House Sitting in Wyndemere, Madison, WI

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Dismiss
Confirmed Holiday Availability
1. Jennifer

AVAILABLE THIS WEEKEND!!!

Madison, WI, 53719

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

6 repeat clients

"Jennifer was absolutely wonderful! She made our first weekend out of town as new puppy parents worry free. She took the time to briefly meet us and Bearle be... (more)"

2. Hannah

I'm probably as active as your dog!

Junction Ridge, Madison, WI, 53717

Dog Boarding, House Sitting, Doggy Day Care

5 repeat clients

"My dogs were at ease with Hannah. I received photos of my dogs while I was away, which was fantastic. The girls seemed less stressed out than when they come ... (more)"

3. Fran

How about a long walk today?

Parkwood West, Madison, WI, 53705

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

3 repeat clients

"When visiting Madison, we arranged with Fran to watch our Golden while we took our daughtwr out for a birthday dinner. Fran was very accommodating to our eve... (more)"

4. Michelle

At-home CPA who loves fur babies!

Hill Farms-University Neighborh, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"She watched over our dog while we were gone for the night and took great care of Laya. It’s evident she’s a dog lover and enjoys taking care of pets! (more)"

5. Jocelyn

Part Time Dog & Puppy walker/sitter

Fitchburg, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

"Jocelyn is a lifesaver. She was able to take care of my pup while I was away on a short-notice trip. She was extremely accommodating and very friendly! I hig... (more)"

6. 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)"

Confirmed Holiday Availability
7. Andrea

Around the clock care, fenced yard!

Sunset Village, Madison, WI, 53705

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

60 repeat clients

"Andrea was amazing with my dog Otis. She house sat for me so Otis (who has separation anxiety and is timid) didn't have to leave the comfort of his own home.... (more)"

8. Matthew

Top-Notch Professional Pet Services

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

"Matt is a passionate dog lover! I would trust him with my dog which is saying a lot becuase my dog loves to run away and actively pursues the challenge of g... (more)"

9. 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)"

10. Jessica

Making them happy when you're gone!

Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Everything went perfect! All three of my dogs had a great time Jessica took care of everything. Fish were fed and my home was well kept!!! 5 stars! (more)"

11. Heather

a person who says hi to dogs first

Wisconsin Co-Op Housing, Madison, WI, 53705

House Sitting, Drop-In Visits, Dog Walking

"Heather is a fantastic dog caregiver! As the owner of two very different (and slightly odd) dogs, I can 100% vouch for Heather's ability to gain a dog's trus... (more)"

12. Brenna

Graduate student animal lover!

Vilas, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Brenna did a fantastic job. My dog can be labor-intensive, but I felt like Brenna had everything under control. And she kept in contact with me, which I ap... (more)"

13. Ashley

Fun walks & fresh air for your dog!

Madison, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

About: Hi there, I am Ashley! I have grown up with 5 dogs throughout my life and miss the constant energy! We have 2 cats currently that are quite active,... (more)

Confirmed Holiday Availability
14. Kaylyn

Professional, Positive, Pet Sitter

Middleton, WI, 53562

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

"We were very pleased at how well Kaylyn cared for our old New Foundland. She made sure he received all his medication on time. It was also great that she wou... (more)"

15. Jillian

I would love to play with your dog!

Fitchburg, WI, 53719

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Jillian was great! She genuinely enjoys spending time with dogs and taking care of them. She also has lots of experience with her own dogs. (more)"

16. Abigail

Pre-Vet Grad. 10 yrs of Animal Care

Meadowood, Madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

"Abby has a natural instinct and a way with all animals, especially dogs. She has an observant eye if she notices unusual behavior and understands canine body... (more)"

17. Lauren

Lauren on the West Side

Madison, WI, 53717

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I am one of those pet parents who will leave 9 pages of instructions for a dog walker. When I met Lauren, she was already three steps ahead of me. She asked ... (more)"

Confirmed Holiday Availability
18. Christine

A tired dog is a good dog

Prairie Hills, madison, WI, 53711

House Sitting, Drop-In Visits, Dog Walking

37 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
19. 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)

20. Kellsey

Love going on long walks!

Middleton, WI, 53562

House Sitting, Drop-In Visits, Dog Walking

"Kellsey has genuine love for animals, especially dogs. Her friends and family have entrusted her with their beloved pets to dog sit, play, and go for walks.... (more)"

Pet parents in Wyndemere, Madison, WI love dog sitters on Rover.com. 423 owners have reviewed sitters in Madison, giving them an average rating of 4.9/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Wyndemere house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Wyndemere, Madison, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Wyndemere house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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 Wyndemere, 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: