Dog Boarding in Highlands Community, Madison, WI

Find a loving dog sitter to watch your dog overnight at your sitter's home.

Pick up
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Highlands Community dog boarders

1 / 1
Sitter Profile Image: Katie & Samuel W.
Verified Enhanced Background Check
Katie & Samuel W.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
17 reviews
10 repeat clients
20 years of experience
MIDDLETON, WI, 53562

Amazing people who love and care for my pup while he is with them - they also send the cutest pictures and updates! They were also super understanding when I got stuck in traffic on the way to pick my dog up.

Profile image
Alexandrea P.
Sitter Profile Image: Cleda W.
Verified Background Check
Cleda W.
Star Sitter
from
$60
per night
5.0 out of 5.0 stars
201 reviews
82 repeat clients
11 years of experience
Spring Harbor, Madison, WI, 53705

So glad I found Cleda! Organized, friendly, responsive. But most importantly, Roux loves her. Leaving both my pets and traveling out of the country for 2 weeks was tough. But every morning I awoke to an email and pictures letting me know that all was going well. Highly recommend!

Profile image
Margaret C.
Sitter Profile Image: Lindsey C.
Verified Enhanced Background Check
Lindsey C.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
24 reviews
7 repeat clients
10 years of experience
Madison, WI, 53705

Lindsey was great with my dog! She made sure to update us with photos and activities throughout the days. Thank you Lindsey for showering my fur baby with love and lots of walks!💕

Profile image
Jennifer V.
Sitter Profile Image: Mary Z.
Verified Enhanced Background Check
Mary Z.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
18 reviews
8 repeat clients
10 years of experience
Regent, Madison, WI, 53726

Mary and her family were absolutely wonderful sitters for Grizzy! They took great care of him during a cold snap, making sure he was warm and comfortable. Mary sent wonderful updates and absolutely adorable pictures, and I would recommend her to anyone!

Profile image
Meghan D.
Sitter Profile Image: Edith S.
Verified Enhanced Background Check
Edith S.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
49 reviews
18 repeat clients
20 years of experience
Waunakee, WI, 53597

Edith was so amazing. We knew right from the beginning that she would take care of our baby. We wouldn't hesitate to come back again. Everything went so smoothly, I wouldn't worry one bit about booking. Thank you again! -Anne & Anthony

Profile image
Anthony T.
Sitter Profile Image: Michelle S.
Verified Enhanced Background Check
Michelle S.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
17 reviews
4 repeat clients
30 years of experience
Orchard Ridge Community, Madison, WI, 53711

Michelle and her family were stellar! Our two golden retrievers were with them for the weekend. She sent pictures and updates each day and checked in with us on questions. Couldn't be happier with the care they received or her communication! Great experience.

Profile image
Colleen W.
Sitter Profile Image: Kristin & Bruce M.
Verified Enhanced Background Check
Kristin & Bruce M.
Star Sitter
from
$35
per night
5.0 out of 5.0 stars
83 reviews
21 repeat clients
2 years of experience
Madison, WI, 53719

Kristin, Bruce, and their family took great care of Tony for our weekend away. We received regular updates with photos of Tony while we were away. We would definitely book a stay again. Thank you so much!

Profile image
Hannah & Eli W.
Sitter Profile Image: Julie Z.
Verified Enhanced Background Check
Julie Z.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
40 reviews
9 repeat clients
25 years of experience
Sunset Village, Madison, WI, 53705

Julie was absolutely fantastic. She knows dog behavior very well and I completely trusted her with my 12 week old puppy who is very nervous. Julie went above and beyond to make sure my puppy was comfortable and well taken care of. Highly recommend!

Profile image
Taralinda W.
Sitter Profile Image: Christine N.
Verified Background Check
Christine N.
Star Sitter
from
$44
per night
4.9 out of 5.0 stars
102 reviews
58 repeat clients
27 years of experience
Prairie Hills, madison, WI, 53711

Skipper had a blast with Christine. She is very attentive and very calm. She responded quickly to my inquiry. She is perfect for a dog with anxiety issues. I appreciated her flexibility and her requirement to see vaccination records. Skipper loved having other dogs to play with and we loved getting photos during his stay. We will definitely call on her again for Skipper's staycation!

Profile image
Tammra S.
Sitter Profile Image: Ryan & Martha M.
Verified Enhanced Background Check
Ryan & Martha M.
from
$37
per night
5.0 out of 5.0 stars
20 reviews
6 repeat clients
14 years of experience
Stone Meadows, Madison, WI, 53719

Ryan, Martha and their family were great! They were really good about being responsive and sending updates. Flóki was very welcomed into their home and tried to make everything as normal as possible as if he Flóki was with me. They let us do a meet and greet to see if the setting would be a great fit and go over all of the information they would need for sitting. Thank you!

Profile image
Jill H.
Sitter Profile Image: Robert N.
Verified Enhanced Background Check
Robert N.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
143 reviews
47 repeat clients
20 years of experience
Orchard Ridge Community, Madison, WI, 53711

Robert did an amazing job watching my dog, Bear. He was very communicative and send pictures throughout the day. I would highly recommend him.

Profile image
Shaina S.
Sitter Profile Image: Daseanna M.
Verified Enhanced Background Check
Daseanna M.
Star Sitter
from
$43
per night
5.0 out of 5.0 stars
8 reviews
5 repeat clients
4 years of experience
Madison, WI, 53705

Daseanna was so great. She was communicative and provided great updates on Penny while I was away. I could tell Penny was throughly cared for and enjoyed her stay with Daseanna.

Profile image
Carol B.
Sitter Profile Image: Emily B.
Verified Enhanced Background Check
Emily B.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
17 reviews
3 repeat clients
8 years of experience
Fitchburg, WI, 53711

Emily and her family took amazing care of my dog Dove! They welcomed her as part of the family and did a great job gauging and responding to her energy level as needed. Emily was excellent with communication, updates, and giving Dove her daily pill. I knew Dove was being so well taken care of, and I (and she) look forward to having her stay with Emily again in the future!

Profile image
Geoffrey H.
Sitter Profile Image: Robert L.
Verified Background Check
Robert L.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
253 reviews
48 repeat clients
40 years of experience
Capitol, Madison, WI, 53703

Dottie loves to stay with Bob! We sure appreciate the updates and can enjoy time away, knowing that our precious girl is in good hands. Thank you!!

Profile image
Ann H.
Sitter Profile Image: Ronalisa E.
Verified Enhanced Background Check
Ronalisa E.
Star Sitter
from
$30
per night
5.0 out of 5.0 stars
12 reviews
3 repeat clients
6 years of experience
Madison, WI, 53704

Ronalisa did wonderfully! Floyd is high energy and can be pushy- so at first I was worried as we had never boarded through Rover before. But it was quickly apparent than Rona was confident and capable even with young and crazy dogs like Floyd. She always got back to me quickly and sent the cutest videos of them playing fetch, swimming, and hiking around. Her dogs are also great too! They helped Floyd play appropriately but still have fun. I would love to board with Rona again

Profile image
Katy B.
Sitter Profile Image: Ryan & Jocelyn R.
Verified Background Check
Ryan & Jocelyn R.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
75 reviews
21 repeat clients
20 years of experience
Greentree, Madison, WI, 53711

Our dog Preston had a great time staying with Ryan and Jocelyn and their children. We received daily updates and pictures and i could clearly see that Preston was being love and was happy. They have a beautiful fenced in backyard that Preston enjoyed exploring. I would not hesitate recommending them as pet sitters and will definitely be using them again!

Profile image
Tracey H.
Sitter Profile Image: Nicole P.
Verified Enhanced Background Check
Nicole P.
Star Sitter
from
$35
per night
5.0 out of 5.0 stars
18 reviews
5 repeat clients
39 years of experience
Cross Plains, WI, 53528

Nicole did a great job taking care of our dog, Kevin, and keeping us updated on his stay along with plenty of photos each day. Her and her family seemed to give Kevin lots of exercise and attention. Highly recommend!

Profile image
Lesley S.
Sitter Profile Image: Elena "Sofi" R.
Verified Enhanced Background Check
Elena "Sofi" R.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
24 reviews
7 repeat clients
5 years of experience
Capitol, Madison, WI, 53715

Sofi was great! She frequently shared photos of Ollie during his time with her and communicated how he was doing while staying with her and her dog.

Profile image
Susan S.
Sitter Profile Image: Amy G.
Verified Enhanced Background Check
Amy G.
from
$42
per night
5.0 out of 5.0 stars
19 reviews
5 repeat clients
26 years of experience
Fitchburg, WI, 53711

Amy was awesome!!! We were so grateful to know that our little dog was in such capable and loving hands while we were on vacation. She was very communicative and provided great updates. We will definitely book with her again!!! Thanks Amy!!! 💕🐾

Profile image
Lisa M.
Sitter Profile Image: Hope R.
Verified Enhanced Background Check
Hope R.
Star Sitter
from
$40
per night
5.0 out of 5.0 stars
29 reviews
3 repeat clients
15 years of experience
Eken Park, Madison, WI, 53704

I could not ask for a better care provider for my Maltese Ollie, who has been cared for by only family members until recently! Hope went above and beyond to ensure that Ollie was comfortable while I was away. She invited Ollie and me to her home before committing to caring for Ollie. She was honest in sharing his daily joys and stressors, which was refreshing! She also provided suggestions to improve Ollie's comfort the next time I am away - too awesome!

Profile image
Susan S.
1 / 1
View more sitters

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.

  • World-class support

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

Dog Boarding FAQs

Frequently asked questions about Rover