House Sitting Windyhill

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

End
Search

Windyhill, 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: Grace F.
Verified Background Check
Grace F.
from
$65
per night
5.0 out of 5 stars
• 15 reviews
6 repeat clients
22 years of experience
Easton, MD, 21601

“Grace is the absolute best!! We have a whole farm here and she handles them all excellently. Even our one dog who doesn't particularly love anyone but Mom and Dad cannot get enough of Grace.”

Profile image
Sarah H.
Sitter Profile Image: Lily K.
Verified Enhanced Background Check
Lily K.
from
$75
per night
5.0 out of 5 stars
• 14 reviews
4 repeat clients
11 years of experience
Oxford, MD, 21654

“Lily was terrific! She was enthusiastic and caring with Bailey and Beau and was a great communicator with us about details concerning our home and the pups needs. Would not hesitate to use her again.”

Profile image
Vivian E.
Sitter Profile Image: Maura M.
Verified Enhanced Background Check
Maura M.
from
$60
per night
5.0 out of 5 stars
• 6 reviews
3 repeat clients
7 years of experience
Easton, MD, 21620

“Maura and Will treated Ozzie like he was part of the family! He felt right a home at their house, and I believe thoroughly enjoyed having another canine companion to play with. Maura will be my go-to any time I travel in the future.”

Profile image
Beth D.
Sitter Profile Image: Johanna T.
Verified Enhanced Background Check
Johanna T.
Star Sitter
from
$75
per night
4.9 out of 5 stars
• 18 reviews
3 repeat clients
15 years of experience
Cambridge, MD, 21613

About: My dog passed and I miss her company! So I love having visitors to keep me company and play with while working from home :) Work from home, I'm free to walk the dogs first thing the the morning, around noon and anytime in the evening and spend the whole day with them if needed :) Quiet home, no children, no smoking, no other dogs or cats - just fish n two birds, half way fenced Yard, but very safe. We can walk around the neighborhood, there is a park down the street as well and the back yard.

Sitter Profile Image: Stephanie R.
Verified Background Check
Stephanie R.
from
$75
per night
5.0 out of 5 stars
• 7 reviews
2 repeat clients
10 years of experience
Oxford, MD, 21654

“Stephanie took great care of my dog Sammy. I am thankful I found her. She was wonderful.”

Profile image
Mary O.
Sitter Profile Image: Catherine H.
Verified Enhanced Background Check
Catherine H.
from
$200
per night
38 years of experience
Seaford, DE, 19973

About: Building Trust with Pets • Peace of Mind for Their People • Loving • Reliable • Personalized • Attentive • Compassionate • Trustworthy • Gentle • Patient • Experienced • Enriching • Dependable • Safe • Professional • Nurturing • Heartfelt Pet care is a natural part of my daily routine. I intentionally schedule my days to provide dependable visits, walks, playtime, feeding, medication (if needed), and plenty of one-on-one attention. I enjoy staying active, so walks and outdoor time are something I genuinely look forward to. I treat every pet like a member of my own family and make sure they receive consistent, loving care while you’re away. I care for pets in their own home where they’re most comfortable and their routine stays consistent. I follow each owner’s instructions carefully for feeding, fresh water, walks, playtime, medications, and any special needs. I also spend quality time providing companionship, affection, and enrichment—not just completing a checklist. During each visit, I make sure the home is secure, clean up after the pet, and send updates with photos so owners know their pet is happy, safe, and well cared for.

Sitter Profile Image: Summer B.
Verified Enhanced Background Check
Summer B.
from
$125
per night
5.0 out of 5 stars
• 2 reviews
20 years of experience
Wye Mills, MD, 21679

About: ✨ Schedule & Availability I currently maintain a full-time position but please do not hesitate to reach out and we can talk about options to accommodate your pets needs. ‼️Currently can only guarantee afternoon services on Monday and Tuesday. ✅House sitting includes Morning and Evening services with overnight care. ✨My Experience I have experience caring for both dogs and cats with a wide range of personalities, energy levels, and care needs. In addition to caring for my own pets over the years, I have multiple years of providing care to clients, and volunteered with animal rescue and shelter organizations. I currently work full-time, but I still maintain availability outside of my work schedule for pet care, drop-ins, walks, feedings, and quality time with your pets. I’m reliable with routines and make sure pets receive the attention, consistency, and care they need while their owners are away. I understand how important trust is when someone is caring for your pets and entering your home. I treat every animal with patience, respect, and attention to their individual comfort level and routine. I’m experienced with shy pets, senior animals, anxious pets, and pets that may need a calmer approach or extra time to adjust. I always prioritize safety, clean environments, secure doors/leashes, and careful attention to instructions so owners can feel confident their pets are being cared for like family.

Sitter Profile Image: Busara C.
Verified Enhanced Background Check
Busara C.
from
$65
per night
5.0 out of 5 stars
• 92 reviews
16 repeat clients
5 years of experience
Dover, DE, 19904

“Busara was an incredible dog sitter! From the moment she came for the meet and greet, I was impressed. My dog was calm and took to her immediately, which gave me so much peace of mind. She even took notes about his care, showing how attentive and thorough she is. After the meet and greet, she sent a detailed care summary and promptly accepted the booking. Throughout our trip, she communicated amazingly, sending multiple updates and photos of our baby every day through out the day. It made being away so much easier knowing he was happy and well cared for. When we returned home, everything was in perfect condition. She brought in our mail, watered our plants, and most importantly, our dog was happy, relaxed, and clearly well loved. I would absolutely recommend Busara to anyone looking for a trustworthy, caring, and professional pet sitter. We will definitely be booking with her again the next time our family travels!”

Profile image
Danielle K.
Sitter Profile Image: Rachael B.
Verified Enhanced Background Check
Rachael B.
from
$80
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
10 years of experience
Queen anne, MD, 21657

About: I have 8 animals of my own, both dogs and cats. I also work part time as a Kennel Technician so I am very familiar with different animal personalities and how I’m expected to care for them! Neighbors, friends, family & clients have relied on me to care for their furry friends and I’ve loved getting to know each one. I am pet CPR & First aid Certified. I work as a nanny from 11-5 as well as dog sitting overnights frequently. I work as a nanny from 11-5 in Southampton. College is online so that won’t be a problem right now. My scheduled days can change but shifts are no longer than 6 hours at a time, Mon-Fri. I live in Sayville. I have plenty of time in the morning & afternoon for long walks and fetch! My weekends are completely free. I will take wonderful care of your pets as if they were my own. My pups love to play outside and get lots of attention so I want to share the love!! It’s always fun getting to know your dogs and cats. I have built a trusted clientele over the last 3 years of being on Rover. I am very responsible and will care for your house just as well as your pets! I know it takes a lot to entrust someone in your home so I won’t let you regret it.

Sitter Profile Image: Chelsea R.
Verified Enhanced Background Check
Chelsea R.
Star Sitter
from
$100
per night
5.0 out of 5 stars
• 12 reviews
4 repeat clients
12 years of experience
Frederica, DE, 19946

“Krose had a great day with Chelsea! Chelsea arrived early with a goodie bag with treats and a toy. We appreciated the photos throughout the day. We were happy to see he was relaxed when we arrived home. We would definitely use Chelsea again!”

Profile image
Jeanne S.
Sitter Profile Image: Carla C.
Verified Background Check
Carla C.
from
$25
per night
5.0 out of 5 stars
• 27 reviews
9 repeat clients
4 years of experience
Salisbury, MD, 21804

“Carla is a true pet lover, responsible and very caring. Trustworthy and respectful of property and responsive to communication.”

Profile image
Glenn S.
Sitter Profile Image: Danielle D.
Verified Enhanced Background Check
Danielle D.
from
$80
per night
5.0 out of 5 stars
• 4 reviews
3 repeat clients
5 years of experience
Salisbury, MD, 21804

About: Im familiar with giving medication, and providing exceptional care for all animals. I've cared for pets most of my life, and I have 5 years of experience in an animal shelter caring for cats and dogs. It's very rewarding, and it's the best part of my day when I see the happy tails, hear the purring and receiving those kisses. I dont live in Denton, I live in Salisbury. I do travel for my clients,[up to 50 miles] only if youre in need of a sitter for more than 3 days. We can discuss even further during a meet n greet. My full time work is as a gig worker. I make my own schedule, so I am able to care for your pets at any time. I love animals! I provide a safe, and caring environment when I care your pets. I love them like they're my own. Care would be in your home, and I usually stay overnight, unless you would like daily care, then I would come a couple times per day to provide meals, scoop litter boxes, take daily walks, etc.

Sitter Profile Image: Michael P.
Verified Enhanced Background Check
Michael P.
from
$90
per night
5.0 out of 5 stars
• 75 reviews
38 repeat clients
10 years of experience
Arnold, MD, 21012

“Lolly and Trixie love Michael. My husband and I do too. The dogs love him because he’s gives them lovies and pets and lets them lay all over him. We love him because he’s reliable, on time, follows instructions (especially with medications), sends us pictures, and has a genuine love for his job. All of this is a priceless combination. You’ll never go wrong hiring Michael to take care of your beloveds.”

Profile image
Teresa C.
Sitter Profile Image: Laurie H.
Verified Enhanced Background Check
Laurie H.
from
$75
per night
45 years of experience
Annapolis, MD, 21401

About: I truly adore cats and their unique personalities. I'm a retired empty nester, who is flexible, attentive, patient, affectionate, and I believe great cat care includes a fresh, spotless litter box every day. Your cat will get plenty of love, attention, and a comfortable environment giving you a peace of mind while you're away. Being retired gives me a flexible schedule and plenty of time to devote to your pets, providing attentive, dependable care without rushing or juggling another job. Whether in my home or yours, I follow each pet's normal routine, providing plenty of love, attention, exercise, fresh water, clean spaces, play time and personalized care.

Sitter Profile Image: Jarren C.
Verified Enhanced Background Check
Jarren C.
from
$28
per night
15 years of experience
Frankford, DE, 19945

About: Ive been taking care of little to small pups ever since a little girl. Our family has had breeds anywhere from chihuahuas to lab to boxer. Im looking forward to meeting new pups, as well as giving them the exercise and cuddles they need or desire. If you have any specific questions or concerns, please feel free to reach out anytime! I love puppies, so anytime is puppy time. But, I'm currently available only early mornings, mid day and evenings. I do have a child at home so that will have to be taken into consideration. I work a 8-4 schedule, but I am free to leave if I absolutely need to. I can definitely do grooming. Your pet will be fed based on owners normal schedule. Dogs can be let out ever 2-6 hours depending on availability. Any rule you apply for your pet to adhere to, I will delegate that.

1 / 1
View more

The median cost per night for house sitting in Windyhill is $55

Pet parents share their Rover experiences - Windyhill

1 / 1
5.0 out of 5 stars

Kelly has become our go to pet caretaker! She is amazing with our animals, sends tons of pictures and is generally awesome! Thanks for everything Kelly!

Profile image
Stephen W.
House Sitting
5.0 out of 5 stars

Kelly as per usual was amazing! She truly loves our dogs and sends us constant pictures throughout our time away. She is trustworthy and super friendly. We appreciate you Kelly!

Profile image
Stephen W.
House Sitting
1 / 1
Find pet care near you

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 house sitting

  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.

Popular requests for house sitting - Windyhill

Select a filter and find qualifying sitters offering house sitting.

Sitters in Windyhill average 3
repeat house sitting clients

FAQs for House Sitting - Windyhill

Frequently asked questions about Rover

As of October 2026, there are 260 sitters on Rover offering House Sitting across Windyhill. 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 Windyhill 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 Windyhill 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.

<b>Tip:</b> 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 Windyhill 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 , 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 .

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 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 .

sitters on Rover set their own , 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.

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

  • 96% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 96% 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.

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge