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House Sitting in Westchester Gardens, 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.
Confirmed availability
4th of July
1. Allison & Raymon

LOVING, ACTIVE DOG SITTERS!!

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

"Allison stayed at our house and took care of our dog & cats last night. She was great! She kept us informed about how everything was going and sent lots of p... (more)"

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2. Gracie

I promise a tail-wagging good time!

Madison, WI, 53718

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

"Evie had another great stay with Gracie over the Christmas break. She was obviously well-looked after and very happy to be hanging out with Gracie and her p... (more)"

3. Carly

Let me love them while you can’t

Schenk-Atwood, Madison, WI, 53706

House Sitting, Drop-In Visits, Dog Walking

"if I could give 10 stars I would. My little puppy had an accident that required him to be watched while he went through the healing process. We asked Carly t... (more)"

4. Marlena

I'll run with your dog!

Monona, WI, 53716

House Sitting, Drop-In Visits, Dog Walking

"Marlena was great taking care of our two dogs and two cats while we were away for the weekend. She sent us regular updates with pictures, and also left the h... (more)"

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5. Faith

Grew up with Dachshunds, Have a Cat

McClellan Park, Madison, WI, 53718

House Sitting, Drop-In Visits, Dog Walking

"Faith was nice and accommodating while staying at my place with my dog and two cats. She sent regular updates and I felt better that my dog and cats could s... (more)"

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6. Kayla

i love playing with dogs

Monona, WI, 53716

House Sitting, Drop-In Visits, Dog Walking

"Kayla house sat and pup sat for our 2 Labrador retrievers; who need constant exercise. She took very good care of them; both in making sure they ran, played ... (more)"

Confirmed availability
4th of July
7. Stephanie

will give: love, exercise & care

Madison, WI, 53704

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

About: Hello! I’m Stephanie && am a COMPLETE dog lover. Leaving my dog is always the hardest/most stressful part of taking trips and I want to serve as a ... (more)

Confirmed availability
4th of July
8. Sarah

Dog hair everywhere, don't care!

Worthington Park, Madison, WI, 53714

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

"Sarah was amazing with Capone! She sent us updates all weekend and knew he was in good hands! We came back to a nice note and summary of the weekend. I would... (more)"

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9. Erica

Will love your dog as my own

Elvehjem, Madison, WI, 53716

House Sitting, Drop-In Visits, Dog Walking

"Erica is the best dog sitter we have ever had. She sent me pictures everyday and kept me updated on how my dog was doing! She also brought our mail in and le... (more)"

Confirmed availability
This weekend
10. Johnathan

Home full-time, fenced backyard

Carpenter-Ridgeway, Madison, WI, 53704

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

About: I have raised a duck hunting dog and now have a sweet lab named hiccup. I love spending my time with dogs. I am available almost all the time as ... (more)

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11. Jamie

I am a Certified Vet Tech

Marquette, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

"If I could describe Jamie in one word it would be selfless. She gives everything she has every single day without asking for anything in return. She does h... (more)"

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12. Bea

Walks-Exercises-Treats-Happy Pet.

Sun Prairie, WI, 53590

House Sitting, Drop-In Visits, Dog Walking

"Bea did an amazing job! It was nice to come home to relaxed, tired dogs. I would definitely recommend Bea to anyone that is looking for a Rover. She let m... (more)"

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13. Jess

Confident, reliable and resourceful

Schenk-Atwood, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

"We had a nice meet and greet with Jess and hired her to pet sit for us. She did a great job, had good communication, and even brought in the mail without be... (more)"

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14. Camille

I provide lots of cuddle & playtime

Tenney-Lapham, Madison, WI, 53703

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

"Camille is the best dogsitter ever! She is always enthusiastic and gives so much love and attention to my dog Shag! Shag is always happy to see Camille walk ... (more)"

Confirmed availability
This weekend
15. Katerina

Patient Dog-Lover Avail. Full-Time

Bluff Acres, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

"Katerina was great with my fur kids! She kept me up to date with concerns she had and assured me they were happy and receiving lots of cuddles. This was my... (more)"

16. Daniel

Lover of all, big and small!

Eastmorland, Madison, WI, 53714

House Sitting, Drop-In Visits

"Daniel took great care of our dogs so we could get away for a weekend. He kept me updated and did a great job winning over my grumpy old man. We came home to... (more)"

17. Jon

Wants doggo friends!

Mayfair Park, Madison, WI, 53714

House Sitting, Drop-In Visits, Dog Walking

About: I love animal care work, but moved on to another career path and miss caring for animals. I'd get to know your dog and figure out what type of care... (more)

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18. Angie

Our pup loves playmates!

Madison, WI, 53718

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

About: We have a very active 1.5 year old yellow lab who loves to play and nothing burns him out like a good play session with another pup! Since we can’t... (more)

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19. Kiana

Perfectly pawfect.♡

Berkley Oaks, Madison, WI, 53704

House Sitting, Drop-In Visits, Dog Walking

"Kiana was a wonderful house sitter! She stayed at my home, with a dog and a cat, for just under a week and things went very well. Kiana sent me regular updat... (more)"

Confirmed availability
4th of July
20. Abby

Pet mom to 3 amazing dogs!

Mayfair Park, Madison, WI, 53714

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

About: Hi I'm Abby, I have been an animal lover since i was a tiny tot, my family always had pets in the house from dogs, cats and to even birds! I am 2... (more)

Dog lovers in Westchester Gardens, Madison, WI love house sitters on Rover.com. Over 423 pet owners have reviewed house 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 house sitting in Madison can be when you book with Rover. Wondering how much it might cost to book house sitting? Check out our average house sitting rates to get an idea before contacting a house sitter near you.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Westchester Gardens house sitter in seconds on Rover.com. If you're looking for trusted dog sitters while you're away, whether it's for one night or a whole month, you can find a house sitter in Westchester Gardens, Madison, WI who meets your and your dog's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Westchester Gardens, 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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.