House Sitting Woodwind Estates
Find a loving house sitter to watch over your pets and your home.
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.
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.
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!
“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!”
“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!”
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.
“Faith is a fantastic petsitter! We were out of town for 8 days and didn't have to worry about a thing back home. It was wonderful to find a caring person who could spend this much time with our pets. Boarding can be so stressful on our big dogs, but Faith was able to do overnights and wasn't intimidated by our Dobermans in the slightest. She was a perfect fit, and we were so blessed to find her on Rover. It was our first experience with the service platform being new to Southern Maryland, but we will be repeat customers for sure.”
“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”
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.
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.
“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!”
“We could not have left our dog, Waldo, in better hands than Stacey's! Stacey feels like family and Waldo felt that, too. We're grateful for her photo and video updates and attentive care. We strongly recommend Stacey!!”
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
“Anh took terrific care of our pups. She was responsive, sending daily updates and getting in touch with any questions she had about dog care. I absolutely recommend her for puppy care and will request her for future needs.”
“This is the 3rd or 4th time we have booked Vanessa! She’s amazing! She stays at our house for us. She watches our dogs and cat and she loves them like her own. I’m glad that when my wife and I go out of town we can leave without having to worry about our animals while we are gone. She’s an amazing sitter for our animals! She’s extremely attentive and very friendly! We will definitely continue booking Vanessa every time we go out of town!! It’s always a struggle to find someone who will take care of your animals the way you do, but for us, Vanessa is that person!!”
About: I’ve cared for pets for several years & genuinely love spending time with animals. I have experience feeding, walking, playing with, & giving attention to dogs & cats of different sizes & personalities. I’m reliable, patient, & always make sure pets feel loved & happy! I have a flexible schedule & enjoy making time for pet care throughout my week. I’m available for walks, playtime, & I make sure every pet gets plenty of attention. I make sure all pets get exercise & care, I’m dependable, commutative, & will always do my best work. I will make sure I work to your pet’s routine & needs. I provide a safe, loving, & comfortable environment for every pet in my care. I pay close attention to each pet’s needs, routines, & personality to help them feel relaxed & secure. I can follow feeding schedules, give plenty of playtime & potty breaks, along with putting them in a crate if needed. My goal is to make pets & owners feel comfortable as much as possible.
“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!”
The median cost per night for house sitting in Woodwind Estates is $50
Pet parents share their Rover experiences - Woodwind Estates
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!
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 Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Woodwind Estates sitters!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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