Dog Boarding in Chestertown

Your dog stays overnight at a reliable dog sitter's home whilst you're away

445 results for Dog Boarding in Chestertown, MD

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Rich B.

(41)
12 repeat clients
from $40.00
per night

It was our first time leaving our new rescue, so we were nervous, but Rich was fantastic and accommodating! He sent us regular updates and kept our pup entertained. Would highly recommend

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Jenn S.

(60)
25 repeat clients
from $49.00
per night

It’s true, Oliver came home exhausted, happy and miraculously eating dog food out of a bowl like a normal dog! We told Jenn and Bob that we’d accidentally created a picky hand fed dog, she confidently said “I’ll get him to eat” and she did. We got daily photos and updates. They treated Oliver like their own and said he’s welcome back any time. He had a ball playing with the other dogs.

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Michelle M.

(551)
255 repeat clients
from $45.00
per night

Taking care of our shy, fearful dog takes patience and generosity, qualities that Michelle has in spades. During our two-week trip, Michelle updated us daily with photos and comments about how he was doing, which helped to reassure us he was handling our absence well. We would recommend Michelle highly!

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Jessica R.

(18)
7 repeat clients
from $40.00
per night

Second time for Cody. When he stays with Jessica, it’s easy for me to just leave and enjoy my trip without worrying about his care especially over the holidays . Flexible and on top of his care -thanks!

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Danielle S.

(42)
8 repeat clients
from $40.00
per night

Danielle is fantastic! She is super responsive and gives me regular updates so I know things are going well and mymdogmisnhealthy and happy. Would 100% recommend her!

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Tarina L.

(37)
11 repeat clients
from $50.00
per night

Tarina is the best and this was my second time and will be coming back again, my fur baby loves her home and family. She kept me updated with his time in her home and sent me pictures and videos 🤎

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Thomas H.

(9)
5 repeat clients
from $35.00
per night

Tom did a wonderful job caring for our two beagles on short notice. He has plenty of space for them to roam in a nice fenced-in yard, and they both got along great with Maxx. I know they were well cared for while I was gone. Great communication as well. I would absolutely recommend Tom to anyone looking for someone to watch their dogs.

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Patrick & Bahiya A.

(69)
22 repeat clients
from $52.00
per night

Wonderful caregivers for our dog - he was so excited to see Pat & Bee again! Love the walks, playtime in their fenced yard, and pleasant communications and photos all the way through the visit.

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Paris V S.

(239)
56 repeat clients
from $55.00
per night

Communicated so much and sent tons of pics. Felt like my dogs were happy and safe and she made sure my old lady was looked after and loved. Would use again, dogs came home happy and worn out.

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Theresa C.

(114)
42 repeat clients
from $49.00
per night

Theresa was a wonderful sitter for our Maxx. She kept him busy throughout the day. She also sent numerous photos during the stay and we could clearly see Maxx was having a great time. Her fenced in backyard was perfect for letting young Maxx run out some of his puppy energies along with other puppies. I would highly recommend Theresa for anyone looking for a competent and trusted sitter.

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Carlie H.

(59)
24 repeat clients
from $42.00
per night

Carlie and her family are so awesome with my Finnigan! They even made fall crafts with his paw prints! He's sleepy but like a good return home from an awesome vacation sleepy! I wouldn't want anyone else to have him at this point.

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Briana & Isaiah S.

(64)
15 repeat clients
from $50.00
per night

Briana and Isaiah were great. They accepted my request last minute and accommodated me and Lulu’s needs perfectly. They sent updates and pictures during my baby’s stay with them. Thank you!

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Jacob & Megan W.

(76)
46 repeat clients
from $42.00
per night

Jacob and Megan did a great job taking care of Molly. We loved getting the updates and pictures of her on walks and playing with the other dogs.

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Katelyn M.

(86)
23 repeat clients
from $45.00
per night

Katelyn is wonderful! She only watches one dog at a time, so your furry baby will get lots of attention. She sends lots of updates and pictures through the day.

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Lindsay G.

(77)
29 repeat clients
from $49.00
per night

This was our first time using Lindsay and our 2 dogs were very well taken care of. We had regular communication and she sent frequent adorable pictures. I would definately use her again and recommend her services.

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Dawn D.

(10)
2 repeat clients
from $60.00
per night

Dawn did a great job looking after my 5 year old lab. I would recommend her to anyone.

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Gisel D.

(38)
17 repeat clients
from $55.00
per night

Gisel was so wonderful. She sent me pics and videos frequently while she took care of my pup. He seemed to have a great time and i feel like she went above and beyond caring for him. I feel like she truly loved Rocky for the time he was there and I plan on using her in the future when i need someone to love my pup when I'm gone. I was 100% satisfied. :)

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Barbra F.

(61)
23 repeat clients
from $55.00
per night

Barb and her husband took great care of Lewis, gave him his medications and were so attentive. I could tell Lewis was really happy there and they enjoyed him too! So great!

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Jillian & Richard A.

(43)
20 repeat clients
from $45.00
per night

Jillian gave me peace of mind leaving my pet Brooke with her. She sent me pics and gave me a progress report 2 times a day. I will definitely be using her again in the future!!!

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Shuling J.

(122)
52 repeat clients
from $45.00
per night

Shuling was wonderful! She even sent pictures of my puppy throughout her stay there :) She was very responsive and kind and took great care of my pup. I would definitely recommend her!


Find Dog Boarding in Chestertown

The alternative to dog boarding kennels

Are you looking for Dog Boarding in Chestertown to take care of your beloved dog? You are in the right place! We currently have 445 experienced, loving and background-checked dog care specialists in Chestertown. Our sitters offer a variety of pet services such as home dog boarding, dog walking and doggy daycare. Make an informed decision based on reviews, response rates and contact at least 3 approved Dog Boarding professionals. Your dog will be delighted to be looked after by our loving dog sitters.