Search Deals onPossibility Playground Vacation Packages
Possibility Playground Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Sturtevant/Racine
Price was $509, price is now $445 per person
$445
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Sturtevant. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Apple Holler and Franksville Park are located nearby.
The Pfister Hotel
Price was $1,777, price is now $1,392 per person
$1,392
per person
Aug 28 - Sep 1
found 22 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
Price was $1,267, price is now $1,001 per person
$1,001
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the bar and the helpful staff in our reviews. Popular attractions American Family Field and The Rave-Eagles Club are located nearby.
Potawatomi Hotel & Casino
Price was $1,287, price is now $1,076 per person
$1,076
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and 7 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Potawatomi Bingo Casino are located nearby.
Baymont by Wyndham Mequon Milwaukee Area
Price was $976, price is now $820 per person
$820
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Mequon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Lynden Sculpture Garden and Walter Schroeder Aquatic Center are located nearby.
Hyatt Regency Milwaukee
Price was $935, price is now $787 per person
$787
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.
The Ingleside Hotel
Price was $761, price is now $644 per person
$644
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
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.
AmericInn by Wyndham Brookfield
Price was $674, price is now $572 per person
$572
per person
Sep 10 - Sep 16
found 15 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Brookfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Milwaukee County Zoo and Mayfair Mall are located nearby.
Hawthorn Extended Stay by Wyndham Milwaukee Airport
Price was $731, price is now $622 per person
$622
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Oak Creek. Enjoy free breakfast, free WiFi, and free parking. Popular attractions South Milwaukee Performing Arts Center and South Milwaukee Downtown Market are located nearby.
Embassy Suites by Hilton Milwaukee Brookfield
Price was $1,022, price is now $881 per person
$881
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
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.
The Iron Horse Hotel
Price was $1,208, price is now $1,046 per person
$1,046
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Harley-Davidson Museum are located nearby.
Home2 Suites by Hilton Milwaukee Downtown
Price was $1,092, price is now $966 per person
$966
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions American Family Field and Riverside Theater are located nearby.
3-4 Night Vacations in Possibility Playground
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Possibility Playground
Price found within the past 48 hours. Click for updated prices.
Possibility Playground Last Minute Hotel Deals
The Harborview on Lake Michigan, an Ascend Collection Hotel
135 E Grand Ave Port Washington WI
Book a stay at this business-friendly hotel in Port Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff ...
Sybaris Pool Suites Mequon
10240 Cedarburg Rd, Hwy. 57 Mequon WI
Stay at this hotel in Mequon. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Walter Schroeder Aquatic Center and Lynden Sculpture Garden ...
Chalet Motel Mequon
10401 North Port Washington Rd Mequon WI
Stay at this motel in Mequon. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Country Inn & Suites By Radisson, Brown Deer - Milwaukee North
5200 West Brown Deer Road Milwaukee WI
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Milwaukee River Walk and Walter ...
Four Points by Sheraton Milwaukee North Shore
8900 N Kildeer Ct Milwaukee WI
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Fairfield Inn & Suites by Marriott Milwaukee North
7035 N Port Washington Rd. Milwaukee WI
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
AmericInn by Wyndham Glendale/Milwaukee
5110 N Port Washington Rd Milwaukee WI
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.
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