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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Christine

compassionate, experienced care

Prairie Hills, madison, WI, 54235

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

25 repeat clients

"Christine on many occasions has house sit and watched our dogs, we always knew that they were in goods hands. Christine has a love of dogs and it shows. If... (more)"

Confirmed Holiday Availability
2. Kelsey

Animal loving college student

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I have owned animals all of my life especially dogs. Being in college I do not have the opportunity to own pets. I love going for walks and do that... (more)

3. Whitney

I'll treat your furbaby like my own

Verona, WI, 53593

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Whitney was great! She came in for a drop-in visit while we were away for a day trip. Silly Millie got into things she wasn't supposed to and Whitney gladly ... (more)"

4. Ben

I've got a passion for animals

Vilas, Madison, WI, 53711

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

1 repeat client

"Ben was patient with Winnie while she warmed up to him. The Rover app wasn't working properly so I only saw a couple of updates. Ben left a detailed message ... (more)"

5. Amy

Love and Patience!

Regent, Madison, WI, 53726

Drop-In Visits, Doggy Day Care, Dog Walking

3 repeat clients

"Amy is great with my two (kind of high maintenance) beagles. She "dropped in" with one of them and walked the other while I was at work, and both of them wer... (more)"

6. Skylar

Dog loving academic!

Regent, Madison, WI, 53726

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Skylar did a great job with Dozer and was so good about posting updates so that I knew he was safe and happy while I was out of town. Couldn't have asked for... (more)"

Confirmed New Years Availability
7. Emma

Furry or scaly, I love them all!

Appalachian Ridge, Madison , WI, 53705

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I'm a Horticulturist who is looking for winter work while the ground is frozen. I adore pets of all kinds, grew up with Belgian Tervuren and now ow... (more)

8. Stephanie

Attentive animal lover just for you

Madison, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"I have hired Stephanie two time now to take care of my cat while out of town. She does an excellent job! She is also great about communicating and always se... (more)"

9. Cindy

I will be your dogs best friend!

Hill Farms-University Neighborh, Madison, WI, 53705

Drop-In Visits, Dog Walking

"Cindy did a great job taking care of my boy when I had a long Saturday trip. She sent me lots pictures of him playing and then when he got stung by a bee off... (more)"

10. Sheryl

Let us spoil your dog!

Sunset Village, Madison, WI, 53705

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

About: My aunt was a dog breeder and I grew up around dogs from their inception. I helped with the breeding process, whelping, weaning, training for the r... (more)

11. Adam

A friend of All Hunds

Orchard Ridge Community, Madison, WI, 53711

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

2 repeat clients

"Adam has provided great care for our dog. I would highly recommend him to other people! (more)"

12. Michelle

Reliable Dog Lover

Oakbridge Community, Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

1 repeat client
No Reviews Yet

About: I've always been a huge dog lover, tried to take in every stray as a kid, I grew up around dogs like basset hounds, Labradors, poodles and beagles.... (more)

Confirmed New Years Availability
13. Christina

Anything fluffy, fuzzy, & floppy!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Christina set my mind at ease during the meet and greet. She did drop in visits with my dog while I was away and each time she came over she let me know when... (more)"

14. Amy

Energetic and passionate dog lover

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Amy is a caring and attentive sitter. She has watched my dog multiple times while I have had to travel for business. I received numerous updates on how my pu... (more)"

15. Kayla

Medical student dog lovers

Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"2 Years ago Kayla rescued an aging Black and Tan Coon Hound, the love and care she gave this dog was beyond wonderful. Even when Ruby was diagnosed with term... (more)"

Confirmed Holiday Availability
16. Shauna

Recommended and experienced sitter

Spring Harbor, Madison, WI, 53715

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Shauna took great care of my cat while I was away for the holidays. She communicated well throughout the booking process and stay, was able to administer hi... (more)"

17. Emily

Dog and outdoors lover!

Blackhawk, Madison, WI, 53717

Dog Boarding, Drop-In Visits, Dog Walking

"I would highly recommend Emily as a dog caregiver! I've spent a lot of time with Emily, and she treats my dog with love and care as she does her own personal... (more)"

Confirmed Holiday Availability
18. Kimberly

Unconditional love for "fur"-babies

Middleton, WI, 53562

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

2 repeat clients

About: My name is Kim! I'm 21 years old and currently work at a pet boarding facility. I've lived with dogs, cats, and one mini pig my entire life (I curr... (more)

19. Matthew

Animal Lover

Madison , WI, 53719

House Sitting, Drop-In Visits, Dog Walking

About: I love dogs, they are like family to me. I have a dog of my own and I give him the love he desires. I've had 3 dogs in my past, two of them were La... (more)

Confirmed Holiday Availability
20. Lindsay

Owned by 3 experienced w/ many more

Madison, WI, 53719

Drop-In Visits, Dog Walking

About: I have owned dogs all my life and have experience with dogs ranging from 10-110 pounds, and all ages, temperaments and activity levels. I am famili... (more)

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Learn About Premier

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: