Dog Sitting Highland

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

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Over 44
pet parents in Highland have booked dog sitting

Highland, Find top rated dog sitting

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: Sarah T.
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Sarah T.
from
$30
per visit
5.0 out of 5 stars
11 reviews
1 repeat client
7 years of experience
West Park, NY, 12493

Sarah took great care of our kitties over 5 days with drop in visits. She was very communicative and sent some very nice photos. We returned to happy and relaxed cats! I would definitely book her again.

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Sharon C.
Sitter Profile Image: Amanda L.
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Amanda L.
from
$14
per visit
5.0 out of 5 stars
2 reviews
5 years of experience
Highland, NY, 12601

About: I really love being around animals as they bring a lot of joy. Over the years I have pet sat for various family friends, co-workers, colleagues, and friends of friends pets. While pet sitting not only have I been responsible to feed the pets, give them water, let them out to relieve themselves, clean up after the pets, and take them out for a walk but I also have looked after the house. Additionally, I have been working for a company so couples beloved dogs can attend their weddings. Previously, I have volunteered by fostering dogs and dog walking. I am available most weekends and off most holidays. I do work full time so if it is anything during the week I do not get home until after 5 pm. Anything during the week I need to know ahead of time so I can plan accordingly. I would care for your pets as one of my own. I am flexible and come to your pets home so they are comfortable in their own environment.

Sitter Profile Image: Alesandra P.
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Alesandra P.
from
$50
per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
5 years of experience
Poughkeepsie, NY, 12601

About: I grew up around animals, from birds and hermit crabs to cats and dogs, my household has always been filled with pets. I have also fostered medically fragile dogs and volunteered at the Westchester Humane Society. I am passionate about ensuring all animals receive the best possible care and I will give your pet the same love I give my own. I currently work part time and I’m a full time grad student, but I have my own transportation so my schedule is open and flexible. I will schedule a meet and greet with you and your pet to learn all about their unique quirks, likes, dislikes, and routines prior to beginning services with them. I ensure a safe environment by using non-retractable leashes on walks and will send you updates while I am with your pet. Your pet's safety is my top priority.

Sitter Profile Image: Meghan S.
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Meghan S.
from
$20
per visit
1 repeat client
10 years of experience
Poughkeepsie, NY, 12601

About: I've been lucky enough to have a dog in my life since I was 8 years old, and now I'm 20! My dog is 13 years old, and caring for her has taught me so much about patience and responsibility. She takes multiple medications, so I'm very comfortable with medication schedules and making sure pets receive the care they need on time. I've also looked after other pets for family and friends like my friend's 3 cats, Rocky, Pepper and Sage, during school breaks, and the cutest dog in the world, Abby. These experiences helped me become confident caring for pets with different personalities, routines, and needs!! I truly love spending time with animals, cuddling, playing, keeping them company, or just making sure they stay active and happy. I'm an outdoorsy person who enjoys hiking and walking, so I'd be happy to take your dog on walks and adventures if needed. I'm reliable, attentive, and comfortable with feeding and following special instructions to ensure your pet feels safe, loved, and well cared for! I’m planning to have an internship, so I’ll be working full days but will be able to periodically check in on your animals!! I love to play and spend time with them, and you can trust they’re in great hands! My puppy is 13 years old, and is on many medications, has specific feeding times and diet, but she still loves to play and go on walks! I’m super organized and take very good care of her.

Sitter Profile Image: Kaya F.
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Kaya F.
from
$20
per visit
5.0 out of 5 stars
5 reviews
3 repeat clients
8 years of experience
New Paltz, NY, 12561

Pup had the best time with Kaya! Hope to book again next time we’re in town!

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Heather B.
Sitter Profile Image: Emma M.
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Emma M.
from
$25
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
New Paltz, NY, 12561

About: I’ve had dogs and cats for the last 10 years, and my friends and neighbors have trusted me to walk and feed their pets too! I love cats and dogs of all kinds! I work Wednesday-Monday during the day so I can walk, feed, or play with pets in the afternoons and evenings or I can house sit overnight. I am used to high-energy dogs and cats that need someone to play with and get their energy out, or to take them for a long walk.

Sitter Profile Image: Margaret S.
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Margaret S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
18 reviews
5 repeat clients
17 years of experience
Wappingers Falls, NY, 12590

Needed someone for a last-minute drop in for the next day and Margaret willingly accepted. She was timely and send photos while there. Will definitely contact her again.

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Jennifer M.
Sitter Profile Image: Mario C.
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Mario C.
Star Sitter
from
$32
per visit
5.0 out of 5 stars
108 reviews
34 repeat clients
20 years of experience
Poughkeepsie, NY, 12601

Thank you Mario for meeting with Buster. He absolutely loved you!!! He cannot wait to see you next week. Mario has a very calm demeanor and listened attentively to all of our instructions. We have already booked several dog visits with him.

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Sharon L.
Sitter Profile Image: Michelle P.
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Michelle P.
from
$30
per visit
8 years of experience
Hyde Park, NY, 12538

About: I've house sat, walked and cared for dogs ever since I was 14. My coworkers, neighbors and their friends are returning customers due to high detailed and enthusiastic care. I always tell people I will take care of your pets faster than your kids lol. Hi im currently working a part time job so depending on my schedule I can spend time with your furry friend before or after my shift. I follow clients pet plans with feedings, walkings and medications if needed. I will work with you on any adjustments you need for your fur baby.

Sitter Profile Image: ANN E.
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ANN E.
from
$20
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
30 years of experience
Hyde Park, NY, 12538

About: Volunteer with Guiding Eyes for socialization of 2month old puppies in my home in the past. Have 30 yrs + experience with my own rescue dogs. Now down to 1 senior dog who cannot walk long distances. Looking for new walking buddies! Retired and looking for new opportunities mostly during the week. Have volunteer work also, so prefer morning walks at this time; can come to you or you can drop off. I believe dogs thrive on exercise and daily walks; also great time to continue training and encourage obedience. Most dogs love to work out and be with their humans outside.

Sitter Profile Image: Breanna S.
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Breanna S.
from
$38
per visit
5.0 out of 5 stars
18 reviews
4 repeat clients
20 years of experience
Highland, NY, 12528

Breanna S. is a reliable and professional dog walker. She is always punctual and ensures my dog gets a safe and enjoyable walk each time. Breanna communicates well and provides updates after every walk, which I really Breanna is a great choice for anyone looking for dependable pet care. I highly recommend her services.

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Anthony M.
Sitter Profile Image: Kayla M.
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Kayla M.
from
$30
per visit
5.0 out of 5 stars
100 reviews
27 repeat clients
15 years of experience
Pleasant Valley, NY, 12569

Kayla was great. She was very comfortable with the dogs which put me at ease. She was able to give Arlo his medication and didn't seem overly worried about watching a dog with his medical condition which was a relief (Arlo has epilepsy). I received updates and pictures which I loved. I would definitely recommend and I would use Kayla again =)

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Sharon P.
Sitter Profile Image: melanie t.
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melanie t.
from
$30
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
poughkeepsie, NY, 12601

About: I have 2 pet cats that are my everything, and been pet sitting my first cat since I was 12! For about 7 years, I've pet sat for multiple people including friends and family. The animals include cats, dogs, and birds. I have done drop-in visits as well as overnight shifts and dog walking. I would love to pet sit for your fur babies and give them lots of love and care. My pets are my world, so I would treat your pets the same!!! I am a graduate student at Marist University, so my schedule frequently changes between semesters. Please reach out to me to discuss scheduling and I will let you know if I am available , thank you! I will give your fur baby unlimited attention as well as efficient care. I can take them out on walks, feed them as needed, clean during potty breaks, brush them as needed, and give them lots and lots of love!!!

Sitter Profile Image: Kenniqua B.
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Kenniqua B.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
18 reviews
3 repeat clients
10 years of experience
Marlboro, NY, 12542

About: Hi. My name is Kiki and I love dogs!! I have years of hands-on experience working with dogs of all breeds, sizes, and temperaments. I was a manager at a cage-free dog daycare for 5 years, where I handled everything from group play supervision to administering medications and managing daily care routines. I also volunteered for 3 years at Second Chance Dog Rescue, helping with socialization, walking, and basic training. In addition, I’ve provided trusted pet sitting services in Peekskill, NY for 5 years until the family relocated. I’m trained in pet CPR, comfortable administering all types of medications, and have a dog of my own—so I truly understand how important it is to find someone reliable and compassionate to care for your pets. I have a car, am highly dependable, and treat every animal as if they were my own. Although I work full-time and attend school, I have large daily time blocks available between commitments, which I dedicate to pet sitting, walking, and drop-in visits I care for every pet like my own, ensuring they feel safe, loved, and comfortable while following their regular routine, my skills are administering medications, and giving personalized attention. Every pet has a specific personality so I try to respect that much like people.

Sitter Profile Image: Stefanie A.
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Stefanie A.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
41 reviews
16 repeat clients
31 years of experience
PLEASANT VALLEY, NY, 12569

So grateful we found Stefanie! Super sweet, communicative, and thoughtful. Our very shy cats came out for her which is rare for them with people they don’t know. Will definitely book again :)

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Courtney B.
Sitter Profile Image: Bianca W.
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Bianca W.
from
$25
per visit
5 years of experience
12590

About: Hi! I'm so glad you're here! I know how important it is to find someone you can completely trust with your pet and that's exactly the kind of care I strive to provide. Whether your pup needs a fun walk to burn off energy or they just want a friendly face while you're away, I'll make sure they feel safe, loved, and cared for every step of the way. I treat every pet as if they were my own, following their routine closely so they stay comfortable and stress-free. I have five years of experience with both my own and family members' dogs, giving me hands-on experience with daily walks, feeding, playtime, and providing lots of love and attention. You can expect dependable communication, plenty of photo updates, and personalized care based on your pet's unique personality and needs. I know every animal is different, and I take the time to earn their trust while making sure you have complete peace of mind. I currently work part-time, giving me flexibility for dog walks and drop-in visits throughout the week. I'd love the opportunity to meet you and your furry family member! Your pet's safety and well-being are always my top priorities. I understand that every pet has their own routine, personality, and needs, so I'll take the time to follow your care instructions carefully and make sure they feel comfortable during every visit. Whether we're out for a walk or spending time together at home, I'll provide a calm, caring, and dependable environment while treating your pet and your home with the utmost respect. My goal is to give you peace of mind, knowing your pet is in safe and caring hands. Here are the Services I offer and What to Expect: 30 Minute Dog Walks include a fun stroll around your neighborhood or a nearby trail to give your pup the exercise, fresh air, and mental stimulation they need during the day. 30 Minute Drop-Ins include potty breaks, feeding, playtime, and of course plenty of snuggles to keep your pet happy and comfortable while you’re away.

Sitter Profile Image: Ann Marie N.
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Ann Marie N.
from
$25
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Poughkeepsie, NY, 12603

Great experience. Ann Marie is very thoughtful and a good communicator.

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Nancy S.
Sitter Profile Image: Sophia G.
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Sophia G.
from
$22
per visit
5.0 out of 5 stars
3 reviews
7 years of experience
Highland, NY, 12528

About: Aside from growing up with two dogs throughout their puppy and elderly stages of life, I have lots of experience with animals that are not my own. I have a passion for caring for animals of all kinds—to the point where I consider the squirrels that come to my college dorm window my friends! I love helping out the pet owners in my community and often volunteer to watch dogs for free, just because I enjoy it. I have lots of experience with dogs that have special needs (i.e. injuries or medicine), and I take the responsibility of pet care seriously. I approach all animals with the same love and care as if they were my own, and i understand uniquely how worried we can get about our pets when we’re away. Part of my petsitting M.O. is frequent updates (especially photos) to give owners peace of mind. I have a special place in my heart for dogs, but am a lover of all animals and have experience with cats and bunnies as well. I look forward to meeting you and your furry friends! I am a college junior currently at home for summer break. I will be taking two vacations in the next few months, but other than that my schedule allows for extremely open and flexible hours! I approach all pets with gentleness and respect, and i make sure to provide ample time for them to get used to my presence before interactions. I follow instructions thoroughly, so detail there is always appreciated, and I like to be in consistent contact with owners in case there are questions, concerns, or updates. I understand strangers can be nerve wracking for pets and their parents, so I do my very best to earn trust and be patient!

Sitter Profile Image: Colleen V.
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Colleen V.
from
$28
per visit
5.0 out of 5 stars
9 reviews
12 years of experience
Highland, NY, 12528

Colleen was great with all 4 of our cats. We appreciated the time she took to win over our cats, especially our skittish one, we also appreciated all the personal updates and extra care.

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matthew. E.
Sitter Profile Image: Deanna B.
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Deanna B.
from
$25
per visit
17 years of experience
Highland, NY, 12528

About: I’ve taken care of animals for over 15 years. I pet sat many times as a child and continued through adulthood including, walking, feeding, administering medicine, baths & snuggles! I also volunteered at a local animal shelter as a dog walker. Currently 3 cats and a rambunctious German Shepard/Siberian Husky 3 years old. I have cared for all kinds of pets including but not limited to goats, chickens, horses, pigs, donkeys etc I’m currently working full time but have a very flexible schedule and can move my hours around to meet your needs especially for early morning and later evening check ins or during work hours! I have worked with leash trained and non leash trained dogs if you have a fenced in yard. I prefer leash trained dogs for public walks with a standard leash. I love animals, their snuggles & kisses too! I have kids & animals so drool & slobber don’t bother me!

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

Dog parents share their Rover experiences - Highland

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5.0 out of 5 stars

Amanda did a great job updating us on our pet. She made sure to send us pictures and kept up with his routine! We really appreciated her. She also made sure that on July 4 to play calming music for my pet since we were away. We will be booking her again because our pet was very comfortable with her!

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udara j.
Drop-In Visits
5.0 out of 5 stars

Was able to come over on short notice when I had to change my work schedule around. Very responsive and kept me in the loop on everything.

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

Amruta is amazing! From the meet and greet I knew she would be a good fit for us. Tux was drawn to her immediately and is always so excited when she walks through the door. I have a very specific feeding routine for tux and amruta is diligent about following it. I am so happy to have found Amruta because I am now at ease when I go to work, knowing she dropping in to care for Tux. I cannot recommend her enough!

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bettina a.
Drop-In Visits
5.0 out of 5 stars

Angellina did a great job caring for our pets. We felt comfortable knowing she was there and will definitely be using her in the future. She had great communication with us throughout her drop ins and was respectful of our home. We are very grateful for her!

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

This was my very first time leaving my dogs with a sitter, and I couldn’t have asked for a better experience. I have two mixed-breed pups (Dogo Argentino and Pitbull), and they can be a handful—but from the moment we met Rubina we knew we made the right choice. She was calm, confident, and genuinely loving. She was punctual every day, attentive to their needs, and went above and beyond to make sure they were comfortable, happy, and cared for. I received regular updates, photos, and messages, which made me feel completely at ease while I was away. Both of my dogs absolutely adored her—and that says a lot! It’s not easy to trust someone new with your pets, especially for the first time, but she exceeded every expectation. I came home to two relaxed, happy dogs and a spotless home. I can’t thank her enough for treating my pups like her own. If you’re looking for someone responsible, kind, and truly passionate about animals, I highly recommend her. She’s officially our go-to sitter from now on!

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

I was invited on a trip over Labor Day weekend at the last minute, and I was fortunate enough to find Kevin to do drop in visits with my dog and cat. He followed all of my instructions to a T and provided EXCELLENT customer service. I honestly couldn’t have picked anyone better! He was great with my dog, who is 14 years old and has a few medical issues. I was able to enjoy my trip without being worried, and I came home to my house exactly the way that I left it. I will definitely use him again in the future.

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Heather G.
Drop-In Visits
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  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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Meet local sitters who will treat your dogs like family

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Sitters in Highland average 5
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FAQs for Drop-In Visits - Highland

Frequently asked questions about Rover

The average cost for Dog Sitting in Highland on Rover is $27.75 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 Dog 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 Dog Sitting. For more information on service fees, click here .

As of August 2026, there are 1,163 sitters on Rover offering Dog Sitting across Highland. 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 Highland 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.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Highland choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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

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

A Meet & Greet is a short introductory meeting between you, your dog, 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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Highland with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

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

  • 95% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 99% can help with daily exercise

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

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

Sitters on Rover set their own 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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