Pet Sitting 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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Over 89
pet parents in Chestnut Hill have booked pet sitting

Chestnut Hill, Find top rated pet 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: Allison L.
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Allison L.
$28
total per visit
5.0 out of 5 stars
5 reviews
1 repeat client
14 years of experience
Allston-Brighton, Boston, MA, 02135

Allison was great with motek. Took notes of her routine and sent great pictures and updates.

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

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

Sitter Profile Image: Julie J.
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Julie J.
Star Sitter
$28
total per visit
5.0 out of 5 stars
239 reviews
73 repeat clients
22 years of experience
Brookline, MA, 02445

Julie provides a truly special experience for the pets she cares for. My two special needs cats get playtime, cuddles and everything else they would need two feel comfortable while I'm away. She also goes above and beyond to care for my home. Thanks Julie!

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Melissa L.
Sitter Profile Image: Kayla W.
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Kayla W.
$18
total per visit
5.0 out of 5 stars
2 reviews
4 years of experience
Allston-Brighton, Boston, MA, 02135

About: Hi! I'm a lifelong dog lover with years of hands-on experience caring for dogs of all ages and personalities. I grew up with two family dogs, spent two years walking dogs through Wag!, and now have a dog of my own who I trained myself using positive reinforcement. In addition to professional dog walking, I've also cared for the dogs of family and friends, whether that meant walks, drop-in visits, or overnight care. I understand that every dog has their own personality and routine, and I always take the time to make them feel comfortable, safe, and cared for. I know how important it is to trust someone with your pet, and I treat every dog as if they were my own. Whether your pup needs an energetic walk, plenty of playtime, or just some extra love and attention while you're away, I'm committed to providing dependable, compassionate care and keeping you updated along the way. I have a flexible schedule and do my best to accommodate my clients' needs whenever possible. I understand how important consistency is for dogs, so I'm committed to being reliable, punctual, and communicating clearly if anything comes up. Whether your pup needs a midday walk or regular weekly visits, I'll make sure they receive the care and attention they deserve. Your dog's safety and comfort are always my top priorities. I take the time to learn each dog's routine, personality, and any special instructions before every visit. During walks, I stay alert to our surroundings, use secure leash handling, and make sure your pup gets plenty of exercise while staying safe. I'll also send photo updates so you can feel confident your dog is happy and well cared for.

Sitter Profile Image: Elisabeth K.
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Elisabeth K.
$15
total per visit
5.0 out of 5 stars
6 reviews
1 repeat client
18 years of experience
Boston, MA, 02135

Elisabeth was so attentive watching my cat Emma and she made every step of the process so easy for me! Would definitely be reaching back out again soon!

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Kyubin L.
Sitter Profile Image: Adelle W.
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Adelle W.
Star Sitter
$30
total per visit
5.0 out of 5 stars
72 reviews
27 repeat clients
8 years of experience
Allston-Brighton, Brighton, MA, 02135

Adelle did a fantastic job checking in on our two cats while we were away. She communicated well and made the process seamless. This was our first time using Rover and we will be using Rover (and hopefully working with Adelle) again because of our great experience with her!

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Alex B.
Sitter Profile Image: Olivia B.
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Olivia B.
$19
total per visit
5 years of experience
Chestnut Hill, MA, 02108

About: I’ve taken care of dogs since I was a young girl. Growing up, I’ve owned and been trusted to watch a wide range of pets, but I love being around dogs of all ages! I’m currently a graduate student, with classes only taking up half of my week, so I have multiple days I can devote to pet care! Usually, Thursdays/Fridays/Saturdays are my pet days. When entering your home, respect is my top priority. It’s a privilege to be let into your space, and I will respect your home and pet as if they were my own.

Sitter Profile Image: ZILALAI T.
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ZILALAI T.
Star Sitter
$28
total per visit
4.9 out of 5 stars
43 reviews
13 repeat clients
20 years of experience
Allston-Brighton, Boston, MA, 02135

Zilalai was a great sitter for our cat Moogle! She was prompt in her visits and sent photos/notes every day. She was also happy to arrange and meet and greet beforehand to let us and our cat get comfortable with her first. We came home after a week to a happy and healthy cat. Thanks Zilalai!

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Jeremy S.
Sitter Profile Image: Maegan M.
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Maegan M.
Star Sitter
$39
total per visit
5.0 out of 5 stars
207 reviews
46 repeat clients
10 years of experience
Boston, MA, 02135

Maegan took great care of our cat. She clearly knows a lot about cats and made friends with Vera quickly—it was a big relief to have her looking after our girl!

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Maia B.
Sitter Profile Image: Ciana T.
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Ciana T.
$28
total per visit
7 years of experience
Brookline, MA, 02445

About: I grew up with dogs and have loved them my whole life. I've dog sat for friends and co-workers, including overnight stays, and always treat your pet and home with the utmost care. I take pride in leaving your home just as clean as I found it while making sure your pet gets plenty of love, attention, and cuddles so that you don't have to worry while you're away. I work remotely Monday-Friday with a flexible schedule that allows me to take breaks to care for your pet and give them lots of love during the day! I am able and willing to travel to you and take great pride in being a considerate, tidy, and responsible houseguest. My goal is to leave your home looking like it did before I arrived!

Sitter Profile Image: Gabriel B.
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Gabriel B.
Star Sitter
$28
total per visit
4.9 out of 5 stars
80 reviews
18 repeat clients
10 years of experience
Boston, MA, 02130

Gabriel is great. He is dedicated to making sure animals are comfortable with him and provides amazing care. His communication is also great.

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Christopher M.
Sitter Profile Image: Wendy L.
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Wendy L.
$14
total per visit
5.0 out of 5 stars
10 reviews
5 repeat clients
10 years of experience
Boston, MA, 02135

Was able to get Wendy at short notice. She was on time, Communicated promptly with me and made sire Mia had a good time with her. Thanks Wendy

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Rob N.
Sitter Profile Image: Natalia K.
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Natalia K.
Star Sitter
$28
total per visit
5.0 out of 5 stars
237 reviews
73 repeat clients
9 years of experience
Brookline, MA, 02445

Natalia was wonderful!! She was kind, responsive, and clearly loves animals. She took great care of our cats and even brushed them. You can tell from the pictures she sent us that our cats felt very comfortable and playful around her. I’d definitely recommend her as a Rover and would use her services in the future!!

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Calla B.
Sitter Profile Image: Jose Q.
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Jose Q.
Star Sitter
$23
total per visit
5.0 out of 5 stars
22 reviews
5 repeat clients
12 years of experience
Allston-Brighton, Brighton, MA, 02135

Jose is wonderful as always! Came home to happy cats full of love and treats! Jose is communicative, caring and always sends amazing updates with pictures 💗

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Monica W.
Sitter Profile Image: Jana W.
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Jana W.
Star Sitter
$29
total per visit
5.0 out of 5 stars
302 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.

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Korri C.
Sitter Profile Image: Sarah J.
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Sarah J.
$23
total per visit
5.0 out of 5 stars
42 reviews
13 repeat clients
4 years of experience
Boston, MA, 02135

Sarah was terrific with our pups while we were gone for the day. She took them for a walk then came back and gave them dinner. We got cute pics each time.

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Allison B.
Sitter Profile Image: Jane S.
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Jane S.
$24
total per visit
5.0 out of 5 stars
1 review
20 years of experience
Allston-Brighton, Boston, MA, 02135

Jane did such a great job taking care of my cats! She followed all directions and took great care of them. She will be my go-to cat sitter for the future! Thanks so much, Jane!!

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Regina C.
Sitter Profile Image: Sylvia L.
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Sylvia L.
$17
total per visit
4.8 out of 5 stars
6 reviews
6 years of experience
Allston-Brighton, Boston, MA, 02135

⭐️⭐️⭐️⭐️⭐️Above and beyond cat care⭐️⭐️⭐️⭐️⭐️ We could not be happier with Sylvia. She was attentive, kind, punctual, and an excellent communicator before and during our trip. Our cats absolutely adored her, and it showed in every update. What truly set her apart was her initiative: I forgot to even mention the litter box routine, and she still cleaned the litter boxes and the entire area around them, unasked, and handled it professionally. That kind of judgment and care is rare. She made sure our kitties had the best experience: fresh food and water, clean litter, playtime, cuddles, and thoughtful check-ins with photos. We came home to relaxed, happy cats and a tidy space. Her service is unbelievable for the fee she charges…truly above and beyond. We recommend Sylvia without hesitation.

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Heather R.
Sitter Profile Image: Lauren K.
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Lauren K.
$25
total per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
5 years of experience
Boston, MA, 02135

Lauren provided excellent in-home care and walks for our dog. Couldn’t be happier! 🐶

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Riana R.
Sitter Profile Image: Sabina S.
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Sabina S.
$28
total per visit
5.0 out of 5 stars
28 reviews
5 repeat clients
10 years of experience
Allston-Brighton, Brighton, MA, 02135

Sabina did an amazing job. Went above and beyond in taking care of my cat even bringing over a comb, some rub in shampoo, and staying extra one day. Truly a great cat sitter!

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Andrew M.
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The median cost per visit for pet sitting in Chestnut Hill is $25

Pet parents share their Rover experiences - Chestnut Hill

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5.0 out of 5 stars

This is the second time that we’ve used Jasmine and, once again we were very happy with how she took care of our cat, and our house while we were gone. I would recommend her and we’ll use her in the future.

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

Bryana always goes above and beyond to take care of my cat! I felt comfortable and at ease leaving Fenway with her while I was out of town, and appreciate all the photos and details she shared!!

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

Stephanie was great with our three cats — gave them the care and attention they needed, including daily meds for one. She provided timely updates and videos to show how they were all doing. Would absolutely work with Stephanie again for cat sitting.

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

Julia was great with our shy kitty, and even was able to give her some scratches and attention, which is pretty huge! Communication was great, and I would love to have her back in the future.

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

Jordan is the absolute best, and when I got home I could tell my cats had not been lonely, and had gotten a ton of love!

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

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

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

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

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

Michele was very communicative, flexible, kind, and sent lots of photos!! She was very thoughtful, helpful and sweet with my cat, I would 100% recommend her!

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

Avery is extremely professional, warm, and flexible. Clearly cares about the pets. This was our first time booking her and we'll do so again. Our cat also is tough to give medicine to and Avery had no problem with it. 5/5 Recommend.

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

Christina was so good with my cats! She also sent plenty of photos and detailed updates. Everything was taken care of, and I felt good trusting her with my babies.

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

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

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

I booked Claire while traveling out of state to care for my cat, Zelish, and she was exceptional. Claire was incredibly receptive to Zelish’s care instructions, paying close attention to specific details like water quality and regulating the apartment temperature during a severe heat wave. She even thoughtfully offered to water my plants, though it wasn't needed because I thoroughly watered before my departure. Her frequent photo updates gave me complete peace of mind while away. I am extremely grateful for her attentive care and would highly recommend booking with her again.

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

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

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

Lindsey was very quick to respond and extremely kind! She was able to care easily for my socially awkward cat and keep me (an anxious pet parent) updated the whole way. I would recommend to any pet parents looking for a highly reliable sitter!!

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

Dominique did a great job with our felines. They seemed to enjoy their daily visits and we received comprehensive reports on them as well as photos that captured their personalities. We could relax on our trip knowing that they were in good hands!

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

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

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

Revathi was very reliable and great with my cat. She found creative ways to get him to play which I’m so grateful for! She also was a great communicator on anything that needed troubleshooting while we were away. Thank you!!

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

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

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

Alex was fantastic! He was very communicative, great with our cat, and went the extra mile to make sure she kept cool during a heat wave. I'd definitely book him again! Definitely gave us piece of mind on our trip - thanks Alex!

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

Second time booking and just as great as the first. Reliable, communicative, and my cat was well cared for. Highly recommend!

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Meredith P.
Drop-In Visits
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Meet local sitters who will treat your pets like family

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Popular requests for pet sitting - Chestnut Hill

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Chestnut Hill average 6
repeat pet sitting clients

FAQs for Drop-In Visits - Chestnut Hill

Frequently asked questions about Rover

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

Rover makes budgeting the cost of Pet Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Sitting. For more information on service fees, click here .

As of August 2026, there are 11,091 sitters on Rover offering Pet Sitting across Chestnut Hill. Enter your ZIP code to see which available sitters are closest to your home.

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

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

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

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Yes, you can find sitters who have experience with handling special pet needs in Chestnut Hill. On Rover:

  • 91% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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