Dog Sitters in Chestertown, MD

Any sitter, one price
20$ per night

Loving sitters in Chestertown, MD

Loading...
Sign Up

Create your free profile and find a trustworthy sitter near you today!

Add Details

Add your pet care details and dates, then invite as many sitters as you’d like.

Confirm Your Ideal Sitter

Pick a sitter and confirm the sit. Relax knowing your pets are at home instead of in a kennel.

Enjoy Your Trip

Your sitter will send updates while you’re away. After the sit, write a review for your sitter.

Reviews from Dog 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
Sam
Martin and Caitlin are the best house/pet sitters we've ever had. They came fully prepared (they had read through welcome packet thoroughly before they arrived), they sent the best texts and pics to reassure us all was well, and the house was immaculate when we got home. Best of all, they treated Winston like family and he clearly fell in love with them. They are considerate, trustworthy, and detail-oriented. We absolutely would love to have them back (honestly, every time we go on a trip!). They are fantastic and we are truly grateful for the care and love they showed to both our dog and our home.
User
Kara
Denise was by far the best pet sitter we have ever had! She watched our two pups while we were gone for 3 weeks and took amazing care of our dogs and home. She took the time to ask questions and make sure she understood each dog’s needs as well as how to take the best care of our house before we left. She sent videos everyday updating us on how the pups were doing. We were so happy to see how much quality time she was spending with them and how much they loved her. Our dogs were so sad to see her leave and we can’t wait to have her back. Denise made sure that the house was in perfect condition when she left and treated our home as if it were her own. If you are looking for a pet sitter, look no further. Highly recommend Denise!
User
Michelle
Brian was a wonderful sitter for our 11 year old dog and also took great care of our home. He sent me pictures every day and let me know how Macklin was doing which always helps ease my mind. Our home was clean and tidy when we returned and everything in its place. I'd recommend Brian to anyone looking for excellent care by a friendly person!
User
Barbara
This is our second time welcoming Michele and we were so happy to have her back! Our dogs Pedro and Samantha love her and it is clear she loves them! Our house was immaculate upon our return and Michele made her famous lemon chicken recipe which we gobbled up and then we asked for the recipe. We can't say enough great things about her and hope you are lucky enough to get her as a sitter for your pets.
User
Julia
Ryan was one of our best sitters we’ve had! Ryan is so lovely to chat with and we looked forward to meeting him before our trip. He was organized and communicated his plans clearly with us and was easy to communicate with while we were away. Our dog took to him immediately and so we knew we could relax while away. Our home was in great shape when we returned and it was nice to get a debrief from him as well. We’d love to have Ryan back anytime, and so would Steve (our dog)!
User
Linda
Cristina is simply the best house/pet sitter that we have ever had.  She is responsible and dependable and an experienced dog owner. Our Wheaten, Bridie, adores her and misses her when she leaves.
User
Jacqueline
If we could give 10 out of 5 stars for Candace, Brian, and Chris, we would!  They were amazing house and dog sitters for Brown Dog and Scout. They were so accommodating with our timeline and had read our welcome guide to a tee!  It was so reassuring being gone for 2 weeks and knowing our pups were in amazing hands. They sent us daily updates and pictures and it was clear the dogs were so well cared for!  They left the house very clean and even had all of our bedding and towels washed for us when we arrived home. Would absolutely recommend them for a sit and would love to have them back again any time!
User
Velia
Care and compassion for my dogs was at the top of the list of John's attributes. He was the first sitter I have used through zeewoi that was close enough to come meet the dogs before the sit. John not only came for an initial meet and greet, but he made time to meet the pups a second time prior to my departure to better familiarize himself with both the dogs and my home. Having put the fear of God in him about Penny's reactivity (I might have been a bit over the top, but better more attentive than less!), he was cautious with her in the beginning. Later in the sit, they trooped off to the beach on multiple occasions - all good! My 10-yr-old was on some meds for a serious battle with arthritis, and John managed Cooper's needs beautifully. John even made a call and a trip to the vet to re-up Coop's prescription when it was clear he needed to continue the protocol. I received daily updates by  text, including photos and video; communication is hugely important to me. I feel blessed to have had John care for my fur-babies.
User
Caroline
We were so happy with Lynda's care for our senior pup. 

Lynda was extremely accommodating with the key hand over situation we had considering our early flights out of Berlin. She was easy to coordinate with and made this part of the holiday very smooth.

We could also tell Sesame was in the best care. We received updates and photos of Sesame on walks and getting cuddles. We know Sesame can be sassy sometimes but Lynda was great with her little attitudes and handled her with ease. It was also really heart warming to see that Lynda truly enjoyed her time with Sesame and created a strong bond with her. We love to know that our dog is loved and treated with the care we would give her if we were home. 

Both my partner and I were able to fully enjoy our holiday as we knew from updates that Sesame and Lynda were doing well. Our apartment was clean and tidy when we returned and the sheets had also been washed. We would definitely have Lynda back and would recommend her to anyone else looking for an experienced sitter to stay with your pet.
User
Kristin
Melissa and Chris are amazing.  We are very picky about our dog sitters, and we chose them because they have been doing this for a long time and track your wants and needs carefully and follow through with utmost care and integrity.   They offered to come the day before we left to meet Winnie so that we could rest in that she would trust them and connect to them.  Honestly, we would hire them as our only dog sitter all of the time if we could.  I cannot thank them enough and say enough good things about them.  They also took very good care of our house and  plants.

House Sitting FAQs

Pet sitters on Sittsy offer pet sitting free of charge.

The main reasons dog sitters join Sittsy 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 Sittsy.

As of Aug 2024, there are 356 dog sitters in Chestertown, Maryland .
You can filter, sort, expand your radius to find the perfect pet sitter near me.
As a reminder, pet sitters joining Sittsy must pass a background check for you and your dog safety.

Sittsy makes it easy to reach out to multiple dog sitters about your booking.
Typically, 94% of Chestertown, 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 Sittsy must pass a background check before offering their services.

XdK0wkVs1an3kE9wDMITRn10RzNvURKJ0kKmlkFZmK3A6bMijRHEtqTB2mTtZ75A