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 34
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: Mitra M.
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Mitra M.
$19
total per visit
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Boston, MA, 02135

About: Hi there! I'm a reliable, compassionate dog lover who understands that every dog deserves patience, kindness, and individualized care. I know that trusting someone with your pet is a big decision, and I don't take that responsibility lightly. My goal is to make both you and your dog feel comfortable, safe, and confident every step of the way. I believe dogs are family, and I care for every dog as if they were my own. Whether your pup is energetic and loves long walks, prefers a slower pace, or simply enjoys companionship, I'm happy to adapt to their unique personality, routine, and needs. I pay close attention to details, including feeding schedules, medications, preferred walking routes, potty breaks, and any special instructions you provide. I'm attentive during every walk and visit, always keeping your dog's safety as my top priority. I'll make sure they have plenty of exercise, affection, fresh water, and positive attention while they're with me. I understand that consistency is important, so I do my best to maintain the routine your dog is already familiar with. Communication is also very important to me. I'll keep you updated with photos, messages, and details about how your dog's visit or walk went, so you can have peace of mind while you're away. I want you to know that your pet is happy, safe, and well cared for. Whether your dog loves to play, explore, cuddle, or simply enjoys a calm, reassuring presence, I'm committed to providing a positive experience filled with patience, love, and respect. My goal isn't just to walk dogs—it's to build lasting relationships with both pets and their owners based on trust, reliability, and genuine care. I cared for my miniature Sheltie from his energetic puppy years through his senior years, including helping him navigate severe rheumatoid arthritis with patience, love, and compassion. That experience taught me how important it is to be attentive to each dog's unique needs. I strive to provide every pet with thoughtful, reliable care, treating them like family because that's exactly what they deserve. I would be honored to care for your furry family member, and I look forward to meeting you and your best friend! I recently transitioned from my full-time role as a paralegal at a law firm in downtown Boston and am dedicating my time throughout July and August to caring for pets. This allows me to offer a flexible schedule and give each dog the time, attention, and care they deserve. Whether your pet needs a walk, companionship, or extra attention while you're away, I'm happy to work with your schedule whenever possible. My goal is to provide reliable, attentive care that gives you peace of mind and keeps your dog happy, comfortable, and well cared for. I have a fully fenced yard and live near several parks in Brighton's Oak Square neighborhood, providing plenty of opportunities for safe outdoor exercise and enrichment. I don't currently have a dog of my own, as my beloved Sheltie passed away two years ago, which means any dog in my care will receive my full attention. Whether I'm caring for a pet in my home or in a client's home, I prioritize keeping them comfortable by following their normal routine as closely as possible. I carefully follow feeding schedules, walking routines, medication instructions, and any special care requests. I believe consistency helps dogs feel secure, so I take the time to learn each pet's personality, preferences, and needs. My goal is to provide a safe, loving, and low-stress environment where your dog feels cared for, happy, and at home while you're away.

Sitter Profile Image: Eveline L.
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Eveline L.
$25
total per visit
5.0 out of 5 stars
42 reviews
14 repeat clients
15 years of experience
Allston-Brighton, Brighton, MA, 02135

Eveline offered drop-in visits throughout a week for my cat while I was away. She was super reliable and punctual with her visits and provided immediate communications. My main ask was for her to clean the litter box, but she also offered to hangout with my cat and gave him brushing sessions! Eveline was also super accommodating and reliable for picking up and dropping off my keys.

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Michael Y.
Sitter Profile Image: Michele Y.
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Michele Y.
$19
total per visit
5.0 out of 5 stars
6 reviews
1 repeat client
7 years of experience
Allston-Brighton, Boston, MA, 02135

Buddy loved meeting Michele! She was great meeting us before hand and catering to my old guys needs! He had a great visit!

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Stephanie R.
Sitter Profile Image: Kiril Z.
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Kiril Z.
$23
total per visit
5 years of experience
Newton, MA, 02459

About: I grew up surrounded by pets. Both my neighbor and my grandma had cats that loved to explore the outdoors, so I spent many summer days playing and exploring with them. During quarantine, my cousin got an Australian Cobberdog named Rosie. When they were away, I would frequently volunteer to be the one in charge of caring for her. In recent years, when my friends were away they would trust me to walk and take care of their pets. Over the years I have gained a lot of experience caring for cats and dogs of all shapes and sizes, and am so excited to meet your pet! During the months of May-August I am situated in Newton MA. During the months of September-April, I split my time between Amherst MA where I go to school at UMass and Newton. I think pet care is a two way street. I can only provide my best care if I know your pets needs. I preform my best when I know everything I need to know about your pet.

Sitter Profile Image: Luis R.
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Luis R.
$20
total per visit
5.0 out of 5 stars
35 reviews
6 repeat clients
3 years of experience
Jamaica Plain, Jamaica Plain, MA, 02130

Luis is a gentle and kind person who understands shy cats and takes the time to get to know them. I highly recommend him for your kitty care!

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Martha H.
Sitter Profile Image: Tess G.
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Tess G.
$17
total per visit
5.0 out of 5 stars
3 reviews
1 repeat client
3 years of experience
Boston, MA, 02135

About: I’ve watched after friends/neighbors pets (dogs, cats, fish). While I don’t have any pets in my current home, I was raised with both dogs and cats! I am currently on summer vacation, so I will have free time throughout the day or evening to care for your pet(s)! I am very flexible with timing, so I can work around your schedule. My focus will be on building trust with your pet and helping them feel safe while you are away. I am very patient and will focus on what the pet needs in the moment to help them feel more comfortable.

Sitter Profile Image: Anna H.
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Anna H.
$23
total per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
24 years of experience
Allston-Brighton, Boston, MA, 02135

Anna did a great job at caring for my cat. She followed all the instructions I gave her, gave me daily updates, and my cat warmed up to her super quickly. I would definitely book with her again the next time I have to go away!

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Julia B.
Sitter Profile Image: Lani T.
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Lani T.
$34
total per visit
4.9 out of 5 stars
55 reviews
18 repeat clients
20 years of experience
Allston-Brighton, Allston, MA, 02134

Lani did a great job taking care of my cat and my (very old) Chinchilla!! She was totally reliable, showed my pets lots of love and attention and communicated well with me regularly. I will definitely hire her again!

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Alisa G.
Sitter Profile Image: Alyssa M.
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Alyssa M.
Star Sitter
$28
total per visit
5.0 out of 5 stars
19 reviews
5 repeat clients
15 years of experience
Needham, MA, 02494

Alyssa was amazing for my dog and me. Highly recommend. I had a last minute business trip and she was able to drop in to save the evening and walk Louie while I was out of town. And it was her first walk with us. She knew just what to ask during the meet and greet and then again right before the walk to make it be a success for her, me and most importantly Louie! Thx!!!!

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Natalie G.
Sitter Profile Image: Quinlan F.
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Quinlan F.
$19
total per visit
25 years of experience
Allston-Brighton, Boston, MA, 02135

About: I have taken care of pets my entire life! I am lucky to have cared for pets across their entire lives, from puppy/kitten to lovely senior pets. I am currently volunteering at a cat shelter in Boston and would love to bring that experience to your pets. I love pets of all shapes and sizes, but I absolutely adore caring for big dogs and shy cats. I volunteer at a cat shelter in Boston three days a week, but I am otherwise free all throughout weekdays to look after your pets! I am happy to do morning or midday visits to take special care of your pets. I think it is incredibly important that caring for pets does not disrupt their regular habits or schedule! It's so important to gain the trust of people's pets in order to properly care for them, and so I will do everything I can to make sure that your pets feel safe and comfortable while I make sure their needs are met.

Sitter Profile Image: Sydney P.
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Sydney P.
$28
total per visit
4.9 out of 5 stars
66 reviews
25 repeat clients
5 years of experience
Allston-Brighton, Brighton, MA, 02135

Sydney was wonderful to work with. The cats took to her easily, she communicated well and accomplished everything we needed from her. Because of her care we were able to fully enjoy our trip. Thanks again!

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Daniel A.
Sitter Profile Image: Karina v.
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Karina v.
$23
total per visit
7 years of experience
Allston-Brighton, Boston, MA, 02135

About: I’ve been a lifelong dog lover and had the joy of raising my own Boxer for 13 wonderful years. In addition to caring for my own dog, I’ve provided pet sitting for many friends’ and family members’ dogs, both in their homes and in mine. I’m an active person who loves getting outside, and I enjoy having a four-legged companion join me on long walks and adventures. I also have a spacious SUV, making it easy and comfortable to safely transport dogs of all sizes if needed. I understand that every dog has their own personality and routine, and I’m committed to providing loving, reliable care so you can feel confident your pet is in good hands. I work from home mostly and available mornings, lunch and afternoons. Also available on weekends to pet sit at my place or at the pets home. I live in a condo near a park and reservoir with nice path for walking dogs. Happy to stay at pets home as it might be most comfortable for them and their routine.

Sitter Profile Image: Izza Sofia H.
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Izza Sofia H.
$23
total per visit
4.8 out of 5 stars
51 reviews
15 repeat clients
5 years of experience
Jamaica Plain, Boston, MA, 02120

Izza was incredible. She was prompt, took care of everything we asked her to, and sent a bunch of updates every time. We will be using her again when we travel!

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Sadie
Sitter Profile Image: Nimisha T.
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Nimisha T.
$22
total per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
6 years of experience
Allston-Brighton, Boston, MA, 02134

Nimisha was wonderful. My two dogs got walks and cuddles and they loved all the attention they got on their visits. There were many picture updates during visits as well. Will absolutely book with Nimisha again!

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Stephanie B.
Sitter Profile Image: Stuart T.
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Stuart T.
Star Sitter
$23
total per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
1 year of experience
Allston-Brighton, Brighton, MA, 02135

It was the first time we called on Stuart to walk Clare, not just once, but twice in a day, and we’re glad we did. Stuart was conscientious from the start, offering to stop by the day before we needed him to meet us and Clare. We highly recommend him!

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Ted C.
Sitter Profile Image: Mariella G.
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Mariella G.
$19
total per visit
1 year of experience
Brookline, MA, 02446

About: My name is Mari and I am a recent graduate from Johns Hopkins University and working in Longwood! I am a big pet lover and love taking care of pets, since I am not in the stage of my life where I can have one of my own right now. I have a golden doodle of my own at home in Virginia and she is the best part of my life! I cherish spending time with her and get nervous when my family has to leave her, so I understand some of the worries pet parents may have! I have been responsible for pet sitting dogs throughout high school and have extensive experience with walking, feeding, and cleaning up after dogs. I also have been walking dogs in the Boston area for a few months now. I am looking for new client in the Washington Square area! I work a hybrid schedule and normally go in about once a week for a few hours! I am able to drop by at any time needed because of this flexibility. I am willing to follow any instructions provided on caring for your dog in your home! I have experience with letting dogs out and walking them during visits.

Sitter Profile Image: Shilpa J.
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Shilpa J.
Star Sitter
$28
total per visit
5.0 out of 5 stars
69 reviews
30 repeat clients
Allston-Brighton, Brighton, MA, 02135

Shilpa was excellent! She was available on short notice and provided detailed updates on my cats. I would definitely ask Shilpa for help again! Thanks!!!

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Melinda C.
Sitter Profile Image: Sasha P.
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Sasha P.
Star Sitter
$17
total per visit
5.0 out of 5 stars
61 reviews
12 repeat clients
4 years of experience
Boston, MA, 02135

Sasha was wonderful taking care of our cat, even when he got sick in the middle of her care for him! Highly recommend her service for your animals.

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Lane F.
Sitter Profile Image: Linda G.
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Linda G.
$28
total per visit
4.9 out of 5 stars
22 reviews
7 repeat clients
40 years of experience
Watertown, MA, 02472

Linda was terrific. She is reliable, detail oriented, and perceptive. She clearly cares deeply about animals. You can be sure your pet will be well cared for.

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Lisa G.
Sitter Profile Image: Sarah B.
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Sarah B.
$39
total per visit
5.0 out of 5 stars
29 reviews
8 repeat clients
15 years of experience
Boston, MA, 02135

Sarah is amazing! We've booked her twice and both times have come home to a happy and healthy kitty. Our cat absolutely loves her, and we feel so secure knowing she is taking care of him while we are away.

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Emily R.
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The median cost per visit for dog sitting in Chestnut Hill is $25

Dog parents share their Rover experiences - Chestnut Hill

1 / 1
5.0 out of 5 stars

Wendy was excellent. She was reliable a good communicator and made me feel like my dogs were in very safe hands. I will be booking her again

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

Taylor was fantastic! She was easy to coordinate with, responsive, and my dog loved her. Would definitely book again.

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

Sydney is amazing!!! She has lots of experience working with dogs and it shows. Mine can be a bit rowdy at times but she had them sitting and calm within like a minute of being there! She’s super sweet and communicative as well. We would 100% use Sydney again. I had 0 concerns after meeting her and our experience was great!

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

Sabrina is great! Super responsible and responsive, she followed all the instructions for my anxious labradoodle, plus she’s a pleasure to chat with. Highly recommend.

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

mitra is amazing! she took great care of my dog during the drop in visit, and sent a lot of photos and updates :) will definitely love to have her again!!

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Robin P.
Drop-In Visits
5.0 out of 5 stars

Adelle was an excellent caregiver for our aging dog whose loss of hearing and vision causes her to be quite frightened of strangers. Adelle was very kind, reliable, communicative and professional, which allowed us to relax while we were away.

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

It’s hard to tell who has more fun when Megan walks Clare! Today, they explored far beyond what I booked Megan to do. We ‘ve been relying on Megan for two walks each time we call on her, and she’s very responsible, considerate, and loving to Clare, always adding tummy rubs and topping off her food and water before she leaves.

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

Sabrina was so great! Sent pics of the pup throughout and kept me updated every step via text message. Would absolutely use her again!

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

Chloe continues to be such a great sitter for our pup. She is loving and thorough with our dog, and very prompt in communications with us, We will definitely continue to work with Chloe!

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

Tater had a great time with Andy- even protecting him from the dogs on the TV! Andy was on time and very communicative with us.

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Melissa L.
Drop-In Visits
5.0 out of 5 stars

We feel so comfortable leaving out dogs with Michelle! We know they are in the best care. Communication + Care are 10/10 Thank you!!

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Riana R.
Drop-In Visits
5.0 out of 5 stars

Zehra is amazing! Definitely recommend and will request to have her watch my pup again in the future.

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

Tiffany was excellent! Great communication and she took great care of our dog. We highly recommend Tiffany and will be asking her to dog sit for us again.

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

Allison was great with our 12 week puppy Dunkin! She managed a tricky situation where our door was locked and was very communicative during and after the visit. Would totally book with her again.

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

Hannah was great with my dog! She is reliable and trustworthy, and I will book her again in the future.

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Setti R.
Drop-In Visits
5.0 out of 5 stars

Traci is simply a great pet sitter and we just loved her personality. Our Corgis Sami and Tuukka just love her. We highly recommend Traci. Nancy and Sam

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

Grateful once again to Hannah, who took good care of Clare during two walks today, especially with the sky so ominous with the wildfire smoke!

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

Annette was great! She arrived on time and kindly followed our request to take each of our dogs out separately for their walks. Looking forward to booking her again.

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

Riley loved her visits from Colleen and she was well cared for during our weekend away. Super detailed with notes and pictures while we were out!

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

Emily has been a great and reliable sitter for drop in visits with Albert (our indoor bunny). She’s been very caring, communication has been easy and smooth. I highly recommend booking her.

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Pia K.
Drop-In Visits
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  • 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?

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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your dogs like family

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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 Drop-In Visits - Chestnut Hill

Frequently asked questions about Rover

The average cost for Dog Sitting in Chestnut Hill on Rover is $19.26 per visit (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog 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 Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 10,583 sitters on Rover offering Dog Sitting across Chestnut Hill. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Chestnut Hill stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 short introductory meeting between you, your dog, 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.

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:

  • 91% of sitters can help with special care needs
  • 96% 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.

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.

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