House Sitting in Woodwind Estates

Find a loving house sitter to watch over your pets and your home.

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Top rated Woodwind Estates house sitters

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

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Sitter Profile Image: Elizabeth G.
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Elizabeth G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
49 reviews
12 repeat clients
30 years of experience
HUNTINGTOWN, MD, 20639

Liz was an awesome pet sitter. She provided daily updates and photos and asked for information when a possible concern arose. My two dogs came home well cared for and happy!

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Leah M.
Sitter Profile Image: Anna D.
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Anna D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
5 years of experience
Owings, MD, 20736

Anna was awesome! She provided updates and responded to any inquiries within minutes. We've already rebooked her, just waiting on a response.

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Teresa I.
Sitter Profile Image: Faith M.
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Faith M.
from
$45
per night
4.9 out of 5 stars
20 reviews
5 repeat clients
2 years of experience
Chesapeake Beach, MD, 20732

Faith did a great job taking care of Pear and the house. Pear was well cared for, and everything was in good shape when we returned. I reached out a couple of times for updates, and she responded promptly. Overall, we appreciated her care and would happily consider working with her again!

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Aurora R.
Sitter Profile Image: Ashley P.
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Ashley P.
Star Sitter
from
$78
per night
5.0 out of 5 stars
44 reviews
14 repeat clients
15 years of experience
Huntingtown, MD, 20639

We greatly appreciate Ashley taking such wonderful care of our dogs! She kept us updated with lots of pictures and communicated well throughout the entire stay. Our house was left in great condition, and we could tell our dogs were in excellent hands. We would definitely use Ashley again and highly recommend her to anyone looking for a responsible and caring pet sitter. The dogs look forward to having her care for them again soon!

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Kristin L.
Sitter Profile Image: Laura J.
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Laura J.
from
$50
per night
3 years of experience
Huntingtown, MD, 20639

About: While working in a dog shelter, I cared for dogs of all breeds and temperaments, including administering medications. I have also volunteered for the past two years at an animal shelter, assisting with the care, handling, and enrichment of both dogs and cats. I currently work as a dog groomer, where I continue to build hands-on experience in animal care, behavior, and handling while prioritizing each dog’s comfort and well-being. I’m currently a part-time groomer’s assistant, so I have plenty of time to love your fur babies! My schedule is easily adaptable to fit the routines that they already follow to avoid disruption. In past job and volunteer trainings, I’ve received extensive training on canine and feline body languages, how to respect them, and how to safely build trust before things like leash walks, crate time, or play.

Sitter Profile Image: Kendal F.
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Kendal F.
from
$45
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
7 years of experience
Huntingtown, MD, 20639

About: Hello! My name is Kendal, and I’m a dedicated, dependable, and experienced pet sitter with a genuine love for animals and a strong commitment to their care and well-being. With 7 years of experience caring for dogs, cats, and other household pets, I understand how important it is to find someone you can trust to look after your furry family members. Whether it's daily walks, feeding, medication, or simply keeping your pets company while you're away, I provide attentive, personalized care to ensure your pets stay safe, happy, and relaxed. I take pride in maintaining a clean, safe environment and following your pet’s routine as closely as possible. You can expect regular updates, clear communication, and a high standard of professionalism at all times. Services Offered:
 ▪️Drop-in visits
 ▪️Dog walking
 ▪️Overnight care
 ▪️Medication administration 
▪️Personalized care based on your pet’s needs Let’s connect I’d love to meet you and your pets and discuss how I can help make your time away worry-free. I’m currently working part time due to school this upcoming semester. Most of my classes are online so I spend a lot of time at home. I make frequent stops at home during the work day as I’m only 10 minutes from home to let my dogs out of my parents aren’t home. I have an electric fence however dogs would be put on leash. My cats have all their necessities in my room so the pet I would be pet sitting for would stay in the guest bedroom in the basement with me to avoid troubles.

Sitter Profile Image: Pam S.
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Pam S.
from
$60
per night
5.0 out of 5 stars
18 reviews
3 repeat clients
20 years of experience
Hughesville, MD, 20637

Pam was great pet sitting our dogs in our home last minute as we had our usual boarder cancel due to a family emergency. She was very professional, asked lots of questions, and truly cared about keeping my dogs on their typical schedule. Could not recommend her more!

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Jaime A.
Sitter Profile Image: Vanessa S.
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Vanessa S.
from
$85
per night
4.9 out of 5 stars
80 reviews
37 repeat clients
30 years of experience
Prince Frederick, MD, 20678

We are so glad that we found Vanessa to be able to watch our dogs while we were out of town. She is so attentive to the needs of our dogs and treats them like her own. She is very knowledgeable about anxious dogs which makes us feel so much better knowing that she is the one taking care of our dogs when we are away.

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Lizzy K.
Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$35
per night
5.0 out of 5 stars
49 reviews
17 repeat clients
10 years of experience
Huntingtown, MD, 20639

I have nothing but good things to say. Took care of my Atti like she was family. She will be so happy to go back in a couple weeks to play with Blaze again!

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Allyn F.
Sitter Profile Image: Jessie C.
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Jessie C.
from
$40
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
4 years of experience
St Leonard, MD, 20685

About: As a child I've grown up with multiple animals as animals as pets, including a few dogs and a few cats. Professionally, I've had four total years taking care of different animals, which includes supervising dogs as well as helping various animals such as cats, guinea pigs, and other animals get adopted. I have had general experience feeding, walking, bathing, nail trimming, and over all playing with and supervising dogs. I also have had experience taking care of elderly and disabled animals, which includes but is not limited to a 19 year old cat with arthritis and kidney disease. I have experience giving animals oral medications at the correct times and have been consistently. As of right now, I am offering house sitting, drop-ins and dog walking. As of right now, all seven days of the week are generally free for me and I am home most of the time. However, there may be some days where I'm not available, such as certain holidays or family events. If something happens where I can't take care of your animal(s) (such as an emergency), I'll try to let you know ahead of time. I'll always keep your animals supervised regardless of whatever service I'm doing at the time. If your animal takes medications, I'll administer them at the correct times.

Sitter Profile Image: Shemoy S.
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Shemoy S.
Star Sitter
from
$95
per night
5.0 out of 5 stars
33 reviews
12 repeat clients
20 years of experience
California, MD, 20619

Shemoy worked closely with us to make sure our dogs were comfortable before we left them. She treated our babies like her own and always kept us fully updated :)

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Deanna G.
Sitter Profile Image: Emma L.
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Emma L.
from
$27
per night
18 years of experience
Owings, MD, 20736

About: Hi there! If your looking for a dog sitter/walker no need to look any further. I’ve taken care of dogs of a variety of ages and sizes my whole life. I love dogs and have always found them great companions. I have grown up with Golden Retrievers and Cavaliers, so I am comfortable with large and small dogs. I have also had pets in the past with medical issues and am well aware of how to administer medicine and take attentive care if needed. In addition, I have experience with puppies, both my dogs are grown now but I’ve had them since they were puppies. I am used to puppy life with my Cavapoo (Myles), he is very energetic and playful. Hank on the other hand, my Golden, would rather sleep all day, unless we are playing fetch. As a result, I know how to handle pets with different needs, some energetic and some older not so energetic ones. I often dog sit and walk for family and friends, have had paid sitting jobs in the past, as well as bathe and brush my dogs. I am willing and happy to care for your dogs according to your preferences, as well as hangout and play with them so they can have some fun while your away! I work during the week 9-6 sometimes I get off earlier at 4 or 5. I could do morning before work or afternoons after if needed! I also can do most weekends. I am however moving in August so I am only available till the end of summer. I take my dogs on walks around the neighborhood, let them run around outside if there is a safe space. My dogs like to play fetch so I am happy to throw a ball or any other toy to entertain them. I always take my dogs on leash when outside and would make sure to abide by any rules parents might ask of me. I occasionally treat my dogs when they are good pups, so I would make sure to ask the parents about feeding preferences as well as allergies and dietary restrictions.

Sitter Profile Image: Amanda S.
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Amanda S.
from
$75
per night
5.0 out of 5 stars
13 reviews
2 repeat clients
15 years of experience
Huntingtown, MD, 20747

About: I have a rescue dog and I’m very aware of rescues special needs, Iv cared for all sizes of dogs and treat them like my own! Along with cats, pigs and lizards ! I have a full time job , I work four ten hour shifts I am off every Thursday and every weekend and after work hours too if needed I am willing to do morning and evening shifts on the days I work I have a open yard , If your dog needs to be crated that’s fine my dog sleeps on the couch and gets in beds

Sitter Profile Image: Audrey N.
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Audrey N.
from
$55
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Hollywood, MD, 20636

Audrey did great taking care of our sweet Jesse girl. Lots of pictures and videos to keep us updated and help with a mommas anxious heart. Jesse played all weekend and had a blast. Audrey will be our first call if we need a help with our pups again!

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Shayna F.
Sitter Profile Image: Leah H.
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Leah H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
145 reviews
74 repeat clients
22 years of experience
California, MD, 20619

Leah was wonderful! Our pups loved her! This is the first time we’ve had a pet sitter, so we were a little nervous but she eased our worries. She was very prompt with messaging and gave us lots of updates! We will absolutely book her again!

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Sydney M.
Sitter Profile Image: Savanna B.
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Savanna B.
from
$89
per night
5.0 out of 5 stars
21 reviews
5 repeat clients
14 years of experience
Chesapeake Beach, MD, 20732

Savana was responsible in giving the medications on time even before I had time to check in about it. House was in perfect condition, would definitely recommend.

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John S.
Sitter Profile Image: Stacey H.
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Stacey H.
from
$60
per night
5.0 out of 5 stars
23 reviews
9 repeat clients
2 years of experience
Waldorf, MD, 20601

Stacey is the best! She is very reliable and we get regular updates. We have used her multiple times and always appreciate how well she takes care of our pup!

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Jessica R.
Sitter Profile Image: Breonna A.
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Breonna A.
from
$40
per night
14 years of experience
Prince Frederick, MD, 20678

About: I have grown up around dogs my entire life. We had various breeds ranging in size from small to medium. I chose to foster and adopt large breeds once I became an adult. I’ve given baths and administered medicines throughout the years of owning and helping neighbors take care of their babies. I would love the opportunity to help a family care for their babies! I’m currently a CNA looking to transition into the military so I have a pretty open schedule until the process is over and would be willing to work hours into my schedule if needed! I follow whatever the pet parents rules are for their space and understand that everyone is different with how they want their babies cared for! I am a clean person myself and would always clean up any messes that are made throughout my time in your home!

Sitter Profile Image: Sanai F.
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Sanai F.
from
$50
per night
5.0 out of 5 stars
6 reviews
1 repeat client
7 years of experience
Clinton, MD, 20735

Sanai has been an absolute delight! She is incredibly respectful, clean, and kind, and has taken exceptional care of our three-month-old puppy, Obi. My husband and I highly recommend her and fully trust her to care for our fur baby in the future.

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Jay & Yara F.
Sitter Profile Image: Lindsay J.
Verified Enhanced Background Check
Lindsay J.
Star Sitter
from
$31
per night
5.0 out of 5 stars
12 reviews
5 repeat clients
3 years of experience
Huntingtown, MD, 20639

About: Hi I’m Lindsay! I love spending time with our extroverted dog Zoomy 🐾 and with my cousin’s two cats Windex 🐈 and Squirt 🐈‍⬛. Zoomy would love to have some friends come over to play. I am a super responsible and clean person and would love to care for your fur babies while you’re away! Right now I have very flexible scheduling so send me a message! I can do daytime hours or evenings, just let me know. I’d be happy to work with you and your schedule. We have a big yard with an invisible fence for your dog to run around. Plenty of space inside the house to play too! I will make sure to give your dog plenty of water and potty breaks and meticulously follow any instructions you leave me!

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Woodwind Estates pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Liz was so great with our little pup. He's new to staying away from us overnight so we wanted to have someone at the house with him where he's comfortable. We got regular updates of him looking so happy and cozy. When we got home he was happy as can be and clearly had a good time. We will definitely ask Liz to sit for us again next time!

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Lauren R.
House Sitting
5.0 out of 5 stars

My high energy dog was really relaxed and happy after Joe spent the weekend with him. Other animals were also good. What more can you ask? (House was clean and everything in its place. Highly recommend.

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Victoria W.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Woodwind Estates is $50

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 house 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.

Sitters in Woodwind Estates average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Woodwind Estates on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Woodwind Estates house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 812 house sitters in Woodwind Estates. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 86% of Woodwind Estates house sitters respond in under an hour.

House sitters in Woodwind Estates have an average of 16 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Woodwind Estates.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Woodwind Estates house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.