Doggy Day Care Windsor

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Over 13
pet parents in Windsor have booked doggy day care

Windsor, Find top rated doggy day care

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

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Sitter Profile Image: Edith S.
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Edith S.
Star Sitter
from
$40
per day
5.0 out of 5 stars
• 88 reviews
27 repeat clients
20 years of experience
Waunakee, WI, 53597

“Edith is your dream sitter. She posts daily photos and updates of your pet. She obviously loves what she does. She is a lovely soul and my Mimi, who can be shy, had her tail up in the photos which made me feel reassured that she was in a safe, loving environment.”

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Kay C.
Sitter Profile Image: Jamie Z.
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Jamie Z.
from
$40
per day
5.0 out of 5 stars
• 5 reviews
2 repeat clients
2 years of experience
Waunakee, WI, 53597

“Amazing! My pet loved his day with Jamie and enjoyed playing with her dogs. From get going he has been excited with the warmth he was received. She was constantly updating me and also provided pointers for his training.”

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bhavya v.
Sitter Profile Image: Yee Lam C.
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Yee Lam C.
from
$38
per day
5.0 out of 5 stars
• 10 reviews
2 repeat clients
20 years of experience
Sun Prairie, WI, 53590

About: Hi my name is Yee Lam but everyone calls me Suki. I grew up with dogs and am a dog lover. I had a beloved toy poodle named Seven for 15 years, who was truly the best dog and a cherished member of our family. I’m a full-time mom, and when my son (9) and daughter (7) are in school, I have plenty of free time to care for pets—playing with them, feeding them, and giving them all the attention they need. My kids love dogs too, and I think this is a wonderful way for them to learn the joys and responsibilities of having a puppy. I’m available for boarding on weekends and most weekdays after 9 a.m. We have a spacious yard for safe outdoor play, and our neighborhood is calm, family-friendly, and right next to a school, with no major roads nearby, so you can feel at ease knowing your dog will be safe on our walks.

Sitter Profile Image: Kyle & Alaina M.
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Kyle & Alaina M.
from
$25
per day
5.0 out of 5 stars
• 4 reviews
1 repeat client
15 years of experience
Sun Prairie, WI, 53590

“Kirby’s visit went well. Kyle and Alaina met with us twice before taking care of her. This showed they understood Kirby’s anxiety and were very patient!”

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Carla P.
Sitter Profile Image: Kris A.
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Kris A.
from
$25
per day
5.0 out of 5 stars
• 14 reviews
4 repeat clients
16 years of experience
DeForest, WI, 53532

About: I'm currently in a pet-free home with my kiddos and have lived with dogs for much of my adult life. I'm a massage therapist and love giving pups a little TLC with energy therapy and light massage. They love it! The dog you see in my thumbnail photo is KC. She was a rescue dog who was with us for six years and needed lots of training, support and care. Please note I take 3 walking clients per day but only 1 boarder at a time. I teach at a technical college and am a personal trainer, working part-time from home and part-time out of the home. I'm often home for long hours during the day. My three kids are in public school, so dogs may have 1 to 4 dog-lovers in the home after 4pm. I offer long walks on sidewalks or trails if preferred, treats, water, lots of play and unlimited petting! I offer care in my home and dog walking. Pets are allowed on my furniture if that's what they're used to. Looking forward to meeting your pup!

Sitter Profile Image: Jackie G.
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Jackie G.
Star Sitter
from
$50
per day
5.0 out of 5 stars
• 71 reviews
18 repeat clients
20 years of experience
SUN PRAIRIE, WI, 53590

“Jackie took great care of Millie when we went out of town for the day. Millie had a long walk and got to play in the yard with the hose. She was all tuckered out when she came home at the end of the day.”

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Casey P.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$40
per day
5.0 out of 5 stars
• 15 reviews
8 repeat clients
18 years of experience
Vilas, Madison, WI, 53711

About: We will care for your dog like our own! Since our wonderful dog Stella passed we are looking to add more positive dog energy to our home. I am experienced with senior care; giving medications and supporting older dogs. I also have 4 years experience with dog walking and welcome energetic dogs. Both my husband and I work from home and will keep your dog company and make sure all needs are met. We have two children, ages 8 and 10, who have been raised to love and respect dogs and other animals. We only sit dogs from one household at a time so you can rely on individualized, attentive care. We have a fenced backyard and one friendly dog, Izzy. We will be your dog’s home away from home, with lots of exercise, cuddling, and fun.

Sitter Profile Image: Jenna H.
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Jenna H.
from
$31
per day
5.0 out of 5 stars
• 30 reviews
8 repeat clients
30 years of experience
Waunakee, WI, 53597

“Jenna and her girls took such great care of Merlin! Jenna always responds in a timely manner and has a flexible schedule. I got daily picture updates on how he was doing which was much appreciated. Merlin will definitely be visiting them again! Thank you so much 😊”

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Stephanie D.
Sitter Profile Image: Cynthia H.
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Cynthia H.
from
$45
per day
5.0 out of 5 stars
• 126 reviews
38 repeat clients
30 years of experience
Schenk-Atwood, Madison, WI, 53704

“My pup Popsicle loves Cynthia and gets so excited to see her! Cynthia gives excellent ‘pupdates’ and is super-communicative, so when you’re away from your pup (and missing them), you’ll get beautiful pics and updates. She treats my pup like family, and I’ve hired her again and again!”

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Josephine D.
Sitter Profile Image: Ben K.
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Ben K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
• 133 reviews
29 repeat clients
15 years of experience
Eken Park, Madison, WI, 53704

“Ben is the best! Always so accommodating, and our pup always comes home nice and tired. Super professional, trustworthy, and great with our Lil guy!”

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Ethan S.
Sitter Profile Image: Faith G.
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Faith G.
from
$35
per day
5.0 out of 5 stars
• 3 reviews
29 years of experience
Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53704

About: I’ve always loved dogs and genuinely enjoy spending time with them, whether that means going for a long walk, playing outside, or just keeping them company at home. I’m active and love being outdoors, so I’m especially happy to take dogs on walks and give them plenty of exercise and attention. I’m dependable, communicative, and will treat your pet and your home with the same care and respect I’d want someone to give mine. I’m comfortable following specific feeding, walking, and care routines, and I’ll always keep you updated while you’re away. I have a flexible schedule that gives me plenty of time to fit pet care into my week. I’m available for walks, drop-in visits, feeding, playtime, and check-ins throughout the week and on weekends. I’m happy to work with your pet’s normal routine and schedule! I know how important it is to trust the person caring for your pet and your home. I’ll follow your instructions closely and keep your pet’s normal routine as consistent as possible. I’m attentive, responsible, and happy to provide updates and photos so you know your pet is safe, comfortable, and getting plenty of attention.

Sitter Profile Image: Elena "Sofi" R.
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Elena "Sofi" R.
Star Sitter
from
$35
per day
5.0 out of 5 stars
• 54 reviews
13 repeat clients
6 years of experience
Capitol, Madison, WI, 53715

“Awesome! Very friendly”

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Manuel S.
Sitter Profile Image: Julie D.
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Julie D.
from
$40
per day
4.9 out of 5 stars
• 100 reviews
50 repeat clients
30 years of experience
Lake Edge, Madison, WI, 53716

“Muttley had a great time over the weekend with Julie. He came home a very tired and happy boy. I got a ton of pictures and updates, so I never had to worry about how he was doing while I was away.”

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Melissa R.
Sitter Profile Image: Lenys H.
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Lenys H.
from
$50
per day
4.9 out of 5 stars
• 32 reviews
12 repeat clients
12 years of experience
Mayfair Park, Madison, WI, 53714

About: Dogs and cats have always been a big part of my life, and I know how much joy and comfort they bring. I’d love the opportunity to care for your pets, whether that means daily walks, playful activities, or snuggles on the couch. I’m flexible and attentive, making sure your furry friends feel happy, safe, and loved while you’re away. I’m 22 years old and recently graduated from UWM with a Bachelor’s degree in Criminal Justice. I currently work part-time at a coffee shop and have a flexible schedule, making it easy for me to accommodate pet care needs When I’m caring for your fur baby, I’ll send as many pictures as you’d like, there’s no such thing as too many! I know I’d want updates on my own pets, so I’m happy to keep you connected while you’re away. I follow all instructions carefully to make sure your pets are well cared for!

Sitter Profile Image: Daniel H.
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Daniel H.
from
$55
per day
5.0 out of 5 stars
• 1 review
2 years of experience
Capitol, Madison, WI, 53703

About: I have over two years of experience with dog walking and dog sitting, along with professional experience working at a dog grooming facility and dog hotel. I was responsible for caring for dogs staying at the hotel, making sure they were safe, comfortable, and well cared for during their stay. I’m also a dog owner myself! I have three dogs: Liah, a Shih Tzu, and Lilo and Lady, two Australian Labradoodles. Having three dogs with different personalities has given me plenty of experience with different needs, energy levels, and routines. I genuinely enjoy being around dogs and understand how important it is to have someone you can trust with your pets. I’ll treat your dog with the same care and attention I give my own. Pet care fits easily into my routine, and I make sure every dog gets the time and attention they need. I’m available throughout the week for walks, drop-in visits, and pet sitting, and I’m happy to work with each owner’s schedule and their dog’s normal routine. Your dog’s safety and comfort are always my priority. From my experience working at a dog hotel, I understand the importance of following each dog’s routine, feeding instructions, and individual needs. In a client’s home, I’ll respect their space and follow all instructions carefully while making sure their dog feels safe, comfortable, and cared for.

Sitter Profile Image: Tony D.
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Tony D.
Star Sitter
from
$25
per day
5.0 out of 5 stars
• 202 reviews
70 repeat clients
25 years of experience
Madison, WI, 53718

“Tony watched my dogs for a couple days in a row and he was great! He is very communicative and sent lots of pictures throughout the day. Will definitely request services through him again in the future.”

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Jessica K.
Sitter Profile Image: Tessa S.
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Tessa S.
from
$26
per day
5.0 out of 5 stars
• 20 reviews
7 repeat clients
7 years of experience
Fitchburg, WI, 53711

About: Former full-time human medical provider of 18 years; now available for pup sitting. Takes frequent walks with the neighborhood dog pack. Owner of one special dog named Tennessee. I’m free to organize my schedule between pet sitting, my personal business, pursuing new adventures in the pet industry, hobbies, and full time job in health IT, which is 50% remote. I like routine. I think pets appreciate kibble and potty breaks on a familiar schedule. I will honor your wishes for care, play, walks, and socializing.

Sitter Profile Image: Jackie P.
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Jackie P.
from
$25
per day
5.0 out of 5 stars
• 5 reviews
1 repeat client
25 years of experience
Middleton, WI, 53562

“Jackie is a great choice for any dog sitting needs. She was very communicative and flexible including sending multiple pics of our dog Daisy unprompted. We could tell that Daisy had an incredible vacation with Jackie and look forward to booking again!”

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Aimee C.
Sitter Profile Image: Cecelia G.
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Cecelia G.
from
$30
per day
9 years of experience
Capitol, Madison, WI, 53703

About: I’ve had cats and dogs my entire life, so I understand the different needs of every animal. From energetic puppies and playful kittens to senior pets who need a bit more care and attention, I know how to adapt. Whether it's providing daily walks, offering training, or simply offering companionship, I ensure every pet feels comfortable and loved. I believe in treating each pet as an individual, providing the right care for their unique personality, and making sure they feel safe and happy in your absence. As a student, my schedule is very flexible, which allows me to easily fit pet care into my daily routine. I don’t have classes on Mondays or Fridays, and during the week I have breaks between classes—perfect for walks, playtime, or drop-in visits. I also spend most evenings and nights at home, which makes boarding a great fit for me. I love having animals around and giving them the time, attention, and care they deserve. When caring for pets in my home, I make sure the space is safe, calm, and comfortable. For dogs, I can easily crate them if needed and always keep a leash on hand for safety during walks and potty breaks. I follow their routine closely to help them feel at home. For cats, I have plenty of toys and love spending time playing, feeding, and giving them the quiet companionship they enjoy during visits.

Sitter Profile Image: Sabrina B.
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Sabrina B.
from
$55
per day
5.0 out of 5 stars
• 4 reviews
36 years of experience
Madison, WI, 53704

About: I have always had a special bond with animals, and I am eager to give care and attention to your non-human family, and to accommodate any custom needs that you have! As a small business owner, I have freedom and flexibility to work when I’m needed, so whether you need drop in visits or walks, or someone to keep your babies cuddled and cozy during storms and at bedtime.. I’m here for you! Pet care gives me a chance to see new places and gives me a reason to be active. I love spending time with animals and going for walks, so I can't think of a better way to spend my time! I follow whatever needs each individual family has, since every animal needs different things, just like people! I can do medication administration, feeding, etc. please note, I do not offer bathing or grooming services.

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The median cost per day for doggy day care in Windsor is $35

Dog parents share their Rover experiences - Windsor

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5.0 out of 5 stars

Maria and Bryan did a great job taking care of Augie for the day. He came home happy, healthy, and thoroughly tired out!

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Philip B.
Doggy Day Care
5.0 out of 5 stars

Paula did a great job of looking after Augie during our day trip. He came home happy, mellow, and suitably tuckered out.

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Philip B.
Doggy Day Care
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How to book doggy day care

  1. 1. Search

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Popular requests for doggy day care - Windsor

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Sitters in Windsor average 4
repeat doggy day care clients

FAQs for Doggy Day Care - Windsor

Frequently asked questions about Rover

The average cost of Doggy Day Care in Windsor is $33 per day as of October 2026. Most bookings cost between $32 and $40 per day. On Rover, 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 297 sitters on Rover offering Doggy Day Care across Windsor. Enter your ZIP code to see which available sitters are closest to your home.

Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Windsor commute.

If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.

Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.

A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.

Here are tips for finding the ideal day care fit for your dog:

  • For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
  • For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
  • For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.

As of October 2026, there are 297 sitters on Rover offering Doggy Day Care across the region of WI. Enter your address or desired location to see which available sitters are closest to you.

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in WI ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

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.

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 .

Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 297 sitters in Windsor, 88% respond to messages in under an hour.

You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.

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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