House Sitting Winfield

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

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Over 2
pet parents in Winfield have booked house sitting

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.

1 / 1
Sitter Profile Image: Lora M.
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Lora M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
133 reviews
35 repeat clients
22 years of experience
Finksburg, MD, 21048

Lora is amazing! Very active with communication and attentive towards our puppies. We highly recommend her to anyone looking for great care for their dog when going away.

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

Kerri always does amazing with our girl. She is a timid and nervous dog, but Kerri stayed with her a few days and was so patient. Rose really opened up to her throughout their time together and we could not be more grateful. She always does an amazing job at keeping our house tidy while she stays. She always goes above and beyond!

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

Amber is a true miracle worker and our dog sitting unicorn 🦄 She’s patient, kind, and so understanding with our FOUR older, adoptive, stubborn angels and is the sole reason we are able to take much needed weekends away!

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Jessica B.
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

Hailey took very good care of our cat for almost a week house sitting, We were happy to see our home and cat very happy once we returned! She was very responsive, we would have loved more updates but were very happy with the service she provided. We could see our cat got along with her very well

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Anirudh B.
Sitter Profile Image: Layla K.
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Layla K.
from
$60
per night
5.0 out of 5 stars
9 reviews
1 repeat client
5 years of experience
woodbine, MD, 21797

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

Hannah took care of our 2 small dogs in our home while we were out of town. She kept us updated daily and sent photos. Hannah did a great job and we would highly recommend!

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Donna L.
Sitter Profile Image: Nora A.
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Nora A.
from
$70
per night
5.0 out of 5 stars
22 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: Riley K.
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Riley K.
Star Sitter
from
$34
per night
4.9 out of 5 stars
16 reviews
8 repeat clients
6 years of experience
Owings Mills, MD, 21117

If you’re looking for a great pet/house sitter, Riley is your person. Riley took great care of my pup and fish, checked in daily with me, sent photos and provided daily walks each day. At the end of the stay, Riley summarized Toby’s week, including highlights and household things she did on a sheet of paper. Riley is very reliable and I’ll definitely book her again in the future.

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Bess B.
Sitter Profile Image: Kenneth P.
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Kenneth P.
Star Sitter
from
$45
per night
5.0 out of 5 stars
250 reviews
73 repeat clients
24 years of experience
Germantown, MD, 20874

Ken is awesome. He watched our pup (Wally) for 3 days and in that time, we got lots of pictures and updates. We feel so thankful that Wally can stay comfortable and taken care of at home while we're away.

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Sarah Elizabeth And Paul O.
Sitter Profile Image: Eden H.
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Eden H.
Star Sitter
from
$31
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
5 years of experience
Sykesville, MD, 21784

Eden was fantastic with our older English bulldog! She was reliable, punctual, and took such great care of her. We felt completely at ease knowing our pup was in good hands. I would absolutely recommend Eden and will definitely be using her again in the future. Thank you, Eden!

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Kayla D.
Sitter Profile Image: Samantha R.
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Samantha R.
Star Sitter
from
$40
per night
5.0 out of 5 stars
32 reviews
12 repeat clients
15 years of experience
Halethorpe, MD, 21227

Samantha has cared for our dog (and home) twice now. Again we returned home to a happy pup and clean home. Samantha kept us informed and sent photos, and I wholeheartedly recommend her.

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Deb K.
Sitter Profile Image: Bronte B.
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Bronte B.
Star Sitter
from
$72
per night
5.0 out of 5 stars
197 reviews
57 repeat clients
15 years of experience
Pikesville, MD, 21208

Bronte was WONDERFUL. We had a bit of a situation with a raccoon and our dog while outside in our fenced yard. Raccoon was looking to have our dog as a meal but Bronte was able to get the dog inside safely and alerted us immediately. Bronte was very patient and loving with our dog, will definitely call upon her again.

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Laura G. C.
Sitter Profile Image: Laurie G.
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Laurie G.
Star Sitter
from
$85
per night
4.9 out of 5 stars
33 reviews
15 repeat clients
9 years of experience
Frederick, MD, 21702

We happily had Laurie spend a long weekend with our 2 dogs at our house and everything was great! She sent lots of photos of the dogs and they seemed very much like they enjoyed themselves. She even got my picky dog to eat. Respectful with the house and we returned to happy dogs and a clean house.

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Natalie S.
Sitter Profile Image: Jeffrey G.
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Jeffrey G.
Star Sitter
from
$54
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
25 years of experience
Baltimore, MD, 21212

Jeff was absolutely wonderful! He took such good care of Hazel and our home while we were away. He is an excellent communicator and just an all around good human. I would recommend Jeff any day of the week and will definitely book him again.

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Rachel R.
Sitter Profile Image: Kaila M.
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Kaila M.
from
$60
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
9 years of experience
Frederick, MD, 21702

Kaila was amazing!! She took care of my German Shepherd while I was away for the weekend. She kept me updated the whole time and I’m so grateful she took such a good care of my baby!

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Francis M.
Sitter Profile Image: Keira J.
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Keira J.
Star Sitter
from
$55
per night
5.0 out of 5 stars
13 reviews
6 repeat clients
3 years of experience
Woodlawn, MD, 21244

Keira was great with our old pup Toby while we were out of town. She was knowledgeable about care and Toby was in great hands. She gave updates and photos throughout the stay.

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Morgan G.
Sitter Profile Image: Katharine D.
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Katharine D.
from
$56
per night
5.0 out of 5 stars
2 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: Mabelyn M.
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Mabelyn M.
from
$95
per night
5.0 out of 5 stars
53 reviews
17 repeat clients
5 years of experience
Germantown, MD, 20876

We were so pleased to have had Mabelyn stay at our home to watch our highly anxious dog, Kima, for the weekend. Mabelyn kept in touch with us to let us know how Kima was doing. Mabelyn understood exactly what Kima needed and worked to gain Kima’s trust. I would Highly recommend Mabelyn and we will definitely call her again!

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Virginia F.
Sitter Profile Image: Danielle B.
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Danielle B.
from
$55
per night
5.0 out of 5 stars
5 reviews
1 repeat client
13 years of experience
Mount airy, MD, 21771

Danielle took good care of our little crew when we were gone for several days. We will definitely use her again!

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Amy S.
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The median cost per night for house sitting in Winfield is $50

Pet parents share their Rover experiences - Winfield

1 / 1
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
5.0 out of 5 stars

Nadia stayed at our house with our dogs and was great! Super easy to communicate with and our dogs loved her. Would highly recommend using her for pet sitting!

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Lauren A.
House Sitting
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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

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 August 2026, there are 8,013 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
  • 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.

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