Dog Sitting Chestnut Hill

Book a Chestnut Hill dog sitter to watch your dog in your sitter’s home or yours.

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Over 48
pet parents in Chestnut Hill have booked dog sitting

Chestnut Hill, Find top rated dog sitting

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Sydney K.
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Sydney K.
$30
total per visit
5.0 out of 5 stars
• 26 reviews
7 repeat clients
9 years of experience
Allston-Brighton, Boston, MA, 02135

About: Experience with my family pet rescued seventy-five pounds German shepherd lab mix! Rescued him when he was only 4 months old. Love to go on long walkies! I’m currently working as I got laid off from my 9-5 job. Wanting to earn some money until I figure out my next career path! Fenced in backyard and live right near dog park within 5 min walk! Will always be watching and paying close attention. Open to owners needs :)

Sitter Profile Image: Hannah T.
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Hannah T.
$28
total per visit
5.0 out of 5 stars
• 26 reviews
11 repeat clients
15 years of experience
Brookline, MA, 02446

“Communicative and available last minute, gave timely and detailed updates about the cats. Thank you again!”

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Natalie C.
Sitter Profile Image: Leanne L.
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Leanne L.
$35
total per visit
5.0 out of 5 stars
• 138 reviews
55 repeat clients
20 years of experience
Newton Highlands, MA, 02461

“Leanne was one of the best care-takers I’ve ever had. She did things to care for Dagny that I didn’t even think to ask. And my girl is selective, but she warmed up to Leanne and let her pet her from day one. Leanne is a fabulous sitter. I thank you so much and recommend her fully.”

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Neil B.
Sitter Profile Image: Siyu C.
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Siyu C.
$20
total per visit
14 years of experience
Watertown, MA, 02472

About: I have experience caring for a Labrador and understand the importance of patience, exercise, and daily care. I’m happy to provide dog walking, feeding, fresh water, potty breaks, and loving companionship. I’m responsible, attentive, and will keep you updated with photos and messages so you can feel confident your pet is in good hands. I offer flexible scheduling for dog walking and drop-in visits. I will do my best to accommodate your pet’s needs and keep you updated throughout each visit. I’m happy to discuss availability in advance to find a time that works best for you and your pet. Your pet’s safety and comfort are my top priorities. I follow your care instructions carefully, keep doors and gates secure, and make sure your pet has fresh water. I will treat your home with respect and send regular updates and photos so you know how your pet is doing.

Sitter Profile Image: Julia E.
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Julia E.
$12
total per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
12 years of experience
Allston-Brighton, Brighton, MA, 02135

“Julia was so great with our two cats!! She was so attentive and loving and sent great updates while we were away! Thanks again!!”

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Holly W.
Sitter Profile Image: Sophia V.
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Sophia V.
$28
total per visit
5.0 out of 5 stars
• 1 review
1 repeat client
6 years of experience
Brookline, MA, 02445

“She was great! I have a young puppy and she was able to get her lots of attention!”

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Savannah V.
Sitter Profile Image: Katie D.
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Katie D.
$28
total per visit
5.0 out of 5 stars
• 16 reviews
5 repeat clients
10 years of experience
Brookline, MA, 02445

“Katie was great! Totally reliable and formed a nice bond with my dog (who can be wary of strangers).”

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Mark M.
Sitter Profile Image: Deirdre M.
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Deirdre M.
$34
total per visit
5.0 out of 5 stars
• 29 reviews
9 repeat clients
10 years of experience
Newtonville, MA, 02460

“Deidre has helped me time and again care for my pets. She is communicative, sends pictures and responsible. I have used her a few times now and plan to keep using her!”

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Grace F.
Sitter Profile Image: Silvia P.
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Silvia P.
$28
total per visit
5.0 out of 5 stars
• 5 reviews
1 repeat client
10 years of experience
Boston, MA, 02135

“Silvia was great! Stowe has recently gotten neutered, and she was able help provide extra support throughout the day. She sent multiple pictures and updates at each of her check ins.”

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Kylie K.
Sitter Profile Image: Ella C.
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Ella C.
$17
total per visit
6 years of experience
Allston-Brighton, Boston, MA, 02135

About: I’ve always been the one who my family members trust to care for their dogs whenever they are out of town for an extended period of time or if they simply need a night out. I also have had 2 consistent clients for the past 5 years who have entrusted me to overnight pet sit for their dogs. I am a full-time college student who has flexible weekday and weekend availability. I love outdoor activities like walking around the city as well as just kicking back and spending time indoors. I love any time spent caring for pets! When you entrust me to care for your pet, I will communicate with you by sending updates as well as feeding, spending time with, and walking your pet. I am also willing to stay overnight upon request.

Sitter Profile Image: Hsiao-chia C.
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Hsiao-chia C.
Star Sitter
$34
total per visit
5.0 out of 5 stars
• 22 reviews
3 repeat clients
2 years of experience
Allston-Brighton, Boston, MA, 02134

About: Lifelong animal lover here! Growing up, I had a cat, hamsters, hermit crabs, and fish. I've also had fun experiences with rabbit, ferret, and tortoise sitting for friends! Nothing but glowing reviews, I promise. I am super responsive and always available via messaging. I work a very regular 8-4:30pm job and have plenty of free time to hang out with your fur babies before and after work. See my calendar for availability :) I will always do my best to follow your instructions to a T! Clear communication is appreciated and will be reciprocated!! I promise to take care of your pets (and the things in your home) to the best of my ability.

Sitter Profile Image: Olivia M.
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Olivia M.
$23
total per visit
9 years of experience
Boston, MA, 02135

About: I have grown up with dogs all of my life, so I am very comfortable and familiar with many types! I’ve taken care of dogs since I was 12. Whether it was family, friends, or neighbors, I’ve walked, fed, and bathed pets! Hi! I live in Jamaica Plain and am a registered nurse, so my schedule can vary week to week. This flexibility often allows me to be available on different days and times, including weekdays and weekends. I’m very comfortable around pets and have a calm, attentive approach to care. I love spending time with animals and making sure they feel safe, happy, and well cared for while you’re away. It is my top priority to develop trust with the owner and pet! I love to create a fun and caring environment where everyone feels comfortable.

Sitter Profile Image: Bladen B.
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Bladen B.
$23
total per visit
9 years of experience
Brookline, MA, 02445

About: From dogs and cats to hedgehogs and bearded dragons, I have cared for and loved on them all! I have over 9 years of experience caring for the four-legged animals of neighbors and family friends. I recently moved to the Boston area, and because I run my own business, I can offer flexible scheduling. I’d love to be a reliable dog walker or drop-in visitor for you and your pets! I work remotely, running my own business, which gives me the flexibility to fit walks and drop-in visits into my schedule. I’d be happy to check in on your pet and give them some attention while you’re away! For walks and drop-in visits, I follow your pet’s usual routine and any instructions you leave. I’ll make sure they have fresh water, give them plenty of attention, and take care of feeding or other agreed-upon needs during the visit. I’m also happy to send an update so you know how they’re doing!

Sitter Profile Image: Grace S.
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Grace S.
$25
total per visit
5.0 out of 5 stars
• 28 reviews
9 repeat clients
15 years of experience
Brookline, MA, 02445

“Grace was very receptive to our requests and was a good companion for our puppy during a 1 hour drop in visit. She is also flexible about scheduling. We will be booking again.”

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Fiona L.
Sitter Profile Image: Paige S.
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Paige S.
Star Sitter
$62
total per visit
5.0 out of 5 stars
• 63 reviews
25 repeat clients
25 years of experience
Allston-Brighton, Brighton, MA, 02135

About: I am fully retired and do not work any other job. I am therefore free to spend a large part of each day taking boarding dogs to different parks for play, walks, or outdoor peace and rest in the fresh air. When pet sitting, I take as many walks as possible, with the owner’s permission, both when sitting and boarding. I take tons of pics and keep each owner informed of complete mental and physical health every day. I am able to board one small dog or one cat at a time. I have a large, open condo with plenty of room for ball rolling and play with other toys. If boarding, your dog or cat should meet and see if they are a fit with my cat, Tabullah, and my 18-yr old dog, Bella. Both are very friendly with other dogs and cats. I’ve taken care of dogs of every kind since I was 10. Neighbors, friends and family members have relied on me to walk, bathe, groom, , feed and sometimes administer meds orally or by syringe. I return my boarders and pets in my care at their homes in tip-top form to their human ‘parents.’ I have just moved to a wonderful condo in Brighton, Boston, very near a large Reservoir which is perfect for walking dogs and offers loads of opportunity for possible socialization and stimulation. I also live in a safe, stimulating neighborhood with plenty of beautiful streets to walk on. My husband, Joe, and I often walk together with our guest doggy and keep them well out of harm’s way. In addition to sitting and boarding, I offer short-term walking and pet visiting services. I can offer as many walks as you wish per day for your furry friends if I’m not boarding or sitting other dogs. (I do not try to combine jobs unless one or two 30-minute walks or visits per day can fit easily into my schedule during a sitting or boarding job. ) sit for dogs and cats in their homes, as well do some drop-in visits within one or two miles from my condo. I do light grooming ,nail clipping, bathing, and administer medicine or special care as needed (not as a separate service.) whenever requested as well, but not as a separate service. I am retired and stay home seven days a week, unless I am dog-sitting. So, when boarding or sitting, pets are covered 24 hours a day. It's a routine I love - as walking in the park, or at the nearby Resevoir (with the pups) is something I do every day regardless of whether my husband and I are boarding. I have an extremely sweet and friendly furry companion, Bella, (a 16 yr old puggle) to keep your pup company. I can easily crate dogs for short times for owners who wish it. We love to play games outdoors such as fetch or frisbe, and allow our canine visitors to sleep pretty much anywhere in the house in their dogbeds (this usually ends up being in our bedroom). My one cat, Bullah, sleeps pretty much every night in our condo’s office, and can be kept there if there are any issues with our doggie visitors. I give my complete attention to your pups or kitties. I adore providing my best care and attention to these important members of clients' families. I plan my daily routine around my jobs, with help at home from my husband taking care of my own “babies”! My husband makes my pet care business possible by taking good care of my own pets while I am busy with yours. When there is clear owner permission to leave their pet for up to 2 or 3 hours a day, and they live close enough, I have an occasional meal and a walk at home. Or, only occasionally, Joe takes me to a different location to give a high-quality walk or visit. (Often, I will prepare food and feed a pet during a drop-in visit.) That way, my own pets my best love and quality attention to those pets who have been placed under my care.

Sitter Profile Image: Eliza P.
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Eliza P.
$37
total per visit
5.0 out of 5 stars
• 101 reviews
34 repeat clients
20 years of experience
Newton, MA, 02458

“Eliza is one of a kind and truly wonderful. When we had to leave our dog, Molly, for the first time, we left it to Eliza and there could not have been a better person to keep the dog and us well cared for. Truly appreciative of her flexibility and communication with us throughout the booking.”

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Natalie K.
Sitter Profile Image: Noah B.
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Noah B.
$23
total per visit
14 years of experience
Brookline, MA, 02446

About: I have had extensive experience caring for all animals! Whether for family members, friends, and neighbors, I pride myself on being a reliable and constant resource for them! I also have experience with complex care and medicine administration! I am a graduating undergraduate student matriculating into medical school. My schedule is quite flexible until my start date in July, and I am available for days and nights! I will care for them like they are my own babies! I am very detail-oriented, whether it is dog-walking or sitting, feeding, or more I will always be accommodating.

Sitter Profile Image: Katherine G.
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Katherine G.
Star Sitter
$34
total per visit
5.0 out of 5 stars
• 42 reviews
11 repeat clients
10 years of experience
Allston-Brighton, Boston, MA, 02135

“I have a dog who can be difficult and she immediately liked Katherine. I'm very glad Katherine is visiting my dogs when I'm out of the house.”

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Eva J.
Sitter Profile Image: Michaela R.
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Michaela R.
$38
total per visit
5.0 out of 5 stars
• 3 reviews
10 years of experience
Allston-Brighton, Newton, MA, 02135

About: Whether your pet needs a simple walk and some company or a little extra care, I’ve got you covered. With 10 years of veterinary experience, I’m comfortable caring for pets of all personalities, ages, and needs, from happy, healthy pups to seniors, anxious pets, and animals requiring medications or post-op care. On weekdays, I’m available after 2 PM for consistent one-hour walks or drop-ins. I also offer boarding and sitting, with flexibility to give pets plenty of attention and care without rushing through visits. Safety and trust are my top priorities. With 10 years of veterinary experience, I’m comfortable recognizing changes in behavior or health and making sure pets are cared for according to their individual routines and needs. In a client’s home, I’m respectful of their space and follow all instructions carefully. For boarding, I provide a calm, clean, supervised environment with plenty of attention, exercise, and consistency. I also make sure doors, gates, leashes, medications, and feeding instructions are handled carefully so owners can feel confident their pets are in good hands.

Sitter Profile Image: Anna & John R.
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Anna & John R.
$26
total per visit
5.0 out of 5 stars
• 22 reviews
7 repeat clients
20 years of experience
Watertown, MA, 02472

“Anna took such great care of my cat Mesia while I was away. Her love for animals comes through in all of her attention to detail and consideration. Couldn’t recommend more!”

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Cole M.
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The median cost per visit for dog sitting in Chestnut Hill is CA$25

Dog parents share their Rover experiences - Chestnut Hill

1 / 1
5.0 out of 5 stars

This was our first experience with Christie and she was fantastic! Punctual, very communicative, and so kind to our dog! We will be requesting her services again :)

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Marc C.
Drop-In Visits
5.0 out of 5 stars

Bonnie is amazing! Really appreciated the updates and photos. She left my apt spotless and even took out the trash. 10/10 will book again. Thank you!

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Vanessa B.
Drop-In Visits
5.0 out of 5 stars

Lucy was incredible with Indigo! She was prompt with her responses and punctual with her arrivals! I’m very particular about who cares for my dog and I would absolutely rebook Lucy! Knowing Indigo was going to be well cared for, put my mind at ease

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Kate N.
Drop-In Visits
5.0 out of 5 stars

Julia was caring, reliable, and attentive with our puppy. Communication was great, and we felt completely comfortable leaving our pup in her care.

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Zena G.
Drop-In Visits
5.0 out of 5 stars

Emily was fantastic with our French bulldog, Bruno. He definitely loved hanging with her! I would totally use her again!

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Steffany C.
Drop-In Visits
5.0 out of 5 stars

Gabriella responded quickly to my request, arrived promptly, communicated clearly, and sent lots of pictures of my dog! It was obvious that she took great care of my dog, and I would gladly book her again!

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Jen K.
Drop-In Visits
5.0 out of 5 stars

Jana was very prompt and thorough in communicating. I knew my Ladybug was in good hands for her drop-in visit!

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Lauren B.
Drop-In Visits
5.0 out of 5 stars

Kelsey is amazing! We recently went on a week long trip and she was a huge help! She always checked in and sent cute pictures. She is super reliable and my dog Cruz loved her immediately. Anyone would be lucky to have her!

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emily k.
Drop-In Visits
5.0 out of 5 stars

Giuliana has been my go to person for my pup Cruz. We had back to back vacations and she has been such a tremendous help. Always sending pictures and updates of not only our dog but cat as well. She is amazing as what she does and anyone would be lucky to have her!

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emily k.
Drop-In Visits
5.0 out of 5 stars

Nico was so responsive and helped me out when my previous sitter canceled, my dog was so happy and taken care of! Very prompt and communicative. Will use again

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Gabby K.
Drop-In Visits
5.0 out of 5 stars

I have had a fantastic experience with Quinlan, who provides drop in visits for maybe Dachshund. He is extremely kind, caring, engaging and communicative. Tosh is in very good hands when he is with Quinlan and I highly recommend him!

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Priscilla M.
Drop-In Visits
5.0 out of 5 stars

sydney visited bubba multiple days while i was working all week, i came home to a happy and tired dog, and she was clear with communication and providing updates and taking care of bubba. she made sure to follow instructions well and take great care of bubba. thanks so much sydney, will definitely use you in the future to watch bubs.

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Liam D.
Drop-In Visits
5.0 out of 5 stars

Adelle is great with our older dog who very skittish and can get cranky. She is very kind and understanding.

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Mary D.
Drop-In Visits
5.0 out of 5 stars

Kaitlin always does such a great job communicating with us and is always flexible when we need Ginger care. We absolutely love booking with her!

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Jessica H.
Drop-In Visits
5.0 out of 5 stars

Erica is fantastic with our dog Goose, and helps us out in a pinch. Great communication and very reliable

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Julie M.
Drop-In Visits
5.0 out of 5 stars

Tiffany is truly the best! Hazel loves her. She’s extremely reliable and always makes sure Hazel has the best time.

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Marykate & Demetri H.
Drop-In Visits
5.0 out of 5 stars

Alyssa is a very caring and trust worthy sitter. Communication is easy/smooth and she follows the instructions, so it feels save having her checking in on Albert (Bunny). I can highly recommend Alyssa

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Pia K.
Drop-In Visits
5.0 out of 5 stars

This is the second time I ask them to take care of Frito and they did an amazing job. They sent me pictures of every visit and followed Frito’s care instructions. Totally recommend!

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Matías V.
Drop-In Visits
5.0 out of 5 stars

Andreas did a great job on his drop in with Henry! I really appreciate that he took the request last minute and was very communicative.

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Madeleine K.
Drop-In Visits
5.0 out of 5 stars

Kathleen was wonderful with our senior dog Hildi over the weekend. Hildi loved being with her and going on walks with her while we were away.

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Mayukh G.
Drop-In Visits
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Popular requests for dog sitting - Chestnut Hill

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Sitters in Chestnut Hill average 6
repeat dog sitting clients

FAQs for Dog Sitting - Chestnut Hill

Frequently asked questions about Rover

The average cost of Dog Sitting in Chestnut Hill is $19 per visit as of November 2026. Most bookings cost between $17 and $27 per visit. 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 November 2026, there are 10,375 sitters on Rover offering Dog Sitting across Chestnut Hill. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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!

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.

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.

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 Meet & Greet.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Chestnut Hill with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Chestnut Hill. On Rover:

  • 85% of sitters can help with special care needs
  • 90% can help with giving oral medications or injections
  • 94% 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.

sitters on Rover set their own cancellation policy, 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.

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