Pet Sitting & 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.

Calendar Recently Updated
1. Rick Verified Enhanced Background Check

Experienced, active, & trustworthy

Arbor Hills, Madison, WI, 53713

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

"We had Rick do two drop-in's a day for 4 days in a row for our new 3 month old pup. He was really great with Doc and played and worked on commands with him wh… (more)"

Calendar Recently Updated
2. Ashley Verified Background Check

Treating Your Furbabies Like My Own

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Ashely is awesome!! She is so good with both our dogs. She understands both our dogs and their different personalities. She is our go to when we need someone t… (more)"

Calendar Recently Updated
3. Hannah Verified Background CheckRover 101

Dogs love to run and play with me!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

"Hannah took great care of our big sweetie Fergie and we can’t wait to have her back! (more)"

4. mary Verified Enhanced Background Check

I will care for your pets as my own

Midvale Heights Community, Madison, WI, 53711

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

"We are just always so thankful for Mary!! She takes the best care of our pup and I always feel safe knowing she’s there to meet her needs when I’m out of town … (more)"

Calendar Recently Updated
5. Bryan Verified Background Check

I am the definition of a dog person

Park Ridge, Madison, WI, 53719

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

"Nash loved having Bryan drop in to hang out for a week while I was working. Bryan was great dealing with my last minute instructions. Would definitely consid… (more)"

6. Kim Verified Background Check

Loving and experienced Dog Mom!

Middleton, WI, 53562

Dog Boarding, Drop-In Visits, Doggy Day Care

"Kim was wonderful and sent detailed messages about the drop-in visits. The pictures were great to see that our cat was happy. She watered our plants too which … (more)"

Calendar Recently Updated
7. Laura Verified Background Check

Pet lover looking for a win-win!

Regent, Madison, WI, 53726

House Sitting, Drop-In Visits, Dog Walking

"Laura is awesome! Highly recommend! She treated my pup like her own. She’s a lover of animals. My little guy got lots of loving, snuggling and activity ? (more)"

Calendar Recently Updated
8. Katie Verified Background Check

All dogs love a stroll in Madison!

Sauk Creek, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

"Katie is the best! My puppy loves when she comes to play. She always follows the instructions I leave and takes great care of my pup! (more)"

Calendar Recently Updated
9. Autumn Verified Background Check

Looking for some new furry friends!

Spring Harbor, Madison, WI, 53705

Drop-In Visits, Dog Walking

"Autumn was awesome with our cats! She sent quick responses and photos of how the two of them were doing when she checked in on them and fed them! Would definit… (more)"

Calendar Recently Updated
10. Kayla Verified Background Check

Reactivity, training, play, & sniff

Middleton, WI, 53562

Drop-In Visits, Dog Walking

"Kayla is a responsible, fun, and loving dog owner and caretaker. She is very knowledgeable on dog body language and behavior and has taken courses to learn abo… (more)"

11. Laura Verified Background Check

Caring, kind and flexible

Sauk Creek, MADISON, WI, 53717

Drop-In Visits, Dog Walking

"Outstanding!!!! Thank you Laura!!! (more)"

Calendar Recently Updated
12. Meli Verified Background Check

Responsible Dog Lover!

Middleton, WI, 53562

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

"Meli is a great dog sitter! She came to let my puppy out for a few days. She is trustworthy and sends greats updates and pictures of your pup while you are awa… (more)"

13. Tom Verified Background Check

Home full time.

Spring Harbor, Madison, WI, 53705

Drop-In Visits, Dog Walking

"We are so fortunate to have found Tom. He is a godsend. He has helped us so much with training our new puppy. (more)"

Calendar Recently Updated
14. Ryan & Jocelyn Verified Background Check

Dog Loving Small Family

Greentree, Madison, WI, 53711

Dog Boarding, Drop-In Visits, Doggy Day Care

"Ryan & Jocelyn are wonderful dog sitters and all around outstanding human beings: conscientious, caring, patient, and warm. They have watched my dogs - littl… (more)"

Calendar Recently Updated
15. Cleda Verified Background CheckRover 101

Dogs & Cats LOVE me!

Spring Harbor, Madison, WI, 53705

Dog Boarding, Drop-In Visits

"Cleda was great with my very anxious cat. She sent me pictures each time she checked in on her with a little description on how the visit went! She did everyth… (more)"

Calendar Recently Updated
16. Charlene Verified Background Check

Been pet sitting for many years!

Madison, WI, 53705

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

"Charlene is one of a kind, respectful and welcoming when you meet her and she absolutely loves pets of all kinds. Charlene has cared for my pup a number of tim… (more)"

Calendar Recently Updated
17. Tinaz Verified Background Check

Dog's Best Friend!

Middleton, WI, 53562

Drop-In Visits, Dog Walking

"Our dog and cat had a wonderful weekend with Tinaz! While we were off on a family vacation, our pets were having a fun, pamper-filled weekend of their own. Tin… (more)"

Calendar Recently Updated
18. Molly Verified Background Check

Energetic attentive animal lover

Wexford, Madison, WI, 53717

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

"Molly became my dog sitter through a friends recommendation last year. She watched my dog for a week while I was away in Canada visiting family. My dog loves h… (more)"

19. Emmerson Verified Background Check

Active & Reliable Pet Caretaker!

Hill Farms-University Neighborh, Madison, WI, 53705

Drop-In Visits, Dog Walking

"Emmerson would make a truly wonderful caregiver for your dog! She is kind, patient, empathetic, responsible and up to anything one throws at her. After watchin… (more)"

Calendar Recently Updated
20. Rebecca Verified Background Check

Animals are my jam!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

About: I grew up with cats, but fell in love with both cats and dogs! My experience comes mostly from caring for my friends’ and family’s pets. I hopped on … (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: