House Sitting Chesterton
Find a loving house sitter to watch over your pets and your home.
Over 27 pet parents in Chesterton have booked house sitting
Chesterton, 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 absolutely love Holly! She takes great care of our dog Chloe. She is a wonderful communicator. Very dependable. We know Chloe is well taken care of with Holly, and that allows us to relax on vacation without worrying about our dog being stressed because we are not there.”
“We couldn’t be happier with our experience! Alexia went above and beyond to make sure Cinco was comfortable, loved, and well taken care of. Communication was excellent, and it gave us total peace of mind while we were away. We will definitely be using her again!”
“Our Micki took to Kimberly right away. Our dog can always recognize a fellow dog lover. We received many photos and videos while we were away, which made us feel really good. When we got home, Micki was happy and tired from having so much fun. Thank you Kimberly for treating our dog like the queen she is.”
“Katrina was right on time and Duke was well taken care of and sleepy from his walks after spending the afternoon together. Katrina did great with Duke’s stubborn bulldog ways and would definitely recommend her again!”
About: I have always enjoyed spending my time with animals. I got my first dog when I was in elementary school - sadly he recently passed away - but since coming to college I have been missing my sweet fur baby. Being able to play with and care for someone else's pet while also earning extra cash would be an ideal job experience for me. Getting a new pet really isn’t an option for me right now. With all the free time on my hands, and I would love to get the chance to spend it walking and playing with your fur babies! In the past, I have dog sat for other friends and family and I really enjoyed it and having the extra company is always a plus!
“Meredith did a great job with our two dogs, a four year old and a rambunctious four month old, and our 14 year-old cat. She handled our little circus with no issues!”
About: We have always had pets (Mostly Dogs) growing up and have never met a dog or cat that didn't like us. We are the type of people that animals (Fur Babies) just feel at ease with. From the smallest of toy and lap dogs to the much larger Great Danes and Mastiffs. We will always get along, even the dog that nobody can handle and scares them. My patients never wears thin and eventually all, even the most stubborn pet warms up to me. Any pet under our supervision will always be taken care of from walks, to alone time to calm their nerves if need be but NEVER neglected. We truly believe that your Dogs and/or Cats should and will be treated just you would. Thanks, Between my wife and I we are essentially available 24/7. And hope to accommodate any ones schedule. Our routine will be scheduled around whatever is needed We have a full half acre completely fenced in (Wooden privacy fence). And of course whatever it is you and your dogs like enjoy we will accommodate.
About: I’ve had dogs my whole life and love all breeds. We truly don’t deserve them. My soul dog, Abo, passed away 1.5 years ago and I have been watching and walking dogs for extra money ever since. I’m a college professor working a very flexible schedule and I’d love to walk or watch your dog! I live on the east side of Beverly Shores and also have a place in the city 🌆. I’m down to house sit or watch them at my place. I have local references and would love to meet your dog if I haven’t already 😊 I’m teaching part-time this term, so I have plenty of time to walk your dogs, give them some love, tell them they are good dogs, get some fresh air, exercise and sunshine. ☀️ When I board a dog it is all about them! They are basically on vacation having the best time and getting all the attention and affection they want. 🙂
About: Grew up having a dog (or 2 at times…as well as bunnies…and some other reptiles!). I currently live in an accommodation where I am not able to have a pet and I have become to miss animals more and more! There is no such thing as a bad animal, only a poorly trained one, and I treat them all with love and care. I’m available every Sunday, Monday, and Tuesday all day (and night)! My schedule can be as free as needed on those days and I am open to spending lots of time with your pets to make sure they get the best care possible! I am very careful and thoughtful around pets and other people’s property. I will treat your belongings and animals with the utmost respect and care.
About: I have cared for pets since I was 7 years old! I currently share my home with two kitties and three dogs. I also have some experience with smaller animals, I've had three Syrian hamsters in the past and have cared of guinea pigs and rabbits in a shelter setting. I've even cared for pigs, goats, and horses before! For my professional credentials, I've worked in animal care for a combined five years. I have cared for hundreds of animals in animal shelter and veterinary clinic settings. From shy and fearful dogs to feral cats, to kittens and puppies, to senior animals. I have cared for animals that need medications and/or special diets. I have experience with leash and barrier reactive dogs, exuberant canines, and leash biters. I have completed dog handling in a shelter and feral and fractious cat handling courses through Maddie's University. And I've assisted in moderating 10-15+ dogs in play groups before! Through these experiences I've become proficient in understanding animal body language, able to identify a variety of possible health issues, and learned how to best keep animals safe and happy. All in all I believe my varied experiences with animals professionally and personally will allow me to provide great care to your pet! This is my primary source of income at this time! So my schedule is very flexible. Just reach out and we can work something together. I understand that safety is number one with pets! I will always respect your pets' boundaries. And I want to work with you, the pet parent, to understand your pets' habits, preferences, and any allergies or health issues.
About: I am a licensed veterinary assistant and have three years of experience working in a animal clinic. I am able to quickly identify if there may be a problem with your animal while in my care and can take necessary action to ensure they remain safe. I have a open schedule since i am able to start focusing on my love for animals and helping others they may need help caring for their animals The care my own animals get is they are feed once a day and get treats throughout the day and go on walks or play with there toys or unwind and watch tv and I would treat the animals in my care with the same love or however it is their own cares for them
“Grace took great care of our cats. She took lots of really nice pictures and sent them to us and was super responsive whenever I had a question about anything. She left the house in great condition as well. I would highly recommend her for your kitties.”
About: I've grown up around dogs of all shapes and sizes. I have been around everything from a Miniature Poodle to a Great Dane and I pride myself on knowing how to care for all dogs. I do have a full time job, currently. I am in office Mondays and work from home the rest of the week. I can care for furry friends around my 9-5! I will work to ensure all pets are properly leashed, crates, and/or supervised during my time with them. I am excited to work with your pets and their safety is my priority.
About: I've cared for pets for nearly 20 years. I'm comfortable with dogs and cats of every size and temperament, including seniors and pets with special needs. I can give medications and handle multiple animals at once. As a therapist, I bring patience and a calm presence that helps anxious animals settle in. I work remotely and rarely need to go into the office, so I'm home with your pets for most of the day. That means plenty of attention, regular walks and playtime, and steady routines. I'm available for overnight stays, longer house sits and daytime drop-ins throughout the week. I have my own car and can get to you reliably. I care for your pets in your own home, so they stay comfortable in familiar surroundings. I follow your routines for feeding, walks, medications and bedtime. I keep doors and gates secure, store food and cleaning products out of reach, and watch for any changes in health or behaviour. I send updates and photos, and I'll contact you or your vet right away if anything seems off.
“Diane is amazing! Our dog Juni is really tough. She's petrified of strangers and sometimes nips. She's very slow to warm up and sometimes won't even let sitters let her outside. There have been times when she boycotted eating for days, and even when we have family watch her, she's often sick for days after we get back because of stress. Diane worked with Juni and treated her with kindness, patience, and understanding. She gave her space and even did some emotion/body coding work with her which I thought was really cool. She treated our house with respect and we returned to it spotless. I felt very safe and comfortable having her stay in our home, and I think Juni did too. She was in great spirits when we got back and she even had a great few days of eating, no stress sickness. We so appreciate Diane's willingness to work with her! In addition, she was very communicative and thorough when it came to the details/logistics of the stay, and came by in advance to meet us and Juni. I would recommend Diane to anyone.”
About: Hi! I’m Elizabeth, a lifelong animal lover and proud dog mom to a miniature dachshund! I’ve grown up with dogs my entire life, so caring for them has always been a big part of who I am. I know how important it is to have someone you trust looking after your furry family members. Whether it’s going for walks, playing, giving lots of cuddles, or simply keeping them company, I’ll make sure your pet feels happy, comfortable, and loved while you’re away. I love getting to know each dog’s unique personality and will always treat your pets like they’re my own. I can’t wait to meet your furry best friend! Currently I have my own dog so pet care is already part of my daily routine! We have a routine when I’m wth of a morning afternoon and nightly walk in Lincoln park! As a lifelong dog owner, I understand how important it is to trust your pet’s caregiver. I provide reliable, personalized care tailored to each dog’s personality, routine, and needs, always prioritizing their safety, comfort, and happiness. I’ll follow your instructions, maintain their routine, and share regular updates and photos so you can feel confident they’re in good hands.
“It was our first time using Rover and Bethanie did an amazing job watching our 3 dogs. She was great at communicating with us during our trip and sending pics of our dogs. She also left our home very clean! We would definitely recommend Bethanie and hire her again!”
“Marty has watched my 2 pups twice now and has been amazing each time. For reference one is a senior dog who is very fragile and the other is a rambunctious, playful 5 year old. Throughout his stays, Marty is communicative, he’s polite, and my pups absolutely love him! We will continue using his services for as long as he provides them. Thanks so much for taking care of Joy and Ace, Marty.”
About: I have 2 small cavapoo dogs I have more than 14 years experience of taking care of my 2 dogs and my in laws dogs. We play, go for walks and feed them every day! I currently have a part time job so I have plenty of time to care for your dog. I love meeting new furry friends! I will take care of your dog as if they were my own. I have a fenced in yard and 2 friendly dogs and can easily crate your dog. I love talking them for walks and playing games. Some dogs even like watching movies with me.
The median cost per night for house sitting in Chesterton is $50
Pet parents share their Rover experiences - Chesterton
Lexi was absolutely wonderful! She watched our two dogs and two cats for a full week, and we couldn't be happier. Not only were the animals happy and healthy when we returned, but she also kept the house incredibly tidy. It was such a treat to come home to a clean space and relaxed pets. She kept us updated and was sure to send cute pictures of everyone all week. Highly recommend!
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. 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
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for house sitting - Chesterton
Select a filter and find qualifying sitters offering house sitting.Sitters in Chesterton average 4 repeat house sitting clients
FAQs for House Sitting - Chesterton
Frequently asked questions about Rover
The average cost of House Sitting in Chesterton is $56 per night as of November 2026. Most bookings cost between $27 and $95 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 649 sitters on Rover offering House Sitting across Chesterton. 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 Chesterton 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 Chesterton 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 Chesterton 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 Chesterton. On Rover:
- 87% of sitters can help with special care needs
- 93% 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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