House Sitting Winfield

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Winfield, 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.

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Sitter Profile Image: Addison M.
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Addison M.
from
$35
per night
5.0 out of 5 stars
3 reviews
1 repeat client
2 years of experience
New Windsor, MD, 21776

Was very pleased with how well she took care of Hershey. He does not like fireworks and she sat with him while the fireworks are going off up the road. She’s already scheduled to come back and watch her again. I would recommend her to watch anybody’s pet.

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Tom E.
Sitter Profile Image: Hailey K.
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Hailey K.
from
$50
per night
4.9 out of 5 stars
22 reviews
7 repeat clients
10 years of experience
Sykesville, MD, 21784

We recently had Hailey stay with our 2 older labs (one is blind and requires insulin), 2 cats and a gecko while we were away on vacation for a week. Hailey was wonderful! She kept us updated along with photos of our pups and handled medications and feedings schedules with ease. This was honestly the first time we didn’t worry while on vacation. When we arrived home, our pups and cats were happy and the house was as clean and tidy as it was when we left. I highly recommend Hailey. She is professional, honest, respectful, reliable and very sweet. Thank you Hailey!

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Jennifer G.
Sitter Profile Image: Sofia A.
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Sofia A.
from
$60
per night
4.4 out of 5 stars
7 reviews
1 repeat client
6 years of experience
Mt Airy, MD, 21771

Sofia was wonderful! She took great care of our dog!

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Beth L.
Sitter Profile Image: Kerri L.
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Kerri L.
Star Sitter
from
$70
per night
5.0 out of 5 stars
39 reviews
14 repeat clients
8 years of experience
Westminster, MD, 21158

Kerri was wonderful with our pets. The cat hides and is afraid of everyone, but he took to her immediately. She even got a collar on him which I have not been able to do in the 10 years we have had him. The dog is needy and loves snuggles and Kerri gave her lots of love. We would definitely book with her again!

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Connie G.
Sitter Profile Image: Maxwell N.
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Maxwell N.
from
$35
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
7 years of experience
Westminster, MD, 21157

About: I have experience with and am comfortable with all sizes, breeds, ages and personalities of any dog! I am reliable, friendly, and have good communication skills! I have two cats I take care of day in and day out! I also regularly dog sit one larger dog roughly once a month on weekends! I treat every animal I meet and or sit as if they were my own. As previously stated, I am an animal lover that believes every animal is unique and needs their own personalized care!

Sitter Profile Image: Brian R.
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Brian R.
from
$29
per night
5.0 out of 5 stars
4 reviews
1 repeat client
18 years of experience
Eldersburg, MD, 21784

I liked Brian. did a good job for me and I would book him again. when my flight was canceled he accommodated me and took good care of my dogs.

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Dean M.
Sitter Profile Image: Lora M.
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Lora M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
134 reviews
35 repeat clients
22 years of experience
Finksburg, MD, 21048

Lora is just so wonderful with Sandy. I think Sandy likes her more than us. I never worry about the house or the dog, even with big summer storms. Lora is great!

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Kristi E.
Sitter Profile Image: Nora A.
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Nora A.
from
$70
per night
5.0 out of 5 stars
23 reviews
10 repeat clients
15 years of experience
Mount airy, MD, 21771

Nora has been absolutely fantastic! She does drop-in visits when I am away on vacation or out for work. She communicates well and always sends great pictures of my dogs and cat to let me know how they’re doing.

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Jessica P.
Sitter Profile Image: Travis D.
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Travis D.
from
$50
per night
1 repeat client
20 years of experience
Westminster, MD, 21157

About: I have been around Animals all my life. I have kept and currently keep Exotic Animals. I’m always looking after friend’s or family’s pets, so I thought why not offer my services to others! My entire life revolves around caring for Animals. I have a 2.5 year old Catahoula Bully Mix and currently keep many Reptiles. I look after my parents Cats any time they go out of town and consistently pick up Animal related side jobs whenever I can. I have a fenced in yard at my home but will only be offering care in the client’s home. I am open to any kind of care and any type of Animal. Please reach out for further details!

Sitter Profile Image: Alexander S.
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Alexander S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
19 years of experience
Reisterstown, MD, 21136

Alexander took great care of our dog and home while we were away! We got plenty of updates and came home to a clean house which was greatly appreciated. We highly recommend him and will definitely be booking again in the future.

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Samantha C.
Sitter Profile Image: Amber R.
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Amber R.
from
$50
per night
5.0 out of 5 stars
16 reviews
5 repeat clients
10 years of experience
Westminster, MD, 21158

I cannot say enough about Amber! She is an amazingly caring and thoughtful pet sitter. Gloria was well loved in our absence! I HIGLY recommend Amber's services!

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Cortney G.
Sitter Profile Image: Elizabeth G.
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Elizabeth G.
from
$25
per night
4.3 out of 5 stars
4 reviews
10 years of experience
Finksburg, MD, 21048

Elizabeth was great with my dog. My dog is very high energy at first but that didn’t scare Elizabeth off. She sent me pictures and worked with me on when she came over to my house and when she left. She spent good time with my dog and I would definitely book her again!

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Camden C.
Sitter Profile Image: Paula H.
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Paula H.
from
$31
per night
30 years of experience
Sykesville, MD, 21784

About: Animals have always been a big part of my life. I’ve had cats throughout my life and have also had the joy of caring for a dog. I truly enjoy the companionship that pets bring and love giving them plenty of attention, affection, and care. Now that my kids are grown and out of the house, I have more time to spend doing something I genuinely enjoy! Being around animals! I’d love to spoil your pets with love, playtime, walks, and lots of attention while you’re away. My goal is to make your pets feel comfortable, happy, and cared for just like they were at home. I can stop in before and after work. Or I can stay at your house. I work a 9-5 weekdays. I am available also on weekends. I will follow your expectations while sitting for your pets in your home. I will make sure the home remains pet safe. Making sure your pets environment is safe before leaving them. I will give them lots of attention and playtime.

Sitter Profile Image: Sabrina W.
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Sabrina W.
from
$50
per night
4.8 out of 5 stars
18 reviews
2 repeat clients
4 years of experience
New Market, MD, 21774

Sabrina is the absolute best!!!! I feel so blessed that we found her. She’s such a kind person with the sweetest energy. The animals flock to her!! She’s the only person we’ll be using from now on.

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Ashley L.
Sitter Profile Image: Hannah A.
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Hannah A.
from
$40
per night
5.0 out of 5 stars
28 reviews
9 repeat clients
4 years of experience
Mount Airy, MD, 21771

Hannah took such great care of our 2 sr pups. She communicated regularly when our bulldog's allergies flared up. Our dogs were happy and content when we got home. The house was also nice and tidy.

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Leilani R.
Sitter Profile Image: Katharine D.
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Katharine D.
from
$56
per night
5.0 out of 5 stars
3 reviews
1 repeat client
13 years of experience
Sykesville, MD, 21784

Absolutely fantastic experience with Katharine! She took great care of my dogs and handled giving medicine expertly, and was perfectly comfortable taking care of a giant breed dog. She also sent us pictures periodically of the dogs while she was caring for them which was so nice! Would recommend to everyone!

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Sara T.
Sitter Profile Image: Quinn B.
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Quinn B.
from
$50
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
6 years of experience
Owings Mills, MD, 21117

Quinn was wonderful with our dogs! She kept us informed and sent pictures, and our dogs just loved her. So happy we found her for our vacation. Highly recommend her!

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Michelle L.
Sitter Profile Image: Sarah W.
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Sarah W.
from
$50
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
15 years of experience
Westminster, MD, 21158

We've had Sarah watch our pets a few times and she continues to be fabulous. Sarah is to very vigilant & a strong communicative sitter! Plus our pets absolutely ADORE her, which I am so appreciative of.

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Mark M.
Sitter Profile Image: Ava O.
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Ava O.
from
$45
per night
5.0 out of 5 stars
9 reviews
6 repeat clients
2 years of experience
Walkersville, MD, 21793

First time using Rover and leaving my 10-week-old puppy, and Ava was absolutely fantastic. She sent pictures and videos throughout the day, and I could tell he was having so much fun. She kept him on his schedule and was clearly experienced with puppies. I felt completely at ease knowing he was in such great hands- will definitely be using Ava again!

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Brittania E.
Sitter Profile Image: Riley K.
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Riley K.
Star Sitter
from
$34
per night
4.9 out of 5 stars
16 reviews
9 repeat clients
6 years of experience
Owings Mills, MD, 21117

She is such an amazing caretaker for our many, many animals and is an even more wonderful person! It's obvious she truly cares about animals and is very knowledgeable about and invested in their wellbeing. Plus she does regular check ins throughout the day to make sure we stayed updated on how they were doing compete with pictures!

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Mack B.
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The median cost per night for house sitting in Winfield is $50

Pet parents share their Rover experiences - Winfield

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5.0 out of 5 stars

Navetta was wonderful taking care of our for babies! She was easygoing and very communicative. We got daily updates, pictures, and videos.

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Jennifer W.
House Sitting
5.0 out of 5 stars

Layla was wonderful… she was a life saver and watched our dog Ted on incredibly short notice. She was great and as long as she is available we will not be using anybody else.

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Eddie P.
House Sitting
5.0 out of 5 stars

We recently had Hailey stay with our 2 older labs (one is blind and requires insulin), 2 cats and a gecko while we were away on vacation for a week. Hailey was wonderful! She kept us updated along with photos of our pups and handled medications and feedings schedules with ease. This was honestly the first time we didn’t worry while on vacation. When we arrived home, our pups and cats were happy and the house was as clean and tidy as it was when we left. I highly recommend Hailey. She is professional, honest, respectful, reliable and very sweet. Thank you Hailey!

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Jennifer G.
House Sitting
5.0 out of 5 stars

Ari was amazing with my boys. She’s very patient and considerate of each boys ‘ needs. She was great at giving me updates on their activities complete with photos.

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Audrey B.
House Sitting
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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  • Reservation protection

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    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
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Popular requests for house sitting - Winfield

Select a filter and find qualifying sitters offering house sitting.

Sitters in Winfield average 4
repeat house sitting clients

FAQs for House Sitting - Winfield

Frequently asked questions about Rover

As of September 2026, there are 7,966 sitters on Rover offering House Sitting across Winfield. 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 Winfield 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 Winfield 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 Winfield 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 Winfield. On Rover:

  • 91% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% 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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