House Sitting Chestnut Hill
Find a loving house sitter to watch over your pets and your home.
Over 220 pet parents in Chestnut Hill have booked house sitting
Chestnut Hill, 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.
“Ada stayed overnight at my house with Bailey. She did an excellent job. Bailey loved her. She walked Bailey in the neighborhood and cuddled with her...No wonder Bailey loves her. She also left my house very nice and clean after staying there for 5 days. I will definitely call her again when Bailey needs a sitter.”
“She took excellent care of Ezra. I liked how she kept me updated on Ezra’s activities, schedule and feedings with plenty of photos. You could tell she really likes pups. I would definitely have Kiara take care of Ezra again.”
“Shanna was an excellent caregiver for dog, Tessa, while we were out of town. She was attentive to our girl’s additional needs, administering medications and care for Tessa’s health issues. Shanna kept us updated throughout the week and was responsive to any questions we had. We highly recommend her!”
About: What sets me apart is the hands-on experience I have caring for dogs with all different personalities, ages, and needs. In addition to having three dogs and two cats of my own, I have fostered dogs through Bullies to the Rescue and volunteer with Richmond Animal Care and Control, where I serve as a Volunteer Adoption Coordinator Assistant and a trained Three Paw dog walker. I am comfortable working with dogs who may have behavioral challenges and have experience with senior and sick dogs who need extra patience, attention, and care. I truly take the time to get to know each pet as an individual and adjust my care to what makes them feel safe, comfortable, and happy. I don't just see pet sitting as a job—I genuinely love animals and treat every pet in my care like they are my own. I work full-time Monday through Friday from 7:00 AM to 3:30 PM in East End Henrico, so pet care fits naturally into my routine before and after work. I am available for brief morning visits before work and have much more flexibility after 3:30 PM for longer walks, drop-in visits, and house sitting. I have open availability on weekends and can be flexible with scheduling. For house sitting, I am also willing to travel outside my normal service area when staying in your home. I take scheduling seriously and will make sure I have enough time to give each pet the attention and care they deserve. I care for every pet as an individual and take the time to learn their routine, personality, and specific needs. In a client's home, I follow their normal schedule as closely as possible so their pets feel comfortable and secure while their family is away. I provide plenty of attention, exercise, playtime, companionship, and love, while also respecting pets who need a little space. I am comfortable caring for senior, sick, special-needs, and behaviorally challenging dogs, as well as cats and kittens. I will follow feeding instructions, medication or special-care directions, and any other routines you provide. Most importantly, I want your pets to feel safe, happy, and cared for—and I want you to have peace of mind knowing they are in good hands.
“Did an excellent job taking care of our pet family while we were away for a few days. Left our home in perfect condition. Took time to come out an visit before the stay, and sent plenty of updates and photos during our time away. Highly recommended.”
“Crystal was AWESOME, and I was so appreciative of her taking my very last minute booking. She was so professional and did such a great job with my dog and my home. I came home to an organization house and a very happy dog. I would definitely hire her again!”
About: I have hands-on experience caring for dogs of all sizes, from young puppies to large breeds, and I’m confident handling a wide range of needs and personalities. I’m comfortable administering medications and following detailed care instructions to make sure every pet stays healthy and safe. I also have experience with basic puppy training, helping reinforce good habits and routines. What sets me apart is my patience and understanding, especially with dogs who have separation anxiety or need extra reassurance. I take the time to make pets feel comfortable, secure, and loved while you’re away. I treat every dog like my own, paying close attention to their behavior, energy level, and individual needs so they get the best care possible. Pet care fits naturally into my daily routine, and I make it a priority to give each pet the time, attention, and consistency they need. My schedule is very flexible, which allows me to accommodate morning, midday, evening, and even last-minute bookings when needed. Whether it's walks, drop-ins, or extended stays, I'm able to adjust my routine to match your pet's schedule and keep things as normal and stress-free as possible for them. I'm reliable, responsive, and committed to being there when you and vour pet need me. In my home, pets are treated like part of the family. I have a spacious three-floor condo that gives dogs plenty of room to move around and feel comfortable. I also have a friendly six-year-old dog who gets along well with other animals, helping visiting pets feel more at ease. My two daughters are gentle and respectful with animals, adding to the loving environment your pet will be in. I live in a great area for walks, so your dog will get plenty of exercise, fresh air, and attention throughout the day. I make sure to follow each pet’s routine as closely as possible, including feeding schedules, walks, playtime, and any special instructions. When caring for pets in a client’s home, I focus on keeping things consistent and stress-free by maintaining their normal routine and environment. My goal is always to make sure your pet feels safe, comfortable, and well cared for while you’re away.
“Le’Yana was amazing ! My first time using the app to book someone to watch my dog and I don’t regret it ! Very sweet women , definitely would be booking her again . Thank you”
“Gracie was so great! She took the best care of our senior pitbull who has lots of needs and separation anxiety. She’s a fantastic communicator, easy to coordinate with, and our Miss Honey loved her time with her. Thank you so much, Gracie! We were able to have the best family vacation knowing our girl was in good hands!”
About: I’m a lifelong dog lover and have cared for dogs throughout all stages of life. My days are flexible and I’m easy to get a hold of, so you can expect your pup to get quality care and attention however they need it! I’m currently in between jobs and grad school, so my days are very open! I am up early and live an active lifestyle, so walks and playtime (and chill time) are more than welcome! I am available to care for your pet at my home or from yours. I do have a 10 year old Westie at home who gets along with others just fine! However if you prefer the individualized attention, I am more than happy to care for your pet from the comfort of their own home.
“Carolyn is a wonderful pet/house sitter. This is the second time she’s taken care of our pup, and both times she did a great job. She’s very responsible and careful. She left our house clean and orderly. We hope to use her again.”
“Melanie was a tremendous choice for housesitting and petsitting! She was communicative, professional, and attentive. I never once worried that my babies weren't getting the care they deserve! HIGHLY recommend!!!!”
About: I've taken care of all kinds of animals since I was 16. Dogs, cats, fish, birds, lizards and a rabbit. I have experience in older animals who need medication multiple times a day. I'm currently working part-time with few hours so I have a very flexible schedule and will have plenty of time to meet the need of you and your pet! I stick to a strict schedule if any kind of medicine is involved. Aside from that I am more laid back in my approach to pet-sitting. I love giving treats and extended play times!
“Meghan was such a pleasure to work with. She gave our senior dog the time and attention he deserved and brought out his playful inner puppy. She was great at communicating and we will definitely rebook with her soon!”
“Celeste was great! They house sat for me and took care for my cats, sent me pictures and made sure they got attention, fed, and cleaned the litter box. Would definitely recommend them!”
“Stephenie stayed with our dogs at our house over the weekend, and she was phenomenal! We received lots of updates and happy pictures of the dogs while we were gone that helped put us at ease knowing the dogs were being well taken care of. Stephanie also maintained their routine and gave them their daily medicines. We are so happy to have met Stephenie and will be booking with her again!”
About: I grew up in a multi-cat household and now own 5 cats between my parents and myself! There's no kitty I can't handle - from super social, to shy, to very sassy, I'm known to be able to form a bond with every cat that comes into my care. I'm also a lover of all animals, I owned fish and lizards and have spent a lot of time helping walk and take care of my family's dogs. My animals are my life, and I've been on Rover for almost four years now! I also have a lot of experience working for Happy Cats Concierge LLC in Reston, VA, where I provided a range of services for cats of various quantities, ages, and personalities. Whether your furry friend needs a playmate, cuddle buddy, bodyguard, or just someone to stop by for food and medicine - I got you! My schedule is open and my day-to-day is flexible! Any specific dates I’m unavailable will be reflected on my calendar. Please message me with any other scheduling questions. Inside, outside, leash or no leash, crate, etc., I will honor the owner's wishes for where their furry friend needs to be spending their time. I value consistent routines and attentiveness while your pet is in my care. All of my services will be based in the client's home or neighborhood.
The median cost per night for house sitting in Chestnut Hill is $50
Pet parents share their Rover experiences - Chestnut Hill
This was our first time using Rover, and we couldn't have had a better experience with Michelle. She was responsive, communicated with us, and sent photos to reassure us that our dogs were doing well. She really went above and beyond to care for our dogs and our home while we were out of town for the weekend. We would highly recommend Michelle for any dog sitting service!
Brevin stepped in on short notice to care for our dog and cat over a long weekend, and we couldn’t be happier with how the sit went. He generously came over beforehand to meet the pets and learn how to give our cat his medication, and he sent us updates and photos each day. Both pets seemed comfortable with him from the get-go, which is huge for us since our cat’s comfort level can really affect how well he accepts his medicine! After a challenging family-related trip, it was such a relief to come home to happy pets and a clean house. We’d happily recommend Brevin and look forward to having him sit for us again!
Sarah was an incredible dog sitter! She was wonderful about responding promptly and sending pictures and daily updates. It’s clear that she truly loves animals. She was punctual, left our home neat and tidy, and, most importantly, we could tell when we returned that our dog had been very well cared for. We would definitely have Sarah sit for our dog again and highly recommend her!
Finneas was awesome! He took care of our 4 dogs while we were out of town, and he did an amazing job. My dogs instantly loved him from the moment he stopped by for the meet and greet, and I knew he was the one! He has such a wonderful way with animals -- and my dogs were so happy with him. Thank you so much! We'll be booking you again!
Ada is absolutely wonderful with my pets. My cat is a little bizarre ands likes to snuggle into and bite people’s hair if he likes them. It’s super weird and most people are intimidated by him because of it, but Ada sends me pictures of him snuggling in her hair and she still loves him. My dog was scared of thunderstorms and shaking and being super extra, but she comforted her and when I got home, they both look happy and well taken care of. She even helped when a leak happened in my house and she moved furniture and dried out the floor. She has gone above and beyond to take exceptional care of them ands I would absolute recommend her to anyone. This is the second time we’ve used her, ands we will definitely hire her in the future. She’s a gem.
Peyton took wonderful care of our dogs while we were away! One of our dogs is diabetic and requires oral medication and insulin injections twice a day, and she handled his care with confidence. She went above and beyond trying to get him to eat when he was being stubborn. We came home to two happy, well cared for dogs and would absolutely book with Peyton again. 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 - Chestnut Hill
Select a filter and find qualifying sitters offering house sitting.Sitters in Chestnut Hill average 4 repeat house sitting clients
FAQs for House Sitting - Chestnut Hill
Frequently asked questions about Rover
The average cost of House Sitting in Chestnut Hill is $59 per night as of October 2026. Most bookings cost between $30 and $80 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 1,429 sitters on Rover offering House Sitting across Chestnut Hill. 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 Hill 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 Hill 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.
<b>Tip:</b> 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 Hill 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 Chestnut Hill. On Rover:
- 91% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 96% 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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