House Sitting Chestnut Hill
Find a loving house sitter to watch over your pets and your home.
Over 87 pet parents in Chestnut Hill have booked house sitting
Chestnut Hill, Find top rated house sitting
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Wonderful, trustworthy sitter! She stayed in my apartment with my dog Milo for a weekend and everything went great! I appreciated all of the picture updates which gave me peace of mind. She also left my space very neat when she left. I know my fur baby was well taken care of. I will absolutely rebook!”
“Anna was great with Lucy! She was very communicative and flexible. When our flight was canceled she stayed an extra night to watch Lucy. We will definitely be using her as a dog sitter in the future!!”
“Emily was wonderful with our 10mo puppy, giving him attention and providing enrichment throughout the day, taking him on his midday walk and feeding him lunch. We came home to a happy, wriggly, sleepy puppy. Emily also left the sweetest report card and polaroid shot of Kiwi at the end of the day :)”
“K took great care of my puppy! K took time to discuss the sitting arrangement, my pup’s routine, and provided excellent care while I was away. I will surely book again!”
“Victoria stayed at my house for 5 days and cared for my elderly cat, who needs daily medication. She sent frequent updates and photos and took great care of my dear Nanette. She left the house clean and neat. I wouldn't hesitate to book her again and recommend her highly.”
“Priscilla was excellent in every respect. She came to meet us and our dog Annie before staying here. She impressed us with her ability to put Annie at ease immediately, and her level-headedness made us confident about leaving Annie in her company. Priswcilla sent several photos while we were away and gave us reports on how Annie was doing. When we returned, the house was perfectly clean and tidy, not a thing out of place. And Annie was happy and content. So were we.”
“Sabina was wonderful! Made friends with our reactive dog very quickly! She also took care of him during a power outage, and we are so grateful. We came back to a happy and relaxed lil guy!”
“This is the second time Paige has taken care of my senior dog and cat and Paige is just phenomenal. She truly cares about your pet and gives them lots of love and attention! She is quick to respond and gives lots of photo updates which I really appreciate! Thank you so much, Paige! 💖”
“Ailise is awesome! She was flexible with our last minute modifications. She took care of two of our dogs with very different needs and personalities. She took great care of our home while we were away as well. We were a little nervous leaving our dogs for a weekend with a sitter but we couldn't be happier!”
“Anastasia was amazing with my 13-year-old labradoodle. Great communication and the best pics. So nice to have this confidence when I have to leave, knowing my dog is taken care of.”
About: I grew up with dogs and have loved them my whole life. I've dog sat for friends and co-workers, including overnight stays, and always treat your pet and home with the utmost care. I take pride in leaving your home just as clean as I found it while making sure your pet gets plenty of love, attention, and cuddles so that you don't have to worry while you're away. I work remotely Monday-Friday with a flexible schedule that allows me to take breaks to care for your pet and give them lots of love during the day! I am able and willing to travel to you and take great pride in being a considerate, tidy, and responsible houseguest. My goal is to leave your home looking like it did before I arrived!
“Maddie provided a safe loving environment for my little dog, Lucia! She also went beyond just taking care of her by sending me daily updates & photos- which made me very happy since this was the longest I'd ever been away from her. Maddie also helped out with moving cars due to some ongoing street work requiring them to be moved while I was away. Highly recommend her for your dog sitting needs!”
“Thanks so much Daniella for taking care of our dog Aspen and our cat Amari. We appreciated the daily updates, pics, and videos to check in with us and your responsiveness was top notch! We look forward to working with you again in the near future and would recommend you without reservations. Thank you again!💜”
“We can not say enough good about Luis and the care he took of our two pets: Baloo (a 4 year old hound dog) and Soupbelly ( a 8 month ish old kitten). We were out of the country for a little over three weeks in which Luis attended to every need of both pets. In addition to the usual care, he also took Baloo to nearby off leash parks, which is his favorite thing to do. In addition to graciously sharing his bed with both pets he spoiled them with treats and outings and kept us up to date with lots of pictures, which were so appreciated. Being so far away, it was a relief to know our pets were so well cared for and loved in our absence. And last but not least, he took great care of our house which was an added bonus!”
“Elizabeth was so great & easy to work with when we booked her a little last minute to watch our dog. She was super responsive, flexible, and took great care of our Winnie!”
“Kristina was wonderful with our bernadoodle puppy! She gave us a few updates throughout the night, followed all instructions we left regarding her bathroom routine etc and also sent amazing pictures! Will definitely book her again!”
“Cressida was amazing! Lovely to work with and did a terrific job looking after Molly and the house. This was the first time we left our new dog overnight and Cressida kept us up to date with how they were doing, asked questions when she needed things I had forgotten to mention, and it all went great.”
About: I’ve taken care of dogs and cats big little and everything in between! I love going on walks, playing catch, and giving lots of pets and love. I have experience giving medications, and dealing with elderly pets as well as the little kitties and puppies! I currently work as a PCA, and am busy 12-3 on weekdays for the summer. However, my mornings and early evenings are open. I am also free weekends! I am able to stay with your animals while you are away, or check in on them for walks or play time during the day. Whatever you need!
“Kathleen is AMAZING! Not only was she super thorough about getting to know our dogs and home, but she was also so kind and thoughtful during her stay. She sent us updates and pictures, and even cleaned up and washed the guest room items and towels before we arrived home! Her kindness and generosity of spirit make her one of a kind!”
The median cost per night for house sitting in Chestnut Hill is $60
Pet parents share their Rover experiences - Chestnut Hill
J was amazing with our boy Chase. We chose her for her obvious experience with cats and administering meds. She updated us every day with pics and notes and was able to attend to him when his eye condition acted up. We felt so comfortable leaving him in her excellent care. He took to her right away❤️ We will absolutely be contacting her again in the future!!
Eveline did amazing with Tuxy! She was very responsive and kept up communication / updates. Tuxy was super happy when I got home and I could tell he was well taken care of. Also, Eveline was extremely tidy around the apartment and took care of some chores she didn’t have to do - above and beyond!
Bianca was a great dogsitter and housesitter while we were gone for the weekend! She came over beforehand to meet Goose and asked lots of questions to make sure she was fully prepared. We got plenty of updates during the stay, and we felt like Goose was in good hands the entire time.
K is terrific! I came home to happy, well cared for pups and and the house was in great shape too. I like that they checked in regularly and asked questions, like how the dogs do in thunderstorms when a storm was predicted. Very proactive. I'll definitely ask K to look after the dogs again!
We have a very high energy ACD mix and Danielle was amazing with him!! He can be a bit standoffish at first but he quickly took on Danielle (and her dog Moose) as part of his pack. She sent tons of pictures and updates and was incredibly responsive both to our messages and to Griggs’ needs. She went above and beyond to make our dog comfortable and cater to our needs. It’s tough to find a good sitter and we will definitely be reaching out to Danielle again in the future. Also, her dog Moose is so sweet and we were impressed with how he handled and interacted with our rambunctious pup.
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 $82.69 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 6,666 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:
- 92% of sitters can help with special care needs
- 97% 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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