Pet Sitting in Chestnut Hill

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Chestnut Hill pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Laura B.
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Laura B.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
177 reviews
36 repeat clients
5 years of experience
Midlothian, VA, 23112

Laura was an absolute pleasure !! She took such amazing care of our boy Brutus and was so considerate with her gestures like helping to bring our trash can back off the steeet while we were out of town! Our boy was given so much love and we will for sure use her again in the future! Highly recommend!!

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Madison J.
Sitter Profile Image: Julia H.
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Julia H.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
39 reviews
16 repeat clients
16 years of experience
North Chesterfield, VA, 23236

Julia was AMAZING!! She was communicative and prompt. She took good care of our pups while we were away and I couldn’t ask for someone better!

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Bryanna R.
Sitter Profile Image: Paula H.
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Paula H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
124 reviews
45 repeat clients
20 years of experience
N. Chesterfield, VA, 23236

Paula does such an amazing job! She is patient with our stubborn Otis and gives him so much attention and so many cuddles. She has a flexible schedule and is always quick to respond.

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Erin F.
Sitter Profile Image: Laura C.
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Laura C.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
16 years of experience
Richmond, VA, 23236

Took good care of our boy during a pretty last minute drop-in request!

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Dawn S.
Sitter Profile Image: Jessica W.
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Jessica W.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
81 reviews
22 repeat clients
10 years of experience
Chesterfield, VA, 23832

Jessica was fantastic with providing clear communication, including updates, photos, and how our pupper was doing! Very pleasant experience and would recommend/have again in the future.

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Ian E.
Sitter Profile Image: Caitlyn & Samuel E.
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Caitlyn & Samuel E.
from
$18
per visit
5.0 out of 5 stars
32 reviews
8 repeat clients
20 years of experience
Midlothian, VA, 23114

Cait was amazing with our Goldendoodle, Bella! She spent lots of quality time with her and allowed us to enjoy our family vacation knowing she was taken care of. Updates and photos every visit really helped! Even took care of a few things around the house like bringing in mail and packages. Definitely recommend her!

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Patrick S.
Sitter Profile Image: Kristy B.
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Kristy B.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
314 reviews
120 repeat clients
16 years of experience
Chesterfield, VA, 23832

Kristy was absolutely wonderful for our situation. We have never trusted anyone, outside of our family, to take care of our spoiled rotten pit bull, Lucy. We were faced with the challenge of finding someone who would be responsible and dependable enough to cater to our daily routine - without removing her from her comfort zone “home”. This meant we had to not only trust someone in our home, but more importantly, find someone who understood how unpredictable our rescue put bill could be if faced with other animals. My biggest concern was the care for Lucy while we were on our honeymoon - Kristy agreed to come by ahead of time - so we could meet her, get a feel for each other and see how Lucy responded. While I really liked Kristy - we still worried - but by the second day - I stopped obsessively checking my phone. She kept in contact with us, sent pictures, and responded immediately to all of my texts; she really put my heart and mind to rest. I will DEFINITELY use Kristy again and would recommend her to anyone in need of dependable care for their fur babies. Thank you Kristy ❤️???

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Carmen D.
Sitter Profile Image: DAMACIA J.
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DAMACIA J.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
315 reviews
84 repeat clients
30 years of experience
North Chesterfield, VA, 23236

Damacia was absolutely wonderful with my dog. Easy to work with, gentle, kind, and truly a dog whisperer. Bentley felt comfortable right away, and I could tell he was being cared for with real patience and warmth. I would absolutely trust Damacia again and highly recommend them to anyone looking for thoughtful, compassionate pet care.

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Beth A.
Sitter Profile Image: Emily H.
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Emily H.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
135 reviews
10 repeat clients
13 years of experience
Midlothian, VA, 23114

Emily dropped in to give our dogs a mid-day play and potty break while we were out of town. She was responsive and reliable. One of our dogs is slow to warm up to new people, but Emily was patient and won her over. We will definitely reach out to her again when we need help caring for our dogs.

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Kelli B.
Sitter Profile Image: Cynthia S.
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Cynthia S.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
18 reviews
4 repeat clients
17 years of experience
Richmond, VA, 23235

Cynthia was a great sitter! She was very communicative with me and sent me pictures of my cat while she was there. I felt like I didn’t have to worry about him at all when I was away for Christmas! Absolutely will try to rebook with her anytime I have to leave town!

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Madelyn F.
Sitter Profile Image: Wesley H.
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Wesley H.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
15 reviews
4 repeat clients
20 years of experience
Midlothian, VA, 23112

I will be using Wesley again! Gave me the best videos and pics of our dog while i was on vacation.

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Olivia L.
Sitter Profile Image: Kassandra J.
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Kassandra J.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
91 reviews
15 repeat clients
26 years of experience
North Chesterfield, VA, 23236

Kassandra is amazing! Very thorough with her notes and I felt completely at ease knowing my dog was in the very best hands while I was out of town!

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Devin M.
Sitter Profile Image: Haley B.
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Haley B.
from
$25
per visit
5.0 out of 5 stars
10 reviews
5 repeat clients
15 years of experience
Richmond, VA, 23236

Haley did an amazing job for us in a pinch at Christmas! We truly appreciate you being patient with Biggie and Nipsey, and making sure they were able to get out and eat! We will definitely be looking to book Haley again, hopefully this time not so last minute on our part! 😁

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Jason T.
Sitter Profile Image: Kiara P.
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Kiara P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
247 reviews
65 repeat clients
4 years of experience
Midlothian, VA, 23114

Kiara is great! I really appreciate the wonderful care she gave to my two kitty boys and my home. she was thoughtful and responsive. thanks so much again for everything — we’d be happy to have her watch them again anytime! :)

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Heidi L.
Sitter Profile Image: Erica G.
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Erica G.
from
$15
per visit
15 years of experience
Northwest, Richmond, VA, 23235

About: I’ve been rescuing and working with animals since I was in my early teens. I’ve fostered many litters of kittens, rescued dogs and wildlife. My original dream was to be a vet but instead I’ve continued to care for animals while working for a medical technology company. I currently have a German Sheppard, 3 cats and a lovebird. In the past I’ve had gerbils, a ball python, fish, chickens and many rescue cats and dogs. I love them all so much and would have more if I had the space. -Which is why I’d love to be a part of your babies lives. I work remotely so I’m available to come walk dogs in the mornings, afternoon or evenings. I’m also happy to come house sit and provide company and all day care to your family pets. During the day, my animals are great company to me. On nice days I will work outside on the deck while Ellie and my kitties sunbathe. I would be happy to do the same with your babies.

Sitter Profile Image: Amber C.
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Amber C.
from
$22
per visit
4.9 out of 5 stars
47 reviews
13 repeat clients
8 years of experience
Midlothian, VA, 23112

Amber did so great with my pup! I have never used Rover before and had to a only a few days to figure out care for my dog while I was away. She was prompt with her response and came to meet Monarch. Monarch instantly warmed up to her which means a lot and helped me trust that Amber was a great fit for her. I received updates and check ins from her. I would recommend Amber and would rebook her again!

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Kaitlin K.
Sitter Profile Image: Peyton B.
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Peyton B.
from
$13
per visit
20 years of experience
Jackson Ward, Midlothian, VA, 23112

About: Growing up my family always had at least one or more pets of various breeds so I have 20+ years of experience around animals. I have cared for dogs, cats, fish, lizards, rabbits, goats, and hedgehogs. Personally, my husband & I have 2 dogs currently, 9 & 10 years old, one having epilepsy & is dependent on medication. I have helped raise/care for/train puppies, kittens, baby rabbits, & baby goats. The only pet I'm not comfortable with is snakes, my little sister has one but I only look at it from 3ft away in its enclosure, haha. I work part time Tu/W/Th 8A - 5P, I do not mind caring for pets those days, however I will be gone all day. Otherwise, I'm available for your pets needs! My personal routine with my pets: My husband helps me care for our pets daily but his schedule is a bit different than mine, so our dogs are let out at least within 4-6 hours those days. Otherwise, we let them out every 2-4 depending on their needs (which they have been trained to lets us know if they need to go sooner). Our medical dog is on a 12 hr medication schedule. I'd prefer to care in my clients home due to one of my dogs having a reactive past, it was quite a transition when we inherited our other dog. If you have a specific routine, I'm ready to follow it to the T! I'm comfortable walking dogs on leash, hanging out/playing with them in a fenced yard, or just chilling inside. As mentioned, I have experience with medically dependent pets. I have an escape artist, so I'm always vigilant of their proximity to me and prepared to run/chase in the event something happens. I can stay at the home with the pets or I can visit throughout the day!

Sitter Profile Image: Haley S.
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Haley S.
from
$20
per visit
5.0 out of 5 stars
21 reviews
5 repeat clients
15 years of experience
Midlothian, VA, 23112

Haley was great with our cat Puffin!! We loved the photos she sent us and Puffin looked like he enjoyed their visits! We will be using Haley again in the future! :)

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Lierin R.
Sitter Profile Image: Cindy T.
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Cindy T.
from
$18
per visit
5.0 out of 5 stars
301 reviews
82 repeat clients
20 years of experience
north chesterfield, VA, 23235

About: Hi, I'm Cindy! I’m a stay-at-home mom of 2. I’m an animal lover with years of experience caring for pets. In our home, we only board small(In stature) dogs, medium dogs that are on the smaller side and small breed puppies. Our Jack Russell is afraid of larger breeds and we’ve found many small dog owners have the same issue. If your pet weighs more than 25 pounds but is still small in stature(like corgis), feel free to ask! Your pet will receive plenty of love, attention, and playtime. I’m home with your pets most of the day, except for short errands. My 2 dogs, a Jack Russel named Flower and a Goldendoodle named Cupid love having friends over! I treat them like family—whether it's cuddling on the couch or romping in our large, fenced backyard. For added safety, I stay outside with them, and we have locked gates and security cameras. All pets are fed separately for safety. I carry separate liability insurance for added peace of mind.

Sitter Profile Image: Amanda W.
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Amanda W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
55 reviews
17 repeat clients
15 years of experience
Chesterfield, VA, 23832

After the meet & greet took place, I knew Amanda would be the perfect person to care for my dogs. She’s reliable, compassionate, attentive, and patient with dogs that have special quirks and needs. I highly recommend Amanda as a resource for your animal needs!

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Brittany J.
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Chestnut Hill pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Julia did a great job as always! Our dog loves when she comes over and our skittish cats come out to great her.

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

I Loved Kassandra & how well she took care of my fur baby! She made sure she was able to potty, eat, stretch her legs out & get some loving on while we were gone. She’s great at communicating and keeping me updated. I’ll be using her for as long as she’s ever available to come check on my Kitana 😊

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Sabrinna A.
Drop-In Visits
5.0 out of 5 stars

Eileen provided expert and loving care for our dog, Murphy! They are so kind, attentive and wonderful communicators while they are caring for Murphy. We are so grateful for their loving care while we are away. We love that Murphy can stay home where he is most comfortable and happy. Thank you!

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Katherine J.
Drop-In Visits
5.0 out of 5 stars

Jessica was wonderful to work with. She was quick to respond, very friendly in all communication, and gave regular updates during the visit. She followed all care instructions carefully, and I felt very comfortable leaving Orion in her care. I would definitely recommend her!

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

Wesley accepted a last minute request to care for our dog and I am so thankful. Our dog immediately took a liking to Wesley making me feel very comfortable making my decision to move forward with the visits. Wesley was timely with our initial meet and throughout the three drop in visits completed this weekend. I received notes and pictures with each visit which was much appreciated. I highly recommend Wesley and I personally look forward to using his services again!

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

Christell is amazing! She is professional, communicative, and so helpful. I highly recommend booking her for your pet care needs.

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

I know I can count on Kristy to do a great job checking in on my dog. It’s wonderfully knowing he is well cared for and I highly recommend her.

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

Emily is amazing always but this time specifically I had her take care of my dog, my parents dog, and my grandparents dog. They all had special requirements and she did great! My parent’s dog was slow to warm up but Emily easily won him over. She is the best and I can’t recommend her enough!!!

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

Melissa did a great job watching Pete my cat. Melissa used to watch the cat I had before he passed. I’ll definitely have her watch Pete in the future.

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

Thank you so much!! Sara was amazing as always, I know Remi will safe and well cared for when she is with Sara.

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

We reached out to Abby last minute to drop in and care for our dog, Chloe, while we were away for the weekend. Our dog has some separation anxiety and tends to damage curtains and blinds when left alone with friends so we wanted to give Rover a try. Abby was amazing! We really appreciated the meet and greet visit first before leaving Chloe alone with someone new. Abby dropped in each time as requested and made sure Chloe had food, water, treats, belly rubs, and walks. She was very attentive to Chloe and provided us with feedback and photos of each visit, which made us feel more comfortable that Chloe was in good hands. She also brought in our packages which was appreciated. We will absolutely be working with Abby again in the future!

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

Janini took excellent care of my cat and was very communicative and responsive. I would highly recommend her!

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

Madeline is wonderful! Very patient with my kitty when giving his meds. Would 100% recommend her to take care of your furry babies!!

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

Amber did so great with my pup! I have never used Rover before and had to a only a few days to figure out care for my dog while I was away. She was prompt with her response and came to meet Monarch. Monarch instantly warmed up to her which means a lot and helped me trust that Amber was a great fit for her. I received updates and check ins from her. I would recommend Amber and would rebook her again!

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

Caitlyn jumped in when our previous dog sitter had to cancel last minute. She made the process very easy and took a lot of the stress worrying about our pup before our trip. She communicated quickly and gave great updates! Highly recommend.

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

Carina has been an amazing dog sitter, very responsive and is able to handle my energetic dogs. She has really taken the time to earn the trust of my (2) border collies and has been great at meeting time schedules. She is good at communicating and highly recommend her to anyone who needs a dog sitter!

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Danny S.
Drop-In Visits
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Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Chestnut Hill pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet 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 pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

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

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

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet 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 pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.