House Sitting Chesterfield
Find a loving house sitter to watch over your pets and your home.
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!”
“I'm so lucky to have found Ami. She was caring, my puppy loves her from the start. I felt very comfortable leaving my dog in her care. She was also very punctual and sent constant updates and great pictures.”
“Elias did a wonderful job with Birdy. We are so happy to have found Elias. The house was neat as a pin. Birdy was well cared for. She had an immediate connection with Elias.”
About: I have over 10 years of pet care experience including walks, overnight stays, and short visits. I also grew up with dogs and have lived with a few different cats in my adult life. I am new to the Rover app but am happy to provide references upon request. I work Monday-Friday 11-5 in Brattleboro. I can do overnights any day of the week, but just know that on these days I will be away for 6-7 hours depending on distance from your house. I love taking dogs on long walks and can do so 2-3 times a day. I am super communicative and experienced at house sitting while pet sitting. I am very respectful of people's homes and pets' routines. I will make sure to keep your house as clean - and your pet as happy - as you left them.
“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.”
“Hayley is AMAZING!! One of my cats is very social and the other is shy. She got BOTH of them playing, brushed them, and made sure they knew they were loved on top of the bare minimum of feeding them and giving my old lady her meds. She even checked to make sure my hamster was still breathing while I was away since it was always during my hamster’s sleep time that she was there. Highly recommend. Will be using again if I ever am going away and she is available”
About: I have been working as a veterinary assistant for 3 1/2 years. I am experienced in giving oral and injectable medications. I love dogs and cats of any size! I currently work 3 1/2 days a week and I’m doing pet care on my days off. I love spending my time meeting and taking care of new pets! I treat every pet like they are my own. I always send updates to the pet parents throughout my visits so everyone can be stress free!
“Louisa was absolutely fantastic. She sent daily pictures of our cat, fed him at his scheduled feeding times, and even replaced one of our flimsy keys for us. We returned to a very happy kitty and a very clean home. Thanks Louisa! We will definitely try to book you during our extended trips out of town.”
“We had a great experience with Lori house sitting our American Bully & Pit mix. Lori asked questions ahead of time, reviewed our instructions, and sent us text and photo updates. We couldn't have asked for anything more. We really appreciated all of her communication.”
“Everything went smoothly. The dogs warmed to Stephanie really quickly, even Callie who is shy and usually takes a while to win over. They had lots of walks and cuddle time, just what they love!”
“Grace was fantastic! She was warm, bubbly, and instantly connected with our dogs—they were snuggling with her before we even left the garage. She was incredibly flexible and kept us updated with pictures throughout the stay. She gave us so much peace of mind, especially with our 14-year-old senior dog. We’d love to have her back anytime!”
“Kendra watched our two senior dogs and house sat for us for a little over a week while we traveled out of state to visit family. She sent regular updates with photos and videos, took care of everything, and when we came back dogs were in excellent spirits and the house was as clean as we left it (possibly cleaner). Would use her again in a heartbeat.”
“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.”
About: Throughout my whole life there have been multiple dogs in my family. I have had my own dog before, and trained her from eight weeks old. Also, I have dog/house sat for dogs of friends and family over the years! I work in the schools so I am looking to pick up a side hustle while on summer break! I’m looking forward to a flexible schedule that incorporates my love for dogs and walking, it’s a two for one! I am very flexible and will do whatever you and your dog needs to be happy and healthy! I know what it is like to have a fur baby so I get what it’s like to do the best for them:) I am also an active person so I am able to meet the variety of needs for any dog!
“Michael was great watching Bonnie while we were out of town! He took great care of her and provided updates each day. The house was perfect when we got back and Bonnie was so chill. Will definitely be reaching out for his help again!”
“Yes, yes, Karen took great care of our pet, Cinder, and our home while she was here. Easy communicator, responsible, and kind. I am so glad to have found Karen and look forward to calling on her again!”
About: i’ve taken care of dogs and cats, senior dogs, administered meds, plants, and kept in constant contact with owners even if it is just to send pics or videos saying hi to their pets :) i am able to stay at your place of residence and not disrupt your pets established routines and so they feel safe and comfortable even with someone new taking care of them i don’t mind different levels of checking in with me. i have had people not want to be bothered on vacation just leave me local emergency numbers all the way to some clients wanting short videos of our walks and facetimes to say hi to their dogs.
About: I’ve been caring for pets for over 35 years, and I just love it! I have to travel for work which means I can’t have my own right now, so looking after others is a true joy. I naturally treat every animal as if they were my own — and making sure they feel secure, loved, and happy while their parents are away. With every sit, I bring both reliability and heart. Over the years I’ve cared for dogs, cats, parrots, chickens, and more — each with their own unique personalities and quirks. I’ve played with energetic puppies who needed training and adventure, given gentle support and patience to sweet seniors, reassured nervous or shy animals with steady routines & space, and comforted sick or elderly pets in their final days. One of the most important lesson I learnt came from my own senior dog, who had arthritis. Beyond medication, what mattered most were the little things. I could see from her body language that her favorite time of day was simply sitting together in the sun while I gently massaged her and talked to her. Those quiet moments made her feel safe and deeply loved — and they taught me how much presence and empathy matter in pet care. I work remotely with flexible hours, which means I can spend plenty of time with your pets — for walks, play, belly rubs, or simply quiet companionship so they don’t feel alone. While I’m new to Rover, I’ve been sitting through other platforms where I’ve built excellent reviews and references. Having hosted sitters myself, I also understand the trust (and nerves!) that come with leaving your pets and home in someone else’s care. That’s why I believe clear communication is key, and I’ll always keep you updated with photos, feedback, and check-ins so you can relax knowing your pets are safe, loved, and well cared for. My work is remote so I can be anywhere as long as I have wifi. I only work part-time with flexible hours which gives me the space to adapt to your pets needs & also have the time to for plenty of walks, cuddles & play. When caring for pets in their own home, I make sure their routines stay consistent so they feel secure — from feeding and walks to playtime and rest. I pay close attention to each animal’s signals, balancing structure with the affection, stimulation, or quiet companionship they need. Safety is always a priority. I follow your instructions carefully, ensure food and medications are given correctly, and keep doors, windows, and gates secure. I maintain a calm, clean environment so pets feel relaxed, and I treat every home with the same respect as my own. I’m a naturally tidy person who cleans as I go, so you’ll return to a home that feels just as you left it. Having hosted sitters myself, I fully understand the trust (and nerves!) that come with leaving your pets and home in someone else’s care. That’s why I believe strong communication is key. I’m happy to provide updates, photos, and even video calls as often as you’d like — so you can relax knowing your pets are safe, loved, and well cared for while you’re away.
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.
Meet local sitters who will treat your pets like family
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
As of August 2026, there are 240 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 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 Chesterfield. On Rover:
- 81% of sitters can help with special care needs
- 100% 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.
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