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Pet Setting & Drop Ins in High Crossing, 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.
Confirmed availability
4th of July
1. 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)"

Calendar Recently Updated
2. Michelle

Large fenced in yard. Active family

Sun Prairie, WI, 53590

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

About: We are an animal loving family who has two dogs of our own and also work with a local rescue to foster dogs until they find their forever homes. Ou... (more)

3. Melissa

Sebastian's love dogs!

Dane County, WI, 53590

Dog Boarding, Drop-In Visits, Dog Walking

"Two years ago I met Melissa through a friend who recommended her to help me rehome an 8 year old Labrador Retriever who had been retired from a breeding kenn... (more)"

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4. Gracie

I promise a tail-wagging good time!

Madison, WI, 53718

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

"Gracie has taken care of our dogs on two different occasions, one home stay and one drop in, and she is outstanding. She gives great updates and we always co... (more)"

5. Marlena

I'll run with your dog!

Monona, WI, 53716

House Sitting, Drop-In Visits, Dog Walking

"Marlena was excellent! She replied promptly, took meeting my kitty very seriously and checked-in with photos and updates. I will use Marlena again for sure f... (more)"

6. Tammy

Pet Sitter

Cottage Grove, WI, 53527

House Sitting, Drop-In Visits, Dog Walking

"i have known Tammy for many years and she has taken care of my dog many times. She is good with dogs and has several dogs as well as a cat. Tammy has always ... (more)"

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7. Ellen

Work from home, flexible schedule

Elvehjem, Madison, WI, 53716

Drop-In Visits, Dog Walking

"Ellen has a love for dogs that shows in her care for them. She is very organized and diligent which is great if you have any special instructions for your do... (more)"

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8. 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)"

Confirmed availability
4th of July
9. 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)"

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10. 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)

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11. Courtney

A home away from home

Madison, WI, 53718

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

About: My name is Courtney and I'm the proud owner of two pups - a 12 pound Pekingese mix, Oliver, and a 70 pound Bernese Mountain Dog puppy named Sulliva... (more)

12. Daniel

Lover of all, big and small!

Eastmorland, Madison, WI, 53714

House Sitting, Drop-In Visits

"Dan was very good with my dog Howard, a Newfoundland. Howard was a handful and most other sitters had an issue with him going to the bathroom or chewing thin... (more)"

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13. Amanda

Responsible, active, pet owner

Cottage Grove, WI, 53527

Dog Boarding, Drop-In Visits

"Amanda was great; would definitely recommend! (more)"

14. Jessica

Compassionate and loving!

Rolling Meadows, madison, WI, 53714

Drop-In Visits, Dog Walking

"Jessy is my sister in law. And Im proud to say so. She has and is a very good mother to her children, and an inspiration to others in being an awesome child ... (more)"

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15. 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)"

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16. Grace

Nature Walks, Love and Attention!

Reston Heights, Madison, WI, 53718

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

"Grace would be a responsible and loving pet sitter. She grew up in a family who were always surrounded by all kinds of animals. Grace also had a horse of her... (more)"

Confirmed availability
This weekend
17. Robin

Dog Lover with 30+ years experience

Heistand, Madison, WI, 53714

Dog Boarding, House Sitting, Drop-In Visits

"Robin has shared her life with a dog since she was 4 years old. I can't imagine her not sharing her home with a dog. As a young girl she shared her life wit... (more)"

18. 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)

19. Afiqah

Dog Lover in the House :)

McClellan Park, Madison, WI, 53718

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

"Afiqah is the best dog sitter I've ever met. She is a dog & cat lover. She's willing to spend her time with the dogs/cats that she takes care of. She even ha... (more)"

Confirmed availability
This weekend
20. Katerina

Patient Dog-Lover Avail. Full-Time

Bluff Acres, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

"Katerina was very friendly and accommodating. Stevie liked her instantly and he was happy and well taken care of. (more)"

Dog owners in High Crossing, Madison, WI turn to pet sitters on Rover.com for their pet sitting needs. Over 423 pet owners have reviewed pet sitters in Madison, giving them an average rating of 4.9/5. Pet sitting can be affordable, no matter where you live or what your price range may be. Curious about how much pet sitting costs in Madison with Rover.com? Check out our average pet sitting rates near you to get an idea before getting a conversation started with a pet sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect High Crossing, Madison pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in High Crossing, Madison who can provide the care your pet needs, when they need it.

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 High Crossing, 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.