House Sitting Chesterfield
Find a loving house sitter to watch over your pets and your home.
Over 17 pet parents in Chesterfield have booked house sitting
Chesterfield, 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.
“Mila was wonderful with our senior dog, 2 cats and a bird for a weekend housesit. She was super sweet and all of my guys took to her right away. Awesome communication and sent lots of cute pics!”
“Ben took great care of our sweet but shy Niela-Phyu, a 75lbs female Great Pyrenees for 10 days at our house. We came back to a happy, obviously often brushed dog in a clean house (which is a challenge with a shedding dog in summer and well watered garden). Notes on walks, events (tick removal ;) - thx) etc on top of many updates awaited us on return. Can only highly recommend Ben and thank you again for an amazing job.”
“What a dear person. Nadine is a natural with knowledge and a love of animals. She showed great judgement, and was kind enough to let me know when our cat was in for the night. She was thoughtful, and clearly is great with animals. Our cat was thoroughly in love.”
“I 100% recommend Kathleen! She really saved us! Our pet sitter canceled the morning we were supposed to leave for a seven-day vacation. I posted a job on Rover and she responded immediately, and very kindly stepped in to help, even though she had just finished another pet sitting gig. She took care of our beloved older dog, Dewey and our nine chickens. She was thoughtful, loving, reliable, and responsible. She texted with us almost daily, which we had asked her to do, and which set our minds at ease. She went above and beyond by giving our chickens daily treats and giving our dog LOTS of love. She is warm, respectful, and a good communicator. She also left the house in immaculate condition--in some ways cleaner than we left it. An ideal house and pet sitter in every way!!”
“Kiersten is very easy to communicate with and took great care of my dog, Luna. She sent me lots of pictures of their time together and was very flexible when our plans changed. I would definitely hire her again.”
About: Dogs are always a joy to play with and be with, they bring joy and happiness! And always make my mood better. Dogs are the best! I’ve walked dogs and fed them at certain times with certain medication too. I can do daytime trips for dogs or sitting, I love to walk dogs and I also love to play with them. It’s a very enjoyable time, I have 3 dogs of my own and I always take them on walks near my home. I make sure to always keep them in an area that’s controlled, I give them enough space to run around and do there business but I also make sure there behaving and not doing anything that’s not good.
About: I've taken care of big dogs, small dogs, in between dogs. I've taken care of young kitties, mature kitties, and elder kitties. They all were adored by me. I currently work remotely, so I have plenty of time to be present for the needs of those I'm caring for. Working this way allows for a more spacious and flexible day and week. I am easily adaptable and can work within the needs of the homes I visit. Every home and every care situation is unique and requires fluidity.
About: I have taken care of many animals, from aquatic to a variety furry friends. I am always willing to offer a hand in any kind of care or training that is needed to be kept up while their humans are away so that you can be sure the critters are getting the best care and love while you’re away. Hello! A little about me, I am an all around animal lover! Every morning and night our 3 girls go on long walks and every afternoon we set time aside specifically for playtime. Going to lakes in the summer and fall is one of their favorite activities, especially if we are going out on a boat! I have 3 female dogs, both very friendly. We have an underground fence, though I would keep your fur baby on a leash when we go outside. We have a nice yard, about half an acre, live near a stream and love taking walks around the neighborhood.
About: I have Joyfully shared my entire life with pets for 70 years now!! I speak Fluent Feline and Canine and have been a pet parent to dogs, cats, hamsters, mice, turtles and fish as a child and provided daycare for birds. I am also a Certified Level ll Reiki Energy Practitioner. My services include Housesitting, Drop-ins and both dog and cat walking! My beloved Josie used to love going outside on a harness and leash since she and brother Shadow were feral-born barn kitties and then “indoor only” rescue pets for 15+ years! My “Platinum Spa” Services include pet massage and Reiki sessions for an additional fee for Housesitting and Drop In clients. My Passion to care for other people’s pets as a new career/business stems from the tragic loss of both my feline companions at the end of 2024. I have decided to no longer own pets myself and to get my “Pet Love Fixes” by Pampering My Client’s pets as if they were my own!! I have maximum flexibility with scheduling 24/7 for all services in the 5 Colleges Area of Western MA. I am also available to travel outside my local area to provide pet, plant and housesitting services upon request. I provide a full menu of services at client’s homes including multiple walks daily on leash, outings to local dog parks and hiking trails, specialized diets and medications, senior and disabled pet care, active playtime, basic training reinforcement, photos and text updates on how your pet is doing with each visit. My exclusive pet massage and Reiki treatments can enhance your pet’s health and happiness under my care!!
“Julie was amazingly flexible, as our schedule was unknown, and was there when we needed her. More importantly, she was good with Ricky, took him out for walks as well as for his sanitary needs, and kept us regularly informed, with pictures. If we are in the area again we will seek her to assist us, and Ricky, again.”
“Bri was the perfect fit for our energetic dog. She provided updates and pictures while we were away. It put our minds at ease knowing she was taking such great care of our dog. I would definitely book with her again!”
About: I have taken care of dogs since I was in elementary school. I would pet sit for friends and neighbors, along with work at vets office for a few years in college. I currently have a black lab named York with my partner. I work an 8-4 job Monday thru Friday, so I am available for early morning, afternoon, and evening check ins. Along with overnights and weekend availability. My focus is to treat your pet like they are my own. Which means good play time and making sure they get their meals on time. I am able to do walks, handle administration of medications, dietary requirements.
About: We have two black labs, Claire and Ivy, and we dote on them! I’m the go-to friend in my community when people need dog sitters and my whole family falls in love with every dog we’ve cared for. Currently I’m a stay at home mom with two almost adult children under my roof. We have ample time freedom to play with your doggies! We live off grid on 39 acres with many trails on and around our property. We love to go for long walks with our girls to get the sillies out!
The median cost per night for house sitting in Chesterfield is $60
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 - Chesterfield
Select a filter and find qualifying sitters offering house sitting.Sitters in Chesterfield average 3 repeat house sitting clients
FAQs for House Sitting - Chesterfield
Frequently asked questions about Rover
The average cost of House Sitting in Chesterfield is $23 per night as of October 2026. Most bookings cost between $21 and $33 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 October 2026, there are 235 sitters on Rover offering House Sitting across Chesterfield. 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 Chesterfield 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 Chesterfield 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 Chesterfield 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 , 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 .
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 .
sitters on Rover set their own , 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 Chesterfield. On Rover:
- 89% of sitters can help with special care needs
- 92% can help with giving oral medications or injections
- 94% 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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