Maplewood Vacations from $388

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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.
Wildwood Lodge

Wildwood Lodge

2.5 out of 5
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Milwaukee (MKE)
8.4/10 Very Good! (1,006 reviews)
Interstate noise is bad if you are in a room facing it. Also, if you are traveling with a medium- to large-sized dog, there's really not a great place to exercise them. On the plus side, the staff could not have been nicer.

Reviewed on Jul 7, 2025

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 2
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
8.6/10 Excellent! (1,350 reviews)
By the marina and view

Reviewed on Jul 5, 2025

Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Milwaukee (MKE)
9.2/10 Wonderful! (123 reviews)
This property is very unique and like home. The beds are very comfortable. Communications with staff was very easy. Staff was very welcoming.

Reviewed on Jun 26, 2025

Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 2
found 9 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
9/10 Wonderful! (1,000 reviews)
Amenities were excellent, the service was great as well. If you are the first floor you will likely have a lot of issues sleeping. 12am to 6am is quiet hours and it stays quite loud. 1878 was an excellent restaurant.

Reviewed on Jul 6, 2025

AmericInn by Wyndham Hartford WI

AmericInn by Wyndham Hartford WI

2 out of 5
per person
Sep 9 - Sep 14
found 6 hours ago
Roundtrip non-stop flight included
Cleveland (CLE) to Milwaukee (MKE)
8.4/10 Very Good! (484 reviews)
Great location, free breakfast and great rates!

Reviewed on Jul 4, 2025

Maplewood Hotel Deals

Okauchee Lake Vacation Rental w/ Boat Dock!
Okauchee Lake Vacation Rental w/ Boat Dock!
Oconomowoc
Outstanding Outside
"The good: Outside: the dock, swim pad, accessories, deck, outdoor furniture, neighborhood, location. Inside: everything worked, A/C was mostly sufficient with fan blowing into bedroom. The not so good: there is clearly a known ant problem on the center peninsula of the kitchen, saw spray in the utility ..."

Reviewed on Jul 8, 2024

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Okauchee Lake Vacation Rental w/ Boat Dock!
3 Bedroom Okauchee Lake
3 Bedroom Okauchee Lake
Oconomowoc
9.2/10 Wonderful! (10 reviews)
Great
"Great stay!"

Reviewed on Jun 25, 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
Get rates
Lakefront Wisconsin Escape w/ Boat Dock & Kayaks!
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 family-friendly 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.