Pet Sitting Windward Cove

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

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Windward Cove, Find top rated pet sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Gina G.
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Gina G.
from
$14
per visit
20 years of experience
Grasonville, MD, 21638

About: As a mom and lifelong animal lover, I understand how important trust is when someone cares for your pet. I offer dependable, attentive care in a calm home setting. I’m patient, nurturing, and detail-oriented — making sure your dog feels loved, exercised, and safe at all times. My open schedule allows for consistent supervision and care. I’m flexible with my time and available most days and weekends which allows attentive care :) I care for pets in my home, offering a secure and relaxed setting while you’re away. They will be comfortable safe and always loved :)

Sitter Profile Image: Bryan J.
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Bryan J.
from
$22
per visit
5.0 out of 5 stars
• 8 reviews
6 repeat clients
20 years of experience
Chester, MD, 21619

“Bryan did an excellent job dropping in on our two elderly dogs and my cat 4x a day for three days. I highly recommend him. He followed my instructions with medications for my dogs precisely. Walked and spent time with them all and sent great pictures and reports daily. We are very pleased with Bryan’s outstanding care for our fur babies. I already rebooked with him for future dates.”

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Joanna Z.
Sitter Profile Image: maranda c.
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maranda c.
from
$22
per visit
5.0 out of 5 stars
• 15 reviews
4 repeat clients
10 years of experience
Centreville, MD, 21617

“Fantastic job with taking care of our pets. She took some of the best pictures and kept us thoroughly updated. We would happily use her again.”

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Justin A.
Sitter Profile Image: Summer B.
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Summer B.
from
$30
per visit
5.0 out of 5 stars
• 2 reviews
20 years of experience
Wye Mills, MD, 21679

“Excellent and thorough! Clearly loves dogs and cats. She was on time and did everything I listed for my pets. The Rover site was easy to use and it gave me quick access to pick Summer as our sitter. Will definitely have her back!”

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Mary Ann W.
Sitter Profile Image: Sydney T.
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Sydney T.
from
$30
per visit
5.0 out of 5 stars
• 15 reviews
8 repeat clients
17 years of experience
Wye Mills, MD, 21679

“Sydney met with me and Jojo beforehand and then did a drop-in visit with Jojo. Jojo loved her visit. It was nice knowing I can count on Sydney while I am at work and I received a report card, pictures & a video! Thanks so much!”

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Cheryl C.
Sitter Profile Image: Brigid S.
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Brigid S.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
• 11 reviews
3 repeat clients
18 years of experience
Chester, MD, 21619

“Very friendly, knowledgeable, competent, reliable. Came to the house for last minute weekend care of our cats. Sent pictures during the weekend. We definitely recommend Brigid.”

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zetasean s.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$25
per visit
5.0 out of 5 stars
• 8 reviews
1 repeat client
10 years of experience
Chester, MD, 21619

“Thank you Hannah for this trial run. Taking the time to get to know my boys & their schedules We are looking forward to our vacation now knowing they will be well taken care of while we are gone”

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Julie B.
Sitter Profile Image: Lena M.
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Lena M.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
• 27 reviews
8 repeat clients
20 years of experience
Stevensville, MD, 21666

“Lena was a calm, caring presence for my senior kitty -- just what he needed. I so appreciated her photos and videos as well. Will definitely use her again!”

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Laura T.
Sitter Profile Image: Josiah S.
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Josiah S.
from
$10
per visit
3.7 out of 5 stars
• 3 reviews
12 years of experience
Centreville, MD, 21617

“Josiah was wonderful! We will be requesting him again!!😊😊”

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Alayne K.
Sitter Profile Image: Jacqueline G.
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Jacqueline G.
from
$20
per visit
1 year of experience
Chester, MD, 21619

About: What sets me apart from other sitters is trustworthiness, reliability, punctuality, and care. I care for others' animals just as I would my own! With love, attention, and energy. I’m typically available from Thursdays - Sundays. Please reach out to confirm 24 hours in advance so I can make sure my schedule aligns with yours. I can adhere to any guidelines you set for me while in your home. I am a trustworthy and respectful sitter who will take loving care of your furry family members like they're my own!

Sitter Profile Image: Chloe T.
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Chloe T.
from
$32
per visit
4.9 out of 5 stars
• 20 reviews
4 repeat clients
17 years of experience
Easton, MD, 21601

“Chloe was a great sitter for my cat Melody! Her reports have me peace of mind while out of town and I loved getting photos of my baby. Would book with Chloe again!”

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Allison F.
Sitter Profile Image: Imani W.
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Imani W.
from
$14
per visit
5.0 out of 5 stars
• 2 reviews
1 repeat client
20 years of experience
Easton, MD, 21601

About: I’ve taken care of dogs since I was 8 my family and friends always ask me to take care of walking ,feeding , and administrating medicine . I work at the Easton Elementary i usually get off anywhere between 3:55-4pm so I can do check ins and or walks Monday through Friday after I get off from work on the weekends I have a very flexible schedule so I can do anytime I had 2 dogs they passed away this year due to older age couple of months ago but I have a backyard with a closed off fence top to bottom so your pets will be very safe and have a good yard to run around and stretch

Sitter Profile Image: Ryan L.
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Ryan L.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
• 16 reviews
6 repeat clients
25 years of experience
Annapolis, MD, 21409

“Ryan is absolutely amazing! Ryan came over for a meet and greet before our first scheduled visit to get to know our dog and answer all of our questions. Ryan put me at ease knowing that Napoleon will be well cared for.”

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Stephanie H.
Sitter Profile Image: Marley W.
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Marley W.
from
$30
per visit
5 years of experience
Grasonville, MD, 21638

About: I’ve taken care of my own dogs since I was 8. I had a medium sized low energy dog and now I have a high energy bigger dog so I have a good range of care. I’ve always been the one neighbors have reached out to to take care of their dogs Currently I am unemployed so I am pretty openly available! It really just depends on your dogs needs and how I can best provide for them! I am really good with handling dogs and getting them to listen. I’m super athletic so I’ll love taking your dogs on walks and playing! Super openly available for all there needs.

Sitter Profile Image: Zachary S.
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Zachary S.
from
$20
per visit
15 years of experience
Chester, MD, 21617

About: I’ve taken care of dogs my entire life whether that is my own dogs at home or helping out a neighbor or friend! I would love to help your dog as well I’m currently a student at Salisbury university but I am commuting so I only have classes on Tuesday and Thursdays. I am available almost any other time besides then! I will be there for whatever your pet needs may be! I love taking care of dogs of all sizes and know what it takes to make sure they will be ok while you are gone

Sitter Profile Image: Cristina M.
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Cristina M.
from
$25
per visit
5.0 out of 5 stars
• 9 reviews
25 years of experience
Stevensville, MD, 21666

“Cristina is an excellent pet sitter! Our sweet kitty is in end stage cancer and Cristina took such great care of her, ensuring she got her shot and monitored her food/water intake to assure us that all was well while we were away. I would definitely hire Cristina again!”

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Sue M.
Sitter Profile Image: Crystal D.
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Crystal D.
from
$25
per visit
5.0 out of 5 stars
• 10 reviews
4 repeat clients
17 years of experience
Ridgely, MD, 21660

“Couldn’t be more flexible and a bigger help.”

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Ken S.
Sitter Profile Image: Amanda M.
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Amanda M.
from
$25
per visit
5.0 out of 5 stars
• 1 review
15 years of experience
Chester, MD, 21619

About: I love playing with dogs and walking them. I've grown up around all types of dogs small and large. I'm very fun and outgoing as well as criminal justice trained ensuring your pets safety. I have taken care of our families dogs as well as watching other family friends pets. I have watched animals with allergies and medication needs. Dogs of all ages are welcome. I will meet any needs of the dog/dogs and ensure to have them back to you safe worn out and happy. I work part time so most of my day is running errands or cleaning the house. If they love car rides they are more than welcome to drive around with me. I will adjust my schedule to meet the needs of the dog or animal. Also absolutely love my kitties. Open to all animal requests just ask! Im a full time optician and part time cook. With plenty of notice I will take off my parttime job to care for your babies. Your pet will be loved as family. Your pet will be able to sleep with me and get full access of my apartment. Toilet bowl lids will always be closed

Sitter Profile Image: Idi C.
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Idi C.
from
$50
per visit
5.0 out of 5 stars
• 37 reviews
12 repeat clients
6 years of experience
Stevensville, MD, 21666

About: I've taken care of dogs for years! From energetic pups to laid back senior puppies. I have owned bunnies, guinea pigs, pups, and cats as well! My husband and I work remotely which means one of us, if not both of us, is home all day and can give your animal friends all the attention and play time they need! My home, provides a safe, clean, and comfortable environment for your pet. It’s a spacious townhome with plenty of indoor room for your pet to relax and feel at home. While we don’t have a fenced yard, pets in my care receive regular leashed walks and outdoor time, along with visits to nearby parks for exercise and fresh air. My husband and I work together to maintain your pet’s routine so they feel secure and at ease. We provide feeding, playtime, and mental stimulation through toys and activities, along with regular updates so you always know how your pet is doing. We only care for one family’s pet at a time to reduce stress and give your dog the undivided attention it deserves. We have experience with energetic puppies, senior dogs, pets with mobility issues, anxiety, and noise sensitivities. Whatever your dog needs, we’re happy to accommodate.

Sitter Profile Image: Shacja S.
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Shacja S.
from
$25
per visit
5.0 out of 5 stars
• 7 reviews
3 repeat clients
45 years of experience
Ridgely, MD, 21660

About: Active Dog Loving Grandparents We enjoyed the pleasure of having pets our entire lives, they have brought us a sense of peace and joy and best of all unconditional love. Our best friends have been Boston Terrier’s, German Sheppard’s, American Bulldogs and Boxers. They are all unique in their personalities but all love to be loved, just like us. We are retired so one of us are at home all the time. We live on a great fence property with an awesome nieghborhood that we love to take walks around multiple times a day (weather permitting.) The dogs usually have a grand time taking a run around the property and playing. Should it be too warm of course they enjoy the air conditioning ? Now that our children are grown and married with children/dogs we occasionally keep their Boxer brother (Duke) and sister (Honey) and our grandchildren too. You can feel safe leaving your pets in our care. We will look after them and love them like our own! In fact, they may not want to leave as our grand-dogs do? Can provide a bath prior to your return if you would like. Look forward to meeting you and your baby soon. Grandma J

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  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

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FAQs for Pet Sitting - Windward Cove

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to 25,000 in eligible veterinary care reimbursement.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and request a Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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