Pet Sitting Woodwind Estates

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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Over 76
pet parents in Woodwind Estates have booked pet sitting

Woodwind Estates, 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.

1 / 1
Sitter Profile Image: Ashley P.
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Ashley P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 54 reviews
16 repeat clients
15 years of experience
Huntingtown, MD, 20639

“Ashley was amazing with Cocoa Bean! Cocoa is a 91 pound XL bully who is sweet but excitable and Ashley handled her perfectly. Our whole family loved the detailed updates and many pictures Ashley sent each day. It was clear that Cocoa and Ashley formed a real bond and Cocoa got endless pets and stick time in the yard. Ashley also thoughtfully brought in packages, took our garbage to the curb and back, and fed and watered our misanthropic hedgehog, Mister Bear.🤣 When our flight was rerouted Ashley stepped right up to add an extra visit for us with little notice. We 10/10 recommend Ashley!”

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Jessica S.
Sitter Profile Image: Kelly B.
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Kelly B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 46 reviews
13 repeat clients
10 years of experience
Chesapeake Beach, MD, 20732

“Kelly did a great job taking care of our cat while we were out of town! She was great at communicating, gave me peace of mind, and even helped clean up a broken picture frame that had fallen while we were gone. I would definitely have Kelly take care of our cat again!”

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Kara W.
Sitter Profile Image: Jennifer J.
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Jennifer J.
from
$17
per visit
40 years of experience
Chesapeake Beach, MD, 20732

About: ​Dogs have been a central part of my life for as long as I can remember! I currently have two wonderful dogs of my own, so I fully understand the peace of mind that comes with knowing your pup is in safe, loving hands. ​What I offer for your dog: ​Active Walks & Exercise: Customized walks tailored to your dog’s pace, energy level, and favorite sniffing spots. ​Medication Administration: Experienced and confident administering oral, liquid, or topical medications accurately and on time. ​Personalized Attention: Whether your dog is a high-energy ball-fetcher or a calm cuddle bug, I adapt to their routine and personality. ​Reliable Routine Care: Timely feedings, fresh water, and attentive supervision to keep your dog comfortable and happy. I maintain a very flexible schedule with wide availability most days of the week. Whether you need last-minute drop-in visits, consistent midday dog walks, or customized care times, I’m easily reachable and happy to accommodate your pet's regular routine. ​I make every visit smooth and worry-free by following your exact entry and security instructions—whether using keypads, lockboxes, or garage codes. If we aren't able to meet in person prior to your booking, I am fully equipped to handle seamless remote onboardings via detailed written notes, photos, or a quick phone call. During every visit or walk, I treat your home with total respect, keep safety as my top priority, and send detailed Rover cards with clear photos so you always know your pet is secure, comfortable, and well-cared for.

Sitter Profile Image: Amanda S.
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Amanda S.
from
$17
per visit
5.0 out of 5 stars
• 13 reviews
2 repeat clients
15 years of experience
Huntingtown, MD, 20747

“I have booked Amanda two times now. She has been the best! I am able to go away and feel confident my pets are safe, well loved and under amazing care.”

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Naomi L.
Sitter Profile Image: Beth C.
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Beth C.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
• 29 reviews
8 repeat clients
12 years of experience
Chesapeake Beach, MD, 20732

“Beth is so sweet, you can tell she loves animals. We are thankful she is able to drop-in to let out new puppy out and give him some loves during the day. Thank you!”

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Katrina S.
Sitter Profile Image: James R.
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James R.
from
$15
per visit
6 years of experience
Huntingtown, MD, 20639

About: I have taken care of many different types of animals for 6 plus years for all my local friends and family with the utmost joy. I have a remote job which allows me to work from home so my schedule is very flexible to take care of animals whenever needed. I treat every animals like my own and will take care of them with the utmost care. I follow any guidelines the animal owner has for me to take care of each animal with care.

Sitter Profile Image: Shyann N.
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Shyann N.
from
$12
per visit
5.0 out of 5 stars
• 7 reviews
1 repeat client
20 years of experience
Prince Frederick, MD, 20678

“Shyann was so helpful and wonderful with our babies! Our plans changed the day of the reservation and she was more than willing to accommodate and help us with everything. We will definitely use Shyann again.”

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Lindsay G.
Sitter Profile Image: Daniela H.
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Daniela H.
from
$25
per visit
5.0 out of 5 stars
• 3 reviews
5 years of experience
Prince Frederick, MD, 20678

About: I’ve been taking care of dogs and cats for friends and neighbors for the past 5 years. I absolutely love animals and treat every pet like they’re my own! 🐾❤️ Our family homeschools, so there’s almost always someone home. Your dog will be welcomed as part of our family, with plenty of attention, love, and companionship. They’ll rarely have to be home alone 😊 We have a Boston Terrier who is used to having other dogs around and does well sharing her space with them. I keep dogs on a leash when we go outside since we don’t have a fenced-in yard, and I take them out multiple times throughout the day for potty breaks and fresh air. When I need to leave the house, I crate the dogs for their safety and peace of mind. I want every pet staying with us to feel comfortable, cared for, and part of the family!

Sitter Profile Image: Rose K.
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Rose K.
from
$20
per visit
5.0 out of 5 stars
• 13 reviews
3 repeat clients
15 years of experience
North Beach, MD, 20714

“Great job checking in on Sam. Pics were wonderful to see. Went the extra mile when asked, thanks Rose!”

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David H.
Sitter Profile Image: Gabrielle S.
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Gabrielle S.
from
$15
per visit
1 year of experience
Prince Frederick, MD, 20678

About: I volunteer at the animal shelter multiple times a week and walk many kinds of dogs or different sizes, energy levels and backgrounds. I love doing it! I work part time but am usually home around 1:30 and am able to walk and take care of dogs full time Friday-Sunday. I have a wide open yard with fully green grass, a 3 story house and live in a neighborhood with side walks and dog parks.

Sitter Profile Image: Myah D.
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Myah D.
from
$15
per visit
5.0 out of 5 stars
• 5 reviews
2 repeat clients
3 years of experience
Huntingtown, MD, 20639

“I couldn't be happier with the cat-sitting service provided by Myah over Christmas! Allison was content and well-cared for, and we appreciated the daily updates. Myah's reliability and genuine love for our cat made our holiday worry-free. Highly recommend!”

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Daisy W.
Sitter Profile Image: dylan f.
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dylan f.
from
$15
per visit
10 years of experience
Prince Frederick, MD, 20678

About: I've loved pets for as long as I can remember. I have a true passion for caring for any animal in need and will always treat them with the same love and dedication as my own! Pet care fits seamlessly into my daily routine. I manage my time carefully to ensure pets get consistent attention, dedicated exercise, timely feedings, and structured drop-in visits or walks throughout the week and on weekends I prioritize the safety, health, and well-being of every pet in my care. I provide a calm, comfortable environment where pets can relax freely, alongside wholesome, high-quality, non-GMO organic treats and food tailored to their needs!

Sitter Profile Image: Christina B.
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Christina B.
from
$20
per visit
5.0 out of 5 stars
• 13 reviews
6 years of experience
Owings, MD, 20736

“Christina took great care of our two cats while we were away. she was very kind and her communication was great. Definitely will be using her again!”

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Huston H.
Sitter Profile Image: Carrie N.
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Carrie N.
from
$30
per visit
5.0 out of 5 stars
• 18 reviews
6 repeat clients
10 years of experience
St Leonard, MD, 20685

“Amazing dog sitter!! She is very kind and trustworthy. She also sent lots of photos of my dog, which I loved. I would definitely recommend her and will be rebooking with her!”

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Jordan C.
Sitter Profile Image: Avery R.
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Avery R.
from
$20
per visit
5 years of experience
North beach, MD, 20714

About: I have had dogs my entire life. My mom always watched dogs when I was younger and at some points had up to 5 dogs in the house. I have walked dogs over the past few summers. I am reliable, safe, and friendly with pets kinds but especially dogs. I am a current college student and in my time of break I have a pretty clear schedule. I am available everyday during the week and most weekends at this time until I go back to school. I can do anything requested from walking dogs to staying with them for a few hours. I will make sure to abide by your schedule. I can be there when your animals need me.

Sitter Profile Image: Amanda D.
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Amanda D.
from
$30
per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
30 years of experience
North Beach, MD, 20714

About: Promo Code for $40 off first time booking for Pet Owners that it is their first time using Rover- AMANDD61392 Friends and Family call me the animal whisperer. I have had a dog/dogs my whole life. I have taken care of dogs from brand new puppies, to babies that were at the end of their life. I'm currently not working full time away from home, so for any boardings that are on week days or weekends, you and your fur babies are good to go. I do have one small dog at home BUT, if you prefer your dogs to be alone while here, my dog is easily brought to his grandparents house:), which they are always happy about. I will update when my work schedule changes. I have a fenced yard (tall privacy wooden fence with sliding deadbolt), and can easily crate dogs if needed. Any animals would have free range of the house and the yard. Your babies are my babies while I am taking care of them.

Sitter Profile Image: Layla O.
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Layla O.
from
$25
per visit
6 years of experience
Dunkirk, MD, 20754

About: I have experience caring for both dogs and cats through helping friends, neighbors, and family. I’m comfortable with feeding routines, walks, playtime, and giving lots of attention. I really enjoy being around animals and making sure they’re happy and well cared for Hii! 🐾 I work part-time, so I have a flexible schedule and plenty of time to give your furry friends the love and attention they deserve! I’m available after 1 PM Monday through Thursday, and my weekend availability may vary by day, with additional time often available. I can’t wait to meet your pets! ❤️ I provide a safe, clean, and calm environment, follow routines, secure doors, monitor behavior, and give pets consistent attention, comfort, and supervision at all times.

Sitter Profile Image: Victoria A.
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Victoria A.
from
$20
per visit
5 years of experience
Port republic, MD, 20676

About: I love animals with all my heart. I’ve never met a pet who hasn’t loved me. I agree with the statement that animals are very energy in tune and I’d like to think so am I! I’ve done lots of dog sitting and cat sitting jobs for people close to me and they’re satisfied with how I did, so you 100% will be too. Your pet is in responsible, attentive hands. I have a free schedule and I’m in desperate need of a side hustle. I have too much free time and I think this would be the perfect thing to book my schedule with, especially because of how much I love being outside and animals. I’m very mindful of the safety even of my own animals so your pet is in the best of hands. Although my yard is not fenced, I take my dog out for walks leashed and for the few times she has escaped, I’m not near any major roads for there to be any accidents or for her to be in harm’s way. I am very vigilant and I would never put your animals or my own at risk because pets are apart of the family and I’d never let anything happen to a family member, even yours.

Sitter Profile Image: Rosie J.
Verified Enhanced Background Check
Rosie J.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
• 14 reviews
3 repeat clients
22 years of experience
Lusby, MD, 20657

“Rosie was quickly responsive to my last minute request, was prompt, sent pictures, and communicated a concern that helped make her care the best for our Natty. Thank you, Rosie!”

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Colleen D.
Sitter Profile Image: Uduak U.
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Uduak U.
from
$20
per visit
5.0 out of 5 stars
• 16 reviews
6 repeat clients
12 years of experience
Upper Marlboro, MD, 20772

“Uduak was wonderful! She was communicative with my husband and I, and very patient with my pup who is not comfortable with new people. Uduak followed instructions to a tee, and also used her discernment in caring for Mozzy (even cleaning up an accident he had without us requesting she do so). 10 out of 10 would recommend. We will definitely be using her services again in the future.”

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Loren H.
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The median cost per visit for pet sitting in Woodwind Estates is $20

Pet parents share their Rover experiences - Woodwind Estates

1 / 1
5.0 out of 5 stars

Beyond happy with Lindsay. To say she went a ove and beyond is an understatement with my pups. 10 out of 10!

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Brian J.
Drop-In Visits
5.0 out of 5 stars

Liz is the best ! She takes great care of my pup and even cleans up after her. She’s very flexible and understanding! I love working with Liz !

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Lacey W.
Drop-In Visits
5.0 out of 5 stars

Stephanie has been such a wonderful sitter for our cats. She has relieved a lot of their anxiety which they experience with new people in the house. We never have had to worry about them when we’re gone and Stephanie is watching them. Highly recommended!

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Carol N.
Drop-In Visits
5.0 out of 5 stars

Beth was amazing - she took excellent care of our 2 cats and now we have found our cat sitter when traveling❤️

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Gaynor F.
Drop-In Visits
5.0 out of 5 stars

Karlie did an excellent job of taking care of our fur-baby. We will definitely be using her services again. Kakes really liked her and how attentive she was with her. She took care of her like she was her very own. Great job all the way!!!

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Sarah P.
Drop-In Visits
5.0 out of 5 stars

Kelly did a great job looking after our 2 cats. Her daily updates really eased our worries leaving our cats for a long vacation. We will definitely use her the next time we need a cat sitter.

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Kellie B.
Drop-In Visits
5.0 out of 5 stars

Samantha was fantastic with my dog. She went above and beyond. She let me know when she arrived, sent photos and videos, topped off his water, and as she left gave an update on her visit with Moose. Would 100% book her again!!!!!

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Gabbie E.
Drop-In Visits
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Book with peace of mind

  • 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

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Popular requests for pet sitting - Woodwind Estates

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Woodwind Estates average 6
repeat pet sitting clients

FAQs for Pet Sitting - Woodwind Estates

Frequently asked questions about Rover

The average cost of Pet Sitting in Woodwind Estates is $17 per visit as of November 2026. Most bookings cost between $16 and $28 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 3,292 sitters on Rover offering Pet Sitting across Woodwind Estates. Enter your ZIP code to see which available sitters are closest to your home.

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 Rover's Trust & Safety page.

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 Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.

Yes, you can find sitters who have experience with handling special pet needs in Woodwind Estates. On Rover:

  • 87% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, 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 use the 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 Meet & Greet.

sitters on Rover set their own cancellation policy, 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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