House Sitting Chestnut Hill
Find a loving house sitter to watch over your pets and your home.
Over 86 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!”
“Emily was so great with my cat! She paid a lot of attention to his behaviors and I could see he was having a good time when she sent update photos. We booked her for housesitting, and she did a perfect job. Would recommend her!”
“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!!”
“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.”
“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!”
“Emma is courteous, punctual, friendly, followed my instructions to a "T," and clearly loves dogs. I will 100% ask her back for house- and dogsitting as well as dog walking!”
“Ciana was great with my two French bulldogs. Very communicative and provided good updates. She also went above and beyond with my older dog - hand feeding him when he wouldn’t eat. Very respectful of my home. Would def book again!”
“Traci is wonderful. We’ve done day walk and overnight housesit stay. Our Remy (German shepherd) greatly enjoyed his time with Traci. He was well taken care of, and the house too. Looking forward to future times together!”
“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!”
“Priscilla was very conscientious about understanding our dog, his personality and his needs while we were gone. This was very re-assuring to us that he would be in fine, capable hands! Everything went well and we would definitely recommend Priscilla and DogVacay to others! We are already looking at our calendar for future stays!”
“My wife and I are first time dog owners who recently got a puppy. Anastasia took care of him for an evening while we were away and did a fantastic job! Theo was so comfortable with her and the peace of mind knowing that he was safe and well cared for is all I could ask for. Will definitely be working with Anastasia again!”
“Once again, Amy took such good care of our elderly cat, administering medications and providing ample pets and cuddles. She left our home clean and tidy. We came home to a happy, healthy cat.”
“Paige is absolutely wonderful and I am so happy to have met her! I think she is incredible and has a gift with animals and my pets did so well in her care! Romeo and Yoshi were comfortable with her right away and that really put me at ease. Paige provided multiple updates a day with lots of photos, it honestly feels like you're right there with them! My cat Yoshi can be a little sassy but I was so glad to see him get close and cozy with Paige and Romeo really took a liking to Paige and I'm sure he loved going on his walks! I would definitely recommend booking with Paige!!”
“Ailise did a wonderful job housesitting with my cavapoo Freddie over the long weekend! She sent great updates, videos, and photos of my boy, and I felt confident that he was safe in her care. She left my apartment in great condition. I highly recommend Ailise and would definitely book with her again! Thank you :)”
“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!”
About: I've had pets all my life, from dogs and cats, to tadpoles. I am currently a cat mom of 3 but love a good slobber from g' boys and girls with tails that wag. I am open to long walks in the park the the adventurers, or quiet time with my shy or sedentary babies. Doesn't matter the age, they are all babies to me. I am looking to get out of the human driven industry and spend time happier, with my furry friends. I would love to make this a regular job. When caring for others babies, I always listen carefully to humans directions but am super mindful to take body language cues from my furry friends. I think its important to meet the pets where they are at, and be patient just like you should a person who cannot speak for themselves.
“Amazing as always! We all are big fans of Kathleen’s, over and over repeat customers. She’s done a great week of house sitting for our puppy and a cat, and I couldn’t be more comfortable with her thorough reports, being responsive and reliable. Needless to say, she’s our person of choice whenever we need an eye for our furry kids. Much much grateful 🙏”
“10/10 experience! We needed a last minute sitter for our pets and we are very picky about who takes care of them. Hsiao-chia took our long instructions with such grace! Our pets loved her and she made sure to check in with us - easing my anxiety lol. We will certainly use her in the future!”
The median cost per night for house sitting in Chestnut Hill is $63
Pet parents share their Rover experiences - Chestnut Hill
Danielle looked after our two large dogs for two days and one night. Our dogs require special attention given their size and health conditions. Danielle gave our lab with elbow dysplasia his medicine and ensured he had adequate exercise in a safe environment. We came home to two happy and healthy dogs, who were fed, watered, exercised and loved. We were at ease while away from home knowing they were in good hands with Danielle.
Brooke is a lifesaver for us! We had an unexpected family trip and we needed someone to house-sit with our Basset Hound for a weekend. Our dog has glaucoma, and so is blind. And she has had some back surgery in recent months that require careful attention to detail in terms of not stressing out the dog's back (no jumping, no falling, no big missteps on stairs, etc.). The combination can leave some to feel intimidated about her care. Brooke jumped right in and helped. She showed up about an hour early to do a walk through of our place and to do some practice walking of our dog and to understand feeding, meds, and the like. She bonded immediately with our dog and it was clear she was comfortable with her. While we were away, Brooke sent many photos and notes just to reassure us. Our dog was doing her usual stuff, which meant she was relaxed and enjoyed Brooke's company. Brooke waiting until we were back in our place to give us a final report before she headed out. We would highly recommend Brooke for house-sitting / dog-sitting, even in some complicated circumstances.
Stina did a fantastic job housesitting and looking after our two cats while we were away for the weekend. Her communication was excellent, and she truly cares and is very knowledgeable about cats. We came home to two very happy cats and a clean house. We will definitely book her again in the future!
We couldn't be more pleased having J stay overnight in our home with our 14 year old kitty, Ricky. She sent wonderful photos of him and let us know how he did while she was with him. J is very sensitive, capable, and calm and brings a reassuring and creative energy with her that made me feel very relaxed being away from our beloved Ricky! We will absolutely have her come back again.
This was our, hmm I've lost count time Dawson has watched our pets and he did an amazing job as always. He kept us updated and all of her animals and our home very safe and sound. Anyone would be lucky to have Dawson watch their home and pets! Super professional, communicative, and caring. He even brings up our mail and packages! 5/5⭐
We had a surprise weekend and we’re in NH when our dog sitting plans fell through. Eveline did an amazing job making us feel comfortable with her meeting the dogs for the first time without us. She walked the dogs and left many updates and they seemed to love her! We will definitely be using Eviline’s services again!
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 $83.25 per night (as of September 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 September 2026, there are 6,614 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
- 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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