Pet Setting & Drop Ins in Westchester Gardens, Madison, WI

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

Tip: Contact sitters now to confirm availability.
1. Michelle

Large fenced in yard. Active family

Sun Prairie, WI, 53590

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

"Michelle was fantastic! She was so nice and friendly and my dogs seemed to warm up to her right away (which is what is most important of course!). Our larg... (more)"

Confirmed 4th of July Availability
2. Allison & Raymon

LOVING, ACTIVE DOG SITTERS!!

Capitol, Madison, WI, 53703

House Sitting, Drop-In Visits, Dog Walking

"Allison was so caring and positive dropping in on my Lincoln. I was nervous, as I always am, about leaving the pup behind, but Allison's updates and photos c... (more)"

3. Jennifer

Great with high energy dogs!

Worthington Park, Madison, WI, 53714

Drop-In Visits, Dog Walking

"Jennifer is the best - she is so good with our Siberian husky. We’re really particular about who we ask to watch our dog, and Jennifer has made us feel confi... (more)"

4. Rebecca

Patient, playful, and dedicated

Capitol, Madison, WI, 53703

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

"Rebecca was incredibly accommodating to my schedule and went out of her way to make sure the stay went well. My cats had a great time with her. I would for... (more)"

5. Gracie

I promise a tail-wagging good time!

Madison, WI, 53718

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

"Gracie has taken care of our dogs on two different occasions, one home stay and one drop in, and she is outstanding. She gives great updates and we always co... (more)"

6. Marlena

I'll run with your dog!

Monona, WI, 53716

House Sitting, Drop-In Visits, Dog Walking

"Marlena was excellent! She replied promptly, took meeting my kitty very seriously and checked-in with photos and updates. I will use Marlena again for sure f... (more)"

7. Faith

Grew up with Dachshunds, Have a Cat

McClellan Park, Madison, WI, 53718

House Sitting, Drop-In Visits, Dog Walking

"Faith is a dog lover at heart and loves being around them and caring for them. She is responsible and understands that owners see their pets as an extension ... (more)"

8. Carly

Let me love them while you can’t

Schenk-Atwood, Madison, WI, 53706

House Sitting, Drop-In Visits, Dog Walking

"Carly was my dog sitter multiple times and always did a spectacular job. She would keep my two dogs and I never had to worry. She always left my apartment cl... (more)"

Confirmed 4th of July Availability
9. 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)

10. Anamaria

Catch Dog Training Academy Student

Sherman Village, madison, WI, 53704

Drop-In Visits, Dog Walking

"Ananaria has helped me numerous times with my dogs. I was looking for a reliable, responsible dog sitter and she certainly has lived up to that. Her knowledg... (more)"

11. Matthew

Lover of all dogs, very attentive!

Ridgewood, Madison, WI, 53704

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

"Matthew LOVES babysitting our pup. He says he "feels honored" every time we ask him, instead of it being a chore. I highly recommend him! (more)"

12. 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)

Confirmed 4th of July Availability
13. Julie

Playcare fun may cause drowsiness.

Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53714

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

"Julie is a true dog lover. Our pug, Rooney, always has a fun filled day when visiting Julie and her dog Duncan. When we drop Rooney off he is so excited; h... (more)"

Confirmed 4th of July Availability
14. Charli

A Dogs Best Friend

Nobel Park, Madison, WI, 53704

Drop-In Visits, Dog Walking

"Charli did a wonderful job with my special needs pets. She gave updates and photos and went the extra mile to make sure they were safe and happy. I would def... (more)"

Confirmed 4th of July Availability
15. 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)

16. Daniel

Lover of all, big and small!

Eastmorland, Madison, WI, 53714

House Sitting, Drop-In Visits

"Dan was very good with my dog Howard, a Newfoundland. Howard was a handful and most other sitters had an issue with him going to the bathroom or chewing thin... (more)"

17. Jessica

Compassionate and loving!

Rolling Meadows, madison, WI, 53714

Drop-In Visits, Dog Walking

"Jessica is my cousin and she has always had a soft spot for any animal, especially dogs. Shes had dogs her whole life and has alot of experience with them. I... (more)"

Confirmed 4th of July Availability
18. Bethany

Certified Veterinary Technician

Worthington Park, Madison, WI, 53714

Dog Boarding, Drop-In Visits, Doggy Day Care

About: My name is Bethany Heil and I am a CVT of 14 years with experience in foster care as well as pet-sitting, 3 years of German Shepherd Rescue. 4 y... (more)

19. 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)"

20. Nikki

Love dogs and cats!!

Hawthorne, Madison, WI, 53714

Drop-In Visits, Dog Walking

About: My name is Nikki and I live on the east side. I am going to school and working part time.I own a dog and he is my life. I will treat your dog as if... (more)

Dog owners in Westchester Gardens, Madison, WI turn to pet sitters on Rover.com for their pet sitting needs. Over 423 pet owners have reviewed pet sitters in Madison, giving them an average rating of 4.9/5. Pet sitting can be affordable, no matter where you live or what your price range may be. Curious about how much pet sitting costs in Madison with Rover.com? Check out our average pet sitting rates near you to get an idea before getting a conversation started with a pet sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Westchester Gardens pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Westchester Gardens, Madison who meets your and your pet'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 pet, 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 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: