Dog Boarding Caldwell

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Caldwell, 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: Joanne V.
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Joanne V.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 27 reviews
6 repeat clients
5 years of experience
Waukesha, WI, 53189

“I am so thankful for Joanne and the wonderful care she provided for our 16 yo pup, Ginger! Grateful for the wonderful home environment she welcomed Ginger into while we were gone. Appreciate that she works from home allowing her to be more available to tend to pups’ needs. Joanne kept in touch with us by sending occasional updates and pictures giving us peace of mind the entire trip. Thankful she was able to be flexible when we encountered travel related issues. I would definitely come back. Highly recommended!!”

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Renee P.
Sitter Profile Image: Katy & Dennis "DJ" G.
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Katy & Dennis "DJ" G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 127 reviews
44 repeat clients
35 years of experience
Wales, WI, 53183

“Katy and DJ are wonderful sitters! We are so at peace leaving our dog Milo in their care. They send us frequent updates and pictures. Milo is worn out by the time he comes home. He loves his walks and playing with their pup! I would highly recommend them!”

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Deb P.
Sitter Profile Image: Rachel W.
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Rachel W.
from
$45
per night
4.8 out of 5 stars
• 29 reviews
19 repeat clients
14 years of experience
Burlington, WI, 53105

“Rachel was so amazing to our pup Ryder! She sent us great updates and gave us peace of mind that our boy was left in good hands. He was so loved and spoiled. We will definitely be using Rachel again in the future!”

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Patrick W.
Sitter Profile Image: Kylie S.
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Kylie S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 59 reviews
23 repeat clients
35 years of experience
Eagle, WI, 53119

“Kylie did such an amazing job taking care of our beagle! Our dog needs a lot of affection and we could tell she was in good hands from the daily pictures Kylie sent us. We will definitely want to book with her for future trips!”

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Haley K.
Sitter Profile Image: Kam O.
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Kam O.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 46 reviews
21 repeat clients
20 years of experience
Waterford, WI, 53185

“Kam and her family took wonderful care of my cat Wally. Kam sent me photos every day to show how well my cat was doing. I wholeheartedly recommend Kam’s sitting services!”

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Layni G.
Sitter Profile Image: Jennifer K.
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Jennifer K.
from
$27
per night
5.0 out of 5 stars
• 7 reviews
30 years of experience
Waukesha, WI, 53186

“Jennifer was AMAZING! She took such great care of my dog. We had a last minute trip and needed to find quality care for her, and Jennifer was able to schedule and meet-and-greet the same day for us. She was extremely communicative and provided so many pictures of our sweet girl. We also got to meet her family and her dogs, all of whom were wonderful. I will re-book with her for any trips we have in the future. I can tell she genuinely cared and loved for my baby. Thank you Jennifer!!”

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Emily M.
Sitter Profile Image: Maria & Nayibe B.
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Maria & Nayibe B.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 438 reviews
142 repeat clients
20 years of experience
Menomonee Falls, WI, 53051

“Everything was great and happy they took good care of Nia! I appreciated receiving daily photos/videos. Will definitely use them in the future.”

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Joann marie W.
Sitter Profile Image: Linda V.
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Linda V.
from
$35
per night
5.0 out of 5 stars
• 20 reviews
6 repeat clients
6 years of experience
Riverwest, Milwaukee, WI, 53212

“Linda was excellent and very accommodating for my last minute trip. She also sent a lot of update photos of my puppy to make my first time with rover a great experience :)”

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Jessica
Sitter Profile Image: Debbie L.
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Debbie L.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 81 reviews
22 repeat clients
50 years of experience
Oak Creek, WI, 53154

“Our 11 month old vizsla puppy is a handful and Debbie handled him beautifully with training experience, understanding, and love. He received dedicated one on one care for the 6 days we were away on vacation and we couldn’t be more pleased. Her daily photo updates were comforting and thoughtful. We would love to have Debbie host our pup again in the future!”

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June O.
Sitter Profile Image: Laura N.
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Laura N.
Star Sitter
from
$42
per night
5.0 out of 5 stars
• 39 reviews
10 repeat clients
20 years of experience
Southpoint, Milwaukee, WI, 53221

“Laura did amazing with Romeo, she updated us everyday on how he was doing and was very responsive. Romeo was in very good hands. We would definitely use her again!”

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Kyle A.
Sitter Profile Image: Ashlee K.
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Ashlee K.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 126 reviews
46 repeat clients
7 years of experience
Silver City, Milwaukee, WI, 53215

“Ashlee is absolutely amazing! She provided us with adorable pictures and updates during Boscos stay; we will definitely be requesting future sittings and sending friends her way!”

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Chad T.
Sitter Profile Image: Heather B.
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Heather B.
from
$45
per night
5.0 out of 5 stars
• 18 reviews
3 repeat clients
20 years of experience
Oconomowoc, WI, 53066

“Highly recommend! Heather put my mind at ease while away from my fur baby. She sent daily updates/photos to assure me all was well with my pup. Heather worked with my dog on some behavioral issues as well! She treated my dog as one of her own, truly happy with how the extended overnight stay went; hope to use her again and again in the future”

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jamie r.
Sitter Profile Image: Kathryn H.
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Kathryn H.
from
$40
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
35 years of experience
Pewaukee, WI, 53072

“Amazing experience with Kathryn! Our pup was well cared for during her stay. Incredible timely communication and updates with pictures. Coco is looking forward to another visit in future.”

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Gwen T.
Sitter Profile Image: Doreen C.
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Doreen C.
from
$45
per night
5.0 out of 5 stars
• 166 reviews
55 repeat clients
20 years of experience
Menomonee Falls, WI, 53051

“Thee Best Sitter out there. Partner has stayed with Doreen many times now. He loves it there. He's always excited. Doreen is just the kindest person you'll ever me. She treats our pets as if they're her own. Cannot say enough good things about her. Thank you so much.”

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Tamika C.
Sitter Profile Image: Janice G.
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Janice G.
from
$40
per night
5.0 out of 5 stars
• 23 reviews
8 repeat clients
30 years of experience
Wauwatosa, WI, 53226

“Janice was amazing with our puppy. It was our 1st time leaving him and Janice made us feel totally at ease and sent several pictures and videos throughout the day. Our guy was totally happy and comfortable when we picked him up. He loved his day with Janice and I'm sure he can't wait to see her again. We highly recommended Janice but selfishly want her all to ourselves. 😄”

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Julie P.
Sitter Profile Image: Zachary S.
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Zachary S.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 33 reviews
8 repeat clients
15 years of experience
Fairview, Milwaukee, WI, 53219

“Zachary was very helpful with our dog Otis. He was responsive and asked questions when needed. We felt Otis was in great hands with Zachary. Will use him again!”

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Ben N.
Sitter Profile Image: Sarah K.
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Sarah K.
from
$30
per night
5.0 out of 5 stars
• 27 reviews
6 repeat clients
20 years of experience
Wauwatosa, WI, 53213

“Sarah and her family took great care of Goose while we were gone for a quick overnight! Goose got lots of walks around the neighborhood and played well with their kids, both in the yard and outside. We wouldn’t hesitate to book again in the future!”

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Anna W.
Sitter Profile Image: Kaitlyn S.
Verified Enhanced Background Check
Kaitlyn S.
Star Sitter
from
$54
per night
5.0 out of 5 stars
• 22 reviews
10 repeat clients
12 years of experience
Darien, WI, 53114

“Kaitlyn was great! She was so caring and helpful in responding to my concerns and questions. Also so prompt in all my communications. It is a big plus to know that she is a vet tech and knows what to do! She keeps her home and pet areas so clean and I love all the puzzles she did with our dogs. She sent pictures with the dog’s activities from each day. I will definitely use Kaitlyn again! She is GREAT!!”

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Naomi J.
Sitter Profile Image: Ben D.
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Ben D.
from
$42
per night
5.0 out of 5 stars
• 5 reviews
1 repeat client
2 years of experience
Wauwatosa, WI, 53226

“Porter absolutely loved Ben and his dog Melvin! Ben regularly updated me with pictures and administered medication that Porter needed. I really appreciated how attentive was! I plan to rebook him later this month!”

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Elizabeth G.
Sitter Profile Image: Carol &  Steve B.
Verified Enhanced Background Check
Carol & Steve B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 27 reviews
8 repeat clients
25 years of experience
Muskego, WI, 53150

“Ollie had the best time at Carol & Steve’s! He loved their yard and all the attention they gave him. Carol is a great communicator and sent lots of adorable pictures during his stay. It gave me peace of mind knowing he was enjoying himself and being taken care of by such kind people. Thanks, again!”

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Amanda G.
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The median cost per night for dog boarding in Caldwell is $45

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 - Caldwell

Select a filter and find qualifying sitters offering dog boarding.

Sitters in Caldwell average 11
repeat dog boarding clients

FAQs for Dog Boarding - Caldwell

Frequently asked questions about Rover

As of November 2026, there are 892 sitters on Rover offering Dog Boarding across Caldwell. 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 Caldwell 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 Caldwell 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 Caldwell.

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 Caldwell. On Rover:

  • 88% 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 Caldwell 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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