House Sitting Flagg

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Flagg, 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: Laurel M.
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Laurel M.
from
$40
per night
5.0 out of 5 stars
• 13 reviews
6 repeat clients
25 years of experience
Oregon, IL, 61061

“Laurel did an excellent job watching our critters. She is so attentive and communicative. When we returned, everyone was happy, healthy, and seemed like they had a fun weekend! Can’t tell you how much it means to be able to go away without worrying about the fur babies at home. 💕🐾”

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Riley R.
Sitter Profile Image: Vanessa H.
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Vanessa H.
from
$35
per night
5.0 out of 5 stars
• 13 reviews
1 repeat client
15 years of experience
Malta, IL, 60150

“Vanessa has stayed with our two boxers for drop in sessions and now a weekend overnight stay at our house. Vanessa is amazing and always updates us on our pups. She made sure our dogs felt calm and safe during 4th of July fireworks and a few storms. Even with the rain Vanessa was able to provide our dogs with enrichment and play time!”

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Erin & Devin W.
Sitter Profile Image: Sara D.
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Sara D.
from
$55
per night
4.8 out of 5 stars
• 10 reviews
2 repeat clients
12 years of experience
Cortland, IL, 60112

“Sara stayed with our motley crew of critters while we went away for a long weekend. They’re somewhat high maintenance and I left feeling confident they’d be well cared for. Sara provided updates whenever asked and everyone was happy and healthy upon our return! Thanks Sara!”

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Rebecca M.
Sitter Profile Image: Michelle E.
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Michelle E.
from
$65
per night
5.0 out of 5 stars
• 44 reviews
15 repeat clients
42 years of experience
Rockford, IL, 61107

“Michelle was the best house and dog sitter we could have ever asked for. She was incredibly attentive and thorough in every aspect including before her stay with our dogs, during and after! She visited us ahead of time to get to know the boys and make sure we had all the details covered. She kept in contact us while we were away and sent photos and kept very extensive notes that were very helpful to read when we returned from our vacation. She is incredibly knowledgeable about training and different personalities in dogs and I would recommend her to anyone!!!!!! I could tell our boys loved having her and were looking for her for a day or two after she was gone. She’s a great lady and I would recommend her with 10 stars!!!!! She even kept up with the shedding and the house was immaculate! A great lady!!!”

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Shannon J.
Sitter Profile Image: Trisha B.
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Trisha B.
from
$30
per night
15 years of experience
Esmond, IL, 60129

About: I have years of experience caring for dogs from all ages puppy to senior. No two are the same. They are all beautiful in their own ways. I am very flexible and dependable. I have two dogs of my own. And have dog sit for strangers and family alike. Strangers are just friends we haven't met yet. I can offer an array of services from basic drop ins and walks, to feedings and overnight stays at my place or yours. I am flexible and willing to work with you to find the best option.

Sitter Profile Image: Leslie P.
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Leslie P.
from
$28
per night
5.0 out of 5 stars
• 10 reviews
2 repeat clients
30 years of experience
Aurora, IL, 60506

“Leslie went above and beyond caring for moose for a week. She helped in numerous ways to make sure our couch was protected from our over eager puppy and even bought him some new toys! She took care of our house well and was so generously flexible when our ac broke mid trip. She clearly loves dogs and I would highly recommend booking her for sitting!!”

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Michaela V.
Sitter Profile Image: Kira S.
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Kira S.
from
$40
per night
5.0 out of 5 stars
• 1 review
17 years of experience
Rockfalls, IL, 61071

“We are happy to have booked Kira for pet sitting our dogs. We would definitely book with her again.”

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Catherine F.
Sitter Profile Image: Aaliyah C.
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Aaliyah C.
from
$55
per night
5.0 out of 5 stars
• 2 reviews
11 years of experience
Aurora, IL, 60506

“Aaliyah was amazing! She took great care of our house and our dog. We have a nervous guy that got freaked out by the thunderstorms but Aaliyah knew just how to make him feel safe and secure. So glad we booked her and would definitely book her again!”

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Brielle F.
Sitter Profile Image: Stefanie J.
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Stefanie J.
from
$75
per night
4.6 out of 5 stars
• 10 reviews
4 repeat clients
10 years of experience
Freeport, IL, 61032

“Stephanie was great. Kept in touch about our kitty every day and sent photos over text. I highly recommend”

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Ann H.
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The median cost per night for house sitting in Flagg is $50

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 - Flagg

Select a filter and find qualifying sitters offering house sitting.

Sitters in Flagg average 4
repeat house sitting clients

FAQs for House Sitting - Flagg

Frequently asked questions about Rover

As of November 2026, there are 191 sitters on Rover offering House Sitting across Flagg. 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 Flagg 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 Flagg 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 Flagg 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 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 Meet & Greet.

sitters on Rover set their own cancellation policy, 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 Flagg. On Rover:

  • 91% of sitters can help with special care needs
  • 93% 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.


Rover.com is the simple, savvy way to find and book Flagg house sitting. It's easy to find the perfect house sitter — many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Flagg on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Flagg house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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