Dog Boarding in Chester, MD

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Sitter Profile Image: Lindsay G.
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Sitter Profile Image: Lindsay G.
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1.

Lindsay G.

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

Lindsay was called on such short notice, during a holiday week mind you, and was so agreeable to taking care of my two dogs! She is the best dog sitter!

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Sitter Profile Image: Juliana C.
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Sitter Profile Image: Juliana C.
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2.

Juliana C.

Reliable Pet Lover
Chester, MD, 21619
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
4 reviews
from
$50
per night

Juliana stayed with our cat, Annabelle, in our home, for a month, while we were in Florida. She was wonderful with Annabelle. She took excellent care of her, as well as taking care of our plants, bringing in the mail, and taking the garbage and recycling out, as scheduled. She communicated with us regularly and sent us photos of Annabelle. Unfortunately, our heat stopped working, and she calmly called us, and was there to receive the repairman, twice! She rolled with the situation and was very responsible with all aspects of staying in and caring for Annabelle and our home. We would definitely welcome having her back! She's a lovely person.

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Sitter Profile Image: Mary L.
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Sitter Profile Image: Mary L.
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3.

Mary L.

Chickens Squirrels Dogs & Kitties!
Stevensville, MD, 21666
2.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
8 repeat clients
from
$59
per night

They were absolutely amazing with Nellie. We couldn't of have had a better experience. Nellie enjoyed her time with them and they treated her very well. It was our first time leaving Nellie with anyone and the random updates on her with pictures and videos helped ease our minds during our time away. We would definitely recommend them to anyone who is looking for pet care/boarding.

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Sitter Profile Image: Michelle M.
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Sitter Profile Image: Michelle M.
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4.

Michelle M.

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

Would absolutely recommend Michelle — She provided great care, daily walks, and great communication including pictures of the dogs every day.

Sitter Profile Image: Mari H.
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Sitter Profile Image: Mari H.
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5.

Mari H.

Dog Lover extraordinaire
Chester, MD, 21619
0.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 repeat client
from
$35
per night

About: Ever since I could walk I have been around dogs. I have been pet sitting for people since I was 10. I love every animal and will treat them like my own. I work part time and am off on the weekends. I can stop by in the mornings, some afternoons, and any evening you need to check on the sweet animals. I will make sure they are well loved and have everything they need. My home is a very safe space for animals. I have an open space behind my home that they can run around and play in.

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Sitter Profile Image: Elaine Y.
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Sitter Profile Image: Elaine Y.
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6.

Elaine Y.

Rover 101
Eastport Doggie B&B!
Annapolis, MD, 21403
10.8 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
222 reviews
111 repeat clients
from
$35
per night

Elaine is simply the best. She's always so kind to work with our schedule and takes care of our little one just like we would. We love her, and, more importantly, our puppy loves her!

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Sitter Profile Image: Candice W.
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Sitter Profile Image: Candice W.
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7.

Candice W.

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

I could not say enough good things about Candice. I was really nervous because this was our first time leaving our one year old dog Lucy overnight. Candice took the time too meet with us and went over all the details of the process and her love of pets. Her dog was so sweet and the perfect playmate for our active lab. I felt at ease leaving our little lady in her care as I knew she would treat her like her own. The communication before and during our trip was so comforting. We got to see pictures and videos from time to time as well as updates on how things were going. It all made the experience really enjoyable for both us and our pet. Honestly the day after we came home I think our Lucy was actually really missing her playmate. This experience has changed the way I look at being able to travel. We have not done so because we felt guilty if we left her behind. Now I won’t hesitate because I know she will be having as much fun as we are and be well taken care of with Candice.

Sitter Profile Image: Renea D.
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Sitter Profile Image: Renea D.
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8.

Renea D.

Rover 101
Barker's B&B: Boarding
Edgewater, MD, 21037
13.2 mi. away
Boarding
5.0 out of 5 stars
87 reviews
52 repeat clients
from
$35
per night

Renea is terrific. She loves the puppies and they love her. We knew our sweet puppies would be well cared for and they were We will be back. Thank you Renea.

Sitter Profile Image: Bhavani K.
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Sitter Profile Image: Bhavani K.
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9.

Bhavani K.

love to workout with pups
Stevensville, MD, 21666
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
1 repeat client
from
$40
per night

For my first Rover experience I couldn't have asked for a better sitter than Bhavani. She was a great communicator from our first contact through to the end of the engagement. Bhavani clearly understood what my dog needed to feel comfortable and gave her a lot of love and affection. I will not hesitate to contact her again in the future.

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Sitter Profile Image: Tom A.
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Sitter Profile Image: Tom A.
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10.

Tom A.

Your Dog’s Best Buddy! ;0)
Annapolis, MD, 21403
10.1 mi. away
Boarding, House Sitting, Drop-In Visits
4.5 out of 5 stars
7 reviews
1 repeat client
from
$51
per night

Tom was great with our dog Jada for the week! He updated us daily and she seemed comfortable and happy. He was also able to give her medications. We would definitely trust Tom for pet sitting again!

Sitter Profile Image: Tommy S.
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Sitter Profile Image: Tommy S.
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11.

Tommy S.

A+ Home w Active Dog & Fenced In
Grasonville, MD, 21638
5.0 mi. away
Boarding
5.0 out of 5 stars
2 reviews
1 repeat client
from
$60
per night

Tommy was great to deal with. Very responsive and seemed to really care for my pup. I appreciated the updates. Will definitely be booking again in the future

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Sitter Profile Image: Michaela P.
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Sitter Profile Image: Michaela P.
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12.

Michaela P.

Dedicated to high quality care
Annapolis, MD, 21403
12.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
20 reviews
7 repeat clients
from
$50
per night

Michela is wonderful! Manny had a great stay and when we came to pick him up, he even ran back into her house to stay longer 😂 10/10 thank you!

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Sitter Profile Image: Samuel T.
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Sitter Profile Image: Samuel T.
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13.

Samuel T.

Dog lovers with a big back yard.
Annapolis, MD, 21403
10.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
17 reviews
7 repeat clients
from
$40
per night

They were great loving host! Definetly dog people who love to share their home! We will hopefully have Kumo stay with them on our next trip! See you guys soon! Joe

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Sitter Profile Image: Makhayla D.
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Sitter Profile Image: Makhayla D.
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14.

Makhayla D.

The Dog Sitter For You
Annapolis, MD, 21401
11.2 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
31 reviews
5 repeat clients
from
$40
per night

My dog is still working through some behavioral issues when around new people. I greatly appreciate Makhayla’s willingness to watch him and help him get start to overcome these problems.

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Sitter Profile Image: Jessica M.
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Sitter Profile Image: Jessica M.
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15.

Jessica M.

Because it deserves the best 🫶
Annapolis, MD, 21401
12.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
1 repeat client
from
$40
per night

My dog was so excited to visit Jessica again, as soon as I took him out of the car he raced up the steps to her home before she was downstairs.

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Sitter Profile Image: Jason B.
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Sitter Profile Image: Jason B.
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16.

Jason B.

Dog lover, large yard,works at home
Edgewater, MD, 21037
12.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
20 reviews
11 repeat clients
from
$44
per night

Our dogs love staying with Jason. He is clear with communication, sends pics, and caters to dogs’ individual needs. I always feel as though my dogs are well cared for and a part of the family when they are with Jason. Highly recommend!

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Sitter Profile Image: Shannon L.
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Sitter Profile Image: Shannon L.
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17.

Shannon L.

Pups and playtime - in home!
Annapolis, MD, 21401
11.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
3 reviews
from
$70
per night

Shannon was an excellent dog sitter. She treated our yellow lab as one of her own and was so calm and comfortable welcoming our dog into her home. Her own dog is so sweet and fun too! My dog made a new buddy while staying with Shannon and her pup. They loved her fenced in yard. Our dog returned home happy because she was taken care of so well. Thanks Shannon!

Sitter Profile Image: Lisa B.
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Sitter Profile Image: Lisa B.
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18.

Lisa B.

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

Lisa is amazing! I knew from our first visit to meet her that she would take good care of our crazy Sheltie. Archie seemed to be very happy at her home instantly and did very well during our long vacation. Lisa loves dogs and enjoys having them around. She wrote to me every day while we were away and sent pictures. She even made arrangements for Archie to have play dates with another Sheltie (with my permission, of course) who comes to her house occasionally for day care. I never had a moment's worry about Archie while we were away, in fact, I was worried that he wouldn't want to come home! We hope to be able to travel more in the future and that Lisa will be available to care for Archie, I think he has found a second home!

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Sitter Profile Image: Jenna C.
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Sitter Profile Image: Jenna C.
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19.

Jenna C.

Loving Petsitter Welcomes All
Annapolis, MD, 21401
13.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
37 reviews
14 repeat clients
from
$60
per night

Jenna is always so accommodating with scheduling and Ellie truly has the best time when she stays with her!! I always feel at ease leaving her with Jenna and Boo 😃

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Sitter Profile Image: Beth H.
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Sitter Profile Image: Beth H.
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20.

Beth H.

Get away with peace of mind
Edgewater, MD, 21037
14.8 mi. away
Boarding
5.0 out of 5 stars
22 reviews
11 repeat clients
from
$60
per night

Beth is amazing!!! I had never left my anxious doggie before so I was a little nervous, but she made biscuit and my self feel so at ease! She sent me pictures of what they were up to throughout the day, and when I went to biscuit up, she didn’t want to leave Beth’s house! 10/10 recommend, she is definitely biscuits new favorite friend :)

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Chester Dog Boarding ratings

Overall Rating:
5.0 out of 5 stars

Dog boarders in Chester are rated on average 5 out of 5 stars based on 50 reviews.


Never beg a friend to watch your dog again, and no more dog kennels. With Rover, you can find your perfect Chester dog sitter in seconds. When you book dog boarding on Rover, your dog will enjoy a loving, relaxing stay in your dog sitter's home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers pet boarding for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care, right in their sitter's home. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach dog sitters in Chester, MD who can provide the care your dog needs, when they need it.

You'll also be able to relax when it comes to price, because the cost of dog boarding in Chester, MD is surprisingly reasonable. No matter your budget or lifestyle, there's a dog sitter on Rover to match your wallet. Wondering how much most people pay for Rover dog boarding services? The average dog boarding rates will give you a good sense of what to expect before checking out the individual dog sitters' hourly rates.

Looking for an on-demand solution to your dog boarding needs when you're short on time? Then you'll love the Rover dog boarding app. The Rover app features hundreds of highly-rated, trustworthy dog sitters, and you can scroll through the options or simply re-hire your regular dog boarder in no time. Your dog sitter can share real-time photo updates via the Rover dog boarding app, and with the app's cashless payment feature you'll be able to compensate your dog sitter quickly and safely, with no need for cash, checks or tips.

In short, when you book Chester dog boarding on Rover, your dog gets the loving care they deserve, and you get to relax, knowing that your pet is in good hands.

Are you a dog lover who wants to know more about how to turn your passion into profit? There's lots of opportunity to earn money with dog boarding in Avon Crest, MD. If you're not sure where to start, visit our page about how to become a dog sitter. We're always happy to include new dog sitters in our dog boarding service listings, and the simple application process means you can start your own dog boarding business in no time. We also take the hassle out when it comes to paperwork, because all our Rover dog sitters have access to helpful benefits including premium pet insurance and cashless payment feature, so you don't have to worry about getting paid on time. Why not apply today?

Reviews from our dog sitters in Chester

Thanks Tabitha for taking our dog on a walk and giving her lots of love! Would recommend her to anyone!

Jess was very considerate of yiidi. They seemed to have enjoyed the walk and yiidi loved jess's company

Shunmarie was a great walker. She handled my big dog great. I will be using her again and recommend her

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