House Sitting Woodwind Estates

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

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Over 17
pet parents in Woodwind Estates have booked house sitting

Woodwind Estates, Find top rated house sitting

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

1 / 1
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: 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: Savannah H.
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Savannah H.
from
$31
per night
5.0 out of 5 stars
13 reviews
4 repeat clients
8 years of experience
Huntingtown, MD, 20639

About: I raised two bigs that I have trained years now and I grew up on a small farm so I have gotten the opportunity to care for animals for some time now! I also volunteer at animal shelters, getting the opportunity to work with all kinds of dogs as well. I am home from playing overseas and am available most days! During week days I can go to others homes to walk or check in pets normally any time of the day. I am comfortable with taking any size pet out for walks or stopping in to give them attention and have no issue taking them out to play and potty based on what the owner wishes!

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

Ashley did a wonderful job taking care of our senior dog and our house while we were visiting family. I think she may have given our pup more attention than she gets when our whole family is home. Highly recommend!

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Lauren E.
Sitter Profile Image: Teresa M.
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Teresa M.
from
$50
per night
20 years of experience
East Carollton, North Beach, MD, 20714

About: I have taken care of dogs for over 20 years, including having my own dogs. I am a travel nurse and I usually volunteer to walk dogs at shelters when I’m on assignment. I work full time as a nurse, but I only work 3 days a week. My schedule is usually free on the 4 days a week that I’m off of work. I am currently living in an apartment while on assignment in North Beach, Md, so I can only take car of pets in your own home.

Sitter Profile Image: Faith M.
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Faith M.
from
$40
per night
4.9 out of 5 stars
20 reviews
5 repeat clients
2 years of experience
Chesapeake Beach, MD, 20732

Our fur babies are family and not pets! She was attentive to their needs and gave them all the love and care in our absence! Our new go-to dog sitter!!

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Melinda J.
Sitter Profile Image: Michelle M.
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Michelle M.
from
$75
per night
5.0 out of 5 stars
19 reviews
7 repeat clients
25 years of experience
Sunderland, MD, 20689

Michelle did a great and perfect job for our 3 doggies We come back after 1 week out of town and everything was cleaned from her , the dog's fall in love with her.We would highly recommend Michelle for other costumers…thanks again Michelle….Antje & Jens

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Jens K.
Sitter Profile Image: Anna D.
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Anna D.
from
$45
per night
5.0 out of 5 stars
8 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: Carrie N.
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Carrie N.
from
$40
per night
5.0 out of 5 stars
18 reviews
5 repeat clients
10 years of experience
St Leonard, MD, 20685

Carrie was wonderful with my 2 babies. She sent lots of pictures and videos while I was gone, which made me feel at ease. If your looking for someone to spoil your puppy while your away, Use Carrie! She even bought them both a new toy, they were happy happy! I will definitely use her again in the future.

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Lisa Y.
Sitter Profile Image: Tosawi L.
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Tosawi L.
from
$38
per night
5.0 out of 5 stars
1 review
5 years of experience
North Beach, MD, 20714

About: My goal is to take your spot as your pet’s best friend .. uhh I mean provide excellent care and service whenever duty calls :) My schedule is fairly flexible, and I am generally available each afternoon. I am sure that we can work out a reasonable time to get your pets situated! Owners rules are law. Whether it’s playtime, supper, potty time, etc I’ve got you covered. I am unable to provide services in my home at this time.

Sitter Profile Image: Shemoy S.
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Shemoy S.
Star Sitter
from
$95
per night
5.0 out of 5 stars
34 reviews
14 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: 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: 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: Leah H.
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Leah H.
Star Sitter
from
$60
per night
5.0 out of 5 stars
146 reviews
74 repeat clients
22 years of experience
California, MD, 20619

We absolutely love Leah!! She's so good with our dogs. Very punctual and responsible. She stays over with our two and leaves or home just the way we left it.

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Dean S.
Sitter Profile Image: Stephanie M.
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Stephanie M.
from
$35
per night
5.0 out of 5 stars
50 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: 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: 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: Anh C.
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Anh C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
10 reviews
5 repeat clients
13 years of experience
District Heights, MD, 20747

Anh was amazing with Pico. She jumped in last minute and handled everything so thoughtfully - including some unexpected tummy issues and his occasional puppy chaos. She kept me fully updated the whole time and sent lots of great photos, which I really appreciated. It made such a difference being able to see how he was doing. Pico is used to being with me all the time, so social interaction is really important for him. Anh adjusted to Pico’s needs and routine and also made him part of hers - giving him so much extra love and attention. You can’t always guarantee that level of care when you’re away, and I’m so grateful I never had to worry. I would absolutely recommend Anh to anyone without hesitation!

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Erin A.
Sitter Profile Image: Victoria A.
Verified Enhanced Background Check
Victoria A.
from
$60
per night
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: Vanessa S.
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Vanessa S.
from
$85
per night
5.0 out of 5 stars
81 reviews
37 repeat clients
30 years of experience
Prince Frederick, MD, 20678

Many thanks to Vanessa for taking such good care of my pup. Vanessa updated me on my pup throughout the trip. My dog is very high energy, and clingy.... she handled her with ease!!

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Peg K.
1 / 1
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The median cost per night for house sitting in Woodwind Estates is $50

Pet parents share their Rover experiences - Woodwind Estates

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
1 / 1
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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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house 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

Sitters in Woodwind Estates average 4
repeat house sitting clients

FAQs for House Sitting - Woodwind Estates

Frequently asked questions about Rover

The average cost for House Sitting in Woodwind Estates on Rover is $43.29 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of July 2026, there are 2,066 sitters on Rover offering House Sitting across Woodwind Estates. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Woodwind Estates walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Woodwind Estates maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Woodwind Estates choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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.

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 .

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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

  • 94% of sitters can help with special care needs
  • 97% can help with giving oral medications or injections
  • 98% 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.

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