House Sitting Chestnut Grove
Find a loving house sitter to watch over your pets and your home.
Over 10 pet parents in Chestnut Grove have booked house sitting
Chestnut Grove, 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.
“Danielle was simply amazing. We received tons of photos and updates throughout the week. She quickly communicated when she had questions and was quick to implement any suggestions. Our girl is so shy and has some trouble on day one adjusting to new sitters- Danielle was so patient and kind with our girl and she was back to her silly, snuggly and fun self in no time! We hope to rebook in the future!”
“Maddie was absolutely awesome! She was super quick to respond and sent us lots of pics while we were away. She also left our house in great condition and Winnie was so happy when we got back! We definitely recommend her! 😊”
“Rosey did an awesome job housesitting our three large, energetic dogs for five days. She has sat for us in the past, and we have always had great experiences. Our dogs love her!”
“Always on time and ready to play! Nathan treats our active fur babies as his own! We never have to worry when Nathan is on the job! He is fine juggling 2 pups with different temperament’s/ keeping them safe and happy!”
“Definitely all 5 stars for Lissette! She stayed in our home with our two dogs for a few days, and we could not have been happier. Lissette is a delight. Conscientious, enthusiastic, and showed lots of love to our pets. She went above and beyond with lots of walks in the neighborhood, lots of playtime in the backyard, and caring for our home. Great communication, too. A real superstar!”
“Dakota did an amazing job taking care of our dog for the entire weekend! Our dog has lots of medication and diet needs, and Dakota handled that with no issues! We returned to a very happy pup!”
About: I’ve grownup with family dogs my whole life. When I was 13 I started a small dog walking business around my neighborhood. When I was 16 I got my own dog who became my best friend. When I was 18 I did an internship at a dog boarding place. I’ve had experience with all kinds of doggy personalities and can’t wait to get to know your pup! I have my own pitbull mixed dog named Coco who I care for daily. We go on adventures outside and spend a lot of time cuddling. She is the most important thing to me in the world. I care deeply for animals and I take the time to get to know each animal individually because making them feel loved and safe is my main goal. I am able to bathe, give medication, etc.. if needed. I am very comfortable with all aspects of dog care.
“Anna was great and our puppy Dot loves her! Anna followed our instructions we left for Dot and was very attentive. She read into Dots needs very well. We are very grateful to have Anna in our lives and have already rebooked with her! Thank you Anna!”
“Bryn was great! My pets can both be shy and slow to warm up to people, and they loved her! Both Piper and Beckett ended up snuggling with her while she stayed with them. I appreciated that she stayed overnight with them, left my apartment as clean as it was when she arrived, and even took my trash out for me. Thanks, Bryn!”
“Tiffanie was great. Even though last minute, she came to meet the dogs before her stay. She took great care of them, sent lots of pictures, was very communicative-commenting on each dog’s personality so you know that she’s spending time with them, and left our house in perfect condition.”
“Ashley was great! She let me know when she arrived and how Buster greeted her. She kept Buster company for several hours during my longer than usual work day— preventing him from getting too anxious about being alone. You can tell Ashley is a true animal lover as well as being very conscientious and reliable. Will definitely reach out to her again for dog sitting!”
“My fiancée and I feel like we’ve hit the jackpot after adding Abi to our lives! She came to our home before our trip to meet us and our girls, ask plenty of questions, and see how the dogs responded to her presence. She is warm and patient, and even our super anxious/epileptic dog took to her quickly (a rare occurrence). She was meticulous in reviewing our care instructions for our needy crew (two dogs on several meds). She texted us pictures while we were away, asked follow up questions, and truly put our minds at ease seeing how much she cared for our girls. We can’t thank her enough for the ways she impressed us, and hope to have her return soon!”
“Our first time using River and I’ve never felt more comfortable with Caroline at our house with our two deaf dogs. She communicated well and sent lots of pictures which was appreciated!”
“Megan was spectacular, stepping in with very short notice to dog sit my puppy for a week when my original sitter canceled a few days before I left. She took very good care of my dog a provided some very cute photos of the fun they were having”
About: when you choose me as your pet sitter, you have nothing to worry about. I care for all pets as if they're my own. I live in an apartment and I'm currently only available to do boarding with one dogs but will consider two if they are bonded pair. before any boarding or housesitting services confirmed, I require we meet in person to ensure all the details are understood and that your dogs are OK with my dog. I have a 30 pound beagle mix named Daisy who is three years old and she will be with me at all times. I am always available for drop in visits and dog walking. prices fluctuate due to various factors but the main ones these days are gas prices and distance of travel. I.e The farther away you are the more likely there is that a added fee will occur before confirmation of service. I provide pet care in services full-time as of November 2021. I am available at any time if you need me. i'm currently available for the following services: housesitting, pet boarding, drop in visit, dog walking for 30 minutes or 60 minutes, and one on one dog training. if your dog is with me, I live in a neighborhood that is very dog friendly. We have two dog parks and I am often at these dog parks at least once a day. However if you have a dog that is not comfortable with that I would not take them there. I would focus on other activities that are more suited to your pet. I also take a lot of pictures and I am constantly in contact with you so you don't have to worry where or what we're doing. I currently work as a therapist with an office in the Madison area, right next to the plow and hearth. My schedule is pretty flexible and it changes weekly as my client needs change. I am almost always around, that makes me a great person for any last minute bookings needed. Your pet’s safety and comfort are always my top priorities. In my home, I provide a calm, pet-friendly environment with plenty of affection, daily walks, and playtime tailored to your pet’s needs. I keep the space clean, secure, and low-stress, with my own well-behaved dog Daisy as a companion if your pet is comfortable. When staying in your home, I’m respectful of your space and your pet’s routine. I follow all instructions closely, maintain regular updates, and work to ensure your pet feels safe and cared for in their familiar environment. I aim to build trust with both pets and their people every step of the way.
“Madelyn did a fantastic job taking care of my two dogs, two cats, and house during a recent overnight trip, and I can recommend her without reservation. It was my first time using Rover so I wasn't quite sure what to expect, but Madelyn made it super easy. She is responsible, enthusiastic, and communicative, and it's clear she loves animals. And judging from the pics she sent, the animals had a wonderful time!”
“Definitely one of my favorite pet sitters that I have worked with since using Rover. Communicated really well throughout the stay. I got lots of picture updates. With the weather changing, he had no issue putting both dogs in sweaters. I felt so confident that they were receiving the best care possible.”
“Emil was very accommodating and kind. He communicates very well. Our dog, Zeus, did very well at his home. He seemed to like Emil and had no issues. Thanks again for being available on short notice!”
The median cost per night for house sitting in Chestnut Grove is $50
Pet parents share their Rover experiences - Chestnut Grove
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?
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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. Search
Browse profiles of sitters near you who offer house sitting
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Popular requests for house sitting - Chestnut Grove
Select a filter and find qualifying sitters offering house sitting.Sitters in Chestnut Grove average 4 repeat house sitting clients
FAQs for House Sitting - Chestnut Grove
Frequently asked questions about Rover
The average cost for House Sitting in Chestnut Grove on Rover is $27.75 per night (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of August 2026, there are 494 sitters on Rover offering House Sitting across Chestnut Grove. 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 Chestnut Grove 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 Chestnut Grove 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 Chestnut Grove 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 Chestnut Grove. On Rover:
- 100% of sitters can help with special care needs
- 100% 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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