Pet Setting & Drop Ins in Woodlands, Madison, WI

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

1. Danielle

I am dog's best friend!

Verona, WI, 53593

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

26 repeat clients

"Danielle did a fabulous job!!! Our cats were very well taken care of. Danielle also went above and beyond when she came and stayed longer when there was seve... (more)"

2. Whitney

Reliable & caring dog/cat sitter!

Madison, WI, 53719

Drop-In Visits, Dog Walking

4 repeat clients

"Whitney was very conscientious when caring for Wrigley!!! (more)"

3. Crystal

Animal Lover

Middleton, WI, 53562

Drop-In Visits, Dog Walking

18 repeat clients

"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)"

4. Christina

Anything fluffy, fuzzy, & floppy!

Prairie Hills, Madison, WI, 53711

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

20 repeat clients

"Christina did a great job taking care of my cats! She takes the time to play with them and engage with both of them even though one can be standoffish. The p... (more)"

5. Amy

Reliable & Conscientious Caretaker

Hill Farms-University Neighborh, madison, WI, 53705

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

9 repeat clients

"Amy did a wonderful job! She was flexible last minute to watch/walk our lab on Thanksgiving. Our pup was nice & tired after his long walks. Would recommend ... (more)"

6. Kiersten

Corgis are my spirit animal.

Regent, Madison, WI, 53726

Drop-In Visits, Dog Walking

6 repeat clients

"Kierstin was awesome...so sweet...and she made her available to help out with a urgent medical need at the last minute. I would definately use her again in ... (more)"

Confirmed Holiday Availability
7. Cleda

I love dogs and they love me!

Spring Harbor, Madison, WI, 53705

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

About: I have a small dog myself and she is a diva. If I can handle her, I can handle any dog. We frequent the dog park and I've interacted with many dogs... (more)

8. Joseph

We love dogs! Fenced yard freedom!

Middleton, WI, 53562

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

"Joe's fun and laid back demeanor shows in his pets' (dogs) personalities. When they get too excited he doesn't get overly excited, but does have limits and ... (more)"

9. Kelsey

Want a 4 day weekend get-away?

Madison, WI, 53705

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

2 repeat clients

"Kelsey is wonderful! She walks our golden doodle puppy on a regular basis and also has popped last minute to help us out in a pinch! She's on-time, trustwo... (more)"

10. Celia

Dogs big/cats small I love 'em all!

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Celia is so great! This is the second time I’ve hired her and I all absolutely continue to do so. She’s so good with my shy cat that sometimes needs coaxing ... (more)"

11. Maryrose

I'll walk any dog in any weather.

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"MaryRose is one of the most responsible people I know, and a fantastic dog caregiver. She is excellent at setting dogs of all ages, sizes, and breeds at ease... (more)"

12. Joy

New best pal for your dog!

Middleton, WI, 53562

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

1 repeat client

"I've known Joy for several years now. She has a 5 year old Sheltie of her own and she is a fantastic owner. She has puppysat for my two dogs on several occas... (more)"

13. Michelle

At-home CPA who loves fur babies!

Hill Farms-University Neighborh, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"If you want more bang for your buck, Michelle is outstanding! As a dogsitter, she's a natural - our golden, Abbie, took to her immediately. She also sent r... (more)"

Confirmed Holiday Availability
14. Sarah

Looking to meet some furry friends!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Sarah has watched my dog for me several times while I was away on vacation for a few days. She has always taken good care for him, taking him for a walk at l... (more)"

15. Dr. Elisa

Active dog-loving veterinarian!

Madison, WI, 53719

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

2 repeat clients

"Elisa goes above and beyond to make sure your furry friends are comfortable, safe, and having the time of their lives. She's experienced with dogs of all tem... (more)"

Confirmed Holiday Availability
16. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

62 repeat clients

"Andrea treats your dogs as if they were her own. Animals are a big passion of hers especially dogs. She has rescued many dogs all around the US including two... (more)"

17. Danae

fun and friendly and dog lover!

Wyndemere, Madison, WI, 53717

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

"As a long time friend of Danae's, I have seen, countless times, the love and affection she shows towards all animals. She is especially good with dogs, and s... (more)"

Confirmed Holiday Availability
18. Kristy

Home almost full-time, fenced yard

Oakbridge Community, Madison, WI, 53717

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

2 repeat clients

"Kristy is one of the kindest and most caring people I know, with both her two-footed and four-footed friends! She's had her own dog, Moose, trained as an emo... (more)"

19. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

4 repeat clients

"Thank you so much! We love having Bruno spend time with you so we can relax and not worry about him. Thank you! (more)"

20. Glenis

Every Dog Has its Staycay

Spring Harbor, MADISON, WI, 53705

Dog Boarding, Drop-In Visits, Doggy Day Care

20 repeat clients

About: Missing our Bayley (Treeing Walker Coonhound), so need a pooch fix. We'll care for your dog(s) (max. of three/night) while you go away to play....... (more)

Dog lovers in Woodlands, 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.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Woodlands pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Woodlands, Madison, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Woodlands pet sitters and avoid the kennel.

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 Woodlands, 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: