly after surgery, and who need medication administered

Availability updated 19 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Evan A.
Verified Enhanced Background Check
Sitter Profile Image: Evan A.
Verified Enhanced Background Check

Evan A.

Amateur caretaker gone Pro!
Florence, MA, 01062
10.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per day
5 out of 5.0 stars
5 reviews
Profile image

Evan was great with my dogs - they loved being with him and he took super care of them, tired them out on nice long walks and sent videos of snuggling them. Cannot recommend him strongly enough!

Availability updated 47 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Gail H.
Verified Background Check
Sitter Profile Image: Gail H.
Verified Background Check

Gail H.

Long walks and yardtime
Haydenville, MA, 01039
7.4 mi. away
Boarding, House Sitting, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
7 reviews
1 repeat client

I've known Gail for over 20 years. In all that time, Gail has been a consistently loving, attentive, and attuned caregiver. She makes sure her animals are engaged, known, and attended to while providing respectful boundaries. Gail is friendly, professional, resourceful, utterly reliable, not to mention funny and smart! Your pets will be happy as clams in Gail's care.

Availability updated 39 days ago
Sitter Profile Image: Leah B.
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Sitter Profile Image: Leah B.
Verified Enhanced Background Check

Leah B.

Big or Small, I love them ALL.
Westhampton, MA, 01027
8.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 5.0 stars
5 reviews

Where do I begin?? Leah is absolutely incredible with, not only dogs, but ALL animals. She's an animal-whisperer! She puts their needs first and I never worry about my dog when she's with her. If you're looking for someone who you can trust with your furry family members, Leah is the person to contact!

Availability updated 45 days ago
Sitter Profile Image: Susan R.
Verified Background Check
Sitter Profile Image: Susan R.
Verified Background Check

Susan R.

Stay in a home, not a kennel!
Florence, MA, 01062
9.3 mi. away
Boarding, Doggy Day Care
from
$30
per day
5 out of 5.0 stars
39 reviews
13 repeat clients
Profile image

Sophie was well taken care of during her evening stay with Susan - and Susan was able to take the reservation even last minute. So appreciated!

Availability updated 37 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kristin B.
Verified Background Check
Sitter Profile Image: Kristin B.
Verified Background Check

Kristin B.

Home full time, 4 acres yard space
Goshen, MA, 01032
3.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
15 reviews
4 repeat clients
Profile image

I was passing through the area and Kristin was very accommodating about fitting my dog into her home for the few hours in the afternoon and evening that I needed. Thanks to her dog Maggie and her family my dog Sadie felt welcomed and gave her the love and attention she craves. Thanks Kristin!

Availability updated over 1 year ago

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The median cost per day for doggy day care in Chesterfield is $37

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Sitters in Chesterfield average 3 repeat doggy day care clients

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