Dog Sitting in Chester

Dog sitters in Chester, Maryland who will care for your furry friend at home without any charges!

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There are 6,652 dog sitters near you

Sitter Profile Image: Cindy
Cindy

Chester, Maryland

40+ Five-Star pet sits; Columbia University faculty (teaching remotely)

5.0
• 57 reviews
Owner Image

It was a pleasure to have Cindy care for my cat Stella while I was away on an unexpected last-minute trip. Cindy sent frequent updates and photos, which provided a great comfort to me since I had only been home from a long trip 3 days before suddenly having to leave again. Stella seemed quite comfortable with Cindy's company! I returned home to a relaxed kitty and tidy apartment. Thank you, Cindy!

Sitter available from Oct 1
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Sitter Profile Image: Maureen
Maureen

Chester, Maryland

Never cancelled a sit, all boosters, non-smoker, traveling solo

5.0
• 55 reviews
Owner Image

Maureen was a treat from start to finish with our home and cat, Poppy! She is perhaps one of the most organized sitters we have encountered on zeewoi. Her resume speaks for itself. She was eager to sit, despite it being a somewhat short notice (about 10 days). Upon arrival we received pictures of Poppy to let us know that she was in good hands. We also got daily updates in the evenings, which we enjoy. Maureen stayed at our home during the coldest stretch of the year, and came prepared with heating blankets, etc, which we appreciated as we only have space heaters currently. We would be happy to host Maureen any time. Her communication and experience are certainly top notch and your pet will be in great hands!

Sitter available from Oct 1
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Sitter Profile Image: Shauna
Shauna

Chester, Maryland

Non-smoking medical professional

5.0
• 48 reviews
Owner Image

Shauna was a wonderful house and pet sitter. I got occasional photos of Buzzi (the cat) -- enough for me to see that Buzzi was very happy. Periodic updates from Shauna revealed no problems. The house looks great; now I just have to keep it that neat and clean.

Sitter available from Oct 1
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Sitter Profile Image: Elena
Elena

Chester, Maryland

Quiet, reliable and responsible cat (and small dog) lady

5.0
• 47 reviews
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This was our first time using a Trusted Sitter, and I'm so grateful Elena chose to stay with our precious pup. He's a senior dog that requires a little extra attention, and Elena was so kind and caring with him. From our very first zoom call to get to know one another, I knew Elena would be a great fit. She was very organized, told us what she needed to know, and was very flexible when our dates changed a bit. Elena sent several pictures of Beamer every day. My kids eagerly awaited to see what their brother was up to while we were away. He looked so happy in all of his pictures. She took him for walks and gave him plenty of cuddle time. Elena also took such great care of our home. We arrived back to a spotless house! Our experience with Elena was more than I could have hoped for using Trusted Sitter. It was like having an old friend stay over. I highly recommend Elena, and hope she will be available to stay the next time we go on vacation!

Sitter available from Oct 1
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Sitter Profile Image: Olivia
Olivia

Chester, Maryland

Hi! I am Olivia, and my partner's name is Belrie. We look forward to meeting you

5.0
• 35 reviews
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I am so fortunate because I had to cancel this sit at the last moment and Olivia and Belrie were extremely understanding. All our communications leading up to the sit were phenomenal, and I can't wait to have them stay with Pearl soon.

Sitter available from Oct 1
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Sitter Profile Image: Todd
Todd

Chester, Maryland

Caring, responsible and reliable house and pet sitters since Nov 2020

5.0
• 35 reviews
Owner Image

Once again, Todd and Janis were wonderful sitters. They were easy to communicate with, sent adorable photos, and took great care of our home.

Sitter available from Oct 1
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Sitter Profile Image: Monica
Monica

Chester, Maryland

Non-smoking remote worker eager to love your pets as my own!

5.0
• 32 reviews
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Monica was an outstanding house sitter. She communicated well, took very good car of our cat, and was very gracious after a falling tree limb took out the internet. We would definitely invite her to sit again.

Sitter available from Oct 1
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Sitter Profile Image: Brandi
Brandi

Chester, Maryland

Solo sitter with the need to please loving animals while their owners are away.

5.0
• 27 reviews
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This was the 2nd time Brandi housesat for us. She did an amazing job again and when I got home, I couldn't even tell that she has even stayed in our guest room because she is so neat! She kept me posted about all of our pets and sent photos. I would definitely trust Brandi to take care of our pets and home again!

Sitter available from Oct 1
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Sitter Profile Image: Lisa
Lisa

Chester, Maryland

English/Theater Teacher (remote), Animal Spoiler, Humane Society Volunteer

4.85
• 34 reviews
Owner Image

What a great experience we had with Lisa. She was so good with Cella. She was very tolerant of Cella's early rising. She's a tiny little thing, but has a big personality and knows what she wants. Lisa was so good at reading her needs. We were able to have a zoom interview with Lisa before we confirmed the sit. She stayed in touch with us daily and kept us updated on how things were going. When we arrived home, Lisa had washed all of the bedding and towels. She vacuumed and thoroughly cleaned the kitchen and bathroom. We couldn't be more pleased with Lisa as our sitter for Cella. We hope we'll be able to have her again. She was awesome.

Sitter available from Oct 1
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Sitter Profile Image: Sidney
Sidney

Chester, Maryland

“Stop worrying about the potholes in the road and enjoy the journey” ~ Babs Hoff

4.78
• 32 reviews
Owner Image

Sidney did a great job taking care of our dog and cat over a long weekend. We got regular updates and he was very responsive.

Sitter available from Oct 1
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Reviews from Dog Owners

4.93
253,301 reviews
4.93
253,301 reviews
4.96 Organised 4.96 Reliable 4.95 Clean and tidy 4.97 Self-sufficient 4.91 Pet care
User
Jeff
My dog had a medical emergency while in John’s care and I credit him with saving my pup’s life. You couldn’t ask for a better sitter in a pressure situation. He also communicated regularly during the stay, keeping me posted on how my pup was doing. Would recommend John to anyone who needs a sitter they can trust.
User
Wendy & Rob
Joe and Casey were very easy going and reliable. We organised the sit way in advance with a video chat and we had adequate communication leading up to the sit. We handed over the house and animals after a fairly swift explanation of everything. Being experienced sitters Joe and Casey didn't need us to over explain anything (hopefully they felt the same) and we could see very quickly that they were animal lovers. They asked us how much communication we needed whilst away and we said "no news is good news". So we received just the right amount of updates along with the most adorable photos and reassuring words about all the animals. It was clear that they quickly understood the character of each of the animals. We forgot to mention that Tipper likes to dig dirt beds around the garden which creates quite a mess and it was obvious that these were kept under control. The garden and pool were well cared for. We enjoyed a relaxing couple of weeks away knowing that the animals were being loved and the dogs definitely looked for Joe and Casey when we arrived home. Our pets, home and garden were well respected and cared for and we would not hesitate to invite Joe and Casey to sit for us again.
User
Lisa
Jasmine is a five-star sitter.  She is everything you want in a sitter when you go away and leave your beloved pet and home.  She is reliable, communicative, respectful, and flexible.  We had no worries about our dog or home while we were away, and will be having Jasmine sit for us again soon.  Our home was immaculate when we got home, and our dog was obviously well-cared-for.  Can't say enough good things about this wonderful human.
User
SOPHIA
I've always been lucky with my sitters through zeewoi, and this time was no exception. George, Larissa and their four lovely children were the absolute perfection in house guests and I cannot praise this wonderful family too highly. 

They did all the usual things you'd expect, gave my beautiful girls all the love and care I could wish, walked them at least once every day despite the best the British weather could throw at them, and sent me regular updates and photos so I could see how much love they were getting. 

They also left the house cleaner and tidier than I think I've ever seen it! I'm a bit worried that all they did for the week was walk and play with the dogs and then clean the house - I'm beyond grateful, the place looks amazing!

They really are the very nicest people too, George has a hilarious sense of humour (thanks for the funny texts George!) and Larissa is calm, kind and an inspiration as a mother. 

I really can't wait to have them back to look after the girls again in the summer and wish the whole family a wonderful trip until then. 

If they come and house sit for you then you are in for a real treat!
User
Leslie
I’m sure most folks say the nicest things about their sitter, but honestly, if there were a “super star” status available then Denise would win the prize as sitter of the year!

From the start, Denise was an excellent communicator.  While we were still in the decision phase, Denise was always available to chat either by FaceTime, telephone or text.  It was so easy to choose Denise; as you can see from her countless 5 star reviews, she truly is the only pet sitter you’d ever need and the one everyone hopes to have.  

Denise came to our house eager to meet us, our pets and the quirks of our house.  Denise has an excellent sense of humor and immediately put us all at ease.  Our pets took to her as if she was a long lost friend (even our finicky Siamese cat was loving on her from the start).  

While we were gone, our dog had a non-emergency health issue come up and just like that Denise was taking her to our vet, and administered the dog’s meds like a champion (Denise is also a nurse BTW).  Additionally, Denise brought our pup to her scheduled groom appointments and even made future appointments for us to make our return home as seamless as possible.

Denise was even above and beyond helpful to our neighbors and they appreciated her giving them access to our refrigerator when theirs broke down on Thanksgiving Eve!  

When we got home we were super impressed by how perfectly immaculate our house was!  Most sitters leave the house clean, but Denise met and may have even exceeded our military standards of clean and orderly.  Seriously, our house felt like we never left it.  Everything was spotless, shinny and clean.  She didn’t miss a beat!!  Our pets were so happy to see us but honestly, I felt like our pup and kitty were disappointed when we walked in the door (I believe they were expecting to see Denise!).  Haha.  

If you are ever fortunate enough to have Denise apply for any of your sits then I can’t recommend her enough.  Seriously, you can stop reviewing applicants and just go with Denise.  She was awesome in every sense of the word and I hope she’ll come back and stay with our pets again.
User
Koni
Robyn was a great pet sitter and house sitter.  She  went way over and beyond my expectations!!!! She sent a photo of her and my dogs and they were looking at her like they were in love.  And my cats are not very friendly, but she won them over also.  I would highly recommend Robyn as a pet sitter and house sitter.  She is a very sweet lady.  I would love to have her watch my babies again and again.
User
Courtney
Wendy sat for us on three occasions this Summer and I can’t say enough good things about her. The dogs were well taken care of and she was, organized, tidy, and responsible. It’s great to find a house/pet sitter that you can rest easy knowing everything is taken care of. We are hoping she will want to spend more time in the PNW!
User
Courtney
Amara was a WONDERFUL sitter for our home and our dogs for the weekend. We were so comfortable with her being in our home, and she provided regular updates and photos of our babies. The house was clean upon arrival home - we would have no hesitation recommending her to others and hope she would consider coming back to spend more time with our dogs!
User
Cassandra
Jim sat for my extremely shy rescue pup and new kitten for two weeks -- my pup struggles with new people, and is very fearful of men in particular. And yet, Jim was more successful with her than any sitter I've ever had: I can't recommend him highly enough. He has wonderful patience, a calm energy, and is a great communicator. He consistently updated me with photos and videos of my sweet girls enjoying the world with him, taking my dog on hikes and adventures to her favorite streams. He went above and beyond both for her (in meeting her needs and taking the time to get to know her personality), and also in caring for my home. I returned to such a cozy environment, a repaired wood stove, an organized wood pile and an at-peace dog and cat. Choosing Jim as a sitter is ensuring that your pets and home are getting the best of care, and his actions exemplify his kindness, generosity and thought taken in consideration of others. I hope to have him return many times in the future; the experience was a privilege both for myself and my pets.
User
Linda
Christina handled Bridie's first-ever time without us perfectly.  We returned after 5 days to a happy, well-cared for and well-exercised pup --- and an emaculate house.  Christina knows dogs and helped us with a few Bridie issues.  We got photos and some updates while away. She was flexible and very sensitive to all of our needs.  Chrisrina is the best sitter that we have ever had.

House Sitting FAQs

Pet sitters on Zeewoi offer pet sitting free of charge.

The main reasons dog sitters join Zeewoi are:
- They can't have their own dog right now but want to share their love for animals by helping out locally.
- They are work from home professionalist and want to pet sit in different cities.
- Many retired teachers, nurses, firefighters, and others enjoy traveling and caring for dog on Zeewoi.

As of Aug 2024, there are 1,387 dog sitters in Chester, Maryland .
You can filter, sort, expand your radius to find the perfect pet sitter near me.
As a reminder, pet sitters joining Zeewoi must pass a background check for you and your dog safety.

Zeewoi makes it easy to reach out to multiple dog sitters about your booking.
Typically, 94% of Chester, Maryland dog sitters respond within 24 hours.
Once you create your profile, dog sitters can apply to care for your pets, and you can also invite them!

Yes! dog sitters joining Zeewoi must pass a background check before offering their services.