Pet Sitting & 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.

Search Results

Confirmed availability: Memorial Day
Erika R.
1.
Loves long walks and winter cuddlesVerona, WI, 53593
Drop-In Visits, Doggy Day Care, Dog Walking

Erika was wonderful! Very accommodating and professional, even on short notice! Sent me lots of pics and loved hanging out with my pooch! Five stars (more)

from
$18
per visit
Confirmed availability: Memorial Day
McKenna A.
20 years experience with all breedsBlackhawk, Middleton, WI, 53562
Drop-In Visits, Dog Walking

McKenna was amazing with our little puppy! So caring, thoughtful, and flexible. Great to know our four legged family member was in such good hands! (more)

from
$18
per visit
Calendar Recently Updated
Ashley E.
3.
Treating Your Furbabies Like My OwnMadison, WI, 53705
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Ashley is fantastic! She was on time, communicative, and took such good care of my older kitty. I loved her updates and photos, would absolutely want to book … (more)

from
$18
per visit
Confirmed availability: Memorial Day
Hillary L.
Caring, experienced and reliable!Summit Woods, Madison, WI, 53711
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Hillary was amazing! She sent daily updates of my cat, kept him entertained and well fed. She was very creative in entertaining my cat in ways I wouldn't have i… (more)

from
$25
per visit
Anna P.
5.
Perfectly sane cat lady!*Madison, WI, 53711
Drop-In Visits

Anna was amazing! She was the next best thing to me while we went on vacation. I received lovely notes and pictures each day. It was a wonderful first experien… (more)

from
$20
per visit
Confirmed availability: Memorial Day
6.
Gen 
Verified Background Check
Rover 101
Not your average pet care service!Middleton, WI, 53562
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Amazing! Gen was so great, we were first time Rover users because we just needed someone to come let our pup out and give him dinner during our wedding, and she… (more)

from
$25
per visit
Confirmed availability: Memorial Day
15 Years of Pet Lovin'!Madison, WI, 53705
Drop-In Visits, Dog Walking

Jessica is always so quick to respond, thoughtful and is great with Catdog! Goes above and beyond, giving him time to sit on the porch (his favorite) and is sup… (more)

from
$15
per visit
Calendar Recently Updated
8.
Not enough dogs in my lifeMadison, WI, 53705
Drop-In Visits, Dog Walking

Shelbi is a fantastic caregiver - Shelbi cared for our 3 year old German Shepherd while we were in the hospital during the birth of our daughter. Zeus warmed … (more)

from
$20
per visit
Calendar Recently Updated
9.
Animal Lover and Experienced SitterMiddleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

Helped out very last minute! (more)

from
$15
per visit
Calendar Recently Updated
10.
Reliable & caring dog/cat sitter!Madison, WI, 53719
Drop-In Visits

Oh my gosh, I just can't say enough good things about how well loved my pets (2 cats) and home felt with Whitney checking in while I was out of town. I loved s… (more)

from
$16
per visit
Calendar Recently Updated
11.
Energetic lover 🥰 of Fur-babies!Middleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

Donna is the SWEETEST dog sitter! She always goes above and beyond to give the animal what they need. If asked to take the dog for a walk, she’ll be sure to giv… (more)

from
$22
per visit
Calendar Recently Updated
I pawsitively love dogs and cats!Old Middleton Greenway, Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

It’s evident that RuthAnne loves what she does! I felt like our aging golden retriever was well cared for during walks and drop-ins and communication was super … (more)

from
$20
per visit
Calendar Recently Updated
13.
Dog owner & med student!Spring Harbor, Madison, WI, 53705
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sophie is a wonderful sitter who cares so much about animals. She has a lot of experience with caring for dogs and just genuinely loves them. She also did a gre… (more)

from
$18
per visit
Confirmed availability: Memorial Day
14.
Outgoing, student, dog loverMiddleton, WI, 53562
House Sitting, Drop-In Visits, Dog Walking

We absolutely love Camille! Always kind and understanding with our older dog. Very professional and a great a communicator with lots of photo check in skills 😊 (more)

from
$25
per visit
15.
Keep your pets happy at home!Junction Ridge, Madison, WI, 53717
Drop-In Visits, Dog Walking

Katie did a fantastic job with our pup! She was very prompt, super communicative, and sent us TONS of pictures—which is exactly what we wanted! (more)

from
$25
per visit
Calendar Recently Updated
16.
Tom 
Verified Background Check
Home full time.Spring Harbor, Madison, WI, 53705
Drop-In Visits, Dog Walking

Tom's care of my Ragdoll cat Phoenix was exceptionally great. It was outstanding! It's easy to see how Tom cares about and has compassion for animals. He wen… (more)

from
$17
per visit
Calendar Recently Updated
17.
love adventuring with furry friendsMadison, WI, 53719
House Sitting, Drop-In Visits, Dog Walking
15 years of experience

About: I’ve had pets since grade school, I’ve had two of my very own cats and a dog, and I’ve been cat sitting and dog sitting for about 5 years. They will … (more)

from
$25
per visit
18.
Cared for as if you were homeMiddleton, WI, 53562
House Sitting, Drop-In Visits

Kate watched our furbaby for us while we were away on a two-week trip to England. It took us about two-seconds to think if who we would trust our pups with, and… (more)

from
$25
per visit
Confirmed availability: Memorial Day
19.
Daily visits to the dog park!Marbella, Madison wi, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Extremely reliable and was a life saver on my long days at work. Always got a picture and a map of where her and my pup walked. Will definitely use again!!! (more)

from
$50
per visit
Confirmed availability: Memorial Day
Professional, kind, reliable personSpring Harbor, Madison, WI, 53705
House Sitting, Drop-In Visits, Dog Walking

Clarissa was fantastic! We hired her to drop in on our dog during a 2 day trip. She went above and beyond to make sure my dog would eat his food (he gets anxiou… (more)

from
$20
per visit

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.

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