Greendale Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Greendale Vacation
Say farewell to planning hassles and hello to a Greendale vacation package. With the finer details organized before you go, you can focus on discovering the best of this city, starting with Historic Third Ward, which is great for shopping, festivals and history. Every trip to Greendale needs a well-thought-out itinerary. Fill yours with major attractions such as American Family Field, Wisconsin State Fair Park and The Rock Sports Complex. Stop dreaming and start doing. Explore the multitude of options on Expedia today and put your Greendale vacation plans into motion!
Top Greendale Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Pleasant Prairie-Kenosha by IHG
Price was CA $654, price is now CA $647 per person
CA $647
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.8/10 Excellent! (536 reviews)
Rooms were spacious and clean. Only downside is parking in front is minimal if you park in back and use the entrances available had a hard time using key card and if you went around to the back of hotel you had to exit property and go back around
Reviewed on Jan 16, 2026
Greendale Hotel Deals
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Mar 1 to Mar 2
CA $172
CA $203 total
Mar 1 - Mar 2
includes taxes & fees
9.4/10 Exceptional! (1,927 reviews)
We felt like royalty!
Reviewed on Feb 1, 2026
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
The price is CA $176 per night from Feb 16 to Feb 17
CA $176
CA $207 total
Feb 16 - Feb 17
includes taxes & fees
9.6/10 Exceptional! (2,550 reviews)
Everything about our stay deserves 5 Stars....from the moment we walked in to the moment we left and everything in between. The staff people we interacted with were nothing short of pleasant & eager to help, the room was not only comfortable, but fun & unique and the art galleries added a special ...
Reviewed on Feb 6, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Feb 16 to Feb 17
CA $137
CA $161 total
Feb 16 - Feb 17
includes taxes & fees
9.6/10 Exceptional! (2,042 reviews)
GREAT HOTEL. You can tell its family owned. Clean. Luxury. The amenities are above and beyond....for instance the complimentary happy hour and light food bites...more like a meal. Staff was super friendly and knowledgeable. After our stay we looked at their other locations so we can be sure to stay ...
Reviewed on Feb 6, 2026
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.
Discover the most popular places to visit in Greendale
Harley-Davidson Museum
5/5(13 reviews)
Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.
Milwaukee Art Museum
5/5(12 reviews)
Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.
Potawatomi Bingo Casino
Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area.
What to do in Greendale
Milwaukee Scavenger Hunt Walking Tour and Game
CA $68
per adult
Explore a world of travel with Expedia
- 4 Star Hotels in President Heights
- Pet-Friendly Hotels in College Heights
- B&B in Franklin
- Chalets in Franklin
- Cheap Hotels in Franklin
- Family Hotels in Franklin
- Hotels with Free Airport Shuttle in Franklin
- Hotels with Kitchenettes in Franklin
- Pet-Friendly Hotels in Franklin
- Spa Hotels in Franklin
- Franklin Hotels
- Inns in Franklin
- Motels in Franklin
- Hotels near General Mitchell Intl.
- Farmstay in Greenfield
- Aparthotels in Greenfield
- B&B in Greenfield
- Cabin Rentals in Greenfield
- Cheap Hotels in Greenfield
- Greenfield Hotels
- Motels in Greenfield
- Guest Houses in Hales Corners
- Hales Corners Hotels
- Pet-Friendly Hotels in Maitland Park
- B&B in Milwaukee Airport Station
- Hotels near Milwaukee Airport Station
- Hotels near Milwaukee County Sport Complex
- Delta Hotels in Mitchell West
- Pet-Friendly Hotels in President Heights
- Hotels near Rock Snow Park
- Hotels near St. Sava Serbian Orthodox Cathedral
- Flights to Greenfield
- Flights from Waterloo (ALO) to Milwaukee (MKE)
- Flights from Bangor (BGR) to Milwaukee (MKE)
- Flights from Buffalo (BUF) to Milwaukee (MKE)
- Flights from Detroit (DTW) to Milwaukee (MKE)
- Flights from Fargo (FAR) to Milwaukee (MKE)
- Flights from Fort Lauderdale (FLL) to Milwaukee (MKE)
- Flights from Green Bay (GRB) to Milwaukee (MKE)
- Flights from Los Angeles (LAX) to Milwaukee (MKE)
- Flights from Minneapolis (MSP) to Milwaukee (MKE)
- Flights from New York (NYC) to Milwaukee (MKE)
- Flights from Chicago (ORD) to Milwaukee (MKE)
- Flights from Seattle (SEA) to Milwaukee (MKE)
- Flights from Syracuse (SYR) to Milwaukee (MKE)
- Flights from Sault Ste. Marie (YAM) to Milwaukee (MKE)
- Flights from Edmonton (YEG) to Milwaukee (MKE)
- Flights from Hamilton (YHM) to Milwaukee (MKE)
- Flights from Halifax (YHZ) to Milwaukee (MKE)
- Flights from Kitchener (YKF) to Milwaukee (MKE)
- Flights from Kelowna (YLW) to Milwaukee (MKE)
- Flights from Ottawa (YOW) to Milwaukee (MKE)
- Flights from Windsor (YQG) to Milwaukee (MKE)
- Flights from Regina (YQR) to Milwaukee (MKE)
- Flights from Thunder Bay (YQT) to Milwaukee (MKE)
- Flights from Sudbury (YSB) to Milwaukee (MKE)
- Flights from Toronto (YTZ) to Milwaukee (MKE)
- Flights from Montreal (YUL) to Milwaukee (MKE)
- Flights from Vancouver (YVR) to Milwaukee (MKE)
- Flights from Winnipeg (YWG) to Milwaukee (MKE)
- Flights from Saskatoon (YXE) to Milwaukee (MKE)
- Flights from London (YXU) to Milwaukee (MKE)
- Flights from Abbotsford (YXX) to Milwaukee (MKE)
- Flights from Calgary (YYC) to Milwaukee (MKE)
- Flights from Victoria (YYJ) to Milwaukee (MKE)
- Flights from St. John's (YYT) to Milwaukee (MKE)
- Flights from Toronto (YYZ) to Milwaukee (MKE)
- Apple Holler
- Basilica of Saint Josaphat
- Bristol Vacations
- Brookfield Square Mall
- Brookfield Vacations
- Cabela's
- Discovery World
- Erin Hills Golf Course
- Harley Davidson Factory
- Harley-Davidson Museum
- Hartland Vacations
- Jackson Vacations
- Mequon Vacations
- Milwaukee Art Museum
- Milwaukee City Hall
- Visit College Heights
- Visit Maitland Park
- Milwaukee Public Library
- Visit Wilson Park
- Milwaukee Vacations
- Mitchell Park Horticultural Conservatory
- Moose Mountain Falls Waterpark
- Pettit National Ice Center
- Potawatomi Bingo Casino
- Regency Mall
- Reiman Publications Visitor Center
- Sanders Park
- Silver Lake Vacations
- Spinning Top and Yo-Yo Museum
- Twin Lakes Vacations
- Washington County Fair Grounds
- Whitefish Bay Vacations
- Wind Point Lighthouse
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
