Dog Sitting Jamaica Plain

Book a Jamaica Plain dog sitter to watch your dog in your sitter’s home or yours.

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Over 409
pet parents in Jamaica Plain have booked dog sitting

Jamaica Plain, 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: Catarina A.
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Catarina A.
$17
total per visit
4.8 out of 5 stars
• 136 reviews
53 repeat clients
10 years of experience
Roxbury, Boston, MA, 02121

“Catarina has been the best cat sitter we have ever had! She’s been our pet sitter for 2 years now! She very great with our pets needs including medication, we always trusted leaving our pet with her. I highly recommended her!”

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Milana B.
Sitter Profile Image: Mercedes F.
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Mercedes F.
$17
total per visit
5.0 out of 5 stars
• 4 reviews
5 years of experience
Allston-Brighton, Boston, MA, 02135

“Mercedes was communicative, punctual, and reliable. I would be happy to have her watch my cat again!”

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Prinnapa Y.
Sitter Profile Image: Carolina S.
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Carolina S.
$28
total per visit
5.0 out of 5 stars
• 7 reviews
3 repeat clients
2 years of experience
North Dorchester, Boston, MA, 02125

“Our pup wasn’t feeling well today and Carolina was very helpful and accommodating! She was so patient and very communicative of his extra needs today!”

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Elizabeth S.
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: Emma S.
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Emma S.
$28
total per visit
5.0 out of 5 stars
• 18 reviews
9 repeat clients
7 years of experience
Brookline, MA, 02445

About: I’ve loved and taken care of dogs my entire life and have devoted so much time and energy to learning about what’s best for them. I treat all dogs like my own and love them more then people!! Anyone who knows me will attest that having me take care of your dog will ensure the same level of love and care you give them. I’m currently in school, part time so I will have lots of time to play with your pup. At school, there’s a large outdoor grassy courtyard, all fenced in, with balls to play and run around and a nice heated and A/C area where I will have a bed for them to relax on, right next to me. I live in an apartment, I have availability Tuesday/ Thursday all day, Friday Mornings and Saturday/Sunday basically all day to check in, walk and play with your pup, and make sure to give you updates with photos every time, unless you request otherwise. I volunteer at the MSPCA, animal shelter, 1 to 2 times a week. Trusting your dog with another individual is hard and that is why I want to ensure that you know the care and safety of your pet is my top priority. I will treat your dog as my own and ensure that they’re getting the best of care and will give my full attention and energy towards your pet during our time together. I will offer plenty of enrichment, playtime, cuddling/affection, training and whatever else your dog may need. I take great care to be aware of your dogs body language as well as other dogs to ensure your dog is safe and comfortable in my care. I will adhere to any rules you have with your pets strictly. I will be sure to tell you all about our visits and will be sure to communicate with you, if something were to happen. I will take lots of photos and videos of your pet and be sure to update you throughout our time so you can always know what we are up to!!

Sitter Profile Image: Adina G.
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Adina G.
$25
total per visit
5 years of experience
Roxbury, Roxbury, MA, 02119

About: Hi folks, I've always loved animals and it is a personal goal of mine to befriend any animal I meet (furry or not). At a party, you are most likely to find me at either the snack table or hanging with the animals or children. Especially with dogs, I give off a very playful energy, but I'm also a big snuggler and will give scritches to a furry friend for hours. I have experience living with and caring for dogs, cats, and rats. In addition, I have some training knowledge and will give positive reinforcement for good behavior and avoid reinforcing undesirable behavior. I'm currently working part time and usually have availability in the late mornings or early afternoons. If I plan ahead I can potentially be available later in the day, in the evenings (I'm a night owl), or even some weekends. In your own home or if I go on walks, I will ask questions to gain knowledge about temperament, comfort around other animals, and general house rules and preferences. I always ensure harnesses and leashes are secure and I have enough strength and good reaction time to hold on tightly if a dog pulls. When I approach a shy animal that is unfamiliar with me I am patient and offer a sniff of my hand first before giving pets, and I will pull away as soon as the animal signals discomfort.

Sitter Profile Image: Lena O.
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Lena O.
$34
total per visit
4.9 out of 5 stars
• 20 reviews
6 repeat clients
10 years of experience
Jamaica Plain, Boston, MA, 02130

About: I’ve worked with dogs and cats for the last few years as I’ve been working on my bachelors and masters degrees. I love spending time with animals and would have a dog or cat of my own if I didn’t enjoy occasional trips as much as I do! I love being outside and work well with active pets. I’ve provided some basic medical care, such as pill administration and wound care for dogs. I’m currently working part time remote and in office and really enjoy spending extra time I have with pets. I’m especially free for weekends/extended weekends. I offer pet sitting services for clients in their home. I typically will try to get dogs on two long walks/dog park visits/hikes a day depending on what’s agreed on prior and the dogs’ fitness abilities. I also love hanging out with cats and playing with them during the day. Your pet can expect lots of pets and and quality time with me as a sitter.

Sitter Profile Image: Denzel G.
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Denzel G.
$20
total per visit
5.0 out of 5 stars
• 14 reviews
5 repeat clients
12 years of experience
Roslindale, Roslindale, MA, 02131

About: I've been taking care of dogs since I was 14 years old. Helping walk, feed, and dog sit for multiple days at a time for neighbors. I continue to help out neighbors and friends when asked upon I work part time so I have lots of spare time to play with some awesome dogs. My schedule is very flexible so I can work mornings or overnights with your dog I will be sure to show all dogs lots of love and if asked I can have your dog crated in your house. Brush him/her as well.

Sitter Profile Image: Natalie J.
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Natalie J.
$23
total per visit
5.0 out of 5 stars
• 9 reviews
1 repeat client
Allston-Brighton, Brighton, MA, 02135

About: Howdy! My name is Natalie and any dog I've met I have loved like my own. Growing up I had my fluffy 90lb Labradoodle and two sweet guinea pigs. Aside from my own pup, neighbors, friends, and family have relied on me to walk and feed their dogs and care for their cats. I currently have a full time job where I have to go into the office Monday-Thursday but an available for walks and drop-in on Friday, Saturday, and Sunday. I live in a small apartment in Brighton MA across the street from a wonderful reservoir and less than a mile away from several parks! I am a very active person so would be a great host for an athletic or active dog! However, if your dog is less active, I can easily bring my activity level to where your dog is happy and comfortable. I allow pets on my bed and couch, unless you prefer them not to.

Sitter Profile Image: Louise T.
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Louise T.
$19
total per visit
5.0 out of 5 stars
• 2 reviews
5 years of experience
Jamaica Plain, Jamaica Plain, MA, 02130

About: I have experience taking care of a wide variety of animals, from dogs and cats to lizards and horses. So I can adapt to your pet's needs. I am currently taking classes online as a college student and have a flexible schedule well suited to taking care of pets who need love, time, and attention. My home currently is not suitable for bringing your pets into, however, I am happy to come to your home and take care of your pets there.

Sitter Profile Image: Emma & Thomas Y.
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Emma & Thomas Y.
$20
total per visit
5.0 out of 5 stars
• 16 reviews
5 repeat clients
20 years of experience
Cambridge, MA, 02139

“Absolute pleasure working with Emma, she went above and beyond when we got stuck away from home because of the blizzard. Thank you for braving the snow and the wind to keep them happy and fed! We finally made it home to find happy and well taken care of cats. Thank you so much and we look forward to trusting our cats with you in the future, I'm sure they will be excited to see you again :)”

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William D.
Sitter Profile Image: Alexa R.
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Alexa R.
Star Sitter
$15
total per visit
5.0 out of 5 stars
• 53 reviews
14 repeat clients
7 years of experience
Belmont, Brookline, MA, 02446

“Alexa was an amazing sitter and so easy to work with! She was always on time and provided great updates and lots of pics of my cat. Would definitely recommend her!”

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Jenna K.
Sitter Profile Image: Tauryn D.
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Tauryn D.
$32
total per visit
5.0 out of 5 stars
• 8 reviews
7 years of experience
Roslindale, Boston, MA, 02131

“Tauryn was amazing with our two dogs! She was punctual and communicative. The pictures she sent were so cute. They both seemed so happy when we returned from our trip! We will definitely use her for drop in care again!”

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Caitlin S.
Sitter Profile Image: Emma B.
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Emma B.
$28
total per visit
5.0 out of 5 stars
• 6 reviews
10 years of experience
Allston-Brighton, Boston, MA, 02135

About: Caring for animals has been a part of my life for as long as I can remember. I've grown up with dogs of all sizes, from energetic Huskies and Labs to smaller breeds like Havanese, so I'm comfortable with different personalities, energy levels, and care needs. I'm experienced caring for multiple pets at once and am confident managing busy households. While babysitting, I've often cared for children and dogs together, which has taught me how to stay organized, attentive, and calm in any situation. I’ve helped care for my mom's Husky with two torn ACLs, giving me experience with pets who need extra patience, gentle handling, and special attention. I'm comfortable administering medications, treating ear infections, and following detailed care instructions to keep your pet healthy and comfortable. I've also lived with cats throughout college, where my roommate had two cats, and I'm now the go-to pet sitter for both of my brothers' two-cat households. I'm just as comfortable caring for cats as I am with dogs. I'm an active person who does long walks everyday and I'd love to have a furry friend join me for walks and adventures. Whether your pet loves long walks and playtime or prefers a quiet companion, I'll make sure they feel safe, loved, and well cared for while you're away. I work full-time but have a flexible schedule. I work remotely on Tuesdays, Wednesdays, and Fridays, which gives me flexibility for walks, drop-in visits, and pet care throughout the day. On Mondays and Thursdays, when I'm in the office, I'm available for early morning and evening walks or visits. My weekends are wide open, so I have plenty of time for longer walks, overnight stays, and lots of quality time with your pets! Your pet's safety and comfort are always my top priorities. I carefully follow each pet's routine, including feeding schedules, medications, and any special care instructions. During walks, I stay alert, keep dogs securely leashed, and avoid unsafe situations or extreme weather. At home, I make sure pets have a calm, clean, and secure environment where they can feel relaxed. I know every pet is different, so I take the time to build trust and provide care that's tailored to their individual needs.

Sitter Profile Image: Lily H.
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Lily H.
$16
total per visit
1 year of experience
Boston, MA, 02115

About: I've taken care of and have a love for dogs ever since I was little. I have 4 dogs that I help take care of when visiting home. I also have watched my neighbors dogs regarding feeding and playing time. I have a love for dogs, and enjoy spending my time with them. Some special skills I have is caring for older dogs, as I have 4 back home that I care for when I visit. I know when dogs want space, want to play, and when they need basic care such as bathroom breaks. I give my full attention when watching to give the dogs the best care they deserve! I am currently a college student who does not have class on Tuesdays and Fridays and am free on weekends. I am great with time management and very reliable when it comes to planning my weeks. I am very quick to respond to any inquiries about my skills and schedule. I am very flexible and punctual. I plan to care for your pets in your home by taking good instruction on how you would prefer me to watch your fur babies. Regarding playing time, feeding time, and bathroom time, I am very reliable and trustworthy when it comes to the care you expect from me!

Sitter Profile Image: Ailise C.
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Ailise C.
Star Sitter
$43
total per visit
5.0 out of 5 stars
• 22 reviews
7 repeat clients
20 years of experience
Jamaica Plain, Boston, MA, 02130

“Ailise did a great job checking in on our dog, Ollie! He’s a nervous & anxious dog who likes to bark with unfamiliar people, but she did a great job making him feel comfortable. She cuddled with him on the couch and sent us pictures! Would 10/10 recommend Ailise!”

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Madie W.
Sitter Profile Image: Perla C.
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Perla C.
$27
total per visit
5.0 out of 5 stars
• 5 reviews
3 repeat clients
5 years of experience
Hyde Park, Boston, MA, 02136

“Amazing!!”

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Chloe A.
Sitter Profile Image: Katherine S.
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Katherine S.
$17
total per visit
5.0 out of 5 stars
• 3 reviews
1 repeat client
15 years of experience
Back Bay-Beacon Hill, Boston, MA, 02115

About: I have taken care of all types and sizes of dogs since I was very young. I grew up with a springer spaniel who was very energetic and enjoyed long walks and runs. I have experience taking care of old dogs with lots of medications and assistance needed (carrying up/down stairs, etc.). I look forward to helping out with your pup! I work full-time Monday–Friday, but my schedule is flexible. I’m only in the office two days a week, and those days can vary, which allows me plenty of availability for pet care. I’m available both during the week and on weekends and am happy to work around your schedule and your pet’s needs! My apartment is pet friendly and I have furniture that pets can sit on. I live right next to the esplanade which is great for walks!

Sitter Profile Image: Denise P.
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Denise P.
Star Sitter
$16
total per visit
5.0 out of 5 stars
• 15 reviews
4 repeat clients
16 years of experience
Boston, MA, 02114

“Denise was so sweet and patient with kimchi! Meeting her exactly where she was comfortable. Super sweet person and very communicative. Thanks again Denise ❤️❤️”

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Nipunya K.
Sitter Profile Image: isabella d.
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isabella d.
$25
total per visit
4.6 out of 5 stars
• 38 reviews
11 repeat clients
9 years of experience
Jamaica Plain, Roxbury, MA, 02120

About: Your pets will be in loving, reliable hands with me. I treat every animal like they’re part of my own family, giving them so much attention and comfort that they won’t even notice you’re away🥰 Hi! I work 3 days out of the week 9am to 3pm. And free on weekends! So I have a fairly flexible schedule to care for your loved ones. If you have any questions about my availability scheduling or prices feel free to message me :) When your pet stays in my home, they become part of my family from the moment they walk through the door. I provide a clean, safe, and pet friendly environment where they can relax, explore, and feel completely comfortable. I have 2 cats Emerald and Ivy! They are both 3 years old and they are spoiled. They have there own wall climbing catch tree that and tons of toys.

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The median cost per visit for dog sitting in Jamaica Plain is $25

Dog parents share their Rover experiences - Jamaica Plain

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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

Aly is great!! It’s so great to be able to leave knowing that my dog will be happy and well cared for while I’m gone.

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Esperanza T.
Drop-In Visits
5.0 out of 5 stars

Alissa was absolutely amazing with my husky. She took great care of her, great communication, and very good at accommodating my dog’s needs. I felt very safe knowing that my girl is being taken care of. I definitely will be booking with her again and I highly recommend her :)

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

I highly recommend Mike. He is reliable and he always sends lots of photos and a detailed update on how the visit went. He take a great care of both my dogs.

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Casey
Drop-In Visits
5.0 out of 5 stars

We chose Caleb because he was a cat-forward sitter, and he took great care of our special needs cat! She received plenty of attention and all of her medications as needed. Caleb shined even more caring for our aging and declining senior dogs who started needing extra attention as our trip came closer. We greatly appreciated Caleb and would happily rehire him!

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Kevin F.
Drop-In Visits
5.0 out of 5 stars

Elli was an absolutely great sitter for our Cocker Spaniel. She responded to our Last Minute Request very timely and allowed us to have an evening out of hotel without Winnie while traveling. She was early for Start Time and extremely flexible with our request to be a little late. Clearly she took great care of Winnie!! Very professional with communications. Would highly recommend Elli for taking care of your pet!!

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

Anthony was absolutely amazing! He was originally scheduled to watch my dog Echo from 7–9 PM EST, but when I needed to change the time to 2–4 PM, he was incredibly accommodating and flexible. His communication was excellent, and he was extremely responsive throughout the entire process. He is friendly, approachable, professional, and genuinely great to work with. It was clear that he was reliable and willing to help make things easier for me. I truly appreciate his flexibility and the outstanding service he provided. I would absolutely recommend Anthony to anyone looking for a trustworthy and dependable dog sitter. I would definitely book him again! 10/10

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Robert 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

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

Brianna was so so patient with my Ellie girl! Ellie is an anxious dog and Brianna handled it great! She was super timely and communicative!! Would recommend and will reach out again!!

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Rylee S.
Drop-In Visits
5.0 out of 5 stars

Amanda has been wonderful to work with. She's timely and communicative. We have a nervous dog, Amanda has been patient with them from the start offering them time to get to know her. Will definitely plan to use Amanda's pet sitting services again!

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Corbin
Drop-In Visits
5.0 out of 5 stars

She is great! My puppy loved her and she followed all of the instructions I left! Very communicative as well!

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

Annabel is great. She’s very responsive and was able to visit and quickly learn about our pup’s routine. Happy she’s now a recurring weekly friend :-)

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

Thanks Charlotte! You are so punctual and communicative. Really appreciate the last minute request too!

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Beth Y.
Drop-In Visits
5.0 out of 5 stars

Sienna did a wonderful job with the drop in visits for my senior dog with special needs. She was dependable, sent many updates, and took very well care of Jack. Jack loved her too! Thank you Sienna!

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

Nicole was truly amazing. She helped us out in a pinch and stopped by multiple times to walk our pup when we were out of town. She was on time, a fabulous communicator, and kept our pup safe and happy!

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

Julie was fantastic. A total pro and from the pictures I knew the dogs were really well cared for and went on some great walks

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

Georgia was great! Thank you so much for caring for our furry family member. We will definitely use her again!

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

Jada was wonderful! Pleasant, great with our dog, and made everything very easy. Would definitely recommend her and schedule with her again!

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Emma
Drop-In Visits
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How to book dog sitting

  1. 1. Search

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Popular requests for dog sitting - Jamaica Plain

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Sitters in Jamaica Plain average 6
repeat dog sitting clients

FAQs for Dog Sitting - Jamaica Plain

Frequently asked questions about Rover

The average cost of Dog Sitting in Jamaica Plain is $27 per visit as of October 2026. Most bookings cost between $14 and $43 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 October 2026, there are 10,347 sitters on Rover offering Dog Sitting across Jamaica Plain. 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 Jamaica Plain 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 .

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.

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 .

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 Jamaica Plain 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 Jamaica Plain. 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 , 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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