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
• 25 reviews
6 repeat clients
5 years of experience
Waukesha, WI, 53189

“Joanne was super responsive and sent lots of photos of our dogs! She did wonderful with both of them and you can tell they were well cared for.”

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Megan N.
Sitter Profile Image: Scott & Ashley S.
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Scott & Ashley S.
Star Sitter
from
$47
per night
5.0 out of 5 stars
• 112 reviews
36 repeat clients
20 years of experience
Waukesha, WI, 53186

“Scott & Ashley and their family took such good care of our two dogs. We got daily updates and photos. They took extra care with our little, really old guy with issues. Wonderful sitters. I highly recommend them.”

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Peg C.
Sitter Profile Image: Olivia T.
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Olivia T.
from
$45
per night
5.0 out of 5 stars
• 23 reviews
8 repeat clients
10 years of experience
Muskego, WI, 53150

“Olivia is great with dogs and is my favorite person to have watch my old dog. Fantastic care as usual. She is comfortable administering medications too!”

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

“Kam was totally awesome. Mango seemed right at home with her, her family and her pets. She sent multiple pictures everyday assuring us that Mango was happy and content. I would use her again in a heartbeat if ever I find myself in Milwaukee again”

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Jay N.
Sitter Profile Image: Ashley R.
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Ashley R.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 38 reviews
18 repeat clients
20 years of experience
Mount Pleasant, WI, 53406

“My family had an amazing experience with Ashley. She and her family provided exceptional service while taking care of our dog, during a long boarding. She kept us updated with pictures and messages, which gave us peace of mind knowing our dog was in good hands. When we returned, my dog was happy and well taken care of. I highly recommend Ashley. Thank you for taking such great care of our dog! We will definitely look for availability with you for any future boarding needs.”

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Chris C.
Sitter Profile Image: Joseph & Diana M.
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Joseph & Diana M.
from
$39
per night
5.0 out of 5 stars
• 24 reviews
5 repeat clients
13 years of experience
Muskego, WI, 53150

“Joe and Diana were so wonderful to work with. They were very communicative, sent many updates and photos and it was a relief to have Humphrey in a place where he was safe and comfortable.”

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Rachel H.
Sitter Profile Image: Jenifer D.
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Jenifer D.
Star Sitter
from
$46
per night
5.0 out of 5 stars
• 384 reviews
167 repeat clients
22 years of experience
Pewaukee, WI, 53072

“Jenifer was a caring sitter for Tipper. Tipper was happy with her even though she missed us. Jennifer did her best to get Tipper to eat including sharing treats with her. Thank you.”

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

“Carly's 1st stay with Debbie was fantastic! Carly got a lot of attention and exercise. We rec'd updates & pictures and any doubt I had was totally erased! I will definitely be taking Carly back to Debbie for our next vacation without any hesitation!”

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Kathy L.
Sitter Profile Image: Andrew J.
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Andrew J.
from
$38
per night
5.0 out of 5 stars
• 24 reviews
7 repeat clients
25 years of experience
Sunset Heights, Milwaukee, WI, 53216

“Clark had so much fun staying with Andrew and his family! They have a big fenced in backyard and I got plenty of pictures of Clark playing :) definitely would book again!”

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Jacquelyn S.
Sitter Profile Image: Amanda T.
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Amanda T.
from
$40
per night
5.0 out of 5 stars
• 8 reviews
3 repeat clients
30 years of experience
Mukwonago, WI, 53149

“Amanda and her family did a fantastic job with our 2 dogs. Our vacation was a breeze and we felt at ease knowing our dogs were in good hands! Highly recommend.”

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Dave C.
Sitter Profile Image: Angie F.
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Angie F.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 149 reviews
54 repeat clients
20 years of experience
New Berlin, WI, 53146

“Angie was absolutely incredible! Consistent steady pictures the dog was extremely happy... And I couldn't have felt he was in a safer place. Over the course of two days she sent numerous pictures and a couple of videos which gave me extreme peace of mind! I will definitely use her again in the future whenever I need a sitter. You can definitely trust this lady she's very nice very respectful and pleasant.”

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Scott B.
Sitter Profile Image: Angela K.
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Angela K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 152 reviews
38 repeat clients
25 years of experience
Menomonee Falls, WI, 53051

“Maddie came home exhausted after playing at Angela’s. Angela is always responsive and sends pictures and updates. Maddie really enjoys going there.”

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

“Doreen is a sweet lady who took great care of Buddy. He was in great spirits when I picked him up. I will happily book Doreen again to look after my baby.”

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Kim S.
Sitter Profile Image: Rebecca S.
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Rebecca S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 189 reviews
56 repeat clients
30 years of experience
Town Of Lake, Milwaukee, WI, 53207

“Rebecca and Dave treated our dogs like part of their family while we were on vacation. The daily updates with photos gave us such peace of mind that our girls were being well taken care of.”

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Jamie S.
Sitter Profile Image: Tia & Colin L.
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Tia & Colin L.
from
$45
per night
5.0 out of 5 stars
• 8 reviews
3 years of experience
New Berlin, WI, 53151

“Tia and her husband were amazing! We were nervous to leave our girl with people didn’t know but they loved her so well while we were gone. She gave so many updates and was very flexible with what our dog needed. We did a meet and greet for our dogs then gave her a laid out list of everything about our dog. Tia made us feel super comfortable. We loved that her kids loved our dog and we truly feel like Regan will miss being at their house”

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Denver L.
Sitter Profile Image: Kim F.
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Kim F.
Star Sitter
from
$57
per night
5.0 out of 5 stars
• 589 reviews
230 repeat clients
25 years of experience
Kenosha, WI, 53142

“My 4 year old German Shorthaired Pointer really enjoyed her 10 day visit with Kim and Family. This is Addi's second visit. Thanks for the great care!”

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Kimberly F.
Sitter Profile Image: Tara F.
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Tara F.
from
$30
per night
5.0 out of 5 stars
• 3 reviews
2 repeat clients
20 years of experience
Hales Corners, WI, 53130

“Good communication, flexible with timing, pup was well cared for, no worries while on vacation!”

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John K.
Sitter Profile Image: Mikaela & Shane P.
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Mikaela & Shane P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 42 reviews
20 repeat clients
20 years of experience
Hartland, WI, 53029

“They were great! Mikeale was very communicative & quick with responses, sent daily updates with pictures, and accommodated my short-notice stay. Ruby was very tired when she got home <3.”

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Shunnett M.
Sitter Profile Image: Amanda C.
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Amanda C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 16 reviews
6 repeat clients
18 years of experience
Germantown, WI, 53022

“Amanda was amazing and accommodating with drop off and pickup. She took the time to really get to know all the details with Rusty and his habbits. She gave updates and pictures. Rusty had a great time and was a sad to leave. 13/10 recommend.”

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Maddie
Sitter Profile Image: Kristi B.
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Kristi B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 36 reviews
19 repeat clients
19 years of experience
Franklin, WI, 53221

“I finally found a perfect sitter. My dog is a very picky and shy dog. So whenever I send her to another daycare I always worried so much. But I feel like Kristi treated my dog even better than I do. She updated me with pictures and videos. I feel very comfortable to send my dog.”

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Irene Hyeran K.
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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 - Caldwell

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FAQs for Dog Boarding - Caldwell

Frequently asked questions about Rover

Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.

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.

Depending on the sitter, their home environment, and your dog’s needs, daily exercise 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, 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.

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

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 , 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 .

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.

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