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Holiday Middleton

9401 Old Sauk Road, Middleton, WI 53562

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(866) 374-4058
9.5
Review score
137 reviews
Add review
9.5
Review score
137 reviews
  • 5 star
    61%
  • 4 star
    28%
  • 3 star
    4%
  • 2 star
    4%
  • 1 star
    3%
See all reviews
9.2
Review score
10279 reviews
133 facilities
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Holiday Middleton
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Holiday Middleton community exterior
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street view of Holiday Middleton

Rebecca L DuBey

Friend of resident/client

5.0 out of 5 stars

I love this place!

Middleton Crossing is a wonderful place. I visit weekly to see the friends my mother made when she lived here. The staff are welcoming and caring although I no longer have ties here. I come to visit remaining friends, whose lives I have come to cherish and enjoy. The residents are intelligent, care for each other, and likely, to hold lively conversations at meal times. Meals are delicious and offer a choice between entrees. The common areas are open and cheerful with high ceilings and light[. The rooms are varied and delightful with many floorplans offered. My heart just soars whenever I come here! People are happy here; they great each other kindly and treat each other so nicely. There is a really sense of community here, built on shared activities, bus trips, meals, music guests, card games, puzzle making , and art projects. My mother loved living here, and I keep returning to visit the friends she made because I love it too.

Read all reviews

Holiday Middleton

The Jefferson has been here for over 16 years near beautiful farmland, Pope Farm and corn fields.We have senior care on site to offer Assisted Living. Our staff members have longevity over 15 years and more. We have won "Best Place to Live" 2018 and "Best Place to Work 3 years in a row. We are known for our Chef Prepared Meals with 4 choices daily, every meal. We are also known for our activity and classes! We are 15 minutes from the state Capital and Badger stadium, Lake Mendota, Many Lakes and hiking trails, State Parks, etc.. Next door to Black Hawk neighborhood and a nice walk path meandering around our community quarter mile around.

Learn more about the Best of Senior Living awards and this year’s winners.

See all 2026 award winners

Senior living options offered

  • Independent Living

Holiday Middleton

Pricing

Total monthly costs depend on room type, select services, and the level of care needed

Base fees by care type

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*Prices quoted are monthly rental charges and are provided by the communities themselves. Actual prices may differ due to one-time fees, timing and care services required. Speak with your Senior Living Advisor to learn more.

Reviews

for Holiday Middleton

9.5 out of 10
Review Score137 reviewsWrite a review
Overall Experience
4.4
Cleanliness
4.4
Friendliness
4.5
Care Services
4.5
Staff
4.8
Meals & Dining
4.4
Activities
4.5
Value for Cost
4.3

A Place for Mom has scored Holiday Middleton with 9.5 out of 10 using our proprietary review score based on 25 reviews in the last 2 years. Over all time, Holiday Middleton has 137 reviews with an average "overall experience" of 4.4 out of 5.

Filters

1-20 of 137 reviews

Last Updated: 10/10/25

Overall Experience
Date Submitted
Reviewer
Care Received
Verified Review

A Place For Mom has verified the person writing the review and their connection to the community.

Rebecca L DuBey

Independent Living

Family/friend

October 10, 2025

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

I love this place!

Middleton Crossing is a wonderful place. I visit weekly to see the friends my mother made when she lived here. The staff are welcoming and caring although I no longer have ties here. I come to visit remaining friends, whose lives I have come to cherish and enjoy. The residents are intelligent, care for each other, and likely, to hold lively conversations at meal times. Meals are delicious and offer a choice between entrees. The common areas are open and cheerful with high ceilings and light[. The rooms are varied and delightful with many floorplans offered. My heart just soars whenever I come here! People are happy here; they great each other kindly and treat each other so nicely. There is a really sense of community here, built on shared activities, bus trips, meals, music guests, card games, puzzle making , and art projects. My mother loved living here, and I keep returning to visit the friends she made because I love it too.

Karen

Independent Living

Resident/client

July 2, 2025

5.0 out of 5 stars
Verified Review

A good community

Middleton Crossing is a good place to live. They have a lot of activities like playing cards, bingo, crafts, games, access to therapy, and help with medication management, etc., areas to walk, a library, a great staff (I don't know how they remember names). The food times and serving could use some tweaking. Good for most men, no cooking!

Diane G

Independent Living

Resident/client

June 30, 2025

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

I feel fully relaxed and confident now

From the moment of arrived at Middleton Crossing. I have been treated wonderful in every way and how comfortable at care feel here. The amenities are unless so I need not worry should I need help of any. Nature thanks to [name removed].

Anonymous

Independent Living

Family/friend

June 11, 2025

5.0 out of 5 stars
Verified Review
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Friendly staff

The staff was awesome! From the front desk to the PT department. Very friendly and a lot of fun. Mom did say the food could've been better. She enjoyed the activities such as when they'd bring in music.

Connie C

Independent Living

Family/friend

May 18, 2025

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Felt like home

My mother-in-law lived here for the last 4.5 years of her live and she loved it. The staff treated her like family, she had a lovely apartment with bird feeders outside her window, and she talked often about how good the food was. She had a group of table mates in the dining room and they thoroughly enjoyed each other’s company. Whenever I was there, it was such a relaxed atmosphere. The addition of assisted living services allowed her to have some independence while also giving us the comfort of knowing she was getting the care she needed. Knowing how much she loved it there gave us peace of mind. That is truly what is most important.

Mohammad R

Independent Living

Resident/client

May 16, 2025

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Independent lifestyle and management is very cordial

I like the friends I’ve made here and their sense of humor. We have a lot of fun and laughter here especially at meal times! The shuttle bus is good but could use more hours and days but the driver is excellent

Sheri W

Independent Living

Family/friend

May 16, 2025

5.0 out of 5 stars
Cleanliness
4.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
4.0

Mom's been here almost 15 years

My mother has been living in The Jefferson/Middleton Crossings (the name has changed over the years) for the past 15 years, and it has truly become her home. The staff is not only professional but also kind, compassionate, and genuinely caring. Over the years, we’ve seen them go above and beyond to make residents feel valued and supported. There’s always something going on—fun activities, social gatherings, fitness classes, and games—that keep her engaged and happy. The community is vibrant and welcoming, and it’s clear that the team works hard to foster an environment where seniors can thrive independently while still having help nearby if needed. We’re grateful for the peace of mind that comes with knowing she’s in a place where she’s not just cared for but truly cared about.

Honey R

Independent Living

Family/friend

May 16, 2025

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Sales Director is wonderful

I attended a networking event put on by the sales director and could not have turned out better! I got to meet and speak with a wide ranging network of folks in the industry . Feeling was very welcoming and relaxed. Afterwards chatted with residents who had good things to say and lots of positive vibes. All around good energy. The facilities are clean, bright and the staff is refreshingly friendly and. This community comes complete with some tasteful decor. Learned they host a variety of fun events most days of the week. would definitely recommend! Even a visit and or tour! five stars. For sure

Anonymous

Independent Living

Family/friend

May 5, 2025

4.0 out of 5 stars
Verified Review
Cleanliness
3.0
Friendliness
5.0
Value for Cost
3.0
Care Services
4.0
Activities
5.0
Staff
3.0
Meals & Dining
3.0

Nice Community

The fire alarm has gone off several times at odd hours for a few days and the power went out in part of the building. The staff is friendly and helpful, our frustration it is advertised as a smoke free facility however there has been cigarette smoke coming into the unit several times from a neighbor, staff stated it would cost us a transfer fee to move to another unit. Recently the soup at dinner is served buffet style, residents walk to serve themselves and bring it back to their table which made it more difficult for those with mobility concern

Anonymous

Independent Living

Family/friend

April 30, 2025

4.0 out of 5 stars
Verified Review
Cleanliness
4.0
Friendliness
4.0
Value for Cost
5.0
Care Services
4.0
Activities
4.0
Staff
4.0
Meals & Dining
5.0

Great Place

The staff is helpful. The cleaning person does a great job on my dad's apartment each week. We are so thankful for this service. The dining room is neat, clean, and a very pleasant space in which to dine. Dad really enjoys the food! [name removed], the activities coordinator, interacts nicely with the residents, and provides a good variety of activities in which to participate. Dad really enjoys exercise classes, Euchre, and the musical guests.

Larry K

Independent Living

Resident/client

April 4, 2025

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Middleton Crossings

Great staff and place to live. I have only been here for two months and have enjoyed my stay. There are various activities scheduled, so there is something for everyone to enjoy. Most of the residents are friendly an easy to get along with.

Mike S

Independent Living

Resident/client

March 18, 2025

3.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
4.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Praise to the staff. None to Caesar

Be sure you are personally oriented and that you sign off on your own safety. I repeat. Take nothing for granted. The staff can only work with the tools they are given. They manage to please us all. [name removed], [name removed], [name removed], [name removed], [name removed], [name removed]and even [name removed] make this place fun. I will miss them and my neighbors

Cindy S

Independent Living

Family/friend

March 17, 2025

2.0 out of 5 stars
Verified Review
Cleanliness
3.0
Friendliness
4.0
Value for Cost
2.0
Care Services
2.0
Activities
3.0
Staff
3.0
Meals & Dining
1.0

Would not recommend due to food service.

I would now rate our overall experience as a 2. The food service has been drastically reduced and I feel like we were given a bait and switch. We had lunch at the facility prior to deciding to sign the lease and the meals were all at a set time and we received full waitstaff service. Since my dad has moved in the service has been reduced. Meals are now served during a time window which erodes opportunity for community, petty changes have been made like removing soup spoons and saucers, there are less food choices and a more difficult process for making alternate choices. The meals used to last one hour and now last 20 minutes. We would not have picked Middleton Crossing if we knew these changes would be made.

Anonymous

Independent Living

Resident/client

February 5, 2025

3.0 out of 5 stars
Verified Review
Cleanliness
3.0
Friendliness
3.0
Value for Cost
3.0
Care Services
3.0
Activities
3.0
Staff
3.0
Meals & Dining
3.0

Review for Middleton Crossing, A Sky Active Living Community

I would recommend Middleton Crossing to others. I met with [name removed] while I was at [community removed]. I liked [name removed] and I liked the price as compared to another community I heard from.

Anonymous

Independent Living

Resident/client

January 21, 2025

4.0 out of 5 stars
Verified Review
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Activities
4.0
Staff
4.0
Meals & Dining
5.0

Middleton Crossing

People are friendly, dress is casual, and staff is attentive and helpful. The large, high-ceilinged dining room is inviting: the meals first-rate.

Anonymous

Independent Living

Family/friend

December 17, 2024

4.0 out of 5 stars
Verified Review
Cleanliness
5.0
Friendliness
5.0
Value for Cost
3.0
Care Services
4.0
Activities
4.0
Staff
5.0
Meals & Dining
1.0

Overall, nice place.

Facility is clean and spacious. Onsite staff are available and caring. Food often arrives cold or not cooked (I.e. grilled cheese sandwich comes out with cheese not melted...and cold).

Anonymous

Independent Living

Family/friend

December 6, 2024

3.0 out of 5 stars
Verified Review
Cleanliness
1.0
Friendliness
5.0
Value for Cost
3.0
Care Services
3.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Cleaning needs improvement

The interior really needs updating! They keep the outside looking wonderful. My brother pays big money to live there and they do a terrible job cleaning his room.

AW

Independent Living

Industry reviewer

December 4, 2024

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Great Community with Caring Staff

I have had several clients move to Middleton Crossing over the years. The latest one needed help with some paperwork and also had to visit the post office to confirm his change of address. The Middleton Crossing staff went above and beyond to make sure he could get to the post office(he doesn't drive). They've helped him make friends at the community with other residents...something that isn't easy for everyone. The food is also great at Middleton Crossing! I am there at least once a month to visit past clients and eat a meal. If you're looking for a great, affordable option for independent living, be sure to check out Middleton Crossing!

Mark S

Independent Living

Resident/client

December 3, 2024

5.0 out of 5 stars
Cleanliness
5.0
Friendliness
5.0
Value for Cost
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Love it here!

I have been here a month and love the food, new friends, staff, chef, maintenance and others. I loved the thanksgiving meal and not eating alone any more! I go to wonderful activities and take the shuttle out a lot! We go to Walgreens, restaurants, stores, parks, trips out and so enjoyable!

Anonymous

Independent Living

Family/friend

November 26, 2024

5.0 out of 5 stars
Cleanliness
4.0
Friendliness
5.0
Value for Cost
4.0
Care Services
5.0
Activities
5.0
Staff
5.0
Meals & Dining
5.0

Staff are the best

The staff @ Middleton Crossing are exceptional. Friendly and go above and beyond to ensure the residents are happy and comfortable.

Holiday Middleton

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The features and amenities that are displayed on this page contain marketing information provided by the community. A Place for Mom has not confirmed the completeness of the provided information, and cannot guarantee its accuracy. If you become aware of any information that should be updated or noted, please contact A Place for Mom. A Place for Mom uses the term “assisted living” to indicate that the community provides some level of assistance with daily living activities. It does not indicate that the facility meets official state requirements for level of care.

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