Pet Sitting & Drop Ins in Highlands Community, Madison, WI

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Sitter Profile Image: Melinda N.
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Sitter Profile Image: Melinda N.
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1. Melinda N.

Sorry I was late. I saw a dog!
Maple-Prairie, Madison, WI, 53719
4.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
37 reviews
12 repeat clients
from
$18
per visit

Melinda was a great help and took great care of our pup during her check-ins. She was timely and is a great communicator. We’ll definitely ask her for help in the future!

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Sitter Profile Image: Seán & Leticia W.
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Sitter Profile Image: Seán & Leticia W.
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2. Seán & Leticia W.

Rover 101
Take Care Of Your Best Friend!
Maple-Prairie, Madison, WI, 53719
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
41 reviews
10 repeat clients
from
$16
per visit

Seán & Leticia were great to work with for my first time using Rover. They were respectful of my very nervous cat and took great pictures of my friendlier cat! Seán helped adjust the dates of my booking and checked in with me often to make sure he had all the details right.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Maiya W.
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Sitter Profile Image: Maiya W.
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3. Maiya W.

I'll love them like you love them!
Middleton, WI, 53562
1.9 mi. away
Drop-In Visits
5.0 out of 5 stars
78 reviews
29 repeat clients
from
$15
per visit

Maiya was awesome with our needy cat! He wants all the attention all the time and she was sure to give him lots of love while we were out of town. She offered to bring in the mail too! Such a nice women and definitely a true animal lover!

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Sitter Profile Image: Ann V.
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Sitter Profile Image: Ann V.
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4. Ann V.

Animal Lover and Law Student
Madison, WI, 53711
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
8 repeat clients
from
$20
per visit

Ann was great with my shy cat and let him warm up to her at his own pace. Ann was responsive to messages and I was comfortable knowing she was taking care of my loved one.

Sitter Profile Image: Kim M.
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Sitter Profile Image: Kim M.
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5. Kim M.

Loving and experienced Dog Mom!
Middleton, WI, 53562
1.5 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
94 reviews
40 repeat clients
from
$17
per visit

I chose Kim for my first Rover experience to take care of my cat while I was away for a week. She showed genuine care and interest in my cat , provided daily pictures and updates while I was away , and was always quick to respond if and when needed. She is very trustworthy and she’ll be an obvious choice for the next time I need someone to watch my cat ! I have no hesitation and give my full enthusiasm to recommend her to anybody looking for the right caretaker for your pet.

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Sitter Profile Image: Whitney H.
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Sitter Profile Image: Whitney H.
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6. Whitney H.

Rover 101
Reliable & caring dog/cat sitter!
Madison, WI, 53719
2.5 mi. away
Drop-In Visits
5.0 out of 5 stars
30 reviews
16 repeat clients
from
$19
per visit

Whitney comes highly recommended. She took excellent care of my pet and even did a few "extra" requests while she performed the drop in visits. Really appreciated that.

Sitter Profile Image: Danielle M.
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Sitter Profile Image: Danielle M.
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7. Danielle M.

I am dog's best friend!
Verona, WI, 53593
3.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
37 repeat clients
from
$12
per visit

Danielle was available on super short notice (just a few hours) when our dog-walker fell through; our dogs love her and it was so great knowing we didn't have to worry about the dogs during our day away from home. She's great!!!

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Sitter Profile Image: Jess B.
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Sitter Profile Image: Jess B.
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8. Jess B.

Your weekend/evening needs covered!
Madison, WI, 53719
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
9 repeat clients
from
$24
per visit

Jess and my cat get along so well! Jess is a wonderful pet sitter and always sent me great updates and pictures of my cat. Much appreciated!!! She rules.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sara J.
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Sitter Profile Image: Sara J.
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9. Sara J.

I’ll take care of your PAWfect pup
Junction Ridge, Madison, WI, 53717
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
4 repeat clients
from
$25
per visit

Sara has been timely with her drop in visits, flexible with the craziness of having to exchange keys, and communicative! We appreciate (including Maverick) her greatly with our long work hours.

Sitter Profile Image: Lydia S.
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Sitter Profile Image: Lydia S.
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10. Lydia S.

Here to help with your schedule
Middleton, WI, 53562
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
43 reviews
16 repeat clients
from
$19
per visit

Lydia was a great communicator and very thorough sitter. She followed directions for providing medication perfectly. She also went above and beyond the simple requested drop in for our kitty's basic needs and provided plenty of attention and love. We will absolutely be booking again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jennifer L.
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Sitter Profile Image: Jennifer L.
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11. Jennifer L.

Rover 101
AVAILABLE THIS WEEKEND! TOP RATED!
Madison, WI, 53719
2.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
286 reviews
106 repeat clients
from
$22
per visit

Jennifer was very prompt on responses and great with our dog (who can be a handful). She kept him entertained and even worked on training with him. We knew he was well taken care of and definitely plan on booking visits with her in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dietrich G.
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Sitter Profile Image: Dietrich G.
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12. Dietrich G.

Dietrich is a dog's delight
Walnut Grove, MADISON, WI, 53717
1.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
20 reviews
4 repeat clients
from
$12
per visit

Dietrich has been a wonderful dogsitter for my dog! He is a great communicator thru the Rover App and I appreciate is daily comments and photo. I know that Coco is in great care!

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Sitter Profile Image: Allegra R.
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Sitter Profile Image: Allegra R.
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13. Allegra R.

Rover 101
Dog person for life.
Faircrest, Madison, WI, 53705
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
21 repeat clients
from
$25
per visit

My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!

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Sitter Profile Image: Cleda W.
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Sitter Profile Image: Cleda W.
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14. Cleda W.

Rover 101
Dogs & Cats LOVE me!
Madison, WI, 53705
0.8 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
164 reviews
75 repeat clients
from
$20
per visit

Cleta did an amazing job taking care of our 3 cats while we were gone. She left thorough updates after each visit and took lots of pictures. It made me appreciate our vacation even more knowing our pets were in excellent care!

Sitter Profile Image: Samantha K.
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Sitter Profile Image: Samantha K.
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15. Samantha K.

I’ll take good care of your buddies
Middleton, WI, 53562
1.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
9 repeat clients
from
$20
per visit

We love booking Samantha when she is available. She is always friendly, kind, and does a fantastic job taking care of our cat when we are away. Thanks Samantha for being such a gem!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashley E.
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Sitter Profile Image: Ashley E.
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16. Ashley E.

Treating Your Furbabies Like My Own
Madison, WI, 53705
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
379 reviews
113 repeat clients
from
$26
per visit

Ashley watched our two cats while we were out of town. She described their behavior, played with them, tended to their needs, and sent plenty of pictures! We would definitely have Ashley tend to our cats again.

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Sitter Profile Image: Cindy D.
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Sitter Profile Image: Cindy D.
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17. Cindy D.

Happy to Love your Small Dog!
Madison, WI, 53717
1.8 mi. away
House Sitting, Drop-In Visits
4.5 out of 5 stars
4 reviews
1 repeat client
from
$15
per visit

Cindy has been dog-sitting my chihuahua for almost 12 years; I would never take my dog to another dog-sitter! Daisy is usually timid with new people, but she loves Cindy! Cindy is responsible, reliable, and provides a calm atmosphere for shy dogs to thrive in. She is also flexible and willing to follow any specific instructions you might have related to dog care. Highly recommended!

Sitter Profile Image: Hannah S.
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Sitter Profile Image: Hannah S.
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18. Hannah S.

Love to check on your fur babies!
Madison, WI, 53711
2.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
63 reviews
33 repeat clients
from
$20
per visit

This was the second time Hannah watched our cat for us, this time for a whole week. Our cat was well taken care of and I appreciated getting updates every visit. Hannah even noticed all our cat’s little habits, making me feel confident that she was being well cared for!

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Sitter Profile Image: Bailee B.
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Sitter Profile Image: Bailee B.
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19. Bailee B.

Time with pets is time well spent.
Sauk Creek, Madison, WI, 53717
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$20
per visit

We are so grateful for Bailee who took good care of our dog, Layla, on Easter Sunday. We have used Bailee before and will definitely use her again.

Sitter Profile Image: Anna N.
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Sitter Profile Image: Anna N.
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20. Anna N.

Professional student who loves dogs
Madison, WI, 53705
0.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$15
per visit

Anna is the best choice to care for your dog. She kept us updated on our puppy, did fun activities with our puppy, and even had little treats with him. You can tell that she is a huge dog-lover and will go above and beyond for your dog’s care!

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When it comes to pet sitting, dog owners in Highlands Community, Madison, WI love Rover.com. Over 423 owners have reviewed sitters in Madison, giving them an average rating of 4.9/5. The cost of pet sitting in Highlands Community may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

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 Highlands Community 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 Highlands Community, 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.

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