House Sitting Woodwind Estates
Find a loving house sitter to watch over your pets and your home.
Over 18 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.
“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!”
“Lindsay stayed for 10 days with my 17 year old cat. He takes many supplements and meds and Lindsay followed the schedule precisely. She sent updates and pics everyday to let me know how it was going. She made sure he was well cared for and that he felt comfortable with her. After the first day, he was snuggling with her on the couch. She checked in when she had questions. Lindsay was respectful of my home which made me very comfortable having her stay. She was an excellent sitter and I would highly recommend her. I will absolutely be rebooking with her anytime I need to go out of town.”
“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.”
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.
“We booked Rose when looking for a house sitter for one night at the last minute. Our dogs seemed to take to Rose very quickly and when we returned home it seemed like we hadn't left, which is exactly what we wanted! Rose was kind and professional and sent us multiple photos of our dogs during the trip. There were also no issues at all with our house as everything seemed just as it was when we left. Highly recommend!”
“Anh was wonderful with our dog Wilbur- she sent us updates and was really sweet to him. She stayed over at our place which we appreciated because our pup can get a little anxious. Anh left us a very nice note and left the house very clean. We will definitely be reaching out to Anh again until the future for dog care!!”
“Stacey was absolutely amazing with our two boys. She took them for walks and loved on them while we weren’t able to. She was very communicative and sent us pictures and videos of how happy the boys were. When we came home, she had left the house cleaner than when she arrived. I cannot give her enough stars!”
“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!”
“Courtney was great! We felt very comfortable being away knowing that our pets were getting so much love and attention. We had clear and frequent communications and a plenty of pictures confirming all the good things happening. We'd (and our critters) would be very happy to see Courtney again.”
“Lauren did overnight sitting in my home for a week and took care of my very needy Persian cat and 130lb Great Dane. She is super reliable, communicative, and left the house in better shape than she probably found it. Will absolutely book with her again. Thank you, Lauren!”
About: I use to work for a boarding kennel when I was younger, but since my young teens I have been dog/cat/house sitting. I love animals I will be there new best friend. You will not regret if you choose me to watch your loved one, they will be well taken care of, well loved and spoiled! No request is to much, I have watched all different kinds of animals from dogs, cats, birds, hedgehogs, bunnies you name it I have probably watched them. I work at prince Frederick Safeway. I normally work 4-1pm, 5 days a week. My schedule does change from time to time due to what is going on but I will communicate my schedule prior to watching your babies. Some days are easier than others… Monday, Wednesday and Fridays I’m not normally available until 3pm. Tuesday and Thursdays I’m available anytime after 1pm. This could change just ask and we will work something out! I have a huge fenced in back yard! Lots of room to run and play! I will crate your animal if it is needed, just please bring your crate with you. If not crated during the day I keep all doors shut so they can’t get into anything they aren’t supposed to. I do also have indoor camera to keep an eye on them while I’m away at work. Due to apartment rules I am not allowed to have pit pulls at my apartment, I love the breed! I just have to make sure I am following my landlord rules, I would have to come to you!
“Tia was an awesome, Dog Sitter for our 70 pound, somewhat anxious, rescue dog, Lucy. She instantly knew how to make Lucy comfortable and feel secure, which is no small feat. She was also completely reliable., showing up on time, responding quickly to questions, taking as much time as we needed during our meet and greet. I cannot recommend Tia highly enough.”
“We are so lucky to have found Snowden on Rover! She house sat for 5 nights over Christmas for our senior rescue dog, Maggie, and everything was perfect. Snowden is quick to respond to all communication and Maggie immediately took to her so we knew she was in good hands. Snowden made sure Maggie took her morning meds, took her for walks, and sent us daily pictures. When we got back, Snowden had done laundry, made the bed, washed all the dog dishes and left the house in great shape. We definitely plan to book her again!”
“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!!”
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!
“Shemoy was absolutely awesome with my boy. She visited him before the day and developed a good connection and interacted with him like she had known him forever. She was incredibly loving with him and I was more comfortable that I thought I would be for our first time away!”
“Karima took excellent care of our dog Goose and our apartment while we were away for over a week. She was caring, responsive, and helpful throughout her stay. She sent us daily updates and was very professional. She left our apartment clean and Goose absolutely loved her! I would definitely book with Karima again and suggest her for any of your dog sitting needs.”
About: I've been a dog owner for over 20 years and was a foster parent for a San Diego based rescue group for over 3. I currently volunteer as a dog walker at a local Southern Maryland rescue and also foster with them as well. Our family has cared for, trained and assisted with the adoption of many different breeds from small to large and all ages, puppies less than 12 weeks included. In addition we puppy raise and train service dogs for a non-profit organization based out of NY. Pets bring so much love and joy to our lives and deserve the best care when we are away. I can promise they will receive the same love and attention as if you were home yourself. Current pet is a 13 year old yellow lab and pointer mix that we've had since he was 12 weeks old. He loves long walks, swimming in any body of water and snuggling with his cat brother, Tucker. In addition we have a 2 year old beagle that nothing but fun. References are available upon request. I work remotely and am home during the day. This allows me flexibility to care my own fur-children and yours from either my home or yours. I have a large fenced yard, friendly pups, a dog room and plenty of crates. We often crate and rotate to make sure our pups get enough one on one and would do the same for yours.
The median cost per night for house sitting in Woodwind Estates is $50
Pet parents share their Rover experiences - Woodwind Estates
Lindsay stayed for 10 days with my 17 year old cat. He takes many supplements and meds and Lindsay followed the schedule precisely. She sent updates and pics everyday to let me know how it was going. She made sure he was well cared for and that he felt comfortable with her. After the first day, he was snuggling with her on the couch. She checked in when she had questions. Lindsay was respectful of my home which made me very comfortable having her stay. She was an excellent sitter and I would highly recommend her. I will absolutely be rebooking with her anytime I need to go out of town.
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.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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Popular requests for house sitting - Woodwind Estates
Select a filter and find qualifying sitters offering house sitting.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 August 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 August 2026, there are 2,046 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:
- 92% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 97% 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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