Pet Sitting Winsted

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 24
pet parents in Winsted have booked pet sitting

Winsted, Find top rated pet 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: Stacey G.
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Stacey G.
from
$33
per visit
5.0 out of 5 stars
• 33 reviews
8 repeat clients
15 years of experience
Winsted, CT, 06098

“Stacey was great! She communicated very well with me, took lots of great pictures of my pets and did a great job taking care of them! I will definitely book with her again!”

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Krista K.
Sitter Profile Image: Hunter F.
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Hunter F.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 66 reviews
35 repeat clients
15 years of experience
Collinsville, CT, 06019

“We will be very sad if ever Hunter can't take care of the kiddos. We've told all our friends who need pet sitters to use Rover and to choose Hunter to care for their pets. Thank you so much!!”

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George P.
Sitter Profile Image: Lynsey M.
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Lynsey M.
from
$30
per visit
5.0 out of 5 stars
• 28 reviews
11 repeat clients
8 years of experience
Torrington, CT, 06790

“Lynsey is absolutely phenomenal! She took fabulous care of our wonderful cat, Inga, who is often shy with new people. Lynsey made Inga feel comfortable immediately and this continued for the entire time we were away. Lynsey was reliable, communicative, and it was a true privilege to work with her. We'd give her ten stars if we could, and cannot.say enough good things about her.”

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Christina B.
Sitter Profile Image: Jamilat A.
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Jamilat A.
from
$14
per visit
5.0 out of 5 stars
• 2 reviews
12 years of experience
Torrington, CT, 06790

About: I’ve loved and cared for dogs of all kinds since middle school, walking and pet sitting for family, friends, and neighbors alike. I believe every dog deserves the same level of affection, patience, and care as my own, while also giving each one the individual attention they need to feel comfortable and happy. I work full-time during the week, typically until 4 p.m. Monday through Wednesday and until 5 p.m. on Thursdays and Fridays. I’m available for evening walks on weekdays, as well as full availability on weekends and holidays. I love spending my free time with animals, so pet care naturally fits into my routine and is something I genuinely look forward to. When caring for pets in their own home, I always ensure they feel safe and comfortable in their familiar environment. I follow their owners instructions closely for feeding, routines, and any special needs. I take time to build trust with pets through gentle communication and positive attention while remaining focused on keeping them happy and active.

Sitter Profile Image: Priscilla E.
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Priscilla E.
from
$20
per visit
5.0 out of 5 stars
• 14 reviews
2 repeat clients
20 years of experience
New Hartford, CT, 06057

About: I’ve been around animals my entire life and have hands-on experience caring for a variety of pets, including dogs, bunnies, and birds. Growing up with different types of animals taught me how to adapt to each pet’s unique personality, needs, and routines. I’m comfortable with everything from energetic dogs who need structured walks and play, to smaller animals that require gentle handling and consistency. I pay close attention to behavior, appetite, and mood to make sure every pet is happy, healthy, and comfortable. I currently have open availability, which allows me to be flexible and fully accommodate your pet’s routine. Whether your pet needs early morning visits, midday check-ins, or evening care, I can adjust my schedule to fit their needs. Because I’m not rushing between commitments, I’m able to give each pet focused, unhurried attention during every visit. I care for pets in their own home, where they feel most safe and comfortable. My approach is always needs-based, meaning I follow your pet’s routine closely and adjust to their personality. whether they need lots of interaction or a calm, low-key presence.

Sitter Profile Image: Michelle R.
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Michelle R.
from
$45
per visit
5.0 out of 5 stars
• 1 review
1 repeat client
28 years of experience
Winstead, CT, 06098

About: I’ve worked at animal hospitals for 28 yrs I’m reliable and good with peoples pets I can give meds if needed insulin as well I get lots of waging tails my way I prefer come to your home so your pet is more comfortable and has there familiar surroundings and all the things they’re used to toys their bowls, etc. I can stay the night if needed I like staying with pets at there home this helps also with stomach upsets and stress of being somewhere new and unfamiliar I like the pets to be able to keep there routine

Sitter Profile Image: Kevin D.
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Kevin D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 7 reviews
2 repeat clients
10 years of experience
Burlington, CT, 06013

About: When I was 10 I joined a dog training program through my school, that’s where my training experience began. I provide a premium, low-volume dog care experience for owners who want their dog to have more one-on-one attention in a calm home environment. Your dog won’t be just one of many in a crowded space. I keep my care more personal so each dog gets plenty of attention, supervision, and outdoor time. I have a big yard for dogs to enjoy, but my indoor space is smaller, so I am very intentional about keeping the number of dogs low. That means I can focus on your dog’s comfort, safety, and overall experience much more closely. This is a great fit for dogs who do better with a quieter setting and for owners who value quality of care over high-volume boarding or daycare. I generally only take one to a few dogs at a time unless they are from the same household. I have a lot of experience with senior dogs. I took care of my childhood dog for 17 years of her long, beautiful life. I have experience working with small senior dogs specifically and I know all the little things that they appreciate. I also have experience with large dogs and can handle very big strong dogs. I also love hiking with dogs so if you have an energetic dog you need to burn off energy I am your guy. I have an acre yard with a fenced in front yard in a nice area. Any dog that boards with me would be treated like my own dog and let out very frequently to go to the bathroom and play outside. I would always remain home with your dog. Thank you for considering me and I hope to meet your pet soon! I’m currently a fully remote student so I am fully available. If I board a pet I will be with them full time to make sure they receive the care they deserve. I have a fenced in front yard, and a good amount of unfenced land in the back. My dog is very friendly and would keep your pet great company. He loves dogs and cats. I can easily crate your dog if needed, but would love to give your dog the pet experience and treat them like my own. I live in a nice are and have great access to the woods nearby as well.

Sitter Profile Image: Samantha C.
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Samantha C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 9 reviews
8 repeat clients
3 years of experience
Granby, CT, 06035

“Sam is coming consistently to let out my Daisy and I couldn’t be more at ease knowing she is taken care of every day!! Thank you, Sam!!”

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Debbie A.
Sitter Profile Image: Amanda O.
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Amanda O.
from
$25
per visit
5.0 out of 5 stars
• 8 reviews
10 years of experience
Barkhamsted, CT, 06063

“Amanda was great! She was consistent and made sure my cats had everything they needed. Including taking care of cleaning the cat bowls and picking up after one of them got sick. She gave good updates. Would use again and recommend to others.”

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Jessica P.
Sitter Profile Image: Jaylese H.
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Jaylese H.
from
$25
per visit
5.0 out of 5 stars
• 32 reviews
11 repeat clients
6 years of experience
Plymouth, CT, 06786

About: I've been taking care of my own pets for 6+ years. I make sure pets feel loved and well-cared for, whether it's playtime, feeding, or just giving them some extra snuggles. I understand that each pet has unique needs and preferences, so I adapt my approach to suit their individual personalities. Devoted and loving pet caretaker available around the clock. With a very flexible schedule, I can provide frequent walks, playtime, and feeding to keep your pets happy and healthy. I have a yard for your pet to play in with supervision. I have a small dog and cat that are friendly, But they can be moved to another part of the house if you prefer.

Sitter Profile Image: James E.
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James E.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
• 45 reviews
10 repeat clients
40 years of experience
Bristol, CT, 06010

About: Welcome, y'all! I love watching dogs. We watch kitty cats too 😁. Cheapest rates around! Let me make it easier for you to celebrate your vacation and holidays! Let me sit for your pup. I...love... dogs! My parents were dog breeders for years. As a youngster, I was responsible for many of the chores. As an adult, I have always had pets. I know how important your dog is to you. Your dog is your 'baby'. We are definitely dog lovers in this house! Big dog specialist. I love the little dogs too, though! ☺️💪🎄🎁❤️‍🩹 I will treat your pup like my own. I am a teacher during the day. I'm usually home by 3. I'm home every afternoon and every night and every weekend. I do have flexibility in my work schedule should they need arise. I have a dog lead hooked up to the house and it goes all the way back to the maple tree on the back of the property. 20 ft in either direction gives Fido plenty of room to go to the bathroom. Otherwise, your pup is in the house with me and my family. I am offering dog boarding services. This is a friendly Christian home. Lots of love to share.

Sitter Profile Image: Alexis G.
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Alexis G.
from
$57
per visit
5.0 out of 5 stars
• 6 reviews
2 repeat clients
36 years of experience
Avon, CT, 06001

About: Taken care of different breeds, small and big dogs, cats and small critters. Trained dogs used for disabilities. I walk small dogs with a harness only, and don’t allow them to jump from high places, due to their tiny bones. I make sure they are secured before opening any door where they might run off. I have an Instagram page where I upload dogs I meet , dogs I take care of or watch , dogs that were placed in safe homes. I will take photos to give updates. Can change day to day but if notified ahead of time , can usually work around my schedule. I do check my texts and email if something changes. My dogs are sociable, always keeping an eye out, they are like little kids. There is currently a Japanese Chin, Shitzu, Pekingese, Saint Bernard, a cat, a bird and 3 guinea pigs, in the home.

Sitter Profile Image: Chelsey S.
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Chelsey S.
from
$30
per visit
3.0 out of 5 stars
• 2 reviews
10 years of experience
Simsbury, CT, 06081

About: I have experience caring for both energetic puppies and senior pets. With puppies, I focus on patience, consistency, and reinforcing the training and routines you’re already working on. With seniors, I provide gentle, attentive care and make sure they stay comfortable and stress-free. I truly care about your pet’s well-being and happiness. Pet care fits easily into my daily routine because I work from home and am home most of the day. This allows me to give pets plenty of attention, regular potty breaks, meals on schedule, and companionship throughout the day rather than long stretches alone. I tailor my care based on the service and your pet’s needs. Whether caring for pets in my home or yours, I focus on consistency, comfort, and safety. I follow your pet’s routine closely, provide plenty of attention and companionship, reinforce training for puppies, and offer patient, gentle care for senior pets. I also communicate regularly with updates and photos so you can feel confident while you’re away.

Sitter Profile Image: Alexa F.
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Alexa F.
from
$15
per visit
5.0 out of 5 stars
• 3 reviews
3 repeat clients
3 years of experience
Bethlehem, CT, 06751

About: Hi! I’m Nicole, a 27-year-old animal lover with hands-on experience caring for both dogs and cats. I’m confident in providing attentive, reliable care tailored to each pet’s needs. I’m friendly, patient, and genuinely enjoy spending time playing, walking, and bonding with animals. I look forward to meeting you and giving your pet the care and attention they deserve! I am normally available Wednesday and weekends, For more descriptions and availability check my profile information, can’t wait to meet your family! ! ! I am currently available on Wednesdays, Saturdays, and Sundays only, and I make sure to dedicate focused, quality time to each pet during those days. At the moment, I don’t offer care in my own home since I have multiple pets. However, I’m happy to provide care in your home or take your dog out for walks. I make sure pets feel comfortable in their familiar environment while sticking to their usual routine.

Sitter Profile Image: Lima J.
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Lima J.
from
$22
per visit
4.8 out of 5 stars
• 7 reviews
3 repeat clients
4 years of experience
West Hartford, CT, 06110

About: I’ve taken care of small-medium dogs short-term and long-term. Friends and family know my love for dogs and always call me for dog sitting. I want to get one of my own soon! I’m currently working from home and have lots of flexibility. I also love to go on short and long walks myself and would love to help someone out and walk a pet while I go for my walks! After pet sitting in the past, I’ve been told I did a wonderful job and that their pet loved being with me. I offer a fun and caring environment, follow schedule as provided, and go out for many walks. I’ve usually done sitting at the clients home so the pet is most comfortable in its own home.

Sitter Profile Image: Chelsea W.
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Chelsea W.
from
$20
per visit
5.0 out of 5 stars
• 6 reviews
4 years of experience
Bloomfield, CT, 06002

About: Hi, I am a work from home college student, I have been pet sitting for over 4 years and I have a loving toy cockapoo of my own. I have a large fenced in yard along with plenty of indoor space for cuddles, lounging, and running around. I follow pet parents routine for walk/eating allowing with optional photos/videos. I look forward to hosting your pet where dogs become family I work from home part time so I am always here with a flexible schedule to do walks, take breaks, and keep an eye on our furry friends! I have a large fenced in yard, my care depends on the pets needs, so weather they like long walks, cuddles, lounging on couch or deck, there needs will be catered to and pets will be well taken care of:)

Sitter Profile Image: Nora E.
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Nora E.
from
$40
per visit
5.0 out of 5 stars
• 2 reviews
15 years of experience
Granby, CT, 06035

About: Hello! My name is Nora. I have been petsitting for over 15 years! I first started caring for dogs when a friend found out my love for dogs and how much fun I had running with them and making them happy splashing in the water or just playing fetch! My arm can hold up to all the tug-a-wars any dog throws at me as well as throwing a good tennis ball. I love being outdoors and can go for miles walking any size dog. My experience includes any overnights or day-vacations that require your dog to stay home or while your at work. My availability is pretty open so feel free to contact me and let's set up some walks or sitting for an occasion. Looking forward to hearing from you and your dog/animals. I currently work full-time in insurance, but with a flexible work schedule I am able to petsit almost anytime. I currently have 4 dogs in my household, so any amount of dogs, cats, horses, and farm animals, I am available! When taking care of any pet, whether that be of my own or a petsitting job, every animal is taken care of like my own. My 4 dogs are trained to an electric fence, but have trained to kenneled fence, crate, fenced in yard, and on the leash. I love providing care for each pet with love and no matter the occasion, your pet is in good hands.

Sitter Profile Image: Isabel D.
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Isabel D.
from
$17
per visit
5.0 out of 5 stars
• 10 reviews
2 repeat clients
5 years of experience
Barry Square, Hartford, CT, 06106

“I’m new to Rover but I hit the jackpot when Isabel was assigned to care for my two pups. She thinks of everything and cares for them with such love and kindness.”

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Anne S.
Sitter Profile Image: Brittany F.
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Brittany F.
from
$18
per visit
5.0 out of 5 stars
• 9 reviews
5 repeat clients
20 years of experience
Longmeadow, MA, 01106

About: I have been walking and caring for my own personal animals - 2 dogs, cat, bird, hamsters since I was 5 years old. I also have been dog sitting and walking for numerous neighbors and friends in the area. I work during the day a full-time job. I am available early in the morning and after 4:00pm during the week. I am available on the weekends anytime of the day. I have a fenced in backyard that my 4 year old Brittany Spaniel, Maggie loves to run around and play ball. It is completely fenced in so she can't get out. I love to be outside playing with my dog and bring her on 3+ walks a day around town and at the local park.

Sitter Profile Image: PISHON P.
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PISHON P.
from
$40
per visit
1 repeat client
3 years of experience
West Hartford, CT, 06107

About: Your dog is more than a pet — they’re family. We provide a warm, loving, and secure environment where your furry friend feels safe, happy, and cared for. Whether you’re away for a day or a week, you can rest easy knowing your dog is in trusted hands, getting belly rubs, playtime, and the personal attention they deserve. Because peace of mind isn’t a luxury — it’s a promise. Consider me as your on-call pet sitter. I have currently moved to California all the way from the east coast. Whenever you need me, I’m here ! How I Care for Pets in Your Home – With Safety, Trust, and Comfort at the Heart of It All When I care for your pets, whether I’m house sitting, walking them, or simply dropping in, their safety and comfort are my top priorities. I understand that every pet has a unique routine, personality, and needs — and I take the time to learn and follow your instructions closely to ensure they feel secure and loved in your absence. In your home, I maintain a calm, respectful presence, keeping your pet’s environment clean, stress-free, and familiar. I provide regular walks, playtime, feeding, medication (if needed), and gentle companionship, always with an eye on their behavior and well-being. For drop-ins and walks, I show up reliably and treat your pet like my own — keeping them on safe routes, away from hazards, and paying close attention to their body language and comfort. I always prioritize secure leash handling, water breaks, and positive reinforcement. Your trust means everything to me, and I care for your pets and home with professionalism, love, and integrity.

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The median cost per visit for pet sitting in Winsted is $25

Pet parents share their Rover experiences - Winsted

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5.0 out of 5 stars

Stacey is such a trouper! She made it up to our place despite the treacherous road due to the snow storm. She took great care of our guys and even took pretty great photos of them every day. Leaving pets while we travel is stressful and Stacey was such a great sitter and took all of that worry away from us. We really appreciate her!

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Susan H.
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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  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

How to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  2. 2. Meet In Person

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Popular requests for pet sitting - Winsted

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Sitters in Winsted average 5
repeat pet sitting clients

FAQs for Pet Sitting - Winsted

Frequently asked questions about Rover

The average cost of Pet Sitting in Winsted on Rover is $28 per visit as of October 2026. Most bookings cost between $22 and $44 per visit. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 1,762 sitters on Rover offering Pet Sitting across Winsted. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

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 .

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 , 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 Winsted. On Rover:

  • 90% of sitters can help with special care needs
  • 93% can help with giving oral medications or injections
  • 96% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .

sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

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

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