Maplewood Vacations from $553

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Your Maplewood Vacation

Discover all the amazing things this neighborhood has to offer with a customized Maplewood vacation package. However you picture yourself spending your days here, you'll find endless opportunities for fun, adventure and relaxation. Start your trip to Maplewood with a visit to nearby attractions such as Fowler Lake Park, Oconomowoc Arts Center and Oconomowoc Golf Club. Expedia will help you turn your ideal Maplewood vacation into reality, whatever your budget or travel plans.

The Latest Maplewood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
County Clare Irish Hotel & Pub

County Clare Irish Hotel & Pub

2.5 out of 5
Downtown Milwaukee
Price was $675, price is now $553 per person
$553
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.6/10 Exceptional! (1,008 reviews)
The room was great. The bathroom is sectioned off with dividers rather than separate (the toilet has a door). Parking was tight and info said if you had to double park to give your keys to staff to move your car if necessary (thankfully we found a spot). We had dinner in the pub and our server was incredibly nice. Breakfast was complimentary in the pub; it was fairly limited (various bread and fruit) but they made great omelets.

Reviewed on Oct 13, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $1,210, price is now $930 per person
$930
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.2/10 Wonderful! (1,014 reviews)
Great reuse of available building. Thoughtful layout with carefully constructed design elements make for a comfortable environment. Nice bar and restaurant spaces lend to an easygoing atmosphere. I’ll be back again when in town next time.

Reviewed on Oct 10, 2025

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was $831, price is now $655 per person
$655
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9/10 Wonderful! (1,362 reviews)
The variety of food options were very nice to have .

Reviewed on Oct 13, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $746, price is now $597 per person
$597
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.6/10 Exceptional! (411 reviews)
Fun location. Fun interior. Bay View has a strip of stores, lots of food options and one right downstairs. Room was fun though TV would not turn off unless you unplugged (and I was traveling with high tech daughter so it wasn’t just me). Also a fan blew constantly even when air off and no call for heat. Okay for white noise if that’s your thing:) I do love reimagining older buildings so yes, would stay again if in Milwaukee.

Reviewed on Oct 13, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $744, price is now $599 per person
$599
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.8/10 Exceptional! (2,405 reviews)
Love the love music and dancing

Reviewed on Oct 13, 2025

Maplewood Hotel Deals

3 Bedroom Okauchee Lake

3 Bedroom Okauchee Lake

Oconomowoc
9.4/10 Exceptional! (15 reviews)
Lakeside apartment
"Nice apartment close to our family reunion on a nearby lake. It was above a lively bar but we stayed late at the reunion so were not disturbed by the bar noise. Nice views and well-equipped kitchen. Need to be able to climb a flight of stairs to access the apartment."

Reviewed on Jul 18, 2025

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3 Bedroom Okauchee Lake
Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!

Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!

3 out of 5
Oconomowoc
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Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!
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
Fully refundable
$101 nightly
The price is $117 total per night from Oct 23 to Oct 24
$117 total
Oct 23 - Oct 24
Total with taxes and fees
8.6/10 Excellent! (1,157 reviews)
"Everything was excellent"

Reviewed on Oct 12, 2025

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI
See all 271 properties in Maplewood
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Maplewood

Fowler Lake Park

Explore the great outdoors at Fowler Lake Park, a lovely green space in Oconomowoc. Visit the shops or attend a sporting event in this relaxing area.

Fowler Lake Park

Oconomowoc Golf Club

3/5(2 reviews)

Enjoy a round of golf in Oconomowoc at Oconomowoc Golf Club. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Golf Club

Oconomowoc Historical Museum

You can spend time browsing the exhibits at Oconomowoc Historical Museum in Oconomowoc. Visit the shops in this relaxing area, or simply enjoy its restaurants.

Oconomowoc Historical Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.