Dog Boarding in Great Barrington

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Top rated Great Barrington dog boarders

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Sitter Profile Image: Teresa D.
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Teresa D.
Star Sitter
from
$60
per night
5 out of 5.0 stars
32 reviews
8 repeat clients
16 years of experience
Ashley Falls, MA, 01222

Very happy sitter has a lot of experience with caring for dogs. Rosie shaving a great time playing in big backyard with other dogs and sitter.

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Carrie T.
Sitter Profile Image: Peter K.
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Peter K.
from
$50
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
8 years of experience
South Egremont, MA, 01258

Peter was such a wonderful sitter. His updates were timely and detailed and I felt confident that Nutmeg was cared for, happy, and healthy during her stay. I will definitely ask Peter to sit again if I’m ever in the area again.

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Jana P.
Sitter Profile Image: Brooke B.
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Brooke B.
Star Sitter
from
$40
per night
5 out of 5.0 stars
109 reviews
30 repeat clients
25 years of experience
Pittsfield, MA, 01201

Rocky seemed to really enjoy his overnight. The icing on the cake we believe was his opportunity to play with Brooke's nice dog and her young son! Thanks for the picture!

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J D.
Sitter Profile Image: John S.
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John S.
Star Sitter
from
$72
per night
5 out of 5.0 stars
66 reviews
20 repeat clients
20 years of experience
Norfolk, CT, 06058

Our dog always has a great time staying at John and Orie's house! It's her home away from home in so many ways. We're already looking forward to next time!!

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Kathleen W.
Sitter Profile Image: Mary & Todd H.
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Mary & Todd H.
from
$45
per night
5 out of 5.0 stars
37 reviews
11 repeat clients
40 years of experience
Chatham, NY, 12037

Mary and Todd were amazing! Sent us pics of Oakley having fun on her walks and other pups Communication was terrific and Oakley seemed so happy being there! We can’t wait until her next visit with them! Plus, she made friends with the chickens!!

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Judi P.
Sitter Profile Image: Olivia V.
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Olivia V.
from
$45
per night
5 out of 5.0 stars
8 reviews
10 years of experience
Great Barrington, MA, 01230

Olivia was very professional, accommodating & easy to work with. She accommodated with our flight schedule, kept us on status with our pet through videos & pictures, took him to dog park frequently, & more. I’m returning to Olivia for future out of town trips.

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Lana P.
Sitter Profile Image: Janice A.
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Janice A.
Star Sitter
from
$108
per night
5 out of 5.0 stars
234 reviews
72 repeat clients
35 years of experience
RHINEBECK, NY, 12572

"We love Buddy," Janice said when we picked him up, and I don't doubt it. He's always in good spirits when we pick him up, and we don't have to worry or wonder what's going on in Janice's home when he's there. Looking forward to his upcoming 4-night stay in two weeks.

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Michael S.
Sitter Profile Image: Alex M.
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Alex M.
Star Sitter
from
$55
per night
5 out of 5.0 stars
76 reviews
16 repeat clients
30 years of experience
Torrington, CT, 06790

There are not enough stars for Alex! Our dog Adele always has the most amazing time with Alex and his wife, she loves spending time with them. They go on fantastic adventures and go above and beyond to care for her. I cannot recommend Alex enough!

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William B.
Sitter Profile Image: Robert W.
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Robert W.
from
$31
per night
5 out of 5.0 stars
4 reviews
2 repeat clients
10 years of experience
Lee, MA, 01238

About: I am an all around animal lover who pays close attention to detail every step of the way. Your animal will get attention, cuddles and love all around. Mornings are the best time for me and even early to mid day to take your puppy out. I am flexible with scheduling and am open during the week mainly There are many options available, I have 3 cats and 1 puppy who loves other dogs. I also am able to go to your home and take them out. I am flexible.

Sitter Profile Image: Deanne R.
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Deanne R.
from
$48
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
6 years of experience
Kinderhook, NY, 12106

Jasper seemed very happy and well cared for when we picked him up. He needed a bit of extra care in the beginning of his stay. Deanne followed all of the instructions perfectly. Deanne sent lots of updates and pictures during his stay.

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Chris C.
Sitter Profile Image: Lynette E.
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Lynette E.
Star Sitter
from
$55
per night
5 out of 5.0 stars
60 reviews
20 repeat clients
38 years of experience
Red Hook, NY, 12571

Lynette and Honey were great! Took great care of our pup! He was very happy and content when we picked him up after our trip. Lynette kept in contact with us throughout our trip and sent us pictures and updates. Highly recommend and will use again! Thanks Lynette!

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Jennifer T.
Sitter Profile Image: Franny A.
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Franny A.
from
$50
per night
5 out of 5.0 stars
4 reviews
30 years of experience
Copake, NY, 12516

Franny took wonderful care of my 14 year old Charlie overnight. She’s a very kind person and Charlie felt completely comfortable with her. He also got along well with her dog. I will definitely be using her again.

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Terri L.
Sitter Profile Image: Adrienne H.
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Adrienne H.
Star Sitter
from
$30
per night
5 out of 5.0 stars
75 reviews
24 repeat clients
20 years of experience
Pittsfield, MA, 01021

Adrienne is a wonderful dog sitter! She’s watched my dog twice for me now and it’s been great both times! My dog is very happy and well cared for. I also get updates and photos! Highly recommend sitter!!!

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Danielle S.
Sitter Profile Image: Alister A.
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Alister A.
from
$75
per night
5 out of 4.9 stars
51 reviews
20 repeat clients
10 years of experience
Spencertown, NY, 12165

You and your dog will love Alister! He makes sure your dog gets lots of playtime and exercise. Alister is great with the daily updates and pics! I felt comfortable leaving Chester with him and confident he has the dog experience to handle any situation. I will definitely use Alister again!

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Lannise G.
Sitter Profile Image: Amanda C.
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Amanda C.
Star Sitter
from
$90
per night
5 out of 5.0 stars
10 reviews
2 repeat clients
10 years of experience
Hudson, NY, 12534

I could not be more pleased… My dog had such a good time with Amanda and came home happy and content and tired so I know she had a very good day! And Amanda was wonderful in communicating with me throughout the day to let me know how my girl was doing and sending photos… Highly recommend and will already be booking again!

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Angela C.
Sitter Profile Image: Tetiana M.
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Tetiana M.
from
$60
per night
5 out of 4.9 stars
26 reviews
7 repeat clients
2 years of experience
Pittsfield, MA, 01201

Tetiana is an amazing petsitter! She is communicative, attentive to details and, most importantly, has a loving and giving heart. She and her lovely mom Maria treated my Edna like their own, with play and cuddles and outdoor adventures — many pictures clearly showing to me Edna’s enjoyment. I hope Edna can return to Tetiana’s and I highly recommend her.

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Ann D.
Sitter Profile Image: Christine A.
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Christine A.
Star Sitter
from
$95
per night
5 out of 4.9 stars
82 reviews
27 repeat clients
33 years of experience
Rhinebeck, NY, 12572

Our Newfoundland named Chadwick had a great time with Christine! She was flexible and accommodating and he felt right at home, it was clear from the pictures! (Thanks for sending btw!)

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Gina G.
Sitter Profile Image: Magnolia M.
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Magnolia M.
Star Sitter
from
$65
per night
5 out of 5.0 stars
90 reviews
48 repeat clients
15 years of experience
Hillsdale, NY, 12529

Magnolia took such good care of our dog Uma. She has a great property for playtime and a spacious and cozy home. I felt very at ease after our meet and greet that Uma would be in good hands. She also was flexible with scheduling changes and made an effort to send me updates frequently. I will definitely reach out to her again for future services and highly recommend her to anyone looking for a genuine pet loving caretaker of your animals.

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Brittany C.
Sitter Profile Image: Candice S.
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Candice S.
from
$55
per night
5 out of 5.0 stars
21 reviews
6 repeat clients
10 years of experience
Stottville, NY, 12172

Candice was absolutely wonderful!!!!!!!! This was my first time leaving my baby boy with anyone! I was kept updated with messages and pics. Would definitely recommend and/or book with Candice again.

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Morena B.
Sitter Profile Image: Nicole P.
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Nicole P.
from
$50
per night
34 years of experience
Elizaville, NY, 12523

About: I have had a dog in my family from the moment I was born to now. They truly are family and I believe a house doesn’t feel like a home without a pet. I have been a stay at home mom since 2019 spending most of my time at home caring for my 3 daughters, 2 dogs and my girls cat. We have a recently built new home and a large partial of land in the country perfect for outdoor playing and walks. If your fur baby stays with me I promise that they will be cared for like family themselves. I am home most of the day so they won’t be alone long, cuddles are definitely welcomed and I will respect all rules that you have for your pet! I am looking forward to my home becoming your furbabies beloved vacation spot. If you would like to set up a play date for your pet to meet me and my pets before booking that is welcome but not mandatory..whatever makes you feel more comfortable. Any questions before their stay or check ins during their stay are always welcome as well! 😊 I stay at home with my 3 year old daughter and drive my 4 & 5 year old to school every day. Other than that your pet will not be left alone for long. I spend most of my time at home so they will have plenty of attention and love! My pets are like my children before having children. They are allowed to snuggle on the couch and in bed. When I leave the house they are crate trained. I will respect your wishes and listen to what suits your pets lifestyle best. I have plenty of room at my house for your pets own crate or dog bed. Whatever will make them feel most at home I will do!

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Sitter Profile Image: Teresa D.
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Sitter Profile Image: Teresa D.
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1. Teresa D.

Star Sitter
Dog Mom w/Rich Fostering Background
Ashley Falls, MA, 01222
9.3 mi. away
Boarding, Doggy Day Care
from
$60
per night
5 out of 5.0 stars
32 reviews
8 repeat clients
Profile image

Very happy sitter has a lot of experience with caring for dogs. Rosie shaving a great time playing in big backyard with other dogs and sitter.

Availability updated today
Sitter Profile Image: Peter K.
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Sitter Profile Image: Peter K.
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2. Peter K.

Dogs speak to those who listen.
South Egremont, MA, 01258
4.3 mi. away
Boarding, Doggy Day Care
from
$50
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
Profile image

Peter was such a wonderful sitter. His updates were timely and detailed and I felt confident that Nutmeg was cared for, happy, and healthy during her stay. I will definitely ask Peter to sit again if I’m ever in the area again.

Availability updated 35 days ago
Sitter Profile Image: Brooke B.
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Sitter Profile Image: Brooke B.
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3. Brooke B.

Rover 101
Star Sitter
CRAZY DOG FAMILY
Pittsfield, MA, 01201
19.7 mi. away
Boarding
from
$40
per night
5 out of 5.0 stars
109 reviews
30 repeat clients
Profile image

Rocky seemed to really enjoy his overnight. The icing on the cake we believe was his opportunity to play with Brooke's nice dog and her young son! Thanks for the picture!

Availability updated today
Sitter Profile Image: John S.
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Sitter Profile Image: John S.
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4. John S.

Star Sitter
Retired professional enjoys dogs!!!
Norfolk, CT, 06058
13.3 mi. away
Boarding
from
$72
per night
5 out of 5.0 stars
66 reviews
20 repeat clients
Profile image

Our dog always has a great time staying at John and Orie's house! It's her home away from home in so many ways. We're already looking forward to next time!!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Mary & Todd H.
Verified Background Check
Sitter Profile Image: Mary & Todd H.
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5. Mary & Todd H.

Weekend getaway with active people
Chatham, NY, 12037
14.3 mi. away
Boarding, Doggy Day Care
from
$45
per night
5 out of 5.0 stars
37 reviews
11 repeat clients
Profile image

Mary and Todd were amazing! Sent us pics of Oakley having fun on her walks and other pups Communication was terrific and Oakley seemed so happy being there! We can’t wait until her next visit with them! Plus, she made friends with the chickens!!

Availability updated 9 days ago
Sitter Profile Image: Olivia V.
Verified Background Check
Sitter Profile Image: Olivia V.
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6. Olivia V.

Reliable and Energetic Dog Lover!
Great Barrington, MA, 01230
2.3 mi. away
Boarding, House Sitting
from
$45
per night
5 out of 5.0 stars
8 reviews
Profile image

Olivia was very professional, accommodating & easy to work with. She accommodated with our flight schedule, kept us on status with our pet through videos & pictures, took him to dog park frequently, & more. I’m returning to Olivia for future out of town trips.

Availability updated 33 days ago
Sitter Profile Image: Janice A.
Verified Enhanced Background Check
Sitter Profile Image: Janice A.
Verified Enhanced Background Check

7. Janice A.

Star Sitter
Safe, Loving and Happy farm
RHINEBECK, NY, 12572
29.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$108
per night
5 out of 5.0 stars
234 reviews
72 repeat clients
Profile image

"We love Buddy," Janice said when we picked him up, and I don't doubt it. He's always in good spirits when we pick him up, and we don't have to worry or wonder what's going on in Janice's home when he's there. Looking forward to his upcoming 4-night stay in two weeks.

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Alex M.
Verified Enhanced Background Check
Sitter Profile Image: Alex M.
Verified Enhanced Background Check

8. Alex M.

Star Sitter
Undivided & loving attention 24/7
Torrington, CT, 06790
25.7 mi. away
Boarding, Doggy Day Care
from
$55
per night
5 out of 5.0 stars
76 reviews
16 repeat clients
Profile image

There are not enough stars for Alex! Our dog Adele always has the most amazing time with Alex and his wife, she loves spending time with them. They go on fantastic adventures and go above and beyond to care for her. I cannot recommend Alex enough!

Availability updated 2 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Robert W.
Verified Enhanced Background Check
Sitter Profile Image: Robert W.
Verified Enhanced Background Check

9. Robert W.

I am full of pawsitivity
Lee, MA, 01238
9.0 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$31
per night
5 out of 5.0 stars
4 reviews
2 repeat clients

About: I am an all around animal lover who pays close attention to detail every step of the way. Your animal will get attention, cuddles and love all around. Mornings are the best time for me and even early to mid day to take your puppy out. I am flexible with scheduling and am open during the week mainly There are many options available, I have 3 cats and 1 puppy who loves other dogs. I also am able to go to your home and take them out. I am flexible.

Availability updated 3 days ago
Sitter Profile Image: Deanne R.
Verified Enhanced Background Check
Sitter Profile Image: Deanne R.
Verified Enhanced Background Check

10. Deanne R.

I would love to watch your pets!
Kinderhook, NY, 12106
22.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
from
$48
per night
5 out of 5.0 stars
24 reviews
7 repeat clients
Profile image

Jasper seemed very happy and well cared for when we picked him up. He needed a bit of extra care in the beginning of his stay. Deanne followed all of the instructions perfectly. Deanne sent lots of updates and pictures during his stay.

Availability updated 9 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Lynette E.
Verified Background Check
Sitter Profile Image: Lynette E.
Verified Background Check

11. Lynette E.

Star Sitter
Must be family and big dog friendly
Red Hook, NY, 12571
29.6 mi. away
Boarding, Doggy Day Care
from
$55
per night
5 out of 5.0 stars
60 reviews
20 repeat clients
Profile image

Lynette and Honey were great! Took great care of our pup! He was very happy and content when we picked him up after our trip. Lynette kept in contact with us throughout our trip and sent us pictures and updates. Highly recommend and will use again! Thanks Lynette!

Availability updated 5 days ago
Sitter Profile Image: Franny A.
Verified Enhanced Background Check
Sitter Profile Image: Franny A.
Verified Enhanced Background Check

12. Franny A.

Compassionate dog lover
Copake, NY, 12516
11.9 mi. away
Boarding, House Sitting
from
$50
per night
5 out of 5.0 stars
4 reviews
Profile image

Franny took wonderful care of my 14 year old Charlie overnight. She’s a very kind person and Charlie felt completely comfortable with her. He also got along well with her dog. I will definitely be using her again.

Availability updated 3 months ago
Sitter Profile Image: Adrienne H.
Verified Enhanced Background Check
Sitter Profile Image: Adrienne H.
Verified Enhanced Background Check

13. Adrienne H.

Star Sitter
Dog lover!
Pittsfield, MA, 01021
18.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per night
5 out of 5.0 stars
75 reviews
24 repeat clients
Profile image

Adrienne is a wonderful dog sitter! She’s watched my dog twice for me now and it’s been great both times! My dog is very happy and well cared for. I also get updates and photos! Highly recommend sitter!!!

Availability updated 17 days ago
Sitter Profile Image: Alister A.
Verified Background Check
Sitter Profile Image: Alister A.
Verified Background Check

14. Alister A.

Caring and trustworthy dog lover
Spencertown, NY, 12165
10.2 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 4.9 stars
51 reviews
20 repeat clients
Profile image

You and your dog will love Alister! He makes sure your dog gets lots of playtime and exercise. Alister is great with the daily updates and pics! I felt comfortable leaving Chester with him and confident he has the dog experience to handle any situation. I will definitely use Alister again!

Availability updated 13 days ago
Sitter Profile Image: Amanda C.
Verified Enhanced Background Check
Sitter Profile Image: Amanda C.
Verified Enhanced Background Check

15. Amanda C.

Star Sitter
🐾Pet care from a Licensed Vet Tech
Hudson, NY, 12534
15.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$90
per night
5 out of 5.0 stars
10 reviews
2 repeat clients
Profile image

I could not be more pleased… My dog had such a good time with Amanda and came home happy and content and tired so I know she had a very good day! And Amanda was wonderful in communicating with me throughout the day to let me know how my girl was doing and sending photos… Highly recommend and will already be booking again!

Availability updated yesterday
Sitter Profile Image: Tetiana M.
Verified Enhanced Background Check
Sitter Profile Image: Tetiana M.
Verified Enhanced Background Check

16. Tetiana M.

I care for the dogs
Pittsfield, MA, 01201
17.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 4.9 stars
26 reviews
7 repeat clients
Profile image

Tetiana is an amazing petsitter! She is communicative, attentive to details and, most importantly, has a loving and giving heart. She and her lovely mom Maria treated my Edna like their own, with play and cuddles and outdoor adventures — many pictures clearly showing to me Edna’s enjoyment. I hope Edna can return to Tetiana’s and I highly recommend her.

Availability updated 33 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Christine A.
Verified Background Check
Sitter Profile Image: Christine A.
Verified Background Check

17. Christine A.

Rover 101
Star Sitter
Home Full time...
Rhinebeck, NY, 12572
25.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$95
per night
5 out of 4.9 stars
82 reviews
27 repeat clients
Profile image

Our Newfoundland named Chadwick had a great time with Christine! She was flexible and accommodating and he felt right at home, it was clear from the pictures! (Thanks for sending btw!)

Availability updated 4 days ago
Sitter Profile Image: Magnolia M.
Verified Enhanced Background Check
Sitter Profile Image: Magnolia M.
Verified Enhanced Background Check

18. Magnolia M.

Star Sitter
Ambitious Animal Lover
Hillsdale, NY, 12529
19.8 mi. away
Boarding, Drop-In Visits
from
$65
per night
5 out of 5.0 stars
90 reviews
48 repeat clients
Profile image

Magnolia took such good care of our dog Uma. She has a great property for playtime and a spacious and cozy home. I felt very at ease after our meet and greet that Uma would be in good hands. She also was flexible with scheduling changes and made an effort to send me updates frequently. I will definitely reach out to her again for future services and highly recommend her to anyone looking for a genuine pet loving caretaker of your animals.

Availability updated 7 months ago
Sitter Profile Image: Candice S.
Verified Enhanced Background Check
Sitter Profile Image: Candice S.
Verified Enhanced Background Check

19. Candice S.

Dog lover!
Stottville, NY, 12172
20.3 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
21 reviews
6 repeat clients
Profile image

Candice was absolutely wonderful!!!!!!!! This was my first time leaving my baby boy with anyone! I was kept updated with messages and pics. Would definitely recommend and/or book with Candice again.

Availability updated today
Sitter Profile Image: Nicole P.
Verified Enhanced Background Check
Sitter Profile Image: Nicole P.
Verified Enhanced Background Check

20. Nicole P.

SAHM of 3 girls and 3 furbabies ❤️
Elizaville, NY, 12523
20.4 mi. away
Boarding, Doggy Day Care
from
$50
per night
3 reviews

Nicole is pet mom of two amazing little dogs and wonderful mom to her three girls. She is a selfless person and always thinking of others. You can feel at ease with Nicole taking care of your dogs, knowing they are being cared for the way every pet owner would want their dogs to be treated. You won’t find another person more capable and sweet than Nicole!

Availability updated 17 days ago
Confirmed availability for Memorial Day Weekend

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