Curated Luxury holiday rentals deals in Southern Wisconsin

Search
Add dates
Add dates
1 room, 2 guests
Compare deals on Booking.com

Trusted by over 100,000 travellers every year

back
close
Add dates
Add dates
room 1

Adults

18+
2

Child

0-17
0
Add another room
usp icon

Exclusive member prices

Unlock exclusive member discounts at hundreds of top hotels.

usp icon

The biggest range

Thousands of luxury hotels for you to choose from but all curated for you.

usp icon

The best price

We compare deals and bring you the best price with our price promise.

usp icon

Free cancellation & pay later

A range of fully refundable and pay on arrival luxury and boutique hotels.

Clear filters

Southern Wisconsin

Recommended
Sort by

See the latest prices and deals by choosing your dates

These properties may not be in the centre of Southern Wisconsin, but are nearby and match your search.
Level Chicago - Fulton Market
Full StarFull StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Near West Side, Chicago · 190.26 km from centre

8.4

 

17 reviews

Located in Chicago, one mile from Union Station, Level Chicago - Fulton Market provides accommodations with barbecue facilities and private parking. This 5-star hotel offers a 24-hour front desk, a business center and free WiFi. There's a spa and wellness center with an outdoor swimming pool, fitness center and sauna, as well as a hot tub.

The hotel will provide guests with air-conditioned rooms offering a desk, an electric tea pot, a fridge, a dishwasher, a safety deposit box, a flat-screen TV, a balcony and a private bathroom with a shower. At Level Chicago - Fulton Market every room includes bed linen and towels.

Shops at Northbridge is 1.4 miles from the accommodation, while Willis Tower is 1.2 miles away. The nearest airport is Midway International Airport, 11 miles from Level Chicago - Fulton Market.

Compare price on Booking.com
Compare price on Booking.com
Primary image
DoubleTree by Hilton Chicago - North Shore Conference Center
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Cook County, Skokie · 170.12 km from centre

8.6

 

1,170 reviews

Breakfast available

When you stay at DoubleTree by Hilton Chicago - North Shore Conference Center in Skokie, you'll be in a shopping district, within a 10-minute drive of Lake Michigan and Northwestern University. This hotel is 10.2 mi (16.4 km) from Wrigley Field and 10.6 mi (17.1 km) from Donald E. Stephens Convention Center.

Compare price on Booking.com
Compare price on Booking.com
Primary image
Warwick Allerton - Chicago
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Streeterville, Chicago · 190.50 km from centre

8.8

 

2,938 reviews

Breakfast available

With a stay at Warwick Allerton - Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 11 minutes by foot from Chicago Riverwalk. This family-friendly hotel is 0.7 mi (1.2 km) from Lake Michigan and 0.8 mi (1.3 km) from Grant Park.

Compare price on Booking.com
Compare price on Booking.com
Room
Level Chicago Fulton Market
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Near West Side, Chicago · 190.26 km from centre

9.2

 

599 reviews

With a stay at Level Chicago Fulton Market, you'll be centrally located in Chicago, within a 5-minute drive of Chicago Riverwalk and Michigan Avenue. This hotel is 1.6 mi (2.5 km) from Millennium Park and 1.6 mi (2.6 km) from Grant Park.

Compare price on Booking.com
Compare price on Booking.com
Nader's Motel & Suites
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Western Michigan, Ludington · 198.42 km from centre

8.3

 

204 reviews

Located in Ludington, a 4-minute walk from Stearns Park Beach, Nader's Motel & Suites has accommodations with free bikes, free private parking, an outdoor swimming pool and a garden. With a shared lounge, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The property provides a shared kitchen and free shuttle service for guests.

The rooms at the hotel come with a seating area and a flat-screen TV with cable channels. Certain rooms have a kitchenette with a fridge, an oven and a microwave.

Nader's Motel & Suites has a terrace. Activities such as hiking, skiing, fishing can be enjoyed in the surrounding areas, and guests can relax along the beachfront.

Silver Lake State Park is 29 miles from the accommodation. Manistee County-Blacker Airport is 35 miles from the property.

Compare price on Booking.com
Compare price on Booking.com
Primary image
Kasa River North Chicago
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Aparthotel in Near North Side, Chicago · 189.90 km from centre

9.4

 

220 reviews

Located in Chicago (Downtown Chicago), Kasa River North Chicago is within a 15-minute walk of Michigan Avenue and Chicago Riverwalk. This aparthotel is 1.5 mi (2.4 km) from Grant Park and 1.5 mi (2.4 km) from Millennium Park.

Compare price on Booking.com
Compare price on Booking.com
Lobby
Kasa Magnificent Mile Chicago
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Aparthotel in River North, Chicago · 190.29 km from centre

9.2

 

989 reviews

With a stay at Kasa Magnificent Mile Chicago in Chicago (Downtown Chicago), you'll be a 5-minute walk from Michigan Avenue and 14 minutes by foot from Chicago Riverwalk. This aparthotel is 0.7 mi (1.1 km) from Chicago Theatre and 0.8 mi (1.2 km) from Lake Michigan.

Compare price on Booking.com
Compare price on Booking.com
Elkader Suites
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Northeast Iowa, Elkader · 220.22 km from centre

9.4

 

24 reviews

Breakfast available

Located in Elkader, Elkader Suites is 23 miles from Fort Crawford Museum. The property has a 24-hour front desk and free WiFi is available.

The rooms is fitted with air conditioning, a flat-screen TV with cable channels, a fridge, an electric tea pot, a shower and a desk. Rooms include a private bathroom, while certain rooms have a kitchen with an oven. All guest rooms at the hotel come with a seating area.

An American, vegetarian or vegan breakfast is available at the property. At Elkader Suites you'll find a restaurant serving American cuisine. Vegetarian, dairy-free and vegan options can also be requested.

The area is popular for hiking and canoeing, and bike rental is available at this 4-star hotel.

Compare price on Booking.com
Compare price on Booking.com
WorldMark Galena
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Resort in Hanover, Galena · 167.93 km from centre

7.8

 

117 reviews

Just 8 miles from the Apple River Fort State Historic Site, this Illinois resort offers rooms with cable TV and a fireplace. A heated indoor pool with a hot tub is on site.

A balcony and dining area are provided in every studio and apartment at WorldMark Galena. For added convenience, a microwave, fridge, and tea and coffee-making facilities are also included.

An on-site fitness center is available at Galena WorldMark. Guests can enjoy the resort’s game room or views of the countryside while making use of the outdoor BBQ facilities.

The Shenandoah Horseback Riding Center is 5 minutes’ drive from this resort. The Ulysses S. Grant Home and Historic Site is 7 miles away.

Compare price on Booking.com
Compare price on Booking.com
Cityscape Haven Stylish 2Bed 2Bath Condo with Downtown Chicago Views
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Chicago · 193.39 km from centre

10.0

 

1 review

Just a 12-minute walk from Field Museum of Natural History and one mile from Art Institute of Chicago, Cityscape Haven Stylish 2Bed 2Bath Condo with Downtown Chicago Views features accommodations in Chicago, with a fitness center and a shared lounge. The property is around 1.2 miles from Cloud Gate – The Bean, 1.2 miles from Millennium Park, and 1.4 miles from CIBC Theatre. The accommodation offers a sauna, free Wifi throughout the property, and full-day security.

Offering direct access to a terrace with lake views, the spacious apartment consists of 2 bedrooms. The air-conditioned apartment also features a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 2 bathrooms with a hot tub, a bidet, and a shower. The accommodation is non-smoking.

The apartment also provides a rooftop pool and a hot tub for guests to relax in. The apartment has a picnic area where you can spend the day outdoors.

Popular points of interest near Cityscape Haven Stylish 2Bed 2Bath Condo with Downtown Chicago Views include Chicago Symphony Orchestra, DePaul University, and Adler Planetarium & Astronomy Museum. The nearest airport is Midway International Airport, 10 miles from the accommodation.

Compare price on Booking.com
Compare price on Booking.com
Luxury Suite at Private Beach North Shore Residence
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Highland Park · 158.71 km from centre

9.2

 

5 reviews

Luxury Suite at Private Beach North Shore Residence is located in Highland Park, just a 10-minute walk from Rosewood Beach and 14 miles from Loyola University Chicago. This property offers access to a terrace, free private parking, and free Wifi. Outdoor seating is also available at the guest house.

Towels and bed linen are offered in the guest house. The accommodation offers an air conditioning, a heating, and a private bathroom.

Luxury Suite at Private Beach North Shore Residence has a garden to relax in after a busy day, along with a private beach area.

Wrigley Field is 17 miles from the accommodation, while Six Flags Great America is 20 miles from the property. The nearest airport is Chicago O'Hare International Airport, 21 miles from Luxury Suite at Private Beach North Shore Residence.

Compare price on Booking.com
Compare price on Booking.com
Nuk's Executive Suites
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Brown County, De Pere · 132.63 km from centre

8.7

 

274 reviews

<h2>Comfortable Accommodations</h2>

Rooms feature private bathrooms, air-conditioning, and modern amenities such as free WiFi, flat-screen TVs, and work desks. Guests enjoy river views, balconies, and comfortable seating areas.

<h2>Dining Experience</h2>

The modern restaurant serves Thai cuisine in a romantic ambiance. Breakfast includes continental and à la carte options with fresh pastries, fruits, and juices. Dinner is available in a relaxed setting.

<h2>Facilities and Services</h2>

The hotel offers a fitness center, terrace, lounge, and outdoor seating area. Additional services include a 24-hour front desk, concierge, and free on-site private parking.

<h2>Prime Location</h2>

Located in De Pere, the hotel is a 15-minute walk from St. Norbert College and 5.6 mi from Green Bay–Austin Straubel International Airport. Nearby attractions include Lambeau Field and Heritage Hill State Park.

Compare price on Booking.com
Compare price on Booking.com
Primary image
The Inn at SentryWorld
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Central Wisconsin, Stevens Point · 143.81 km from centre

9.8

 

61 reviews

Breakfast available

With a stay at The Inn at SentryWorld in Stevens Point, you'll be near the airport, within a 10-minute walk of University of Wisconsin-Stevens Point and Green Circle Trail. This golf hotel is 0.5 mi (0.9 km) from Sentryworld Golf Course and 1.8 mi (2.9 km) from Stevens Point Sculpture Park.

Compare price on Booking.com
Compare price on Booking.com
Chez Hotel
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Arlington Heights · 161.80 km from centre

8.5

 

59 reviews

Located in Arlington Heights, 20 miles from Wrigley Field, Chez Hotel has accommodations with a terrace, free private parking, a restaurant and a bar. With free WiFi, this 4-star hotel offers room service and a 24-hour front desk. United Center is 23 miles from the hotel and 360 Chicago is 23 miles away.

The hotel will provide guests with air-conditioned rooms offering a closet, a safety deposit box, a flat-screen TV and a private bathroom with a shower.

Guests at Chez Hotel can enjoy an à la carte breakfast.

Loyola University Chicago is 21 miles from the accommodation, while Lincoln Park Zoo is 22 miles from the property. Chicago O'Hare International Airport is 5 miles away.

Compare price on Booking.com
Compare price on Booking.com
Sheraton Chicago Northbrook
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Cook County, Northbrook · 162.41 km from centre

8.0

 

68 reviews

<h2>Comfortable Accommodations</h2>

Sheraton Chicago Northbrook in Northbrook offers family rooms with air-conditioning, work desks, and free WiFi. Each room includes a shower, hairdryer, and a work desk.

<h2>Exceptional Facilities</h2>

Guests can enjoy a fitness center, indoor swimming pool, and a restaurant serving American cuisine. The hotel also features a bar, minimarket, and outdoor seating area.

<h2>Convenient Location</h2>

Located 1.2 mi from Techny Prairie Park And Fields and 14 mi from Chicago O'Hare International Airport. Nearby attractions include Kohl Children's Museum (2 mi) and Chicago Botanic Garden (5.6 mi).

<h2>Guest Services</h2>

The hotel offers a 24-hour front desk, shuttle service, and paid on-site private parking. Additional amenities include express check-in and check-out services.

Compare price on Booking.com
Compare price on Booking.com
Holiday Inn Chicago North Shore by IHG
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Cook County, Skokie · 173.62 km from centre

7.0

 

642 reviews

Home to the Skokie Conference and Banquet Center, this hotel is located in the heart of Skokie, IL and features an expansive indoor pool and hot tub, on-site restaurant and bar and comfortable guest rooms with free WiFi.

Every room at Holiday Inn Chicago North Shore provides a 36-inch flat-screen TV with premium cable channels, along with a microwave, small refrigerator and coffee maker. In-room dining services are available.

Guests can indulge in one of the restaurant’s signature martinis or grab a bite for breakfast, lunch and dinner at Bar Louie’s, located in the hotel lobby. The restaurant offers free meals for kids.

A 24-hour modern fitness center and a state-of-the-art business center are available on-site. A snack shop and laundry facilities are also on-site for guest convenience.

The Skokie Swift train station is 2 miles away from the hotel, offering easy access to downtown Chicago. O’Hare International Airport is a 15-minute drive away.

Compare price on Booking.com
Compare price on Booking.com
Goldmoor Inn & Resort
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Resort in Galena · 175.14 km from centre

9.6

 

35 reviews

Breakfast available

Located in Galena, 22 miles from Diamond Jo Casino, Goldmoor Inn & Resort provides accommodations with free bikes, free private parking, a garden and a terrace. 6.6 miles from Belvedere Mansion and 7.1 miles from Galena Historic District, the property has a ski pass sales point, as well as a bar. The resort features a hot tub, room service and free WiFi.

Guest rooms in the resort are equipped with air conditioning, a seating area, a flat-screen TV with satellite channels, a kitchenette, a dining area and a private bathroom with free toiletries, a shower and a hot tub. All rooms will provide guests with a fridge.

An American breakfast is available at Goldmoor Inn & Resort. At the accommodation you'll find a restaurant serving American cuisine. Vegetarian and gluten-free options can also be requested.

Guests at Goldmoor Inn & Resort will be able to enjoy activities in and around Galena, like hiking, skiing and cycling.

Galena-Jo Daviess County History Museum is 7.3 miles from the resort, while J Dubuque Monument is 11 miles away. Dubuque Regional Airport is 29 miles from the property.

Compare price on Booking.com
Compare price on Booking.com
MainStay Suites Oakbrook Terrace - Chicago
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in DuPage County, Oakbrook Terrace · 182.80 km from centre

7.6

 

44 reviews

<h2>Comfortable Accommodations</h2>

MainStay Suites Oakbrook Terrace in Oakbrook Terrace offers family rooms with kitchenettes, work desks, and seating areas. Each room includes a refrigerator, microwave, dishwasher, stovetop, and kitchenware.

<h2>Essential Facilities</h2>

Guests enjoy free WiFi, a 24-hour front desk, and a continental buffet breakfast. Additional amenities include a hairdryer, dishwasher, and microwave.

<h2>Prime Location</h2>

Located 14 mi from Chicago O'Hare International Airport, the hotel is near attractions such as Brookfield Zoo (8.7 mi) and United Center (17 mi). An ice-skating rink is also in the vicinity.

Compare price on Booking.com
Compare price on Booking.com
The Hotel & Athletic Club at Midtown
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Resort in Chicago · 185.32 km from centre

8.8

 

152 reviews

The Hotel & Athletic Club at Midtown is part of the Midtown Athletic Club. As part of your stay Guests are provided with full access to the indoor and outdoor lap pools, spa, sauna, steam room, workout facilities, whirlpools, tennis courts, a Yoga studio, a boxing gym, cycle studio, golf simulators, and 190 group fitness classes throughout every week.

Every room at this resort is air conditioned and is equipped with a flat-screen TV with satellite channels. Every room includes a seating area to relax in after a busy day. The rooms come with a private bathroom. For your comfort, you will find bathrobes, free toiletries and a hairdryer.

Free Parking is included for Guests who choose to stay at the property. You will find a 24-hour front desk at the property.

The Hotel & Athletic Club at Midtown is located 1.9 mi from Wrigley Field in Chicago. Lincoln Park Zoo is 2.2 mi from The Hotel & Athletic Club at Midtown, while United Center is 3.1 mi from the property. The nearest airport is Midway International Airport, 9.9 mi from the property.

Compare price on Booking.com
Compare price on Booking.com
The Drake Hotel
Full StarFull StarFull StarFull Star
[missing: cards.star_rating_info]

Hotel in Streeterville, Chicago · 190.05 km from centre

8.5

 

628 reviews

Featuring stunning views of Lake Michigan, the Chicago Drake hotel is 3 minutes' walk from Oak Street Beach and 1 mile from Navy Pier. This hotel built in 1920 includes elegantly designed guest rooms and a chance to enjoy an afternoon tea or cocktails at Palm Court.

Each spacious room at The Drake provides deluxe bedding and marble bathrooms. Guest rooms offer a flat-screen HD TV with HBO and an iPod docking station.
Guests at the Drake Hilton Hotel can explore the shops located on the arcade level of the hotel. A convenience store and foreign currency exchange services are also available.

Lincoln Park Zoo is 2.4 miles from this hotel in Chicago. The John Hancock Center is less than 5 minutes' walk away.

Compare price on Booking.com
Compare price on Booking.com
tripadvisor