Dog Boarding Riley

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Riley, Find top rated dog boarding

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Chelssey H.
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Chelssey H.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 41 reviews
15 repeat clients
16 years of experience
Madison, WI, 53711

“Chelssey was awesome! Great communication prior and during Sunny’s stay which I loved! She also sent pictures which was fun. We will book again with Chelssey.”

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Carol D.
Sitter Profile Image: Nicole P.
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Nicole P.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 35 reviews
8 repeat clients
41 years of experience
Cross Plains, WI, 53528

“We had an excellent experience with Nicole! She was reliable and communicative. Our dog was happy, well cared for, and comfortable the entire time. We really appreciated the regular updates and photos—it gave us great peace of mind while we were away. We would absolutely book with them again and highly recommend them to anyone looking for a quality, trustworthy dog sitter.”

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Heidi K.
Sitter Profile Image: Ryan & Martha M.
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Ryan & Martha M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 63 reviews
28 repeat clients
14 years of experience
Stone Meadows, Madison, WI, 53719

“They did a great job providing updates and showing that our dog was having a great time. They were responsive and easy to work with, and could tell that they really cared for our dog.”

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Kalli V.
Sitter Profile Image: Stefanie B.
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Stefanie B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 113 reviews
43 repeat clients
14 years of experience
Middleton, WI, 53562

“Stefanie and her family were so loving to my little dog Dolly! I cant say enough about how accommodating they were while I was away in Arizona for the week. I highly recommend them for your pups dog sitting needs! Will be using them again in the future for sure. Dolly sure does miss them all!”

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Heather M.
Sitter Profile Image: Katie & Samuel W.
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Katie & Samuel W.
from
$45
per night
5.0 out of 5 stars
• 33 reviews
13 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.”

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Alexandrea P.
Sitter Profile Image: Ronalisa E.
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Ronalisa E.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 45 reviews
15 repeat clients
7 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”

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Katy B.
Sitter Profile Image: Allison C.
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Allison C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 16 reviews
4 repeat clients
5 years of experience
Glen Oak Hills, Madison, WI, 53705

“Our three dogs had a great night with Allison! She was easy to work with and laid back. Dogs got to chill on the couch, luxury access to special beds and blankets. Thanks for a great stay!”

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Ceri J.
Sitter Profile Image: Duane & Lauren S.
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Duane & Lauren S.
Star Sitter
from
$32
per night
5.0 out of 5 stars
• 97 reviews
32 repeat clients
30 years of experience
Ridgewood, Madison, WI, 53704

“Such a treat to have Duane & Lauren take care of my pup, Rapha while I was away. They are very responsive and attentive to the needs of both owner and doggie. Thank you!”

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Russhell C.
Sitter Profile Image: Jessica M.
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Jessica M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 51 reviews
13 repeat clients
25 years of experience
Rolling Meadows, Madison, WI, 53714

“The kids were happy. Good communication, lots of photos and video. It was a great place with a good yard for them to play. She took good care of our perrhijos.”

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Richard E.
Sitter Profile Image: Heather W.
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Heather W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 41 reviews
10 repeat clients
20 years of experience
Brooklyn, WI, 53521

“I would highly recommend Heather! She did a wonderful job of sending photos and updates daily and in general I really felt like our dog was being well cared for.”

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Marta B.
Sitter Profile Image: Hannah P.
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Hannah P.
from
$60
per night
5.0 out of 5 stars
• 16 reviews
8 repeat clients
18 years of experience
Vilas, Madison, WI, 53711

“Hannah and family were just the most wonderful hosts. Kind, warm, and flexible, they made both dogs feel comfortable right from the start. So many great photos of the dogs playing, long walks, and so many lap naps that I was able to not worry! I can’t thank Hannah enough.”

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Nadia N.
Sitter Profile Image: Jennifer J.
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Jennifer J.
Star Sitter
from
$37
per night
4.9 out of 5 stars
• 9 reviews
5 repeat clients
6 years of experience
Lake Edge, Madison, WI, 53716

“Lucy had a great weekend with Jennifer! She got along great with Oscar. Tick season is pretty bad this year and Jennifer made sure to look over Lucy and keep her tick-free!”

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Chuck S.
Sitter Profile Image: Priyanka "Pri" T.
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Priyanka "Pri" T.
from
$59
per night
4.8 out of 5 stars
• 189 reviews
75 repeat clients
20 years of experience
Madison, WI, 53719

“Pri immediately helped our Gracie fit right in. She and Max took an outside walk together right away. So glad to get the daily pics and Updates. We will certainly use her services in the future!”

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Denise S.
Sitter Profile Image: Holly & Ana Maria P.
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Holly & Ana Maria P.
from
$25
per night
5.0 out of 5 stars
• 12 reviews
2 repeat clients
12 years of experience
Schenk-Atwood-Starkweather-Yahar, Madison, WI, 53704

“Leaving our velcro dog behind is always hard, being left by her emotional support humans is harder. But Holly and Ana were so good with her, she got all the snuggles and was treated like one of their own. They gave lots of updates that let me know she was adjusting well.”

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Gina S.
Sitter Profile Image: Mary Z.
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Mary Z.
from
$60
per night
5.0 out of 5 stars
• 19 reviews
9 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!”

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Meghan D.
Sitter Profile Image: Grace R.
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Grace R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 42 reviews
8 repeat clients
11 years of experience
Greentree, Madison, WI, 53711

“Grace was wonderful and kept me updated daily with messages and pictures. Mazzi did get a small cut on his paw while he was outside on the last day, but Grace let me know right away and was able to clean it and put a bandage on it. I really appreciated how attentive and communicative she was. Thank you, Grace!”

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SirJeremy H.
Sitter Profile Image: Emily V.
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Emily V.
from
$50
per night
5.0 out of 5 stars
• 20 reviews
6 repeat clients
18 years of experience
Oregon, WI, 53575

“Emily was great with our big, young and very energetic dog! She has a great fenced in yard and our dog had a blast! He was very tired when he got home! We would definitely use her again!”

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Eric & Christine A.
Sitter Profile Image: Beatrice L.
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Beatrice L.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 17 reviews
4 repeat clients
2 years of experience
Bay Creek, Madison, WI, 53715

“Beatrice was so kind to help me out last minute with caring for my pup. He was very happy to see her, and seemed very relaxed when I picked him up. I am so grateful to have her to help so I can feel at ease when I travel.”

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Talitha H.
Sitter Profile Image: Lee Y.
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Lee Y.
from
$50
per night
5.0 out of 5 stars
• 17 reviews
6 repeat clients
5 years of experience
Midvale Heights Community, Madison, WI, 53711

“Lee was great with our high-energy dogs. They clearly had a lot of fun in his large fenced-in yard, and Lee provided pictures and updates daily! He was also very responsive and flexible when our travel plans changed”

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Dana H.
Sitter Profile Image: Shinduri V.
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Shinduri V.
from
$45
per night
5.0 out of 5 stars
• 31 reviews
9 repeat clients
10 years of experience
Fitchburg, WI, 53719

“Thank you, Shinduri, for taking care of Zeke. I truly appreciate your help, as I didn’t have to worry about him at all. You treated him as if he were your own dog and kept me updated when necessary. I will definitely be rebooking your services in the future. Thank you so much!”

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Kemi A.
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The median cost per night for dog boarding in Riley is $45

Dog parents share their Rover experiences - Riley

1 / 1
5.0 out of 5 stars

I love taking my furry four-legged friend to Jodi. I always have 100% confidence that he will be extremely well cared for. I feel grateful to have a dog-sitter like her.

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Karen L.
Boarding
5.0 out of 5 stars

Jodi was very accommodating with our late booking! She took great care of our pup and kept us posted on her time spent with Jodi. We would certainly ask Jodi to care for our Tuva again.

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Sara & Ian P.
Boarding
5.0 out of 5 stars

Knox was in good hands with Jamie! He was so tired and slept the entire next day, which is very reassuring.

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Sara G.
Boarding
5.0 out of 5 stars

Jamie was wonderful, communication was sketchy due to technology. However, Jamie was able to rearrange the request and make it work for us. Blessing in disguise

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Mary T.
Boarding
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

How to book dog boarding

  1. 1. Search

    Browse profiles of sitters near you who offer dog boarding.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for dog boarding - Riley

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Riley average 10
repeat dog boarding clients

FAQs for Dog Boarding - Riley

Frequently asked questions about Rover

As of November 2026, there are 437 sitters on Rover offering Dog Boarding across Riley. Enter your ZIP code to see which available sitters are closest to your home.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Every sitter on Rover has their own routine. Depending on the arrangements you agree on before the stay, a sitter can follow your dog’s regular feeding schedule, provide a comfortable place to sleep, offer companionship, and support their usual exercise and play needs.

93% of sitters in Riley can provide daily exercise during dog boarding stays. Depending on the sitter, their home environment, and your dog’s needs, this may include walks, outdoor play, indoor enrichment activities, or supervised play with compatible dogs. These activities are not automatically included with every booking, so ask the sitter what a typical day looks like.

During the Meet & Greet, discuss your dog’s usual exercise and play routine, whether they can safely interact with other dogs, and any activities or restrictions the sitter should follow. You can also ask the sitter to send photo and message updates during the stay so you can see how your dog is spending their time.

Preparing for drop-off is easy when you have a checklist! To help your dog settle into their Riley home-away-from-home, we recommend packing:

  • Health and safety essentials such as their ID tags, vaccination records, medication, and emergency vet or secondary caregiver contacts.
  • Food and gear such as harnesses, collars, food (portioned by day), and an item that smells like you.
  • Special instructions such as a list of training cues, medical administration needs, or favorite hang-out spots in your Riley.

Tip: You can upload your dog’s routine and medical info directly onto their profile so your sitter always has the details at their fingertips.

Yes, you can find sitters who have experience with handling special pet needs in Riley. On Rover:

  • 89% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 93% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

You and your Riley sitter can schedule drop-off and pick-up in a way that works best for the both of you—and your dog. Most sitters offer flexible times for drop-off and pick-up but the easiest way to confirm those times will be through in-app messaging. Confirm your arrival time the day of pick-up and drop-off can also help keep the process smooth and organized.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page.

While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.

Many sitters in WI ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.

By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.

If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your dog to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your dog is showing signs of possible illness.

For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.

Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.

Adding another pup to the pack? Most sitters and walkers offer a reduced rate for additional dogs. You’ll find these exact rates listed under the "Services" tab on any sitter's profile. Since every dog is unique, final pricing may vary depending on the level of care required.

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