House Sitting in Chester

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Calendar Recently Updated
Sitter Profile Image: Elizabeth W.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth W.
Verified Enhanced Background Check
1.

Elizabeth W.

Loving your pets like my own!
Chester, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
5.0
15 reviews
from
$28
per night

Elizabeth and her husband took excellent care of my high maintenance dog. She has patience and truly cares about animals. Of course her being in the vet field is a huge bonus as it puts my mind to ease that if anything happens I am confident she will have the resources to take care of it. Her dogs are super friendly and look very healthy and happy which shows the level of care that she takes with animals. I highly recommend and will not be taking my dog anywhere else.

Calendar Recently Updated
Sitter Profile Image: Wendy B.
Verified Background Check
Sitter Profile Image: Wendy B.
Verified Background Check
2.

Wendy B.

I LOVE Animals and they LOVE me!!!
Queenstown, MD, 21658
House Sitting
5.0
26 reviews
5 repeat clients
from
$40
per night

Wendy was so great with our two dogs, 8 chickens, and fish! I highly recommend her! She responds quickly and sends lots of updates. This was the best Ive ever felt leaving my animals! Thank you Wendy!

Calendar Recently Updated
Sitter Profile Image: Gregory G.
Verified Background Check
Sitter Profile Image: Gregory G.
Verified Background Check
3.

Gregory G.

Fenced Yard | Home Full Time
Stevensville, MD, 21666
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
48 reviews
9 repeat clients
from
$75
per night

About: Hey guys, my name is Greg, I have been working from home for about 6 years now, as such I am fairly flexible with availability. I am an animal lover at heart, I have had both dogs and cats all of my life. I have been sitting for rover for a total of 3 years. I have loved meeting and caring for a wide array of breeds in all sizes. Currently, we have one dog (German Short Haired Pointer, who has lots of energy and loves to play) and two cats (Russian Blue and Domestic Short Hair, who generally stick to themselves), which I am sure you will see in the pictures. They are both very good with other animals. Please note if boarding I do require adequate food to be provided by the owners for the duration of the stay. I can't wait to meet you and your pets! Thanks again for trusting and choosing me to be a part of you and your pet's life! If you have any questions or concerns please do not hesitate to ask. As I work from home full time, I am relatively flexible in scheduling visits. Even if there are multiples required. I do stay for the scheduled duration and provide many pictures as well. There will always be someone at the house to play, feed, and care for your little one. Additionally, I have one dog that loves to entertain his playmates. Regarding drop-in visits I respect your home as if it were mine. I have been working from home since before COVID started. Which allows me a great deal of flexibility for drop in visits and dog walks. I have a large fenced yard (1/3 Acre) with plenty of room to run and play. My German short-hair pointer is 5 years old and loves to chase and be chased as well as play fetch.

Calendar Recently Updated
Sitter Profile Image: Heather & Jennifer T.
Verified Enhanced Background Check
Sitter Profile Image: Heather & Jennifer T.
Verified Enhanced Background Check
4.

Heather & Jennifer T.

Trusted Pet Care Provider
Ridgeley, WV, 26753
House Sitting, Drop-In Visits, Dog Walking
5.0
10 reviews
2 repeat clients
from
$65
per night

Heather & Jen were so great with our two dogs. This was the first time we have used Rover for boarding our two dogs and we really appreciated their patience with our 2 energetic doggos, especially 1 who is very anxious. Great communication too. Thanks so much for your help with Reno & June. We really appreciate it!

Sitter Profile Image: Natalia G.
Verified Enhanced Background Check
Sitter Profile Image: Natalia G.
Verified Enhanced Background Check
5.

Natalia G.

The Purr-fect Pet Sitter
Chester, MD, 21666
House Sitting, Drop-In Visits
5.0
15 reviews
1 repeat client
from
$48
per night

Natalia was great with my furbabies while my husband and I were out of town. She provided regular updates and was very attentive to their needs and nuances. I highly recommend Natalia for your dog sitting needs!

Calendar Recently Updated
Sitter Profile Image: Cindy P.
Verified Background Check
Sitter Profile Image: Cindy P.
Verified Background Check
6.

Cindy P.

I love all animals!
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
1 repeat client
from
$50
per night

We were very impressed with Cindy. She was very responsive and sent pictures and videos of our dogs while we were away. She cared for our animals like they were one of her own. She asked questions when needed and left our house in incredible shape. She cleaned it and washed our sheets - when we didn't have that expectation. We will definitely use Cindy again and recommend her to others.

Calendar Recently Updated
Sitter Profile Image: Bill A.
Verified Enhanced Background Check
Sitter Profile Image: Bill A.
Verified Enhanced Background Check
7.

Bill A.

Pets and your home are safe with me
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
10 years of experience
from
$31
per night

About: I really enjoy working with pets not only to play, but to train with them. I like walking and being outdoors and pets make it more fun for me. I currently telework full time so pet care is very easy for me to work into my schedule. I also enjoy fitness so being outside with pets it great for me. I have a job that requires the highest of trust so caring for you pets and property will be of the highest priority for me. I will respect you, your pets, and property.

Calendar Recently Updated
Sitter Profile Image: Jason & Tracy Y.
Verified Enhanced Background Check
Sitter Profile Image: Jason & Tracy Y.
Verified Enhanced Background Check
8.

Jason & Tracy Y.

Rover 101
Reliable & Responsible, Dog Lovers!
Stevensville, MD, 21666
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
61 reviews
26 repeat clients
from
$28
per night

Wow! I never thought that my dog wouldn’t miss us while we were gone for two weeks but, she really didn’t. She adopted Tracy and Jason right away. This says a lot about the care and understanding Tracy and Jason have of caring for other people’s dogs. That, in itself, is a skill and takes patience, observation and understanding. Of course, coming home to Tootsie, after two weeks- she was excited to see me but, remarkably she was relaxed and happy. It sure put my mind at ease have her at home with her familiar smells and routine. Tracy and Jason were great continuation of care for Tootsie. While were were gone as they were our “subs”. We were thrilled with their services and will invite them again to house and dog sit!

Sitter Profile Image: Bohdanna G.
Verified Background Check
Sitter Profile Image: Bohdanna G.
Verified Background Check
9.

Bohdanna G.

Rover 101
I Love Furbabies!
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
5.0
60 reviews
24 repeat clients
from
$30
per night

Always a pleasure to have Bo take care of my 'little man Jasper' and my home. Jasper is so content and calm from all the lovin' when I return.

Calendar Recently Updated
Sitter Profile Image: Michael P.
Verified Enhanced Background Check
Sitter Profile Image: Michael P.
Verified Enhanced Background Check
10.

Michael P.

Rover 101
Compassionate, Reliable, Fun Loving
Annapolis, MD, 21409
House Sitting, Drop-In Visits, Dog Walking
5.0
46 reviews
22 repeat clients
from
$80
per night

Michael was great; did a meet and greet first to make sure Cobbler was comfortable with him, and he took immaculate care of her and my house. Would recommend!

Calendar Recently Updated
Sitter Profile Image: Bhavani K.
Verified Background Check
Sitter Profile Image: Bhavani K.
Verified Background Check
11.

Bhavani K.

love to workout with pups
Stevensville, MD, 21666
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
9 reviews
1 repeat client
from
$100
per night

Bhavani was awesome. Gunner and Magic were well taken care of. Thank you Bhavani!

Calendar Recently Updated
Sitter Profile Image: Jamie P.
Verified Background Check
Sitter Profile Image: Jamie P.
Verified Background Check
12.

Jamie P.

Best Buddy for the Furry Royalty
Annapolis, MD, 21403
House Sitting, Drop-In Visits
5.0
81 reviews
34 repeat clients
from
$37
per night

This was our first time using Jamie and it was a huge success. Jamie took perfect care of our elderly dog in our home and when we came back Mikey and the house were as we left them. We will definitely use her again.

Calendar Recently Updated
Sitter Profile Image: Holly B.
Verified Enhanced Background Check
Sitter Profile Image: Holly B.
Verified Enhanced Background Check
13.

Holly B.

I will love your dog like my own!
Annapolis, MD, 21401
Boarding, House Sitting
5.0
11 reviews
2 repeat clients
from
$60
per night

Holly was amazing with my elderly dog and young cat. She provided numerous pictures and updates. She is a true animal lover and it was evident. I always get anxious about whom I leave my pets in the care of and she 1000% exceeded my expectations. Would highly recommend her to anyone needing their pets cared for.

Calendar Recently Updated
Sitter Profile Image: Jaime A.
Verified Enhanced Background Check
Sitter Profile Image: Jaime A.
Verified Enhanced Background Check
14.

Jaime A.

Make them happy while your away!
millersville, MD, 21108
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
24 reviews
11 repeat clients
from
$65
per night

Jamie stopped by a few days ahead of time to review food and medications. Mika seemed very relaxed when we returned from our overnight away, and Jamie updated us several times with pictures of playtime, eating, and sleeping dog. Great experience.

Sitter Profile Image: Tanaye M.
Verified Enhanced Background Check
Sitter Profile Image: Tanaye M.
Verified Enhanced Background Check
15.

Tanaye M.

Need a dog sitter? I am available.
Grasonville, MD, 21638
House Sitting, Drop-In Visits, Dog Walking
2 years of experience
from
$50
per night

About: Hello my name is Tanaye and I am fairly new to dog sitting and dog walking. I have been a veterinary technician for 2 years and I do have small, medium, and large animal experience. I will take excellent care of your pets, follow directions, and provide medical care such as nail trims, ear cleanings, and giving medication as needed. I work a veterinary hospital Monday through Thursday. I will be able to take care of the pets in the morning, afternoon around 12pm-1pm, and night time. At my house I have a fenced in yard. I do have a cat, a Guinea pig, and a 1 year old lab that is very dog friendly.

Calendar Recently Updated
Sitter Profile Image: Bianca A.
Verified Enhanced Background Check
Sitter Profile Image: Bianca A.
Verified Enhanced Background Check
16.

Bianca A.

Hi! I’m ready to love your pet!
Pasadena, MD, 21122
House Sitting, Drop-In Visits, Dog Walking
5.0
13 reviews
2 repeat clients
from
$55
per night

Minnie and Carlos had a great weekend with Bianca. She gave them extra love, kept them on their normal routine and took great care of the house. Can’t wait for her to stay with them again!!

Sitter Profile Image: Sarah N.
Verified Background Check
Sitter Profile Image: Sarah N.
Verified Background Check
17.

Sarah N.

Loving and open arms to any animal!
Stevensville, MD, 21666
House Sitting, Drop-In Visits, Dog Walking
4.5
4 reviews
1 repeat client
from
$50
per night

Sarah is great with animals. Her family has had pets for many years. Our older dog is anxious and not always comfortable around everyone. Sarah is very helpful with him. He looks forward to seeing her and sitting with her when she comes to our house. We are very comfortable leaving our dogs in her care when we are our of town. She is reliable and trust worthy. She has also helped others with their animals and I have heard good things from the as well. She would be a great sitter for anyone's pets.

Calendar Recently Updated
Sitter Profile Image: Rachael B.
Verified Enhanced Background Check
Sitter Profile Image: Rachael B.
Verified Enhanced Background Check
18.

Rachael B.

I love all pets like my own
Easton, MD, 21601
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
from
$48
per night

She is a Very kind, caring and trustworthy individual. She has shown great patience with our dogs that can be a handful at times. High recommendations from Myself and our neighbors of Rachael.

Sitter Profile Image: Alexis E.
Verified Enhanced Background Check
Sitter Profile Image: Alexis E.
Verified Enhanced Background Check
19.

Alexis E.

Dogs will love you more then anyone
annapolis, MD, 21403
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4.5
4 reviews
2 repeat clients
from
$75
per night

About: I think what sets me aside from other’s is my true passion for all animals, everyone in my childhood neighborhood knew if they found a stray of their friend found a stray you could ALWAYS bring them to my house no matter what it was, at one point we had 7 cats, one just had 3 kittens, 4 dogs, a chinchilla, and a baby turtle! All were found forever home’s except 3 cats and 1 dog we kept bc they felt too much like family we couldn’t let them go! I have training/experience in bottle feeding, giving medications, shots, energetic dog’s, senior dogs/ cats, and pretty much anything else it takes to care for an animal! I’m currently working part time so I have plenty of time on my hands to play with your sweet puppy’s! Open to work with your needs! I had a VERY energetic foster puppy for a few months until she found her furever home, I still get updated pictures of her every week she’s doing amazingly well has lots of new brothers and sisters! I cared for Lola in my apartment by crate training her at night, and during the days we spent most of our time at the doggy park right here in my neighborhood which is right across the street from my house luckily, We also have lots of land and sidewalks to go on since I am in the middle of Downtown Annapolis which everyone knows is SUPER dog friendly! I enjoy long walks and being out in the sun! and hanging by the water!

Calendar Recently Updated
Sitter Profile Image: Kathryn R.
Verified Enhanced Background Check
Sitter Profile Image: Kathryn R.
Verified Enhanced Background Check
20.

Kathryn R.

Cat/dog/animal lover & aficionado
Bowie, MD, 20715
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
42 reviews
17 repeat clients
from
$70
per night

Kathryn houses at for us and cared for our Pack, which includes two elderly dogs and 2 medium-aged dogs. She is wonderful, caring, intelligent and responsible. She asks good thoughtful questions which indicated to me her high level of care. I give her my highest recommendation.

Search Map

Chester House Sitting ratings

Overall Rating:

House sitters in Chester are rated on average 4.8 out of 5 stars based on 11 reviews.


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Chester house sitting needs. On Rover, it's easy to find a loving dog sitter in Chester who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Chester house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Chester for your dog — people who'll treat him like family.

House Sitting