Dog Boarding in Chestertown

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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House Sitting
Drop-In Visits
Doggy Day Care
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Sitter Profile Image: Sabrina G.
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Sitter Profile Image: Sabrina G.
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1.

Sabrina G.

Personalized Pet Care Specialist
Chestertown, MD, 21620
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4.5 out of 5 stars
15 reviews
4 repeat clients
from
$40
per night

Sabrina watched my very shy dog, Ollie, for four days. She was patient with him while took his sweet time becoming comfortable with her. She sent us picture updates the whole time. I would definitely use her again!

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Sitter Profile Image: Lindsay G.
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Sitter Profile Image: Lindsay G.
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2.

Lindsay G.

Loving Pet Family with Fenced Yard
Stevensville, MD, 21666
19.3 mi. away
Boarding
5.0 out of 5 stars
41 reviews
12 repeat clients
from
$49
per night

Oak really enjoyed her stay with Lindsay! She particularly enjoyed her kiddos! Lindsay made the pickup and drop off logistics incredibly easy! I really appreciated her flexibility. Thanks again Lindsay!

Sitter Profile Image: Paris S.
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Sitter Profile Image: Paris S.
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3.

Paris S.

Dogs paradise away from paradise
Edgewood, MD, 21040
18.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
65 reviews
16 repeat clients
from
$39
per night

So thankful with Paris for take care of our Bruno during our Spring break. It was the first time we leave him with someone else . She sent us updates (pictures and videos of him) every day . We highly recommend Paris to take care of your dog . Thank you Paris !! We definitely will count with you again. ~Bruno’s Fam.

Sitter Profile Image: Jeren C.
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Sitter Profile Image: Jeren C.
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4.

Jeren C.

Stay at home mom and animal lover
Centreville, MD, 21617
7.7 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
7 repeat clients
from
$40
per night

Jeren did an amazing job with my dog! She was even flexible with my pick up time when my flight got delayed. Would definitely recommend if your dog likes other dogs and is very shy like mine

Sitter Profile Image: Joy P.
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Sitter Profile Image: Joy P.
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5.

Joy P.

Can't imagine my life without a dog
Kennedyville, MD, 21645
8.9 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
from
$45
per night

Our two goldendoodles had a great time with Joy and her labs, you can tell she loves to care for dogs! Will definitely be back!

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Sitter Profile Image: Jennifer M.
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Sitter Profile Image: Jennifer M.
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6.

Jennifer M.

Enjoy spending time with a pet!
Abingdon, MD, 21009
22.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
17 reviews
8 repeat clients
from
$35
per night

Jennifer was awesome with our two dogs! This was the first time they have ever been away from home, and she made them feel comfortable. I loved the pictures and updates she gave us throughout their stay. I would definitely use her services again, and I highly recommend her.

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Sitter Profile Image: Benita & Ivan V.
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Sitter Profile Image: Benita & Ivan V.
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7.

Benita & Ivan V.

Dog Mommy needs more paws!
Joppa, MD, 21085
22.2 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
17 reviews
3 repeat clients
from
$44
per night

Benita and Ivan are incredible dog sitters! They took great care of our pup, Maple, and sent us several updates over the weekend. They have two dogs that got along great with Maple and took the crew to the dog park every morning! Highly recommended!

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Sitter Profile Image: Sarah & Jeremiah H.
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Sitter Profile Image: Sarah & Jeremiah H.
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8.

Sarah & Jeremiah H.

Big yard, happy dog!
Belcamp, MD, 21017
20.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
7 repeat clients
from
$50
per night

These folks are simply wonderful! I was very nervous leaving Marvin the first time since his rescue, but instantly felt at ease at the drop off. Marvin had a blast with their dog Malia, and he slept like a baby last night. Do not hesitate to book a stay with Sarah, Jeremiah and Malia!

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Sitter Profile Image: Michelle M.
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Sitter Profile Image: Michelle M.
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9.

Michelle M.

Beautiful back yard for your dogs!
Annapolis, MD, 21409
23.0 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
373 reviews
202 repeat clients
from
$40
per night

Michelle is the best. She spoils our fur princess just like we do. We get lots of pictures and comments on how she’s doing. She is super responsive if you need to text her and a reliable second home for Giselle. We consider ourselves lucky to have her.

Sitter Profile Image: Lisa B.
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Sitter Profile Image: Lisa B.
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10.

Lisa B.

Can’t wait to have your pooch over!
Pasadena, MD, 21122
25.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
52 reviews
19 repeat clients
from
$45
per night

Lisa is THE ABSOLUTE BEST thing that happened to our Maggie! We ended up booking with Lisa at the last minute because the sitter that we used previously had an emergency. Lisa was very attentive to Maggie! She sent us daily communications and pictures which helped us feel at ease. We knew that Maggie was in great hands the moment that we met Lisa. Lisa, thank you to you and your family for taking great care of our Maggie. We will most definitely be using yours services in the future.

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Sitter Profile Image: Alana C.
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Sitter Profile Image: Alana C.
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11.

Alana C.

Rover 101
will love your pets like my own
Havre de Grace, MD, 21078
23.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
106 reviews
20 repeat clients
from
$40
per night

Alana was just amazing with our 2 small dogs. We were given quick updates throughout the day while away, with pictures. We’re very thankful we went this route as both dogs came back healthy and happy and our whole family could relax on vacation knowing they were in good hands. Thank you, Alana!

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Sitter Profile Image: Sarah R.
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Sitter Profile Image: Sarah R.
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12.

Sarah R.

Every Dog will Feel at Home!!!
Edgewood, MD, 21040
20.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
17 reviews
8 repeat clients
from
$48
per night

Sarah was amazing! It’s refreshing to meet someone who will love your pet as much as you do! From constant contact w/me regarding my pet to sending me videos and pictures of my pet’s stay w/her, I’m very pleased w/Sarah! I would highly recommend her!

Sitter Profile Image: Janay H.
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Sitter Profile Image: Janay H.
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13.

Janay H.

Just A Bark Away
Edgewood, MD, 21040
20.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$50
per night

Janay was able to watch our little man pretty last second, for a long weekend. She took wonderful care of our ham and sent updates/pictures, keeping me informed! She is so sweet and took care of usi like he was her own, and went above and beyond calming my anxieties... I can't say enough nice things about her, both professionally and as a person! We'll definitely be using her again!

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Sitter Profile Image: Katie F.
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Sitter Profile Image: Katie F.
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14.

Katie F.

A house is not a home w/o dog hair
Dundalk, MD, 21222
24.4 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
61 reviews
21 repeat clients
from
$45
per night

Katie was awesome with Bagel when I had to go out of town for a week! She took him on plenty of walks and adventures and made sure he felt right at home. She kept me totally in the loop with multiple pictures and videos each day. This was my first time using Katie but I saw immediately that she treated Bagel like her own. 10 out of 10, and I will definitely be using her services again!

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Sitter Profile Image: Alessandra G.
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Sitter Profile Image: Alessandra G.
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15.

Alessandra G.

Very passionate about pets !!!
Edgewood, MD, 21040
20.1 mi. away
Boarding, House Sitting, Doggy Day Care
5.0 out of 5 stars
16 reviews
8 repeat clients
from
$40
per night

Alessandra was AWESOME! She cared for Oli like he was a part of the family and she shared photos everyday to keep me informed! I will be using her again! THE BEST!!

Sitter Profile Image: Janice & Charles B.
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Sitter Profile Image: Janice & Charles B.
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16.

Janice & Charles B.

We’d love to welcome your pets!
Clayton, DE, 19938
21.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
2 repeat clients
from
$34
per night

Wonderful people with a great love for animals! I love the way they made my Prince feel at home and special. They sent pictures and updates to let me know that he was ok and to ease my worries. This was the best decision that I have made for my fur baby! I will use Janice and Charles again for the future.

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Sitter Profile Image: Katie K.
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Sitter Profile Image: Katie K.
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17.

Katie K.

Doggo mom
Middle River, MD, 21220
22.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
15 reviews
5 repeat clients
from
$49
per night

Katie did an outstanding job taking care of our 4-legged children while we were away on vacation. She is very thorough and sent us pictures and videos everyday which was a nice touch. Our black pug, Merry, became best friends with Katie’s mom. We plan to use Katie for future pet sitting needs. Would highly recommend!

Sitter Profile Image: Meme & Phil L.
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Sitter Profile Image: Meme & Phil L.
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18.

Meme & Phil L.

Love To Care For Your Fur Babies!
Essex, MD, 21221
20.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
33 reviews
14 repeat clients
from
$42
per night

Thank you to Meme and Phil for making my two dogs feel completely at home. My babies spent a week in their loving care. I received daily heartwarming videos, pics, and text messages. My dogs looked and behaved like they were at home. Honestly, I think my dogs had more fun that week than I did at the beach. Meme and Phil are my first Rover placement, and I have told all of my fur mommy's to consider placement with this loving couple. This review doesn't begin to capture how wonderfully, relaxed I felt that my babies were in an EXCELLENT, safe and fun-filled environment. I am so pleased, that I am scheduling a day visit for one of my dogs to return and play with one of his fav friends who will be there again. ?? Kudos to Meme and Phil for making this more than a visit, but a labor of love!!! I won't be looking for any other Rover placements. All I need is with Meme and Phil.

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Sitter Profile Image: Candice W.
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Sitter Profile Image: Candice W.
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19.

Candice W.

Work from Home Dog Mommy
Annapolis, MD, 21409
25.3 mi. away
Boarding
5.0 out of 5 stars
32 reviews
15 repeat clients
from
$65
per night

Candace was amazing! I have a Great Pyrenees who slobbers a lot and is very timid and Candace handled her p with ease and love. Candace is very easy to communicate with. I recommend her highly!

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Sitter Profile Image: Caitlin “Cc” C.
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Sitter Profile Image: Caitlin “Cc” C.
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20.

Caitlin “Cc” C.

Dog mom life is the best life
Baltimore, MD, 21222
23.6 mi. away
Boarding, Dog Walking
5.0 out of 5 stars
22 reviews
5 repeat clients
from
$50
per night

CC is absolutely amazing! Pleasant and welcoming. You can feel that she cares a great deal about caring for your fur baby and wants to accommodate you in any way. She kept in contact with us throughout the day, sent pictures, and video. We have found a home away from home for our Marlowe!

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Chestertown Dog Boarding ratings

Overall Rating:
4.8 out of 5 stars

Dog boarders in Chestertown are rated on average 4.8 out of 5 stars based on 26 reviews.

Rover also offers Dog Boarding in:

Rover also offers other services in Chestertown:

Boarding