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Pet Sitting & Drop In Visits in Woodwind Estates, MD

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

Tip: Contact sitters now to confirm availability.
1. Christina

Your pups are always welcomed!

North beach, MD, 20714

Drop-In Visits, Dog Walking

"Great job. Very attentive and reliable. (more)"

2. Michaela

Anything for your fur baby

Chesapeake Beach, MD, 20732

Drop-In Visits, Dog Walking

"Michaela has experience with dogs from all walks! She loves taking the time to get to know a dog and figure out the best ways to start a friendship to making... (more)"

3. Krista

Weekends and evenings!

Huntingtown, MD, 20639

House Sitting, Drop-In Visits, Dog Walking

"I have known Krista for 15 years. She’s is an animal lover and has owned many pets of her own. Krista has watched our dogs on numerous occasions. She gives t... (more)"

4. Kelly

I'll run and play with your dog.

Chesapeake Beach, MD, 20732

House Sitting, Drop-In Visits, Dog Walking

"It is with great pleasure that I recommend Kelly H. for your pet sitting because we had the best pet sitting experience with her. Kelly always showed enormou... (more)"

5. Melinda

Home full time/fenced in yard

Owings, MD, 20736

Dog Boarding, Drop-In Visits, Doggy Day Care

"Wonderful, patient, kind and all dogs are treated like her children! Well educated on dog philosophy and behavior! Couldn’t ask for anyone better to take m... (more)"

6. Julie

Mature; will care for any breed!

North Beach, MD, 20714

Drop-In Visits, Dog Walking

"I have used Julie several times and have been very happy with the service and care of my pets. She is always great about giving updates while I am away! I ju... (more)"

Confirmed 4th of July Availability
7. Whitney

Animal lover, vet tech, dog rescuer

Owings, MD, 20736

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"My boys love Whitney and they looked so happy in the pictures she posted! We'll definitely have her back again! (more)"

Confirmed 4th of July Availability
8. Kirsten

Pre-vet student who loves dogs!

Owings, MD, 20736

Drop-In Visits, Dog Walking

"Kirsten is great with our special needs dog during drop-in visits! She checks-in frequently and is very responsible. I would highly recommend her to anyone w... (more)"

Confirmed 4th of July Availability
9. Bianca

Perfection Paws

Sunderland, MD, 20689

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Bianca was great!!!! She updated us every day with multiple pictures and the status of our dogs and how they were doing. I felt extremely comfortable with he... (more)"

10. Nicole

Love the outdoors, and love dogs!

Huntingtown, MD, 20639

Drop-In Visits, Dog Walking

About: As a dog owner I know it can hard to leave our pups with someone when we have to go away. I've had dogs all of my life from little to big, young to... (more)

11. Sarah

I am 24, experienced, and active.

Chesapeake beach, MD, 20732

House Sitting, Drop-In Visits, Dog Walking

"Sarah was a godsend, and really helped me out on very little notice. I'd definitely recommend her! (more)"

12. Lorna

Full-time Student; Ready for Work

North Beach, MD, 20714

House Sitting, Drop-In Visits, Dog Walking

"Lorna is a very caring and compassionate person. I've known her for several years and I wouldn't hesitate to have her care for my many animals. (more)"

Confirmed 4th of July Availability
13. Brianna

Dog-enthusiast who is engaging

Chesapeake Beach, MD, 20732

House Sitting, Drop-In Visits, Dog Walking

"Brianna is Great with dogs. She has taken care of my dog, and grand pup when we traveled on vacation or a long weekend. She walked and played with the dogs. ... (more)"

14. Mandie

Enthusiastic, Reliable Student

chesapeake beach, MD, 20732

House Sitting, Drop-In Visits, Dog Walking

About: I have always grown up around dogs, my own and others. I have been pet sitting now for 3 years, working with many different breeds. I have voluntee... (more)

15. Emily

Flexible and friendly dog walker

Port Republic, MD, 20676

Drop-In Visits, Dog Walking

About: I have been a pet owner since I was little, and that was when our family got our dachshund. I have had multiple sized dogs ranging from 15 pounds t... (more)

Confirmed 4th of July Availability
16. Sarah

Lover of all animals

Prince Frederick, MD, 20678

House Sitting, Drop-In Visits, Dog Walking

"Sarah was amazing. I felt completely confident in her handling my dogs. Usually my dog is slow to warm up to people and very skiddish. Coco warmed right up t... (more)"

17. Pamela

Love Animals, flexible

Prince Frederick, MD, 20678

House Sitting, Drop-In Visits, Dog Walking

About: Hi my name is Pam, and I have 2 german shepherds named gunner who is almost three and Kimber who is almost two. Gunner and Kimber recently had fo... (more)

18. Alexus

Big heart and loves dogs

Prince Frederick, MD, 20678

House Sitting, Drop-In Visits, Dog Walking

About: Hi there! Thank you for taking the time to view my profile. I have a special skill to heal animals, and their energetic field. So if your dog... (more)

Confirmed 4th of July Availability
19. Liana

Flexible schedule and loves dogs!

Sunderland, MD, 20689

House Sitting, Drop-In Visits, Dog Walking

"Liana is an amazing dog sitter. She took care of my dog and helped train her as well. My dog loved her and I will definitely look to her to dog sit for me in... (more)"

Available this weekend
20. Shannon

Love my Fur Babies!!!

Chesapeake Beach, MD, 20754

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

" Shannon is ultimate dog sitter and Walker . She has a very special gift with dogs .She will have your dog jumped for Joy every time she is in their prese... (more)"


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Woodwind Estates pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Woodwind Estates, MD, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Woodwind Estates pet sitters and avoid the kennel.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.