House Sitting Chestnut Hill
Find a loving house sitter to watch over your pets and your home.
Over 206 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.
“I had an out of state house buying trip planned and my boxer randomly got kennel cough and was on medication. So, no kennel for him! I found Kiara on Rover and took a chance. Although I was a little nervous about the idea of someone I don’t know in my house, Kiara worked out perfectly! She kept in regular contact with pictures of Roscoe and what they were doing. She took great care of him, gave his meds as requested, and was a great companion for him during my absence for 5 nights. Oh, and she was a great house sitter as well (she spent the nights here too) I’d recommend Kiara! 5 ⭐️”
“Sarah did an amazing job. I am extremely overprotective and type A about my pets and their schedule and she was amazing. She gave my pets a ton of affection, she administered their medications, she maintained our tidy home and we came home to happy pets and a clean living space, and she sent daily updates with pictures and videos like she said she would. She arrived on time and left at the planned time. We would absolutely hire Sarah again. Our dog is actually searching for her!”
“Ada house sat my dog who was both diabetic and recovering from bronchitis which required shots and other medications twice a day. She not only cared for MMO’s medical needs but provided emotional support for him in my absence. She sent pictures and conducted a River video chat with me to ensure not only Momo’s emotional support but for mine as well. I felt confident my beloved pet was in good hands.”
“Margot is awesome. She watched my dog for an overnight stay. She was trustworthy, communicative, and sent update pics every so often. Reliable sitter. Will definitely consider her for future stays.”
“Jennifer was awesome! She took excellent care of our two dogs, Kona and Milo, while we were out of town. She was very friendly and sent frequent updates letting us know how the dogs were doing. We highly recommend her!”
“Allison did a great job housesitting with my cat Annie! She gave her lots of attention and sent me daily updates and pictures/videos. I would recommend Allison and book with her again.”
“Helena was everything we hoped for in a dog and house sitter. I appreciate so much all of the photos, the detailed updates on their time together, and how proactive Helena was with communicating. We cannot wait to be her repeat clients. If you want someone that you can trust that your dog will quickly be obsessed with, look no further. Seriously, thank you so much, Helena!”
“This is the first time we left our puppy at home. Dianne exceeded our expectations , she is a fantastic pet sitter! We highly recommend her. She is reliable and kind. Also sent us a lot of pictures.”
“Randi and family took such good care of our pups (even when they were acting so needy!) while we were gone. Bad weather delayed us a several hours but Randi worked with us to make sure we were covered. Thanks Randi!”
“Thank you Marissa! Figgy was well cared for and were so thankful to be able to leave her at home instead of at a kennel. Marissa left the house spotless and was extremely flexible when our plans changed.”
“Oli was FANTASTIC to work with! She kept us updated throughout the weekend and shared adorable pics. It created such peace of mind that our dog was in great hands and allowed us enjoy our time away. I would highly recommend Oli and we plan to work with her again in the future!”
“Janet was amazing with our anxious pup, and we cannot thank her enough. She gave our pup space and time to adjust without pressure; she also gave us regular updates and reassurance.”
“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!”
“Sarah was absolutely amazing. We are so glad we found her. She sent lots of photos, stayed in touch with us the whole time and even washed the sheets and blankets from the guest room she stayed in! We look forward to her taking such good care of our pup again for our son’s wedding. It is such a relief to know your precious animals are in good hands. Judging from the way Zeus was looking at her in the photos he can’t wait either! 🐾”
“Tiffany was amazing! In the beginning I was very nervous because I have never left my pet babies with anyone. I usually travel with them. I was kind of paranoid at first. I know I was difficult. Not intentionally, but my pet babies are family. Tiffany had such grace and professionalism. My dogs loved her! Also, my flight was delayed for a day and Tiffany even checked on them the next day, which was outside of the period she was hired. She is a sweet heart, patient, and loves animals. I must emphasize patient because in the beginning I was a helicopter Mom. Anyone would be blessed to have her as a pet sitter. Her professionalism was top notch!”
“Jocelyn is the dog whisperer … one of our dogs is skittish around strangers but she quickly became trusted and loved by both dogs. Great with my birdies too! Really appreciated the photo updates she sends. Can’t wait to use her again in a couple weeks!!!”
“We had an amazing experience with Allyson! From the start, she was communicative, reliable, and clearly cared about our two dogs' well-being. Both pups were so well taken care of, and we loved receiving updates and pictures while we were away. It gave us such peace of mind knowing they were in great hands. We’ll definitely be booking with Allyson again and highly recommend her to anyone looking for a trustworthy and caring pet sitter!”
The median cost per night for house sitting in Chestnut Hill is $50
Pet parents share their Rover experiences - Chestnut Hill
Rebooked Christell and it was a great experience again! She sent lots of photos throughout the day and made sure both of my cats received their meds and food on time and were well taken care of! My scaredy-cat seems to really have taken to her as well, which is always heart-warming to see!
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!
Michelle was wonderful! She went over and above taking great care of our pups! The house was perfect when we got home, too, which an always a plus! She sent many pictures of the pups so we knew they were always happy and very well taken care of! I just wish there were more stars to give her!!
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 - 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 for House Sitting in Chestnut Hill on Rover is $58.83 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 1,426 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.
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 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 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 Hill. On Rover:
- 94% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 98% 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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