Pet Sitting & Drop Ins In Woodlands

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

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Top rated Woodlands pet sitters

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Sitter Profile Image: Maiya W.
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Maiya W.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
107 reviews
32 repeat clients
5 years of experience
Middleton, WI, 53562

Maiya did a fantastic job looking in on our Havapoo puppy all week while we were away. She was professional, courteous, communicative, and most of all, we could tell our pup had a blast with her!

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Jay P. N.
Sitter Profile Image: Natalie B.
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Natalie B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
230 reviews
75 repeat clients
15 years of experience
Hill Farms-University Neighborh, Madison, WI, 53705

Natalie did a great job! She came and fed my kitty twice for 30 minutes each time. She was very communicative and nice. She also clipped my cat’s nails for me!

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Ali R.
Sitter Profile Image: Kim M.
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Kim M.
from
$17
per visit
5.0 out of 5 stars
99 reviews
41 repeat clients
8 years of experience
Middleton, WI, 53562

This is the second time Kim has taken care of our cat while we were away. Just like the first time, Kim did a wonderful job! I always loved seeing the pictures taken during her drop-in visits. We returned home after two weeks to a happy cat! Thank you Kim!!

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Kayci H.
Sitter Profile Image: Cleda W.
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Cleda W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
219 reviews
87 repeat clients
11 years of experience
Madison, WI, 53705

She did such a good job with my cats. I had one who recently had teeth pulled, so both of my cats were getting fed largely different diets. She was able to manage them both. Also my very shy cat was even comfortable coming out to see her every day. Highly recommend

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Ashley A.
Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
25 reviews
6 repeat clients
15 years of experience
Spring Harbor, Madison, WI, 53705

Kaitlyn was wonderful! She took care of our cat while we were out of town and she did the job well and sent photos. We were happy with the service Kaitlyn provided, would highly recommend and we will book again with her in the future.

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Liz T.
Sitter Profile Image: Steve J.
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Steve J.
from
$16
per visit
4.9 out of 5 stars
24 reviews
5 repeat clients
4 years of experience
Madison, WI, 53717

Very consistent and flexible sitter. He not only drops in to check on my meow-meows but also makes sure my plants are alive. Will book again. Thanks Steve!

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Richard N.
Sitter Profile Image: Ryan H.
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Ryan H.
from
$15
per visit
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Stonefield Woods-Ridge, Madison, WI, 53717

Ryan arrived on time and did a drop in visit with our pup as expected. He has a professional demeanor and seems genuinely to enjoy spending time with our pet.

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Tim S.
Sitter Profile Image: Sabrina S.
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Sabrina S.
from
$20
per visit
5.0 out of 5 stars
29 reviews
7 repeat clients
20 years of experience
Madison, WI, 53705

Went with Sabrina again! She does such a great job with my picky, old toy poodle lol. Chewy takes a while to warm up to people so I'm glad he is in good hands with Sabrina. Was a no-brainer going with her and I recommend her!

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Troy S.
Sitter Profile Image: Hannah I.
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Hannah I.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
111 reviews
36 repeat clients
5 years of experience
Wexford, Madison, WI, 53717

Hannah was awesome with our 11 yo rescue dog, very caring and spent quality time with her. Hannah is very responsible, showed up promptly, and Luna was very happy with her visit (we were too)!

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Kathleen M.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
125 reviews
50 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

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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Francesca C.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
61 reviews
19 repeat clients
12 years of experience
Middleton, WI, 53562

We were grateful that Stephanie could help us out over the holidays. She was so gracious to pick up the keys and meet Layla on Christmas Day. Layla loved her. Everything went very smoothly. We highly recommend Stephanie!

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Brian K.
Sitter Profile Image: Anna H.
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Anna H.
from
$20
per visit
5.0 out of 5 stars
34 reviews
9 repeat clients
7 years of experience
Middleton, WI, 53562

It was our first time leaving our kitty for an extended period of time - Anna took excellent care of our girl! She eased my worries with frequent text and photos updates and was very patient getting to know our cat. We also ran into some technical issues (on my end) and Anna was very flexible! We are so grateful for her.

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Robyn Y.
Sitter Profile Image: Mandy C.
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Mandy C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
4 years of experience
Verona, WI, 53593

Mandy is amazing! I would definitely trust her to take care of my cat again. She provides very detailed and funny reports and takes lots of pictures and videos too. Thanks Mandy!

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Alessandra Nicolette B.
Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$18
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
12 years of experience
Junction Ridge, Madison, WI, 53717

Jennifer was such an amazing sitter for my furry babies. She took her time to ask questions and understand well how to care for them. The updates and pictures always were on point and left me feeling that my babies were in very caring and capable hands. Next time I will look for someone to look after my babies I will go for Jennifer.

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Franklin R.
Sitter Profile Image: Yvonne L.
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Yvonne L.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
24 reviews
8 repeat clients
16 years of experience
Middleton, WI, 53562

Yvonne is the best! She was very communicative and I appreciated the pictures and updates everyday. Coto is not fond of people other than his own, but by the end of the booking, him and Yvonne were best friends. Definitely recommend!

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Teresa H.
Sitter Profile Image: Isabel S.
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Isabel S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
32 reviews
9 repeat clients
15 years of experience
Midvale Heights Community, Madison, WI, 53711

Isabel is extremely reliable and patient with our new puppy. She comes over when she says she’ll come, and she takes lots of pictures and notes during her visit, which we really appreciate. She plays with our dog inside and outside and makes sure he gets some good attention while we’re away at work. Would highly recommend her!

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Jennifer V.
Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
555 reviews
170 repeat clients
30 years of experience
Madison, WI, 53719

Jennifer always does an outstanding job with our three cats. We are always able to relax and enjoy our trips when we have Jennifer looking after our girls.

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John M.
Sitter Profile Image: Raymar F.
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Raymar F.
from
$20
per visit
5.0 out of 5 stars
3 reviews
10 years of experience
Madison, WI, 53705

Such a well dog sitter! Came to meet my dog and asked a lot of good questions on how to provide and care for my dog! She came did her thing just like how I told her and she went beyond! Gave me a lot of photos during the care and a lot of note taking on how my dog was! Definitely will book again and recommend her!

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Choua Y.
Sitter Profile Image: Alisyn L.
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Alisyn L.
from
$25
per visit
5.0 out of 5 stars
69 reviews
18 repeat clients
9 years of experience
Madison, WI, 53717

Alisyn did an awesome job with my cat Cleo. She was quick to respond to messages and sent lots of pictures. She even gave her a little Christmas present!

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Sarah W.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
18 reviews
3 repeat clients
30 years of experience
Regent, Madison, WI, 53726

Amy was great! I could tell see really cared about the cats. She did an amazing job catering for my more shy cat, making sure she got food even though she was hiding.

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Stephen G.
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Woodlands pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Natalie was so helpful and wonderful with our cat who needs to take an inhaler! He has given many other sitters a tough time but Natalie was very accommodating and able to administer it with ease. Thank you so much, we will definitely be rebooking for our next trip!

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Hannah S.
Drop-In Visits
5.0 out of 5 stars

Jennifer was stellar. She stepped in quickly when our other sitters bailed at the last minute. Thanks to her our trip to Europe was stress free. We were very happy with her thoughtful care!

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James G.
Drop-In Visits
5.0 out of 5 stars

Ryan was kind and communicative! All went well with drop ins to care for our cat while we were on vacation. Would definitely recommend!

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Camryn V.
Drop-In Visits
5.0 out of 5 stars

Jesse was amazing! She’s so kind and very helpful. I knew my cat was in safe hands. I for sure will be working with her again :)

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Kaitlyn O.
Drop-In Visits
5.0 out of 5 stars

Julia was an absolute godsend for us. My dog had quite a few issues while we were out of town, and Julia was amazing. She gave me constant updates, came to check on him regularly outside of what was originally booked, and made sure that my dog was safe and cared for. She helped ease my worries, and I would definitely rebook her, no questions asked. Our cat also loved hanging out with her!

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Galilea B.
Drop-In Visits
5.0 out of 5 stars

We love Taylor! We always ask her to care for our two kitties when we go out of town. She is very thorough and the cats love her. We have used her services many times now and have had no complaints!

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Annie B.
Drop-In Visits
5.0 out of 5 stars

Lydia is awesome! We were super worried about leaving our dog but both times we have booked Lydia, our dog didn’t even bark when we left.

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Holly A.
Drop-In Visits
5.0 out of 5 stars

Jennifer was such an amazing sitter for my furry babies. She took her time to ask questions and understand well how to care for them. The updates and pictures always were on point and left me feeling that my babies were in very caring and capable hands. Next time I will look for someone to look after my babies I will go for Jennifer.

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Franklin R.
Drop-In Visits
5.0 out of 5 stars

Such a well dog sitter! Came to meet my dog and asked a lot of good questions on how to provide and care for my dog! She came did her thing just like how I told her and she went beyond! Gave me a lot of photos during the care and a lot of note taking on how my dog was! Definitely will book again and recommend her!

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Choua Y.
Drop-In Visits
5.0 out of 5 stars

My little cat Michael just loves his pet sitter ! Michelle takes great care of him and sends me awesome pics 🤗

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Gail S.
Drop-In Visits
5.0 out of 5 stars

We had a great experience with Kaitlyn! We needed a pet sitter last minute. She got back to us right away, and took great care of our two cats.

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Elizabeth K.
Drop-In Visits
5.0 out of 5 stars

Awesome experience with Michelle. Excellent communication, plenty of photos and good care of our animals. We give Michelle a 10 star. Highly recommend. We will contract her again. Thank you!

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Jessica K.
Drop-In Visits
5.0 out of 5 stars

It was our first time leaving our kitty for an extended period of time - Anna took excellent care of our girl! She eased my worries with frequent text and photos updates and was very patient getting to know our cat. We also ran into some technical issues (on my end) and Anna was very flexible! We are so grateful for her.

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Robyn Y.
Drop-In Visits
5.0 out of 5 stars

Meeka was amazing with my 2 kitties while I was away on vacation. Sent lots of photos and gave detailed updates on how they were doing. Was really great knowing they were being well taken care of and entertained as they're still very young and I haven't had to leave them often.

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Courtney S.
Drop-In Visits
5.0 out of 5 stars

Cloey was great with our two cats. She kept us well informed while we were away and the cats seemed to enjoy her company. We would definitely book with Cloey again in the future.

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Beth R.
Drop-In Visits
5.0 out of 5 stars

Cleda did a great job checking in on our cat while we were on vacation. Amazing communication! Will continue to rebook with her for our future trips :)

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Stephanie K.
Drop-In Visits
5.0 out of 5 stars

Natalie is amazing with my dog! She’s very reliable and a fantastic pet sitter! I cannot recommend her enough!

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Madison S.
Drop-In Visits
5.0 out of 5 stars

Great cat sitter. Austin gave detailed updates on our two cats and took lots of pictures. Highly recommend!

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Steve J.
Drop-In Visits
5.0 out of 5 stars

Isabel is a great communicator, reliable, and takes lots of pictures. We will definitely use her services again!

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Karly C.
Drop-In Visits
5.0 out of 5 stars

Evan is an excellent pet sitter and our cat loves him! Evan alerted us and called when he discovered our electricity was off. We really appreciated his help.

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Luanne B.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Sitting FAQs

Frequently asked questions about Rover

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Woodlands.

Rover makes it easy to find Woodlands pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.