Dog Sitting Windham

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

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Over 46
pet parents in Windham have booked dog sitting

Windham, 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: Emily C.
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Emily C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
7 reviews
4 repeat clients
30 years of experience
Raymond, ME, 04071

About: Who's a good dog? All of them. My step-dog is the love of my life, and I'm the person who talks to animals more than humans at a party. I have experience with: Dogs, cats, fish, rodents, horses, chickens, other birds, reptiles, and more. As a former field biologist, I handled a wide variety of animals and completed Institutional Animal Care and Use Committee (IACUC) training. I'm open to caring for almost any critter. Send me a message so we can discuss what your critter needs. New-ish to Rover. Previously, all my clients were by word of mouth in extreme southern Maine and New Hampshire. We recently moved, and I decided it was time to join Rover. My schedule is variable, so just message me so we can discuss what your critter needs. This summer I have lots of availability. Thank you! I am currently not taking client's pets into my own home. I am open to a variety of conditions for home visits/walks/play dates/check-ins. Just send me a message so we can discuss your set up and what your critter needs.

Sitter Profile Image: Alyssa B.
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Alyssa B.
from
$30
per visit
5.0 out of 5 stars
5 reviews
2 years of experience
Gray, ME, 04039

About: I've always had a love for animals, and being able to care for them is something I genuinely enjoy. As someone who works in the medical field, I understand the importance of trust, attention to detail, and treating every family member with compassion—including the four-legged ones! For the past two years, I worked for a luxury dog walking and pet sitting company in Washington, D.C., where I cared for dogs and cats of all ages, breeds, personalities, and temperaments. Whether your pet is a playful puppy, a shy rescue, a reactive dog, or a sweet senior who needs a little extra patience, I'm happy to meet them where they are. Every pet is different, and I love taking the time to earn their trust and learn what makes them feel comfortable. I'm also comfortable caring for pets with medical needs. Because of my background in the medical field, I feel confident administering oral medications, eye drops, and ear medications for both dogs and cats. If your pet has a special routine or requires extra attention, you can trust that they'll be in great hands. Communication is incredibly important to me. For each visit or stay, I'll send detailed updates and plenty of photos! My goal is for you to enjoy your time away without worrying. I also have experience walking up to five dogs at once and am comfortable with everything from leash training to energetic pullers and leisurely senior strolls. No matter your pet's age, personality, or needs, I'll treat them with the same love, patience, and care that I would my own. If I'm staying in your home, I'll care for it with the same respect and attention that I would my own. I'm happy to bring in mail and packages, water plants, keep things clean and tidy, and make sure your home feels just as you left it. My goal is for you to return to a happy pet, a well-cared-for home, and complete peace of mind. I'm currently working part-time while completing my remaining prerequisite courses as I apply to Physician Assistant programs, which gives me a flexible schedule to accommodate your pet's needs. Whether your furry one needs regular walks, drop-in visits, overnight care, or a little extra attention, I'm happy to work with you to find a schedule that fits. Clear communication is important to me, and I'll always be upfront about my availability so you can feel confident your pet is receiving the care they deserve. When caring for pets in a client's home, my goal is to keep their routine as normal and stress-free as possible. I know that pets are happiest when they can stay in a familiar environment, so I take the time to learn their daily schedule, favorite activities, feeding routine, and any special instructions before you leave. I am certified through Red Cross for Cat and Dog First Aid as well. Whether we're going on walks, playing fetch, enjoying cuddle time on the couch, or simply keeping each other company, I make sure every pet receives plenty of love, attention, exercise, and enrichment based on their individual needs. If your pet requires medications or extra care, I'm comfortable following detailed medical routines and will always keep you updated. I also believe caring for your pet means caring for your home. If I'm house sitting, I'll treat your home with the same respect I would my own by keeping it clean and tidy, bringing in mail and packages, watering plants, taking out the trash if needed, and making sure everything is secure while you're away. After each visit, I'll send detailed updates and photos so you can relax knowing your pet is happy, comfortable, and in good hands. My goal is for you to come home to a happy pet, a well-cared-for home, and complete peace of mind.

Sitter Profile Image: Sophia V.
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Sophia V.
from
$15
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
5 years of experience
Windham, ME, 04062

sophia did a great job!!

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sofia m.
Sitter Profile Image: Anna K.
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Anna K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
24 reviews
15 repeat clients
13 years of experience
Ocean Avenue, Portland, ME, 04103

Anna was great! She took care of our dog and reported back very thoroughly. He was such a happy camper - highly recommend using Anna to care for your fur baby.

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Abigail J.
Sitter Profile Image: Amanda C.
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Amanda C.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
15 years of experience
Buxton, ME, 04093

Amanda was great. She did a meet and greet which was great. She communicated when she visited our kitty and provided pictures and a video. We would definitely use Amanda again.

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Christina C.
Sitter Profile Image: Hannah S.
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Hannah S.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
10 years of experience
Rosemont, Portland, ME, 04102

Hannah was amazing. Super responsive, communicative and caring. Exactly what you want from someone watching your pets!! 10/10 recommend and will be using her again. Thanks Hannah!

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Andrew D.
Sitter Profile Image: Claudia & Jason M.
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Claudia & Jason M.
from
$30
per visit
5.0 out of 5 stars
16 reviews
2 repeat clients
10 years of experience
Oakdale, Portland, ME, 04103

About: We are an experienced foster family with many years of experience. Claudia is an animal welfare professional who has been working in animal shelters for many years. Jason (Ilan) is permanently work from home, so there is always someone home with your baby! We have had 13 foster dogs ranging from small puppies to super seniors. We are a positive reinforcement family with experience in reactivity, separation anxiety, stranger danger, resource guarding, and arousal/high energy behaviors! We are able to provide medical care including medications, injections, and breathing treatments! Our home is empty without our own doggies, we so are so excited to give yours all the love! While Claudia works full time out of the house, Jason (Ilan) works from home full time! Your baby will rarely be home alone, if at all! We can easily crate your dog if you would like and have cameras with motion detection in each room so we can ensure your pup is safe. We provide daily updates on your dog so you can know they are doing well. We are experienced handlers who are fear free certified. We are prepared for anything that might happen!

Sitter Profile Image: Katherine L.
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Katherine L.
from
$25
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
East Bayside-India Street, Portland, ME, 04101

It was kinda a last minute booking and had to send pics with directions, and Katherine killed it! I have two cats who manage to be sweet but mischievous at the same time. She dug into the toy drawer and played fetch with them and cleaned up when they tipped the auto feeder over. With my ocd cleaning tendencies, that was very much appreciated.

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Jennifer K.
Sitter Profile Image: Kellie C.
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Kellie C.
from
$25
per visit
25 years of experience
Nasons Corner, Portland, ME, 04102

About: If begging my parents for a dog since birth counts, I’ve been a dog lover for 50+ years. In terms of actual pet ownership, I’ve owned and loved my cats and dogs for the past 25+ years. In addition to having my own fur family, I’ve also happily sat or walked my friends and families. I’m heading into retirement and will have oodles of time to keep your pets company while you’re at work or taking a fabulous vacation. I’m available for house sitting at any time. And currently available for dog walking Friday though Monday. In a few months, my dog walking schedule will free up to 3-4 days during the week. Having raised animals and kids, I know routines help everyone feel confident and safe. I respect whatever you know your animals need. As an example, if you need me to take them on long walks, cuddle on the couch, or bring them for a fetch and swim in the lake, I got you covered.

Sitter Profile Image: James F.
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James F.
from
$20
per visit
5.0 out of 5 stars
13 reviews
15 years of experience
Rosemont, Portland, ME, 04102

About: I have cared for dogs of all sizes from 10lbs to 100+ lbs, ages puppy to senior, all with various temperaments, energy levels and medical needs. I’ve also cared for many cats ranging from 2 years old to 13 years old I’m a middle school teacher on summer break with A LOT of availability. I regularly free weekdays during the day through the evening and even available at night and through the night most days of the week. I have a large fenced in yard with that’s mostly shaded by surrounding trees. With easy access from a back deck. We also have a screened in porch for good airflow on hotter days. I live in a nice and walkable neighborhood and I regularly visit local walking/hiking trails in the area.

Sitter Profile Image: Kelly F.
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Kelly F.
from
$30
per visit
5.0 out of 5 stars
32 reviews
13 repeat clients
40 years of experience
Falmouth, ME, 04105

Kelly was great! She was so attentive with any requests I had and gave detailed updates! I know my kitties were well taken care of while I was away!

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Danielle E.
Sitter Profile Image: Amy S.
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Amy S.
from
$30
per visit
5.0 out of 5 stars
27 reviews
10 repeat clients
30 years of experience
Westbrook, ME, 04092

Amy is incredible, she goes above and beyond to make sure my pup is loved and cared for. My dog Lilo is almost 10 and dog reactive, but Amy not only won Lilo over immediately she was also able to take her for walks while effectively managing Lilo's triggers. She goes out of her way to make sure Lilo has plenty of attention and stimulation and I feel so much more relaxed about having to leave my pup with Amy taking care of her.

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Sonya M.
Sitter Profile Image: Emma C.
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Emma C.
from
$18
per visit
15 years of experience
South Portland, ME, 04106

About: Thank you for checking out my rover profile! My name is Emma! I have a huge passion for animals and have experience working in doggy daycare! I love breeds of all sizes and shapes and use Pawsitive reinforcement training. I’m always very adaptable base on each individual animal. I’m always prepared for treats unless they’re provided. I look forward to meeting your pets and will treat them like they are my own. Please reaching out for additional information ! My schedule is flexible since I currently work part-time, which allows me to dedicate quality time to the pets I care for. I’m available Wednesdays, Thursdays, and Sundays from 9am–3pm, as well as Friday afternoons. This schedule allows me to give pets plenty of attention, exercise, and care during visits or house sitting. I always do my best to work with each owner’s routine so their pet’s day stays as normal and comfortable as possible. I believe every pet deserves care that’s tailored just for them. I use positive reinforcement, patience, and lots of encouragement to help pets feel safe, confident, and happy. I take the time to learn each pet’s routine, personality, and comfort level so I can adapt my care to what they need—whether that’s energetic playtime, calm companionship, or maintaining training cues. I’m also happy to house sit in your home so your pet can stay relaxed in their familiar environment. I’ll make sure they get plenty of attention, exercise, and affection, and I provide regular updates and photos so you always know how your pup is doing.

Sitter Profile Image: Gigi C.
Verified Background Check
Gigi C.
from
$25
per visit
5.0 out of 5 stars
18 reviews
6 repeat clients
10 years of experience
Scarborough, ME, 04074

Gigi has been absolutely fabulous with my dog Thor these past few weeks. She takes excellent care of him. Takes him for a walk around my house, fills up the water bowl and sits on the porch with him. She also gives a great detailed update on the rover card of what he did during her stay with him and sends lots of photos. I have been so happy to have her take care of Thor while we are at work and puts me at ease knowing she is there to let him out on those long days. Will definitely rebook again!!!

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Mary C.
Sitter Profile Image: Briana S.
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Briana S.
from
$17
per visit
4.9 out of 5 stars
11 reviews
6 repeat clients
9 years of experience
Riverton, portland, ME, 04106

Briana took excellent care of our diabetic cat! She really went above and beyond, playing with him and giving him affection, and is one of only 2 sitters who have successfully been able to administer insulin injections.

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Elizabeth S.
Sitter Profile Image: Elizabeth A.
Verified Enhanced Background Check
Elizabeth A.
from
$25
per visit
5.0 out of 5 stars
3 reviews
23 years of experience
Windham, ME, 04062

This was Lola’s first time with me and my 5 furry friends. She did a wonderful job, and went above and beyond. I highly recommend her.

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Ruthann D.
Sitter Profile Image: Tonya O.
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Tonya O.
from
$15
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
38 years of experience
Far North, Standish, ME, 04084

About: Dogs have always been a huge part of my life. I’ve been caring for dogs since I was 10 years old as a pet sitter, but we got our own family dog as a toddler. Over the years, that experience has grown into a true passion, and I now have 2 dogs of my own. I’m used to all kinds of personalities, from high-energy dogs who love long walks and playtime to more relaxed companions who just want cuddles. I’m all about keeping tails wagging with lots of attention, exercise, and love. I work remotely full-time, which gives me the flexibility to provide attentive, consistent care throughout the day. Because I am not tied to an office, I’m able to let sit in your home and be present for walks, feedings, playtime, and companionship—keeping your pets routine as normal and stress-free as possible. When caring for pets in your home, my top priorities are safety, trust, and maintaining a calm, familiar environment. I follow your pets routine closely—from feeding schedules to walks and playtime—so the feel secure and comfortable while you’re away. I treat your home with the utmost respect and make sure your pet gets plenty of attention, affection, and supervision at all times.

Sitter Profile Image: Sundy P.
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Sundy P.
from
$15
per visit
40 years of experience
Westbrook, ME, 04092

About: I’ve had dogs and cats by my side for almost my entire life, gaining hands-on experience with a wide variety of dog breeds, from small to large. Over the years, I’ve cared for puppies and kittens as young as four weeks old through senior aged. learning the unique needs of every life stage. I’ve also spent time fostering dogs, preparing them for successful adoptions by providing love, training, socialization, and medical care. This deep, lifelong experience has given me the knowledge, patience, and skills to confidently care for other people’s dogs and cats as if they were my own. I'm currently taking a break from the corprote world and looking for new adventures. This gives me plenty of time to care for your pet(s) as needed. I will happily care for your pet in a way that keeps them safe and makes you feel at ease. Meeting your pets individual needs.

Sitter Profile Image: Briana M.
Verified Enhanced Background Check
Briana M.
from
$20
per visit
8 years of experience
Windham, ME, 04062

About: I grew up on a farm where I was surrounded by large animals like cattle and horses, which gave me a deep appreciation for working with animals from a young age. My passion for animal care led me to become a veterinary technician, where I spent several years working in a large animal hospital. During this time, I gained extensive experience handling various animals, assisting in surgeries, administering medications, and providing routine care. I also have a 8 year-old German Shepherd named Nala. These experiences have strengthened my skills in animal health and care, and I truly enjoy working with animals of all sizes. Currently work part time so I have plenty of time for your pup/animal! I am very flexible and will do my best to accommodate yours and your animals needs Will love on your pet like my own ! It truly is fun to spend time with different animals and if I could have more than 1 dog I would personally!

Sitter Profile Image: Miranda L.
Verified Enhanced Background Check
Miranda L.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Windham, ME, 04062

About: I have grown up with pets all my life, starting at the age of 7. My family currently has three dogs (one small and two medium) that I care for regularly. I am able to walk the three on a lease comfortably and have played a large role in training them. Although I prefer dogs, I grew up with a cat that I loved and cared for. I am able to provide compassion and care to a variety of pet personalities. With years of experience caring for cats and dogs, I understand how important it is to find a sitter/ walker you can trust. Whether your pet needs playtime, a dependable routine or just company, I’m here to provide loving and reliable care. I am studying for a board exam and working part time. My part time job is flexible, allowing Sat, Sun,Mon, Wed and Fri to have open availability. I am more likely to commit to requests that are received a few days to a week prior. I care for pets in their home by meeting them where they are at; literally and personality wise. With three dogs of my own at home, I am unable to watch your pet outside of their home. In caring for your pet in their environment it helps reduce stress and attempt to maintain any form of routine they have. I am considerate of multiple personalities and consciously make an effort to accommodate the pets needs. With dogs I have watched in the past, I attempt to give them familiarity with their routine, within mine and their comfort. I walk familiar roads/paths, feed them on their schedule (if possible) and attain to any of their needs. I will use any devices/ equipment you typically use and will prioritize safety outside the home (using leases, collars, etc.).

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

Dog parents share their Rover experiences - Windham

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5.0 out of 5 stars

I was able to relax with peace of mind while Nicolette was at my house with my babies. She consistently updated me with pictures and videos and brought her son to help get some energy out with my crazy lab and I could see both of my dogs loved her and had the best time with her and her son.

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

Nicolette was responsive right away when I messaged about doing drop-ins for our dog the following day. She listened to what works well for our dog, and I felt confident that our dog was in great hands! We’ll definitely continue to have Nicolette do more drop-ins for us!

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

Nicole was fantastic with my golden retriever, I booked her four times a week for 13 weeks and she was very reliable, had great communication and was very friendly. Highly recommend her for your pet needs around the Scarborough area!!

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Kassidy K.
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.

Why Choose Rover?

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Sitters in Windham average 6
repeat dog sitting clients

FAQs for Drop-In Visits - Windham

Frequently asked questions about Rover

The average cost for Dog Sitting in Windham on Rover is $27.75 per visit (as of July 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 July 2026, there are 1,016 sitters on Rover offering Dog Sitting across Windham. 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 Windham 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 Windham 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 Windham 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 Windham. On Rover:

  • 99% of sitters can help with special care needs
  • 99% 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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