House Sitting Chestnut Hill
Find a loving house sitter to watch over your pets and your home.
Over 90 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%.
“Zilalai was absolutely wonderful with our old german shepherd! She sent tons of photos of their time together and I could tell my girl was having the time of her life with Zilalai. We will absolutely be using her again in the future. Thank you so much Zilalai!!!”
“Kalle was great!!! She was very thorough in her questions to make sure she understood my instruction s since this was her first time. She went above an beyond what was expected. My Cali was looking for her the day after I returned home.”
About: I love animals and get genuine joy from spending time with them. Have experience caring for pets of family and friends, am the go to cat caretaker for numerous friends in my life and will take any opportunity to walk a dog. I have a gentle approach, am happy to work with you on the best way to care for your pet and am always open to feedback. Here to give so much love to your four-legged loved ones! I work full time, but have flexibility on the weekdays in the early morning or after 5. Weekends am flexible! Happy to work with you to figure out a time that works best. I have a very gentle and caring approach to pets. Happy to play with and snuggle them! If they’re more nervous or need specific types of care, happy to adapt to what they need!
“Anna was wonderful! She stayed at my apartment and watched my dog, Marvin, for about a week and provided daily updates with pictures. Marvin looked like he was having a great time, and he was happy and in great spirits when I got back. I would highly recommend Anna to anyone looking for a dog sitter. Thank you again, Anna!”
“Hsiao-chia was quick to respond and accept my request which I appreciated since it was for the next day. She asked good questions and made me feel good about leaving my 3 pets in her care.”
“Marcy was a terrific sitter for Jasper! She took great care of him as well as our house while we were away. Marcy was a good communicator with us, sending us daily pics and updates, and she matched Jasper's vibe perfectly. I'd be happy to have her sit with him again!”
“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!”
“This was the third time Rachel has cared for our senior dog. She did a wonderful job communicating updates and sending pictures throughout the stay. Moreover, we came home to a very happy and relaxed dog! It's such a relief to find someone you trust in your home and with your pet!”
“Kathleen was incredible. She was attentive, communicative, and most importantly, she took phenomenal care of Bodie while giving him plenty of exercise. It is great to be able to travel stress free knowing our boy is in good hands.”
“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!”
“Belkis has stayed with our pup several times and is always fantastic! Our pup loves being with her and she communicates with us daily so we get to see snap shots of their day. Thank you Belkis!”
About: I’ve cared for pets for years! I dog-sat my grandpas dog and also had a cat when I was younger. I love all animals! I’m reliable, patient and friendly with your pets. I’m currently working part time for the Red Sox on the grounds crew which makes seasonal schedule very flexible. I am available most days during the warm seasons and even more during the winter! I follow your pet’s routine closely: meals, walks, meds, and playtime, so they feel safe and comfortable. I treat your home with the same respect, keeping everything tidy and secure, while giving your pet plenty of love and attention.
“Devika was prompt and personable and connected with my dog immediately. She kept me updated on his well-being and was great to work with. I had to unexpectedly find someone to watch my dog while I was out and was very lucky to find her.”
About: I grew up on a small farm, where my parents always had indoor cats and dogs, and outdoor poultry, etc. Starting in middle school all the way through high school, I had my own pet sitting business where I dog and cat sat in my home, and at other people’s homes. Now as an adult with a cat of my own, I miss those days of getting to visit other animal friends on a regular basis! Looking forward to getting to meet your pet soon. I won’t pretend to be a puppy expert, but I handle every other age / walk of life. I’ve helped raise cats at every stage of life, as well. I love all animals and I’m in-between roles right now, so I would love to make pet sitting the focal point of my life for the time being. I will come to your home and do whatever makes your pet comfortable! I’m down to bring your pup for long walks on the leash, give your cat plenty of play time in addition to the routine feedings and cleanups.
“Alexander was amazing! He was very caring towards our dogs and our apartment. He followed our instructions and was very good at keeping us updated with messages and pictures. One of our dogs had a medical emergency right before our trip and he was quick to adapt to her needs and willing to administer medication. He was on top of reaching out for any issues and we felt like our dogs were in very good hands. We’d love to book with him again for our next trip!”
“I couldn't have asked for a sweeter and more caring sitter than Claudia!! Our fur-baby is our angel and she absolutely ADORED Claudia the moment she met her - my heart overflowed with relief and happiness knowing Claudia would be caring for her. Thank you for everything, Claudia!!!!”
“Sarah was perfect for us! We have an elderly cat and dog and she catered to both of their needs and eccentricities so that we could go on a short trip without worrying about them. We will definitely be calling her back in the future!”
About: I didn’t grow up with a pet (only fish) but I’ve played with and taken care of dogs and cats for friends/family for years. Currently on a career break and I’m not allowed to have pets in my apartment so looking to fill some time playing with and walking dogs. Open to cats as well! I’m currently taking a break from the corporate world, so I have a flexible schedule and plenty of time to walk your pets (for dogs), feed them, take them out for potty breaks, play with them and anything else that make them feel safe and happy while their owners are away! I’m happy to keep your pets company however suitable for them so that they feel comfortable and safe with me. I’ll take time to get to know each of your pets and their routine, personality, needs, and make sure to follow your instructions.
“Very communicative and patient with our puppy! Also let our house in great shape. I felt at ease while traveling knowing Katherine was taking care of our puppy”
The median cost per night for house sitting in Chestnut Hill is $64
Pet parents share their Rover experiences - Chestnut Hill
Jose was wonderful with our 14-year-old French bulldog and her cat sister. He is attentive to both of them and clearly cares about their comfort. When an emergency came up, he made himself available last minute for in-house sitting, which took a huge weight off us. Jose communicates well, sending photos and updates throughout our time away so we always knew how everyone was doing. He also respects our home and left it exactly as he found it. We will absolutely use him again!
Allie was wonderful! I have a senior pup with medical needs and Allie was very thorough marking sure Isley kept his routine and all his meds were administered on time. She kept in touch frequently and sent lots of pics which I love :) will definitely rebook with her again!
Kaitlyn took marvelous care of our dogs and our home when we were away for an extended time. She brought so much reassurance in regular updates and provided quality care with eye drops when one of our dogs needed it. We really appreciate everything she has done as a stellar dog sitter in providing so much love to our dogs. We found them so happy when we returned and highly recommend Kaitlyn!
Phenomenal care for our sweet dog. Provided detailed and friendly updates and took time to give our dog the most attention. We have an anxious dog that at times has trouble with new people, but she was the happiest puppy after the weekend. Will absolutely book again and highly recommend!!!
Rachael was absolutely fantastic! She provided daily updates and lots of pictures. She was very respectful of my house and left it spotless. She was great with communication and I felt very comfortable leaving my dog with her.. I will definitely be using her again in the future for pet care. 10/10 would recommend! Thanks Rachael!
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 on Rover is $83 per night as of October 2026. Most bookings cost between $32 and $111 per night. 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 6,581 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:
- 87% of sitters can help with special care needs
- 91% 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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