House Sitting Crawford Crossing

Find a loving house sitter to watch over your pets and your home.

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Over 2
pet parents in Crawford Crossing have booked house sitting

Crawford Crossing, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Kimberly G.
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Kimberly G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
211 reviews
41 repeat clients
32 years of experience
Baraboo, WI, 53913

Kimberley was awesome with our girls, kept us up to date with daily pics and left our house clean and even tidier than we left it! We appreciated her communication and promptness and love for all animals. I would HIGHLY recommend her !

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Kate S.
Sitter Profile Image: Heather E.
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Heather E.
from
$60
per night
5.0 out of 5 stars
21 reviews
4 repeat clients
15 years of experience
Baraboo, WI, 53913

Heather was fabulous! Our dog, Bodie, loved her. We were at a wedding and we received texts with photos of Bodie a couple of times letting us know he was ok. We will most definitely use her services again.

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willie69 R.
Sitter Profile Image: Amber S.
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Amber S.
Star Sitter
from
$105
per night
5.0 out of 5 stars
22 reviews
2 repeat clients
15 years of experience
Baraboo, WI, 53913

We had an amazing experience with Amber! She went above and beyond in every way. She stayed overnight with our dogs, took them on walks, and kept us updated with plenty of pictures and videos, which gave us so much peace of mind while we were away. The biggest surprise was coming home to our dogs’ feeding station it had been spotless! We had left it pretty messy, and she cleaned it immaculately without us ever asking. That level of care and attention to detail meant so much to us. It’s obvious she genuinely loves animals and treated our dogs like they were her own. They were happy, well cared for, and clearly comfortable with her. We couldn’t have asked for a better sitter and will absolutely be booking with her again. We highly recommend her to anyone looking for someone trustworthy, thoughtful, and truly exceptional!

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Edie M.
Sitter Profile Image: Rebecca R.
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Rebecca R.
from
$80
per night
5.0 out of 5 stars
54 reviews
19 repeat clients
40 years of experience
Baraboo, WI, 53913

I left my 1 year old puppy Mack with Rebecca for a week. I was very nervous to leave him with someone I didn’t know personally. Rebecca was absolutely wonderful!! She sent daily pictures of him. She walked him and played with him and made him happy, as I could tell by the pictures. My house was clean and she was very attentive, that helped settle all of my concerns.

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Shelly K.
Sitter Profile Image: Olivia S.
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Olivia S.
from
$50
per night
5.0 out of 5 stars
5 reviews
20 years of experience
Upper East Side, Baraboo, WI, 53913

Olivia was just what we wanted and needed for our trip. She and Addie safe at the homefront were a superb solution for our family! We won't hesitate one bit to call her again for another booking. Thanks Olivia!

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Gale A S.
Sitter Profile Image: Carlie W.
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Carlie W.
from
$50
per night
5.0 out of 5 stars
55 reviews
24 repeat clients
30 years of experience
Sauk City, WI, 53583

Carlie did a wonderful job taking care of my dogs while I was away. It was clear they were comfortable and happy—they really enjoyed lounging and cuddling with her. She was also very attentive to their care needs, doing a great job managing their medications, potty breaks and even keeping up with their teeth brushing, which I really appreciated.

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Kim C.
Sitter Profile Image: Ashley R.
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Ashley R.
Star Sitter
from
$80
per night
5.0 out of 5 stars
113 reviews
29 repeat clients
30 years of experience
Portage, WI, 53901

Ashley was great! I loved getting all the pictures and updates. Especially for our first time using a pet sitter other than family. Really helped put me at ease that my dog was doing ok! 😌 I will definitely be using Ashley again!

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Ivy F.
Sitter Profile Image: Grace H.
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Grace H.
from
$47
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
9 years of experience
Baraboo, WI, 53913

Grace was exceptional!! She gave both our animals love and care with enthusiasm! She followed all of our directions and was willing to go beyond expectations. I will definitely ask for Grace again. Thank you.

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Caren L.
Sitter Profile Image: Ramon C.
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Ramon C.
from
$70
per night
5.0 out of 5 stars
4 reviews
7 years of experience
Briggsville, WI, 53920

About: Bilingual and able to communicate with families in Spanish, as well. Neighbors and friends have trusted me to care for their pets/homes for almost 7 years. They often say we're (my fiance and I) the only ones they trust to care for their pets. I have experience with senior pets and worked at a rescue previously. Excited to be going full time pet sitting/walking in 2026! I'm very reliable, flexible and am available last minute, 7 days a week and on holidays. I take extra care to keep pets happy, safe and comfortable. I follow instructions given and use caution when necessary to prevent any escapes. I do not do boarding in my home.

Sitter Profile Image: Alissa A.
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Alissa A.
from
$100
per night
5.0 out of 5 stars
27 reviews
5 repeat clients
25 years of experience
Portage, WI, 53901

Our pups were treated just like family. So grateful to found a wonderful place for our Great Danes. Knowing she knows the bread was a great peace of mind.

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Amanda L.
Sitter Profile Image: Elise K.
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Elise K.
from
$45
per night
5.0 out of 5 stars
2 reviews
1 repeat client
3 years of experience
Lodi, WI, 53555

Elise watched my two dogs overnight and took great care of them. She sent photos, kept me updated, and was very tidy.

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Kelsey M.
Sitter Profile Image: Matthew E.
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Matthew E.
from
$75
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
10 years of experience
Cross Plains, WI, 53528

Matthew was great! The dogs were well cared for and I my family was able to have a stress free vacation. I will definitely book again in the future.

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Anne B.
Sitter Profile Image: Kirstyn M.
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Kirstyn M.
from
$40
per night
5.0 out of 5 stars
37 reviews
7 repeat clients
3 years of experience
Portage, WI, 53901

About: I’ve taken care of puppies to senior dogs since I was a little girl. My dad owned a doggy daycare and it was a great experience learning how to care for animals. I currently work full time and I go to school. Pet care will fit into my schedule because I do work night shift. I will have plenty of time to properly care for your pets. I will be there to watch your home and make sure your pet is safe. I will follow all of your instructions to assure that I keep everyone safe.

Sitter Profile Image: Quinn M.
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Quinn M.
from
$28
per night
15 years of experience
Mazomanie, WI, 53560

About: I have been taking care of animals ever since I was little, between dogs, cats, reptiles, and even farm animals such as dairy cows, pigs, goats, chickens, rabbits, and guinea pigs. I can take care of pets at any time of day or night, and I can walk dogs after 4 pm. Tuesday & Thursday, I do have class from 7-10 am. I have a fence for my pets, we play with toys, and we go on walks (depending on the weather). My dog will sleep where she is most comfortable and she always goes to the bathroom on time.

Sitter Profile Image: Victoria S.
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Victoria S.
from
$34
per night
4.5 out of 5 stars
9 reviews
3 repeat clients
20 years of experience
Westfield, WI, 53964

We loved Victoria since the day she came to meet our dog. She was so sweet to Angel and Angel loved her. She did a great job staying with Angel at our house!

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Lee F.
Sitter Profile Image: Skyla S.
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Skyla S.
from
$40
per night
5.0 out of 5 stars
2 reviews
8 years of experience
Spring Green, WI, 53588

Skyla was responsive and incredibly attentive to our dogs. She was very communicative and anticipated the needs of our pets. Would definitely have her watch after our dogs again!!

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Elle N.
Sitter Profile Image: Samuel A.
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Samuel A.
from
$65
per night
5.0 out of 5 stars
22 reviews
2 repeat clients
25 years of experience
Marquette, Madison, WI, 53703

Sam took excellent care of my dogs and home. I was happy to get pics and updates, as well as to come home to a clean house. He even washed the bedsheets ? I recommend Sam for both house and pet sitting!

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Marit S.
Sitter Profile Image: Sara N.
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Sara N.
from
$60
per night
18 years of experience
Lodi, WI, 53555

About: I have been taking care of dogs for my entire life! I have experience caring for big and small dogs of all ages, from puppies to the elderly. I took on the responsibility of training each of my family's dogs, so I am skilled in the area of obedience training for puppies and adolescent dogs. I am a very meticulous person and I follow every direct I'm given to a T, so I will make sure that your fur baby gets the best care and love possible. I am currently a high school student about to graduate and leave for college! From now until the end of the school year, I am available every weekday from 2-10. After May 31st, I will be working part-time, so I will have more than enough time during the summer to care for your fur babies! Although I do not offer services at my own house, I will make sure that your pet is as safe as can be wherever we are! The safety of anybody's pets is a top priority for any pet owner, including myself. Leaches and supervision are some of the most important tools that pet owners can use to keep their pets safe.

Sitter Profile Image: Dawn M.
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Dawn M.
from
$75
per night
35 years of experience
Loganville, WI, 53943

About: I've taken care of many dogs and even more cats over the last 38 years. I love them and will love yours like my own. Semi retired looking forward to helping people out. I have a very flexible schedule and a very dog friendly home. We have one dog in the home sometimes too because I watch my daughter's dog. We have a big country yard, dogs would be monitored with a leash unless the dog is good at obeying commands. Big yard with walking trails.

Sitter Profile Image: Laura R.
Verified Enhanced Background Check
Laura R.
from
$55
per night
33 years of experience
Pardeeville, WI, 53954

About: Hi! I’m Laura — a lifelong animal lover and professional dog trainer with years of hands-on experience with dogs and cats of all breeds, ages, and personalities. I specialize in in-home pet sitting where your pets stay relaxed, routine stays consistent, and your home is cared for with absolute respect. I’m calm, responsible, and deeply experienced with everything from confident working breeds to sensitive, anxious, or quirky dogs. Whether your pet needs quiet companionship, structure, adventure, medication, or extra patience, I tailor care to their exact needs. What You Can Expect Gentle, confident handling Reliable communication + photo/video updates A clean home when you return Safe, respectful care for pets and property Professional judgment in all situations Experience Includes Professional dog training background Puppies, seniors, and special-needs pets Large and working breeds Medication and special-care routines Multi-pet households Basic training reinforcement (upon request) Your pets are family — and I treat them like my own. I travel between Polson, MT and Madison Wisconsin frequently. I run my Dog Training company so I keep busy and can do that from anywhere so the pups are always #1 A mixture of all my years of experience combined with the clients desires and needs for their pet. Each dog I meet is my new best friend!

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The median cost per night for house sitting in Crawford Crossing is $50

Pet parents share their Rover experiences - Crawford Crossing

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5.0 out of 5 stars

Kimberly did an amazing job taking care of my dog and 2 cats! I received regular updates and came home to relaxed and happy pets, as well as a clean and organized home. Highly recommend!

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Heather E.
House Sitting
5.0 out of 5 stars

We had an amazing experience with Amber! She went above and beyond in every way. She stayed overnight with our dogs, took them on walks, and kept us updated with plenty of pictures and videos, which gave us so much peace of mind while we were away. The biggest surprise was coming home to our dogs’ feeding station it had been spotless! We had left it pretty messy, and she cleaned it immaculately without us ever asking. That level of care and attention to detail meant so much to us. It’s obvious she genuinely loves animals and treated our dogs like they were her own. They were happy, well cared for, and clearly comfortable with her. We couldn’t have asked for a better sitter and will absolutely be booking with her again. We highly recommend her to anyone looking for someone trustworthy, thoughtful, and truly exceptional!

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Edie M.
House Sitting
5.0 out of 5 stars

Heather was absolutely amazing for our short trip up north for a wedding. She took great care of our boys, took them for plenty of walks and sent lots of pictures of them enjoying themselves. If we are ever back up that way we will definitely book with her again. Thank you so much for everything !!!

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Taylor K.
House Sitting
5.0 out of 5 stars

Mariah is awesome!! Every time we have used her to watch our dogs, I have felt completely at ease. My family and I can enjoy our vacation and know that our dogs are in great hands. She communicates the entire time and sends lots of pictures. She even got our super picky eater to eat the whole time we were gone!! She is the best!! We have already booked her again and will continue to book with her on future trips! Thank you Mariah for always being the best!!!!

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Amy K.
House Sitting
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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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  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

Sitters in Crawford Crossing average 5
repeat house sitting clients

FAQs for House Sitting - Crawford Crossing

Frequently asked questions about Rover

The average cost for House Sitting in Crawford Crossing on Rover is $38.85 per night (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .

As of July 2026, there are 362 sitters on Rover offering House Sitting across Crawford Crossing. Enter your ZIP code to see which available sitters are closest to your home.

Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:

  • Mail & deliveries: Collecting letters and packages so they don't pile up.
  • Plant care: Keeping your indoor or outdoor garden hydrated.
  • Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
  • Home security: Sitters can stay overnight to keep your home occupied.

The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Crawford Crossing walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.

It’s helpful to think of house sitting as a "home base" service. Most sitters in Crawford Crossing maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:

  • Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
  • Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
  • Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.

Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Crawford Crossing choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

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 .

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 pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet 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.

A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.

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

  • 96% of sitters can help with special care needs
  • 100% can help with giving oral medications or injections
  • 96% 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.

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