Book Exclusive Waukesha County Vacation Packages

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Search vacation packages deals in Waukesha County's top destinations

A modern architectural structure with a curved roof and glass facade.

Milwaukee

Vacations
Milwaukee
A calm lake surrounded by autumn-colored trees and a small gazebo.

Hartland

Vacations
Hartland

Waukesha County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,112, price is now CA $844 per person
CA $844
per person
Oct 30 - Nov 1
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,900, price is now CA $1,313 per person
CA $1,313
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was CA $2,729, price is now CA $1,914 per person
CA $1,914
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,047, price is now CA $1,484 per person
CA $1,484
per person
Oct 20 - Oct 23
found 14 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,863, price is now CA $1,387 per person
CA $1,387
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Top Waukesha County hotels deals

AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

3 out of 5
16865 W Bluemound Rd Brookfield WI
Free cancellation
Reserve now, pay when you stay
The price is CA $111 per night
CA $111
CA $128 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Pool
Breakfast included
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Free cancellation
Reserve now, pay when you stay
The price is CA $104 per night
CA $104
CA $120 total
Sep 10 - Sep 11
includes taxes & fees
Book a stay at this golf hotel in Brookfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Pool
Pet-friendly
Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

3.5 out of 5
1200 S Moorland Rd Brookfield WI
Free cancellation
Reserve now, pay when you stay
The price is CA $169 per night
CA $169
CA $195 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Pool
Breakfast included
Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

3 out of 5
1250 S Moorland Rd Brookfield WI
Free cancellation
The price is CA $136 per night
CA $136
CA $157 total
Sep 5 - Sep 6
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Pool
Hot tub
The Ingleside Hotel

The Ingleside Hotel

4 out of 5
2810 Golf Road Pewaukee WI
Free cancellation
Reserve now, pay when you stay
The price is CA $148 per night
CA $148
CA $167 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Pewaukee. Enjoy free WiFi, free parking, and water park access (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Springs Water Park and Pewaukee Golf Club are located nearby.
Pool
Pet-friendly
Studio 6 Extended Stay Milwaukee Brookfield WI

Studio 6 Extended Stay Milwaukee Brookfield WI

3 out of 5
325 N Brookfield Rd Brookfield WI
Free cancellation
Reserve now, pay when you stay
The price is CA $106 per night
CA $106
CA $120 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this hotel in Brookfield. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Pet-friendly
Parking included
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Waukesha County attractions

The entrance to Veterans Memorial Park with stone archways and flags.

Lac La Belle

9.6/10 (14 reviews)
Commune with nature and explore the great outdoors at Lac La Belle during your travels in Oconomowoc. Visit the shops or attend a sporting event in this family-friendly area.
See properties

Photos of local treasures

Browse Waukesha County vacation photos for more inspiration

A calm lake with a wooden dock extending into the water, surrounded by trees and a clear sky.
A golf course with a putting green, trees with autumn foliage, and a cloudy sky.
A quarry with a large water body and surrounding greenery.
A mural of a guitar with band members painted on it, mounted on a brick wall with windows in the background.
A garden with various wildflowers, a wooden bridge, and trees in the background.

Frequently asked questions

How much are vacation packages to Waukesha County?
CA $844 is all you need to spend for an exciting vacation in Waukesha County. Bundle your flights and hotel into a Travelocity package and watch the savings start to pile up. With such good prices, there's never been a better time to travel.
Where can I get the best vacation package deals for Waukesha County?
There are amazing Waukesha County package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties in all corners of the globe? Keep that in mind when you're ready to cross another destination off your list.
Why should I purchase my Waukesha County vacation bundle with Travelocity?
Whether you're planning an epic vacation or a last-minute trip, we have lots of enticing destinations to choose from at a good price. And on top of that, we provide 24/7 support, superb service and a Price Match Guarantee. Save yourself money and time and reserve your dream vacation now.
Can I save money on my Waukesha County car rental if I combine it with a hotel or flight?
Sure can. And our Waukesha County vacation packages are the perfect way to do it. With just a few clicks you can save cash and time by combining your bookings. Pick up the keys to your rental car then chart your own course. Need to fill your itinerary? Add some activities or experiences to your package and make savings on those too.
Which airport is best for Waukesha County?
General Mitchell Intl. Airport (MKE) and Dane County Regional Airport (MSN) are your top options for jetting to Waukesha County.
What is there to do in Waukesha County?
Waukesha County has hidden surprises around every corner, but make sure you get to Little Muskego Lake and Oconomowoc Arts Center while you're here. These attractions are popular with visitors.