Dog Sitting in Jamaica Plain

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

End Date
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Jamaica Plain dog sitters

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

1 / 1
Sitter Profile Image: Izza Sofia H.
Verified Enhanced Background Check
Izza Sofia H.
$23
total per visit
4.8 out of 5 stars
44 reviews
8 repeat clients
5 years of experience
Jamaica Plain, Boston, MA, 02120

Sophia is EXCELLENT in all respects. She is very conscientious and amazing with dogs. She went above and beyond for us, addressing challenging issues in real time and responding flexibly when situations and needs changed. We are so grateful to have her caring for our dog!

Profile image
Christopher M.
Sitter Profile Image: Julia B.
Verified Background Check
Julia B.
$28
total per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
9 years of experience
Jamaica Plain, Jamaica Plain, MA, 02130

About: I absolutely love dogs, and since I don’t have one of my own, your pet enjoys my full attention in a calm, loving environment. ✨ Flexible Work-From-Home Schedule – I work remotely most of the week and can easily move around my office days to fit your needs. 🔎 Highly Attentive - I might be the most detail-oriented person you'll meet! I catch the little things, follow your instructions carefully, and make sure your pet feels safe and cared for. 📸 Consistent Updates – Expect regular photos and communication for total peace of mind. I’m home most of the week thanks to my flexible work schedule, so your pet will get plenty of attention and companionship. I’m happy to help with regular visits, check-ins throughout the day, or even last-minute requests. I understand the importance of health and safety for both you and your pet, and I am fully vaccinated against COVID-19. I work at a college in educational technology and faculty support, a role that requires organization, attention to detail, and clear communication. I bring those same skills to caring for your pet, focusing on making them feel safe, happy, and loved while I’m with them. I’m highly observant and attentive, following instructions closely and noticing even small changes in behavior. I treat your home with respect and provide calm, consistent companionship, keeping you informed so you can relax knowing your furry friend is in good hands.

Sitter Profile Image: Shoshana R.
Verified Enhanced Background Check
Shoshana R.
$25
total per visit
5.0 out of 5 stars
4 reviews
1 repeat client
8 years of experience
Boston, MA, 02130

Shoshana did a great job! I will be using her again to take care of my cats!

Profile image
Victoria B.
Sitter Profile Image: Angelina T.
Verified Enhanced Background Check
Angelina T.
$28
total per visit
5.0 out of 5 stars
113 reviews
45 repeat clients
13 years of experience
Roxbury, Dorchester, MA, 02121

Tommy did an exceptional job caring for my two fussy cats for 6 days! My cats both need medicine and extra care every day and Tommy was consistent, reliable, and a great communicator. I can tell my cats were well cared for while I was away. Thanks so much Tommy!

Profile image
Laura R.
Sitter Profile Image: Anastasia S.
Verified Enhanced Background Check
Anastasia S.
Star Sitter
$39
total per visit
5.0 out of 5 stars
89 reviews
34 repeat clients
22 years of experience
Boston, MA, 02115

Anastasia was so great with our young puppy. We were a little anxious about leaving her for the first time, but this was an excellent experience. Definitely booking again!

Profile image
Kim D.
Sitter Profile Image: Ashley G.
Verified Enhanced Background Check
Ashley G.
Star Sitter
$23
total per visit
5.0 out of 5 stars
21 reviews
5 repeat clients
15 years of experience
Roslindale, Roslindale, MA, 02131

Ashley was friendly, communicative, and on time. I came home to happy and relaxed cats. From Ashley’s pics, it looked like my cats had a good time!

Profile image
Nichole S.
Sitter Profile Image: Eve B.
Verified Enhanced Background Check
Eve B.
$19
total per visit
5.0 out of 5 stars
6 reviews
1 repeat client
5 years of experience
Jamaica Plain, Boston, MA, 02130

About: I’ve always loved animals, especially dogs, and have taken care of neighborhood pets for years! I am friendly, attentive, and excited to meet your pets! Please feel free to reach out with any questions. I’m easily able to fit pet care into my schedule as I otherwise work remotely or make my own hours! Please reach out with any scheduling questions and I would love to accommodate as best I can! I will do my best to ensure your pet feels safe, loved, and healthy. I’m happy to follow detailed instructions or just stop by and assess what they need and give them some love. :)

Sitter Profile Image: Emily M.
Verified Enhanced Background Check
Emily M.
$28
total per visit
5.0 out of 5 stars
2 reviews
8 years of experience
Boston, MA, 02130

Emily was wonderful to work with. She grasped the care instructions quickly and easily. She carried them out exactly as we wished. And our kitty, Louie, really enjoyed playing with her!

Profile image
Ted W.
Sitter Profile Image: Angelina C.
Verified Enhanced Background Check
Angelina C.
$22
total per visit
5.0 out of 5 stars
23 reviews
4 repeat clients
10 years of experience
Brookline, MA, 02445

About: Forever animal lover! I’ve always had and have loved being around animals. From playing, to walks, to feeding, happy to help you take care of your four legged loved ones. I have availability to help out with your pets in the evenings and on weekends! I’m available to stop by and play, feed, walk or just keep them company. I am able to walk your pup and take them to local parks. I can also take them out to play in your backyard as well!

Sitter Profile Image: Michael P.
Verified Enhanced Background Check
Michael P.
Star Sitter
$28
total per visit
5.0 out of 5 stars
33 reviews
11 repeat clients
20 years of experience
Boston, MA, 02130

Michael is great! Responded to my request to check in on my cats so promptly and I felt secure knowing my cats were in good hands. Got lots of pictures and updates. I definitely recommend booking with him!

Profile image
Hannah H.
Sitter Profile Image: Libbie D.
Verified Background Check
Libbie D.
$17
total per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Jamaica Plain, Boston, MA, 02130

About: Your dog will have an unmatched experience with me and my sweet pup, Tina! I work from home full time, so your dog will always have company, structure, and plenty of attention throughout the day. We live just minutes from the arboretum which means long, enriching walks are part of our daily routine. My pup, Tina, is 4 years old and very chill. She loves having a friend around and I’m committed to making every dog feel safe, loved, and at home and making sure they get the care and affection they deserve.

Sitter Profile Image: Isabel Q.
Verified Enhanced Background Check
Isabel Q.
Star Sitter
$34
total per visit
5.0 out of 5 stars
111 reviews
32 repeat clients
20 years of experience
Brookline, MA, 02445

Isabel was fantastic with our kitty! She sent great updates and photos and followed our instructions to a T. We (and Percy!) look forward to having her care for him again!

Profile image
Erin B.
Sitter Profile Image: Claire F.
Verified Enhanced Background Check
Claire F.
Star Sitter
$42
total per visit
5.0 out of 5 stars
42 reviews
21 repeat clients
23 years of experience
Roxbury, Jamaica Plain, MA, 02130

Claire was communicative and prompt, and took good care of my cats. She was diplomatic in the face of my unexpectedly aggressive cat. Recommended!

Profile image
Nate D.
Sitter Profile Image: Jana W.
Verified Enhanced Background Check
Jana W.
Star Sitter
$29
total per visit
5.0 out of 5 stars
291 reviews
89 repeat clients
30 years of experience
West Roxbury, West Roxbury, MA, 02132

Jana was great with my two dogs! Sent lots of photos and info on how the visit went and she above all made sure that both dogs had a safe visit. I will definitely be using her again.

Profile image
Korri C.
Sitter Profile Image: Sarabeth T.
Verified Enhanced Background Check
Sarabeth T.
Star Sitter
$45
total per visit
5.0 out of 5 stars
43 reviews
7 repeat clients
17 years of experience
Boston, MA, 02130

Sarabeth was great! She was great at reading and recognizing my dog’s boundaries, paying attention to house rules, and providing lots of fun for my dog. Will certainly have her back to watch Mae again

Profile image
Stacey L.
Sitter Profile Image: Jennifer M.
Verified Enhanced Background Check
Jennifer M.
Star Sitter
$45
total per visit
5.0 out of 5 stars
221 reviews
66 repeat clients
30 years of experience
Roslindale, Roslindale, MA, 02131

Jennifer is consistently great with my elderly cat and his multiple meds. She's also been able to roll with the punches when various things have gone wrong while I'm away, and although I wish she hadn't had to deal with any issues, it does make me feel very confident that she can handle whatever comes up!

Profile image
Brennan M.
Sitter Profile Image: Elizabeth S.
Verified Enhanced Background Check
Elizabeth S.
$19
total per visit
10 years of experience
Jamaica Plain, Boston, MA, 02130

About: I’ve taken care of my family pet throughout her life from puppy to end of life. I am familiar with feeding, walking, providing medicine, and general companionship! I am currently in graduate school and working part-time at a yoga studio!! I look forward to adding in pet care as another part time job to get to spend time walking outside and supporting in your pet care needs! I unfortunately cannot have pets in my apartment but prioritize safety and privacy in visiting others!! I am very clean and always tidy up after myself.

Sitter Profile Image: Jacqueline Y.
Verified Enhanced Background Check
Jacqueline Y.
Star Sitter
$18
total per visit
5.0 out of 5 stars
14 reviews
5 repeat clients
5 years of experience
Fenway-Kenmore, Boston, MA, 02215

Jacqueline was great with my kitties! She was very communicative and helpful on keeping an eye on more than just my fur babies. If considering travel, you will have a piece of mind with Jacqueline caring for your pets!

Profile image
Alassandra G.
Sitter Profile Image: Cynthia R.
Verified Background Check
Cynthia R.
$32
total per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
18 years of experience
Boston, MA, 02130

About: Hello! My name is Cynthia, and I’m a registered nurse working in primary care. I’m also a lifelong dog lover and proud owner of two wonderful dogs: Hazel, a sweet senior English Bulldog who loves naps and sunbathing, and Stella, a playful French Bulldog who enjoys playing fetch and relaxing outside in the sunshine. I live in the Roslindale area, close to spacious parks such as the Arnold Arboretum, where our dogs love going for walks and exploring. I have two children, ages 10 and 1, who have grown up around dogs and enjoy spending time with them. Creating a loving, safe, and pet-friendly environment is very important to our family. As a nurse, I am responsible, dependable, and attentive to details. I understand that every dog has unique needs, and I am experienced in administering medications and caring for senior dogs or pets that require extra attention and special precautions. I will treat your dog with the same love, patience, and care that I give my own. Communication is very important to me, and I strive to keep pet parents updated and provide peace of mind while they are away. Whether your pup enjoys long walks, playtime, cuddles, or simply relaxing in a sunny spot, I will make sure they feel comfortable, happy, and loved. I would be honored to care for your furry family member. Please feel free to reach out with any questions. I look forward to meeting you and your pup! Pet care fits naturally into my daily routine. I work Monday through Friday from 9:00 AM to 5:00 PM at a primary care office located just a few miles from home, which allows me to be available and flexible. If needed, I am able to stop home during my lunch break to provide potty breaks, meals, medications, or extra attention. I am off on weekends, giving me plenty of time to dedicate to walks, playtime, and one-on-one care. Since I have dogs of my own, caring for pets is already an important part of my everyday life. I understand the importance of maintaining routines and ensuring that each dog feels safe, comfortable, and loved while their family is away. I treat every dog in my care as if they were my own. I love spending time playing, cuddling, and giving them plenty of attention and affection. I make sure each pet maintains their regular routine and receives the care they need to feel comfortable and happy. Safety is always my top priority. I carefully ensure that dogs are securely leashed before going outside and closely supervise them during walks and playtime. I also have a spacious fenced backyard where pups can safely enjoy fresh air, exercise, and outdoor time. As a registered nurse and experienced dog owner, I understand the importance of being attentive to each pet's individual needs. Whether your dog enjoys playing, relaxing, or requires medications or special accommodations, I am committed to providing loving, reliable, and personalized care while keeping you updated for peace of mind.

Sitter Profile Image: Heather M.
Verified Enhanced Background Check
Heather M.
$28
total per visit
40 years of experience
Jamaica Plain, Jamaica Plain, MA, 02130

About: Hi there! I’m so excited to meet you and learn more about your pet and your current needs. I know finding a sitter can feel a little nerve-wracking, so I focus on being consistent, communicative, and truly attentive to your pet’s routine and comfort. I’ve cared for animals my entire life, from Great Danes to Labs to Frenchies to teacup Yorkies. I’m comfortable with senior pets and medical needs, including administering daily insulin and following strict feeding schedules and dietary guidelines. I’m calm, patient, and detail-oriented, and I focus on helping pets feel safe and settled quickly. I don’t currently have a dog in my home, so your pet will have my full attention and care. I work from home full-time, so I’m available throughout the day for walks, playtime, feeding, and companionship. Dogs get frequent outdoor breaks and attention, and cats get steady check-ins, calm company, and routine-based care. I live directly across the street from the Arnold Arboretum, which is a wonderful, peaceful place for daily walks, and I’m also close to several dog parks for pups who enjoy more active outings. I have two children with me 50% of the time, and they’ve grown up around both dogs and cats. That being said, if your pet is not child-friendly, please still reach out. My children are with me every other week, and I’m happy to coordinate care to make sure your pet is comfortable and set up for success. I know it can feel stressful to leave your pet with someone new, and I take that trust seriously. I follow instructions closely, including feeding schedules, medications, and any special care needs, and I’m thoughtful about each pet’s comfort, boundaries, and routine. For dogs, that means consistent walks, safe supervision, and steady structure. For cats, it means calm energy, predictability, and respecting their space while still making sure they feel cared for and secure. I’m always happy to send updates and photos so you can feel confident and at ease while you’re away. My goal is simple: your pet feels safe, relaxed, and well cared for, and you feel fully informed and supported.

1 / 1
View more sitters

Jamaica Plain dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Allyson did great job taking care of my 2 dogs. She’s easy to communicate with and punctual with arrival times!

Profile image
Austin A.
Drop-In Visits
5.0 out of 5 stars

Thank you Kristen! I hope it wasn’t too hot for you and your little. He may have wanted to stop across from Dane Park. Because he usually goes in there. Thanks again :)

Profile image
Deborah D.
Drop-In Visits
5.0 out of 5 stars

Grace took excellent care of our boy Rua with weekly visits over a few months. We will definitely book again when we need her.

Profile image
Fiona L.
Drop-In Visits
5.0 out of 5 stars

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!

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

Mia is great! Very tentative to our animals! Sends great update pictures. We feel very comfortable entrusting our fur babies to her!

Profile image
Sandy W.
Drop-In Visits
5.0 out of 5 stars

Zilalai is so amazing! She is reliable, flexibility, professional, and goes above and beyond making sure you are well informed. We are so grateful for her!

Profile image
Alexis K.
Drop-In Visits
5.0 out of 5 stars

Nick was the best dog sitter! We had drop in visits scheduled, and he was so intentional with spending time with our pup on each one. We will definitely be booking with Nick for our next trip!

Profile image
Michele V.
Drop-In Visits
5.0 out of 5 stars

Sam was very nice and punctual. He communicated any questions he had right away. My dog definitely liked him!

Profile image
Sarah M.
Drop-In Visits
5.0 out of 5 stars

I highly recommend Elizabeth for all of your dog needs. I have 2 dogs, one is reactive, and she was very thoughtful and gentle with him until they grew trust together. Elizabeth is always on time, and follows through with all her commitments. She is trustworthy, communicative, and friendly. I would recommend Elizabeth to anyone!

Profile image
Timothy K.
Drop-In Visits
5.0 out of 5 stars

Chelseigh was excellent with Petey who is reactive. She was patient, consistent, reliable, and caring.

Profile image
Molly M.
Drop-In Visits
5.0 out of 5 stars

Kaitlyn did a great job with my dog. She was right on time for a drop-in. Her communication is also excellent! She was always very timely with responses to messages and sending me updates. I will definitely use her again!

Profile image
Melinda B.
Drop-In Visits
5.0 out of 5 stars

Emma was very responsive, and so easy and friendly to work with for our very last minute drop in request. She did everything we asked and it was obvious through her pictures our dog was very comfortable with her. Thanks so much!!

Profile image
Emma
Drop-In Visits
5.0 out of 5 stars

Willow loved staying with Jennifer and her pup! She is a great communicator and I am very comfortable leaving Willow with her.

Profile image
Janette K.
Drop-In Visits
5.0 out of 5 stars

Madison was absolutely wonderful with my dog during her drop-in visits. She was reliable, communicative, attentive, and clearly cared about making sure my pup was comfortable and well taken care of. I appreciated the updates and peace of mind while away. I would definitely book with her again and highly recommend her to anyone looking for a trustworthy sitter!

Profile image
Antoinette J.
Drop-In Visits
5.0 out of 5 stars

Chelsea has been an amazing, trustworthy, and responsible friend for our pet dog whenever we go out of town and need someone for drop-in visits / walks. I have been a repeat customer, and feel 100% safe knowing that Chelsea is professional and knowledgeable about all of my dog's needs. I can fully vouch that you won't regret choosing Chelsea for all your Rover needs!

Profile image
Alex J.
Drop-In Visits
5.0 out of 5 stars

Emma was a fantastic dog care person for our beloved Sammi! She went the extra mile to help, when a problem arose. We look forward to booking her again in the future! Thanks, Emma!

Profile image
Ann P.
Drop-In Visits
5.0 out of 5 stars

Sarah was so great with our dog, she took excellent care of him and was very communicative the whole time. We will definitely look to Sarah again in the future!

Profile image
Kyle S.
Drop-In Visits
5.0 out of 5 stars

Ann-Marie did a wonderful job taking care of our 10-year old Bernese Mountain Dog, Zeus. She stopped by to walk and spend time with Zeus three times a day for almost a week and provided helpful updates throughout. She was really great!

Profile image
Allyson G.
Drop-In Visits
5.0 out of 5 stars

Emily is amazing! She is so sweet, genuinely loves and wants to spend time with dogs, and respects a schedule you’d like her to follow. Not only would I request her again in the future, but I also wouldn’t hesitate to recommend her to others.

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

I highly recommend Sarabeth. She did lots of play and snuggles with my herding dog and really tired her out! It’s clear that she pays attention to directions and also engages a dog in a variety of ways. Thanks again!

Profile image
Stacey L.
Drop-In Visits
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Dog Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Jamaica Plain dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.

Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Jamaica Plain.

Rover makes it easy to find Jamaica Plain dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.