Dog Boarding in High Crossing, Madison, WI

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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

Ready to watch your fur babies!

Brentwood Village, Madison, WI, 53704

Dog Boarding, Doggy Day Care

17 repeat clients

"Kersten and Nicholas took great care of our best bud! They sent pictures and updates and even gave us a cute doggy bag of goodies when we picked him up. He ... (more)"

2. Brandee

J&B Dog Care

Sherman, Madison, WI, 53704

Dog Boarding, Drop-In Visits

3 repeat clients

"Brandee and Jason left me feeling confident that my dogs would be well cared for and I would reserve again with them without hesitation. Communication was g... (more)"

3. Melissa

Sebastian's love dogs!

Dane County, WI, 53590

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Rex had so much fun with Melissa and her family! She sent me picture updates and Rex was so happy! Glad I found a perfect sitter for all my future weekends a... (more)"


Home full-time-sun porch-love dogs.

Sun Prairie, WI, 53590

Dog Boarding, Doggy Day Care

61 repeat clients

"Our dogs Nigel and Toby had a great one night stay with Val! We would highly recommend him. Nigel and Toby will be happy to stay again in the future! (more)"

5. Kelly

Fenced yard & lots of love for pups

Eastmorland, Madison, WI, 53714

Dog Boarding, Drop-In Visits, Dog Walking

8 repeat clients

"Kelly and Neil were great from the beginning! They worked with my busy schedule to get a convenient time for an initial meet and greet. I'm so thankful for t... (more)"

6. Kristen & Kurt

Active, professional, work at home

Sun Prairie, WI, 53590

Dog Boarding, Doggy Day Care

7 repeat clients

"Our search for a quality dog sitter is over! Our pup spent 6 nights with Kurt, Kristen, and Margo and he had a great time! I loved the daily updates and phot... (more)"

7. Emily

Large yard and lots of exercise!

Sun Prairie, WI, 53590

Dog Boarding

"Benjamin was well cared for at Emily's. He seemed to enjoy outdoor time in the fenced-in yard. Emily kept in touch with pictures and updates while we were ... (more)"

8. Stephanie

will give: love, exercise & care

Madison, WI, 53704

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

"Stephanie was great! She took the dogs for walks even on the coldest snowiest days, sent me pictures and an update every day and was agreeable to an early mo... (more)"

9. Julie

Happy Tails

Ridgewood, MADISON, WI, 53704

Dog Boarding

23 repeat clients

"We had never left our goldendoodle, Ginger, before and chose Julie based on her wonderful reviews! She was amazing to work with and Ginger thoroughly enjoye... (more)"

10. Nick

Big Fenced yard, Dog Vacation spot!

Whitetail Ridge, Madison, WI, 53704

Dog Boarding, Doggy Day Care

21 repeat clients

"Nick is my go to sitter for my two year old golden. Nick has excellent communication, is very flexible, and makes sure to send lots of pictures! I would reco... (more)"

11. Viri

Fenced yard and yummy treats!

Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53703

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Buddy loved staying a couple of nights with Viri. He was worn out from playing with her pup and is looking forward to staying there again! (more)"

12. Bethany

Certified Veterinary Certified

Worthington Park, Madison, WI, 53714

Dog Boarding, Doggy Day Care

5 repeat clients

"Bethany was super accommodating and did everything to make my dog feel at home and comfortable! She has a nice fenced in back yard with two other friendly do... (more)"

13. Amy Lynn

Do you have a NON-SHEDDING breed?

Sun Prairie, WI, 53590

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

9 repeat clients

"Amy was wonderful as a sitter. She sent me photos of JoJo while we were gone. Answered text messages to ease my mind. When we got JoJo home he was really... (more)"

14. Amanda

Responsible, active, pet owner

Cottage Grove, WI, 53527

Dog Boarding, Drop-In Visits

9 repeat clients

"Amanda did a fantastic job of watching my dog for 1 night. She was flexible on pick up and drop off time and ensured he was well taken care of. Would definit... (more)"

15. Laurie

Fenced in Yard, Love to Play

Eken Park, Madison, WI, 53704

Dog Boarding, House Sitting, Dog Walking

"Great experience. Would highly recommend! (more)"

16. Andrew

Large fenced yard, Friendly husky

Sherman, Madison, WI, 53704

Dog Boarding

"Andrew loves animals and takes great care of his dog. He is always making sure he has the best toys, treats and gets the activity he needs. If you are lookin... (more)"

17. Alesha

Dog enthusiast with love to give.

Ridgewood, Madison, WI, 53704

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

"Anybody would be lucky to have Alesha take care of their dog. She has her own dog that she takes care of whenever she's at home, and constantly misses him wh... (more)"

18. 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)"

19. Macaulay

We are lifetime dog lovers.

McClellan Park, Madison, WI, 53718

Dog Boarding, Drop-In Visits

"Bogey had such a great time and was all tuckered out from playtime with Belle! Also, the photos were much appreciated and made being away from our fur baby a... (more)"

20. Tyler

Large yard, with 2 playful pups!!

Burke Heights, Madison, WI, 53714

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

"My dogs had a great time with Tyler! He sent us lots of pictures. Thank you, Tyler! (more)"

Dog lovers in High Crossing, Madison, WI love dog sitters on Over 423 pet owners have reviewed dog 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 dog boarding in Madison can be when you book with Rover. Wondering how much it might cost to book dog boarding? Check out our average dog boarding rates to get an idea before contacting a dog sitter near you. offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving High Crossing dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in High Crossing, Madison, WI, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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: