Find Free Pet Sitting in Chestertown

Connect with trusted local sitters who care for your pet at no cost. Home safe, pet happy.

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Your neighbors love Zeewoi

Pet owners near Chestertown who have already found a free sitter.

Your neighbors love Zeewoi!

Pet owners near Chestertown who have already found a free sitter.

Pet sitters like these could apply

Rose

With 61-5 star reviews we’d love to partner with you for complete peace of mind

4.98
• 61 reviews
Owner Image

Rose and mark were fantastic. Very professional and caring sitters. I never felt that I needed to worry about anything. They left my home in the condition as if they had never been there. I, absolutely couldn't have been more impressed and pleased.

Sitter available from Oct 1
Annie

Lifelong pet lover, longtime pet sitter!

5.0
• 51 reviews
Owner Image

Annie sat for our cat, Tuna, over a long weekend. She was extremely kind and self-sufficient. When we arrived home, Tuna was relaxed and happy and our apartment was as clean and tidy as we had left it. Annie would be welcome to sit for us again any time, we'd highly recommend her.

Sitter available from Oct 1
Jordan

Spending life's adventure caring for your animal loved ones, big & small, w/ TLC

5.0
• 49 reviews
Owner Image

I could not have asked for a better first experience with zeewoi! Jordan and Nataki were great at communicating from the very start, and they sent me pictures and updates every day. I didn’t have to worry for a moment that my cat Anya was feeling lonely because I could tell she warmed up right away, even though she’s usually quite shy! They also went above and beyond making sure my apartment was tidy for when I got home. So grateful and would definitely be honored for them to sit for me again any time!

Sitter available from Oct 1
Francesco

Caring and loving pet-sitter.

5.0
• 43 reviews
Owner Image

Francesco has been taking care of my furry babies and my place while I'm away for well over a year now, and I couldn't appreciate him more. He is a joy to communicate with, and the most reliable person one could hope for. Being able to count on him while I'm traveling makes a world of difference, because I know I don't need to worry about anything while I'm away. Benny and Zumba love him and are very well taken care of. I know because I come home to two very relaxed and happy kitties. I am super grateful to have found Francesco!

Sitter available from Oct 1
Patti

Fit and fun "young" retired couple offer peace of mind while you are away!

5.0
• 24 reviews
Owner Image

Everything was great even though they were here for some unfortunate circumstances (hurricane and extended power outage). Sent frequent updates and our cat seemed to like them.

Sitter available from Oct 1
Hannah

Experienced housesitters looking to travel and make some furry friends!

4.86
• 28 reviews
Owner Image

Hannah and Joseph were so kind, so communicative, and clean! Kevin seemed so happy in all the photos they sent. Not only did they wash my sheets and towels they used (without my requesting it, simply out of the kindness of their hearts), they ALSO then put my fresh sheets on the bed! 🥹❤️ Such incredible sitters. 10 stars!

Sitter available from Oct 1
Misti

WFH researcher excited to provide quality care to your furry loved ones!

5.0
• 26 reviews
Owner Image

Misti was wonderful! She was able to come by before I left town to meet my dog, Grace, which I really appreciated. She sent daily pics or videos and made sure that Grace got tons of snuggle time, which is a major requirement to keep my dog happy :) Cats and skateboards are evil enemies to Grace and it sounds like Misti experienced both and handled it flawlessly! Misti was a great communicator, left everything tidy for me when I got home and Grace was super mellow and relaxed, which tells me she got all the care she needed while I was gone. I highly recommend Misti - I'll definitely be asking her to sit again!

Sitter available from Oct 1
Lilly

Experienced and zeewoi with excellent references!

4.87
• 38 reviews
Owner Image

Lilly and Thomas stayed at our house and cared for our dogs for a month. I think they took the dogs to the beach nearly every day. Seeing pictures of our dogs on the beach made our time away from them feel so much better. Our house was immaculate when we returned, and we felt so fortunate to have such kind and loving people step in for us in our absence. Anyone would be super lucky to have them in their home.

Sitter available from Oct 1
Gwynn

Intrepid traveler and animal lover

4.93
• 58 reviews
Owner Image

Gwynn was wonderful! She was super communicative, flexible to come to our house beforehand to get oriented, and attentive to details. She connected with our pup, Scout, immediately and we felt so assured that he would be well cared for with her. We hope Gwynn can come stay again another time!

Sitter available from Oct 1
Courtenay

Experienced sitter, 5-star reviews. Meticulous, quiet, non-smoker.

5.0
• 18 reviews
Owner Image

I was thrilled to have Courtenay as our sitter. We had a few last minute changes and she was very accommodating. She is a very pleasant, well spoken person who bonded very quickly with our dog, Pepe. We were in Europe and Courtenay keep us we’ll informed via internet, pictures and all. We came home to a clean house, a happy pet and a delicious pie she left for us in the refrigerator. You would be very pleased to have her as your sitter. Lucy Hottle

Sitter available from Oct 1
Wendy

The Hound and Tabby Nanny is ready to take care of your fur babies.

5.0
• 24 reviews
Owner Image

Wendy was great, she kept us updated on the dogs and all the fun she had hiking with them on the mountain. I returned home to a very tidy house. My dogs just loved her. I will definitely have Wendy sit for me again and would be very lucky to have her do a sit for you.

Sitter available from Oct 1
Julian

Retired professional gardeners available to care for your home, garden & pets.

4.94
• 47 reviews
Owner Image

Julian and Susan were amazing, we came home to happy healthy creatures and a clean, tidy home and yard. They communicated with us during our vacation, both about anything unusual and just to let us know when things were going well (as they were the majority of the time). They are very adaptable and capable people, I highly recommend them for your home and pet needs.

Sitter available from Oct 1
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*Based on the average pet-sitting price of $60 in Chestertown, Maryland, as of January 2025.
Try Zeewoi Risk-Free

Sitters care for free in exchange for a unique travel experience. No money changes hands.

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Sign up for Zeewoi! Fill in your profile with details about you, your home, and your pets, including photos and care tips.

Add Details

Share your dates, pet care tasks and house rules. Once your profile is complete, invite as many sitters as you’d like, or wait for them to apply!

Review Applications

Check out sitters profiles and reviews. Invite sitters for a free Meet & Greet to ask questions and confirm they’re right for your pets and home.

Confirm Your Ideal Sitter

Pick the sitter you’re most comfortable with and confirm the sit. Relax knowing your pets are at home instead of in a kennel.

Enjoy Your Trip

Your sitter will send updates about your pets while you’re gone. After the sit, write a review for your sitter, and they’ll review you too!

Choose a plan that's right for you.

Basic

$20/month
  • Unlimited bookings.
Most Popular

Standard

$30/month
  • Unlimited bookings.
  • See who saves your listing.
  • Home & Contents Plan.

Premium

$40/month
  • All Unlimited features, plus:
  • Premium badge on your listing.
  • Boost your listing in search results.
Verified & Insured

Peace of mind is priceless. Every sitter is rigorously background-checked, ID-verified, and reviewed by pet parents.

Win-Win Exchange

Sitters choose pets they love and dates that fit. They live like locals and enjoy time with animals—all while providing free care.

Secure & Happy

Come home to a happy pet, a tidy house, clean sheets, and fresh plants—no post-vacation chaos.

Reviews From Pet sitter

I used to sit through Rover, but it always felt like a job. I had to accept sits I didn’t really want—like pets I wasn’t comfortable with or dates that didn’t work for me. If I said no, my rating would drop, and I’d lose future opportunities. It was stressful, and I started to lose my love for pet sitting.

Then I found Zeewoi. Here, I get to choose the pets I love, the dates that fit my schedule, and the places I want to explore. It’s not a job anymore—it’s a chance to spend time with animals I adore, and feel empowered to say no without fear. Zeewoi gave me back the joy of pet sitting.
I’m a writer who works remotely, but hotels and Airbnbs add up fast. Zeewoi lets me live in homes full-time while owners are away—not just caring for their pets, but keeping their house safe. Turns out, in a lot of states, leaving your house empty for more than 5 days can mess up your insurance.

It’s a trade that works. Owners avoid risks, and I get free places to write—like that month in a cabin where I finished my book with a snoozing Labrador at my feet. The pets keep me company, the house gives me space to focus, and nobody’s stressing about an empty home.
After retiring and losing our dog, my husband and I sold our house and started traveling full-time. We’re in our late 60s and can’t rush, so Zeewoi is perfect. We care for pets in exchange for free places to stay.

In 3 years, we’ve visited 46 states. We’ve stayed in homes, farms, and apartments, looking after dogs, cats, and even a llama. Owners get free pet care; we get to travel slowly and affordably. It’s meaningful—we help people (new parents, busy workers) and still feel connected to pets after losing ours.

No stress, no hotels. We’re healthier, happier, and forever grateful. Alaska and Hawaii, here we come!

Reviews from Pet Owners

4.93
4.93
4.96 Organised 4.96 Reliable 4.95 Clean and tidy 4.97 Self-sufficient 4.91 Pet care
User
Sheelagh
honeybee was a great sitter for our 3 animals. She communicated very well throughout the sit. Our flight home was delayed and she was great about being able to cover the extra days. Her connection to the animals was wonderful.
We were less organized than intended on her arrival due to some unexpected work issues, and she was great about rolling with the changes (e.g. the closet doors were missing as the painter hadn't finished with them). She used public transport to get to Golden and then drove our car while here. She left a few items behind, and her attention to kitchen cleanliness could be better, but we would definitely have her sit our pets again if the opportunity arises.
User
Lynn
Another amazing sit by Anna and her lovely family - our cocker spaniel Holly has had the best fortnight with these guys with lots of adventures and endless amounts of love and attention!
Highly recommend as 5-star house and pet sitters - thank you Anna - hope to see you again!
User
Branden
Prashant and India were fantastic pets sitters for us. Both were dependable and were even kind enough to allow some service people into the home to do some repairs.

Our dogs were well looked after and we got daily updates on how the dogs were doing. Prashant is very knowledgeable and gave us a few strategies to combat some negative behaviors that we were seeing with the dogs.

Could not recommend them more. They will be missed.
User
Robert & Rebecca
Angela did a great job caring for Willie for 10 days while we were out of town. She was easy to communicate with and kept us informed about Willie, along with sending photos of him out on walks and at the beach. Angela was very accomodating when we needed to come home a day early - Thank you!
The house was left in good shape and it's clear that Angela is organized and reliable and clearly loves her pet charges. I'd recommend Angela and will definitely include her as one of our top sitter choices in the future! Thanks again, Angela!
User
Allison
Megan was the perfect house sitter - got lots of updates and pics of my kitty, communicated well, was flexible and left the place spotless! Would definitely ask her to pet sit again!
User
Paul
I had the pleasure of having Tracey and her two children as house sitters, and I can't praise them enough for the incredible job they did. From the moment they stepped into our home, it was evident that they were dedicated, caring, and attentive to every detail.

First and foremost, Tracey's approach to caring for our house and our beloved pets was nothing short of excellent. She has an innate ability to connect with animals, and it was clear from the daily updates and photos that our pets were happy and thoroughly pampered. The house was kept in immaculate condition, and they treated it with the utmost respect as if it was their own.

Moreover, Tracey demonstrated remarkable responsibility and initiative when our AC system unexpectedly broke down. Without hesitation, she arranged for an HVAC company to come and fix the issue, taking time from her day to ensure our home was taken care of. Her willingness to front the repair costs until I could reimburse her was an act of kindness and trust that you rarely see.

Tracey and her children's thoughtfulness and thoroughness provided me with peace of mind during my time away, which is priceless. I returned to a home that was just as I left it, if not better. Their stay was characterized by an extraordinary level of care and I was particularly impressed by how they left the house in perfect condition, with happy pets to welcome me back.

I wholeheartedly recommend Tracey to any future hosts. Her reliability, compassion, and the ability to handle unexpected situations with grace are commendable. I would welcome Tracey and her children back to house sit in a heartbeat – they are exactly the kind of house sitters that one hopes for on this site!

Thank you, Tracey, for everything. You and your children are welcome back anytime!
User
Heidi
I felt totally confident in leaving Darcy and my house in Elaine’s care and I returned to a very contended dog and a perfectly clean and tidy house. Elaine arrived the day before I left so I was able to get to know her and enjoy an evening meal with her before my very early flight. We kept in contact while I was away via WhatsApp and I was happy to see photos of Darcy relaxing in her usual favourite places. It was lovely to be welcomed back home after my holiday by a very well looked after dog and it was so nice that Elaine was here to welcome me and had the lamps on, flowers in vases and a meal in the oven.  My house was clean and tidy and Darcy has enjoyed a week of lovely walks and neck scratches. I highly recommend Elaine as a completely reliable pet and house sitter and she is a lovely lady to chat to. I was so pleased that I got to know her.
User
Korinda
Laura was an exceptional, reliable, and loving sitter for our goldendoodle Scout, and took such good care of our home!  Scout was excited to meet Laura immediately when she arrived at our home for this sit, and showered Laura with all the hugs and kisses.  Scout has recently been having issues with seizures, so for this sit I was specifically looking for a sitter who had a depth of experience with giving medication and responding calmly in the event of an emergency.  It was a big relief to be able to entrust Scout to Laura's capable and kind hands, and it was extra special that Laura's beloved vizsla had shared the same name.  Laura is wonderfully easy to communicate and coordinate with, and was thorough in her care of our home.  We came back to our garden looking great, house left in even better shape than I left it to Laura, and a very happy Scout!  I cannot overstate how much we appreciated Laura's care for Scout and our home, and heartily recommend her as a pet and house sitter.  If you're lucky enough to get on Laura's schedule, your pups will be with the most wonderful stand-in dog mom you could have hoped for!
User
Carole
Elaine was a welcomed sitter for Cyrus and Purrelli. I returned from holiday to find a very content relaxed dog and a happy fat cat. Purrelli doesn’t eat when he is stressed so seeing a little meat on him let me know he was content and happy :) My condo was left clean and in order, all communications were smooth and there was zero issues. Thx for the great pet care Elaine.
User
Tina
If you’re lucky enough to find Anna as your pet sitter you will have peace of mind and well cared for pets whilst you are away and a clean and tidy home on your return. Anna is thoughtful and kind, she arrived the evening before the sit which allowed for some time to hear about her interesting travels and work, kept me updated with fabulous photos and details of the friendship she was making with the cats and even took the trouble to fix a sticky catch on the cat flap. I can recommend her as a sitter without hesitation. Thank you Anna

Pet Sitting FAQs

From $25/week to $100/week for the cat sitting and from $50 to $150 for the dog, additional rates include from 50% to 100% per additional pet, cheap rates are 40$ for the cat sitting and $120 for the dog sitting. On Zeewoi you can find a pet sitter who will not charge you anything for keeping your pets at home.

Yes, you can find a home pet sitter to stay in your house with your pet overnight and provide 24/7 care for your pets. You can include in your listing time the advisable timeframe that the pet sitter should adhere to and not leave your pet alone in the house. Usually, it's not to leave the pet alone for more than 4 hours.

The pet sitter for the cat should visit at least once a day. For the dogs, the pet sitter should visit at least three times per day, the best solution is if the sitter stays overnight and watches your pets all the time.

Look at the pet sitter with a high rating, and many previous bookings with good reviews, ask the sitter to make a meet and meet before confirming the booking online or in-person, and reach out to the pet owners where the sitter stayed before asking about reference.

Common red flags in pet sitters are bad reviews from previous pet owners, a high cancellation rate after approval, a sitter who doesn't have a background check, a sitter who refuses to meet and greet in person or online, and a sitter who wants to make bookings outside of the platform.

Yes, it is safe to hire a pet sitter it's still advisable to see if the sitter has a background check, good reviews, and past bookings and make a meet and greet before confirmation in this way you can reduce risk to the minimum.

Yes, pet sitters stay all day in your house and also they stay overnight, the sitter can leave your home for up to 4 hours or for a different time that you can discuss during the meet and greet.