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Pet Setting & Drop Ins in Cherokee Garden, Madison, WI

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

Tip: Contact sitters now to confirm availability.
1. Camille

Large Fenced Backyard.

De forest, WI, 53532

Dog Boarding, Drop-In Visits, Dog Walking

"I felt very secure in granting her access to my home. She took very good care of our puppy. Camille's passion for dogs is very evident. She fit the time fram... (more)"

2. Allison & Raymon

LOVING, ACTIVE DOG SITTERS!!

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

"Allison was so great with our two dogs. Usually our younger pup has really bad separation anxiety and has accidents while we’re away, but he didn’t have a si... (more)"

Confirmed 4th of July Availability
3. Jennifer

Great with high energy dogs!

Worthington Park, Madison, WI, 53714

Drop-In Visits, Dog Walking

"Jennifer is the best - she is so good with our Siberian husky. We’re really particular about who we ask to watch our dog, and Jennifer has made us feel confi... (more)"

4. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

"Simply put, Crystal is phenomenal. She has helped with our dog for several months and we have been impressed with her kindness, reliability, attention to det... (more)"

5. Halley

Experienced and loving dog-sitter!

Capitol, Madison, WI, 53703

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Very nice you lady. Halley took very good care of my dog and was thorough with her report and sending pictures. (more)"

6. Rebecca

Patient, playful, and dedicated

Capitol, Madison, WI, 53703

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Rebecca was incredibly accommodating to my schedule and went out of her way to make sure the stay went well. My cats had a great time with her. I would for... (more)"

Confirmed 4th of July Availability
7. Stephanie

will give: love, exercise & care

Madison, WI, 53704

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: Hello! I’m Stephanie && am a COMPLETE dog lover. Leaving my dog is always the hardest/most stressful part of taking trips and I want to serve as a ... (more)

8. Patti

Teacher summer off - runner

Marquette, Madison, WI, 53703

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"If you want your dog to HAVE FUN and BE SAFE, then Patti is absolutely the right choice. She's been our go-to house/dog-sitter for years because she's extrem... (more)"

9. Matthew

Lover of all dogs, very attentive!

Ridgewood, Madison, WI, 53704

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Matthew LOVES babysitting our pup. He says he "feels honored" every time we ask him, instead of it being a chore. I highly recommend him! (more)"

10. Anamaria

Catch Dog Training Academy Student

Sherman Village, madison, WI, 53704

Drop-In Visits, Dog Walking

"Ananaria has helped me numerous times with my dogs. I was looking for a reliable, responsible dog sitter and she certainly has lived up to that. Her knowledg... (more)"

Confirmed 4th of July Availability
11. Julie

Playcare fun may cause drowsiness.

Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53714

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Julie is a true dog lover. Our pug, Rooney, always has a fun filled day when visiting Julie and her dog Duncan. When we drop Rooney off he is so excited; h... (more)"

12. Angie

Our pup loves playmates!

Madison, WI, 53718

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: We have a very active 1.5 year old yellow lab who loves to play and nothing burns him out like a good play session with another pup! Since we can’t... (more)

Confirmed 4th of July Availability
13. Kelsey

Professional Care Provider

Waunakee, WI, 53597

House Sitting, Drop-In Visits, Dog Walking

About: I am a reliable individual who will provide quality care to your dog(s). My hope is that by providing care in your home environment, your dog will ... (more)

Confirmed 4th of July Availability
14. Kelsey

Looking for some new doggo friends

Tenney-Lapham, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

"We've always trusted Kelsey with our dog! We know Aiko will get the exercise she needs and love every minute of it. Kelsey is accommodating to our needs for ... (more)"

15. Carly

Let me love them while you can’t

Schenk-Atwood, Madison, WI, 53706

House Sitting, Drop-In Visits, Dog Walking

"Carly was a tremendous help with my 4 month old lab puppy Grace. Due to my work schedule grace had to be crated for extended hours, but Carly helped me limit... (more)"

Confirmed 4th of July Availability
16. Camille

I provide lots of cuddle & playtime

Tenney-Lapham, Madison, WI, 53703

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Camille is the best dogsitter ever! She is always enthusiastic and gives so much love and attention to my dog Shag! Shag is always happy to see Camille walk ... (more)"

Confirmed 4th of July Availability
17. Charli

A Dogs Best Friend

Nobel Park, Madison, WI, 53704

Drop-In Visits, Dog Walking

"Charli did a wonderful job with my special needs pets. She gave updates and photos and went the extra mile to make sure they were safe and happy. I would def... (more)"

18. Mary & Michael

Your cuties will be loved with me

Ridgewood, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Mary is a kind-hearted animal lover with a big heart for dogs. she will take care of anyone's dog as if it was her own, feed it, bathe it, cuddle it, love it... (more)"

Confirmed 4th of July Availability
19. Sarah

Dog hair everywhere, don't care!

Worthington Park, Madison, WI, 53714

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Sarah has been there to dog-sit for me on a number of occasions, and Izzy is always super happy when I get back in town! For a dog with separation anxiety, t... (more)"

20. Nikki

Love dogs and cats!!

Hawthorne, Madison, WI, 53714

Drop-In Visits, Dog Walking

About: My name is Nikki and I live on the east side. I am going to school and working part time.I own a dog and he is my life. I will treat your dog as if... (more)

Dog lovers in Cherokee Garden, Madison, WI love pet sitters on Rover.com. Over 423 pet owners have reviewed pet sitters on Rover in Madison, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Madison can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Cherokee Garden pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Cherokee Garden, Madison who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Cherokee Garden, Madison donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Madison.

We're proud to support over 200 organizations across the nation, including:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.