Pet Sitting in Winchester

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Top rated Winchester pet sitters

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Sitter Profile Image: Erin F.
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Erin F.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
121 reviews
49 repeat clients
9 years of experience
Woburn, MA, 01801

Lena was happy to see us and not desperate and angry. A tribute to Erin giving her not just the care she needs, but the companionship too while we're gone. We're so grateful for that. Erin goes above and beyond, making sure to take care of the trash and recycling, and leaving the house clean. We're so grateful for her care.

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Sophie and Scott D.
Sitter Profile Image: Shawn V.
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Shawn V.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
76 reviews
22 repeat clients
20 years of experience
Arlington, MA, 02474

Shawn dropped in to take care of our two cats multiple days during our long vacation. It was a huge relief knowing they were in good hands and getting photos each day. She followed our detailed feeding instructions that involved wet food with medication mixed in, and measuring out dry food on a scale. She also gave us detailed updates on their behavior and it was clear she really cared about their comfort and mood while we were gone. Thank you Shawn, would definitely book again!

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Daniel S.
Sitter Profile Image: Natalie J.
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Natalie J.
Star Sitter
from
$28
per visit
5 out of 5.0 stars
99 reviews
36 repeat clients
12 years of experience
Medford, MA, 02155

Natalie took excellent care of my cat. She was responsive and reliable, giving me peace of mind while away. I’ll be booking with her again in the future!

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Jillian G.
Sitter Profile Image: Alina M.
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Alina M.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
44 reviews
17 repeat clients
5 years of experience
Burlington, MA, 01803

Alina was great with my dog, Moose! She was prompt and made sure to take up the whole 30 minutes, and my dog really enjoyed her company! I would recommend Alina to anyone looking for a dog walker in the area.

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Jake W.
Sitter Profile Image: Michael D.
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Michael D.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
33 reviews
14 repeat clients
30 years of experience
Winchester, MA, 01890

About: I grew up caring for dogs of various sizes and breeds. My children and I cherish the love and joy of having a pet to care for and play with. I no longer own a dog of my own, however we still want a furry friend to share our lives with. I'm an elementary teacher by day, however have afternoons, evenings, weekends, school vacations, and summers available to care for your dog. I am not home during most school days, however will not host a dog unless I am also scheduled to be home. There is a lot of space for one or two dogs to play inside our home. When caring for dogs, I will take them for walks in the park across the street or through one of the many walking paths in this area. It's our pleasure to play with your dog; keeping them engaged makes for a fun experience and helps keep their minds off of missing you!

Sitter Profile Image: Elisangela L.
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Elisangela L.
Star Sitter
from
$24
per visit
5 out of 5.0 stars
78 reviews
25 repeat clients
8 years of experience
Woburn, MA, 01801

Elisa was responsive and sent detailed photos with each visit. She also responded well despite my cat having bitten her (a previously unseen behavior) and completed the visits.

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Lisa Z.
Sitter Profile Image: Liz M.
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Liz M.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
10 reviews
3 repeat clients
15 years of experience
Medford, MA, 02155

I asked Liz to drop in on my kiddos for a 2nd time. They really enjoy her visits. And, it provides such peace of mind for me knowing they have a familiar face stopping by to care for them and play with them. Thanks again, Liz!!

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Margot W.
Sitter Profile Image: Bonnie K.
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Bonnie K.
Star Sitter
from
$28
per visit
5 out of 5.0 stars
245 reviews
90 repeat clients
30 years of experience
Arlington, MA, 02474

Bonnie is wonderful! Very accomodating and great at following up. Because I am not computer and internet savvy, I made some mistakes with registering. On her own time, Bonnie worked diligently on her own time to correct my mistake and I got a refund from Rover.com. I know she has a lot of clients but it always feels as if you are her only client. I can't recommend her highly enough!

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Anne D.
Sitter Profile Image: Zijia C.
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Zijia C.
from
$15
per visit
1 repeat client
5 years of experience
Arlington, MA, 02474

Zijia took amazing care of my cat while I was away. My cat is usually shy around new people, but he warmed up quickly thanks to his gentle and patient approach. I came home to a happy, relaxed cat and a clean space. I would absolutely recommend Zijia to anyone looking for a kind and reliable pet sitter.

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Dongfang H.
Sitter Profile Image: Julia B.
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Julia B.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
19 reviews
7 repeat clients
12 years of experience
Somerville, MA, 02144

Julia was fantastic- we really loved her watching our two cats! It was important to us that they have play time and attention while we were away, and they clearly loved her.

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Caroline A.
Sitter Profile Image: Angela R.
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Angela R.
from
$15
per visit
5 out of 5.0 stars
5 reviews
25 years of experience
Medford, MA, 02155

About: I grew up with cats and have always found joy in making sure they’re well loved and cared for at every stage of life. Even after moving away from home, I shared pets with roommates and had the opportunity to love and care for them, just like my own. Now, I’m mom to two tuxedo cats who are smart, rambunctious, and cuddly all at once—and a tween-age beagle mix who’s sassy, full of energy, and a total snuggle bug. Though I’m newer to dog ownership myself, friends and family have consistently trusted me to care for their dogs. With my own dog, I’ve learned how important it is to read and respect each pet’s unique cues, and I’m happy to learn from you about how to best support your pup and to align with your goals. I’m a career special education teacher and high school program director/administrator, which means I’m detail-oriented, responsive, conscientious, and cautious—qualities I bring to every pet I care for, treating them just as I would my own. I have a flexible summer schedule. While my schedule for the fall is not yet solidified, I am consistently available for early morning or late afternoon drop ins. I am very detail oriented, and will ensure that I have the utmost clarity on your pets’ care instructions. I am extremely careful when ensuring that I am following all safety requests (I.e. arming security systems, locking/ closing egresses), and will happily meet your individual requests.

Sitter Profile Image: Shannon S.
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Shannon S.
Star Sitter
from
$22
per visit
5 out of 5.0 stars
71 reviews
10 repeat clients
8 years of experience
Malden, MA, 02148

Shannon is amazing! So responsible and attentive with my dogs. Really pays attention to detail and gives very detailed report cards. Great sitter!

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Alice C.
Sitter Profile Image: Cathalina M.
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Cathalina M.
Star Sitter
from
$30
per visit
5 out of 5.0 stars
344 reviews
83 repeat clients
18 years of experience
Malden, MA, 02148

Needed a sitter while I went away for a week. Cathalina was great with my kitty Domino, who is moody and under the impression he’s a dog. She played with him even after he tried to get her at the start of one of their visits! Hero in my book lol great communication and lots of pics! Definitely will book her again for my next trip!

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Cassandra J.
Sitter Profile Image: Jordan D.
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Jordan D.
from
$14
per visit
2 repeat clients
1 year of experience
Stoneham, MA, 02180

Jordan came to the rescue when our last cat sitter unexpectedly backed out. He's been very accommodating and went to check on our cat same night. He also sent us tons of photos so we know our cat is well taken care of

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Shan L.
Sitter Profile Image: Sara & Ari B.
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Sara & Ari B.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
29 reviews
5 repeat clients
10 years of experience
Medford, MA, 02155

Sara was very accommodating with a last minute request and took great care of Luna! She provided thorough updates and pictures as well. Will definitely book with her again!

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Emily R.
Sitter Profile Image: Blane H.
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Blane H.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
11 reviews
4 repeat clients
10 years of experience
Medford, MA, 02155

Blane was super organized— reached out in advance to come meet the kitties and see the house. The updates we got were so full of love and we 100% knew the cats were in good hands. It was also very easy to ask for a few extra things like making sure the AC was on and the windows were closed when the weather changed. Thanks so much!! We’ll definitely be repeat customers.

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Emily F.
Sitter Profile Image: Maude G.
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Maude G.
from
$19
per visit
5 out of 5.0 stars
13 reviews
2 repeat clients
15 years of experience
Stoneham, MA, 02180

About: Hi guys! My name is Maude, I am a 27 year old small business owner living in Stoneham with my best friend Stella, a 5 year old golden retriever. I’ve always had a passion for animals and have owned dogs for over 15 years, raising them from puppyhood. I know how important your dog is to you and my #1 goal is to return them to you SAFE and HAPPY, along with your peace of mind. We can’t wait to meet you 😊 I know firsthand how stressful it can be to leave your pup with a sitter/walker - my top priority is ensuring that you feel confident in the quality of your dog’s care under my watch and to give your pet my full 1:1 care and attention like I do with my own dog. As a small business owner, I’m able to make my own schedule and can be flexible with fitting your pet’s care into my daily routine. Safety is my number one priority. I know how hard it is to leave your fur baby in someone else’s hands, so my goal is to give you some peace of mind with frequent updates and attentive care.

Sitter Profile Image: Michelle T.
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Michelle T.
from
$15
per visit
5 out of 5.0 stars
2 reviews
4 years of experience
Winchester, MA, 01890

About: I don’t just care for pets, I truly listen to them, bringing calm and steady energy and cater to each animal to make them feel safe and understood. No matter how busy my day gets, I always make sure there’s dedicated time for the pets I care for. Whether it’s a walk, playtime, or just some quiet attention, they’re a priority and I’m fully present with them. When I’m caring for pets in their own home, I make sure to keep their routine as normal as possible. I give them plenty of attention, stick to their feeding and exercise schedule, and create a calm, safe environment where they feel comfortable. I treat their home, and them, with respect, just like they’re my own.

Sitter Profile Image: Jolene G.
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Jolene G.
from
$20
per visit
5 out of 5.0 stars
4 reviews
4 years of experience
Winchester, MA, 01890

Thank you, Jolene, for checking in on my two cats over a holiday weekend with a last minute booking! Jolene’s communication and timing was excellent. While checking on the cats, she filled their bowls, gave them treats, and brushed them. I appreciated her time and attention!

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Emily G.
Sitter Profile Image: Margaret F.
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Margaret F.
from
$17
per visit
12 years of experience
Winchester, MA, 01890

About: Not only have I cared for my own dogs and my friends' dogs, but I volunteer at Zoo New England as an animal Keeper's aid! I've been with Stone Zoo for 2 years now, and transitioned to animal care about a year and a half ago because the education staff knows that I own snakes and have a passion for all animals. I would love to meet your furry, scaly or slimy friends and help you out with their care! I am a freelance opera singer, so my schedule is very flexible. If I'm working on a show in town, I usually have a lot of daytime availability. I do travel for work sometimes, but I always know my schedule well in advance. I have taken dogs for walks, play-dates, given food, medicine, and stayed over night with dogs in their person's house for over a week at a time.

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Sitter Profile Image: Erin F.
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Sitter Profile Image: Erin F.
Verified Enhanced Background Check

Erin F.
Star Sitter

Enthusiastic, flexible pet lover 😊
Woburn, MA, 01801
2.3 mi. away
Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
121 reviews
49 repeat clients
Profile image

Lena was happy to see us and not desperate and angry. A tribute to Erin giving her not just the care she needs, but the companionship too while we're gone. We're so grateful for that. Erin goes above and beyond, making sure to take care of the trash and recycling, and leaving the house clean. We're so grateful for her care.

Availability updated yesterday
Sitter Profile Image: Shawn V.
Verified Enhanced Background Check
Sitter Profile Image: Shawn V.
Verified Enhanced Background Check

Shawn V.
Star Sitter

Keeping pets healthy, happy and ❤️
Arlington, MA, 02474
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
5 out of 5.0 stars
76 reviews
22 repeat clients
Profile image

Shawn dropped in to take care of our two cats multiple days during our long vacation. It was a huge relief knowing they were in good hands and getting photos each day. She followed our detailed feeding instructions that involved wet food with medication mixed in, and measuring out dry food on a scale. She also gave us detailed updates on their behavior and it was clear she really cared about their comfort and mood while we were gone. Thank you Shawn, would definitely book again!

Availability updated today
Sitter Profile Image: Natalie J.
Verified Enhanced Background Check
Sitter Profile Image: Natalie J.
Verified Enhanced Background Check

Natalie J.
Star Sitter

Here to keep the happy tails waggin
Medford, MA, 02155
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per visit
5 out of 5.0 stars
99 reviews
36 repeat clients
Profile image

Natalie took excellent care of my cat. She was responsive and reliable, giving me peace of mind while away. I’ll be booking with her again in the future!

Availability updated 10 days ago
Sitter Profile Image: Alina M.
Verified Enhanced Background Check
Sitter Profile Image: Alina M.
Verified Enhanced Background Check

Alina M.
Star Sitter

I will take care of your pet! 🐶🐱
Burlington, MA, 01803
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
44 reviews
17 repeat clients
Profile image

Alina was great with my dog, Moose! She was prompt and made sure to take up the whole 30 minutes, and my dog really enjoyed her company! I would recommend Alina to anyone looking for a dog walker in the area.

Availability updated today
Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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Michael D.
Star Sitter

A loving experience for your pet!
Winchester, MA, 01890
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
5 out of 5.0 stars
33 reviews
14 repeat clients

About: I grew up caring for dogs of various sizes and breeds. My children and I cherish the love and joy of having a pet to care for and play with. I no longer own a dog of my own, however we still want a furry friend to share our lives with. I'm an elementary teacher by day, however have afternoons, evenings, weekends, school vacations, and summers available to care for your dog. I am not home during most school days, however will not host a dog unless I am also scheduled to be home. There is a lot of space for one or two dogs to play inside our home. When caring for dogs, I will take them for walks in the park across the street or through one of the many walking paths in this area. It's our pleasure to play with your dog; keeping them engaged makes for a fun experience and helps keep their minds off of missing you!

Availability updated 13 days ago
Sitter Profile Image: Elisangela L.
Verified Enhanced Background Check
Sitter Profile Image: Elisangela L.
Verified Enhanced Background Check

Elisangela L.
Star Sitter

LOVE Paws,Claws,Fins,Feathers&More!
Woburn, MA, 01801
2.9 mi. away
Drop-In Visits, Dog Walking
from
$24
per visit
5 out of 5.0 stars
78 reviews
25 repeat clients
Profile image

Elisa was responsive and sent detailed photos with each visit. She also responded well despite my cat having bitten her (a previously unseen behavior) and completed the visits.

Availability updated 5 days ago
Sitter Profile Image: Liz M.
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Sitter Profile Image: Liz M.
Verified Enhanced Background Check

Liz M.
Star Sitter

Your pets next bff!
Medford, MA, 02155
3.8 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
10 reviews
3 repeat clients
Profile image

I asked Liz to drop in on my kiddos for a 2nd time. They really enjoy her visits. And, it provides such peace of mind for me knowing they have a familiar face stopping by to care for them and play with them. Thanks again, Liz!!

Availability updated 5 days ago
Sitter Profile Image: Bonnie K.
Verified Enhanced Background Check
Sitter Profile Image: Bonnie K.
Verified Enhanced Background Check

Bonnie K.
Rover 101
Star Sitter

Your pet is my pet when with me.
Arlington, MA, 02474
2.9 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$28
per visit
5 out of 5.0 stars
245 reviews
90 repeat clients
Profile image

Bonnie is wonderful! Very accomodating and great at following up. Because I am not computer and internet savvy, I made some mistakes with registering. On her own time, Bonnie worked diligently on her own time to correct my mistake and I got a refund from Rover.com. I know she has a lot of clients but it always feels as if you are her only client. I can't recommend her highly enough!

Availability updated today
Sitter Profile Image: Zijia C.
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Sitter Profile Image: Zijia C.
Verified Enhanced Background Check

Zijia C.

Animal Loving Graduate Student
Arlington, MA, 02474
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
1 repeat client
Profile image

Zijia took amazing care of my cat while I was away. My cat is usually shy around new people, but he warmed up quickly thanks to his gentle and patient approach. I came home to a happy, relaxed cat and a clean space. I would absolutely recommend Zijia to anyone looking for a kind and reliable pet sitter.

Availability updated today
Sitter Profile Image: Julia B.
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Sitter Profile Image: Julia B.
Verified Background Check

Julia B.
Star Sitter

Caring Pet Lover
Somerville, MA, 02144
3.4 mi. away
Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
19 reviews
7 repeat clients
Profile image

Julia was fantastic- we really loved her watching our two cats! It was important to us that they have play time and attention while we were away, and they clearly loved her.

Availability updated 3 days ago
Sitter Profile Image: Angela R.
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Sitter Profile Image: Angela R.
Verified Enhanced Background Check

Angela R.

Attentive, caring, & present care!
Medford, MA, 02155
2.7 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
5 reviews

Angela is genuine, loving, caring, and responsible. She has been a pet owner to two cats for several years and raised them since young kittens, and has also adopted and been raising a puppy for over a year now. She is intuitive to her animals’ needs and body language, and her patience is unmatched! Angela’s love for animals runs deep and she has always treated my pets like her own. I can always trust that my pets will be well-loved and cared for in Angela’s hands!

Availability updated 3 days ago
Sitter Profile Image: Shannon S.
Verified Enhanced Background Check
Sitter Profile Image: Shannon S.
Verified Enhanced Background Check

Shannon S.
Rover 101
Star Sitter

Pet Care Specialist
Malden, MA, 02148
3.5 mi. away
House Sitting, Drop-In Visits
from
$22
per visit
5 out of 5.0 stars
71 reviews
10 repeat clients
Profile image

Shannon is amazing! So responsible and attentive with my dogs. Really pays attention to detail and gives very detailed report cards. Great sitter!

Availability updated 5 days ago
Sitter Profile Image: Cathalina M.
Verified Enhanced Background Check
Sitter Profile Image: Cathalina M.
Verified Enhanced Background Check

Cathalina M.
Star Sitter

Provider of loving care
Malden, MA, 02148
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per visit
5 out of 5.0 stars
344 reviews
83 repeat clients
Profile image

Needed a sitter while I went away for a week. Cathalina was great with my kitty Domino, who is moody and under the impression he’s a dog. She played with him even after he tried to get her at the start of one of their visits! Hero in my book lol great communication and lots of pics! Definitely will book her again for my next trip!

Availability updated 8 days ago
Sitter Profile Image: Jordan D.
Verified Enhanced Background Check
Sitter Profile Image: Jordan D.
Verified Enhanced Background Check

Jordan D.

Post-grad pre-work life adventure
Stoneham, MA, 02180
2.8 mi. away
Drop-In Visits, Dog Walking
from
$14
per visit
1 review
2 repeat clients
Profile image

Jordan came to the rescue when our last cat sitter unexpectedly backed out. He's been very accommodating and went to check on our cat same night. He also sent us tons of photos so we know our cat is well taken care of

Availability updated 9 days ago
Sitter Profile Image: Sara & Ari B.
Verified Enhanced Background Check
Sitter Profile Image: Sara & Ari B.
Verified Enhanced Background Check

Sara & Ari B.
Star Sitter

Will love your pet like our own!
Medford, MA, 02155
3.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
5 out of 5.0 stars
29 reviews
5 repeat clients
Profile image

Sara was very accommodating with a last minute request and took great care of Luna! She provided thorough updates and pictures as well. Will definitely book with her again!

Availability updated today
Sitter Profile Image: Blane H.
Verified Enhanced Background Check
Sitter Profile Image: Blane H.
Verified Enhanced Background Check

Blane H.
Rover 101
Star Sitter

Compassionate & Reliable Care
Medford, MA, 02155
2.7 mi. away
Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
11 reviews
4 repeat clients
Profile image

Blane was super organized— reached out in advance to come meet the kitties and see the house. The updates we got were so full of love and we 100% knew the cats were in good hands. It was also very easy to ask for a few extra things like making sure the AC was on and the windows were closed when the weather changed. Thanks so much!! We’ll definitely be repeat customers.

Availability updated 4 days ago
Sitter Profile Image: Maude G.
Verified Enhanced Background Check
Sitter Profile Image: Maude G.
Verified Enhanced Background Check

Maude G.
Rover 101

Dog Owner w/ 15+ years experience!
Stoneham, MA, 02180
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$19
per visit
5 out of 5.0 stars
13 reviews
2 repeat clients

Maude is the owner of a beautiful two year old English Cream golden retriever and has gained a lot of experience caring for her puppy by doing so first hand! She is responsible, reliable and I would highly recommend her caregiving services to any and all pet owners!

Availability updated 10 days ago
Sitter Profile Image: Michelle T.
Verified Enhanced Background Check
Sitter Profile Image: Michelle T.
Verified Enhanced Background Check

Michelle T.

Here for your pets, always❤️
Winchester, MA, 01890
0.5 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
2 reviews

I’ve watched her grow up with a real love for animals and a natural sense of empathy. She’s always been gentle, patient, and caring, even as a kid. I think animals can pick up on that kind of energy because I can’t recall a single bad experience that she’s had with them. She genuinely cares about their well being and treats them with respect, which makes her a great pet caretaker.

Availability updated yesterday
Sitter Profile Image: Jolene G.
Verified Enhanced Background Check
Sitter Profile Image: Jolene G.
Verified Enhanced Background Check

Jolene G.

Big or small, I love them all!
Winchester, MA, 01890
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
4 reviews
Profile image

Thank you, Jolene, for checking in on my two cats over a holiday weekend with a last minute booking! Jolene’s communication and timing was excellent. While checking on the cats, she filled their bowls, gave them treats, and brushed them. I appreciated her time and attention!

Availability updated today
Sitter Profile Image: Margaret F.
Verified Enhanced Background Check
Sitter Profile Image: Margaret F.
Verified Enhanced Background Check

Margaret F.

Dog lover + Zoo Keeper Volunteer!
Winchester, MA, 01890
0.9 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
2 reviews

Margaret has taken incredible care of my dog since he was a year old (and he just turned 13)! She has walked him, fed him, helped him when he needed medical care, and most importantly, she loves him--and the feeling is extremely mutual. She is absolutely one of his top 3 people on the planet. She's conscientious, responsive, and thoughtful, and has a genuine love for animals that they can sense. There's no one I feel more comfortable leaving him with. Cannot recommend her highly enough!

Availability updated 17 days ago

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