Staycation in Milwaukee, WI this Winter | Family-Friendly Hotels with a Pool

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Winter is the perfect season for a staycation! Hotel rates are low and staying overnight in a local hotel with a pool is a great way for your family to break up your regular routine and feel like you are on vacation while staying close to home.

Check in, go for a swim, decompress in the room with some naps or TV and snacks, pick up takeout from a local restaurant, play a board game after dinner, take another swim, snuggle in for a family movie and then hit the sack. The next day, grab breakfast and swim again and then head back home! It’s cost-effective and creates a fun outing your whole family will love while you can also stay safe in this perilous public health environment.

We asked around with other local parents and these are the Milwaukee Area Hotels with Pools that they recommended for a family-friendly staycation!

Staycation in Milwaukee | Family-Friendly Hotels with a Pool

Courtyard by Marriott - Milwaukee Downtown

Milwaukee – Pet-friendly. Large, bright rooms and spacious indoor pool.

300 W Michigan St, Milwaukee | WEBSITE

Aloft Hotel - MIlwaukee

Milwaukee – Downtown hotel on the Riverwalk. Pet-friendly.

1230 Old World Third St, Milwaukee | WEBSITE

Drury Plaza Hotel - Milwaukee Downtown

Milwaukee – Located in the heart of downtown, the Drury Plaza Hotel Milwaukee Downtown is a historic renovation of the 15-story First Financial Centre.

700 N Water St, Milwaukee | WEBSITE

The Pfister Hotel

Milwaukee – Gorgeous, iconic Milwaukee hotel! The pool is on the top floor and overlooks the city. Pet-friendly.

424 E Wisconsin Ave | WEBSITE

Holiday Inn Milwaukee Riverfront

Milwaukee – North Shore. Check out the Kids Stay + Eat Free program. Indoor pool area has been recently renovated.

4700 N Port Washington Rd, Milwaukee | WEBSITE

Hilton Garden Inn Milwaukee Northwest Conference Center

Milwaukee – Located right off I-41 in Park Place Office Park. Full-service restaurant, indoor pool, whirlpool, and sauna.

11600 West Park Place, Milwaukee | WEBSITE

Holiday Inn Express & Suites Milwaukee Airport

Milwaukee – Located near the MKE airport. Pet-friendly. Large pool with basketball hoop plus Children’s Pool with spraying water features.

1400 W Zellman Ct, Milwaukee | WEBSITE

Hyatt Place Milwaukee Airport

Milwaukee – Located near the MKE airport. Pet-friendly. Pool with large windows for the whole family to enjoy.

200 West Grange Ave, Milwaukee | WEBSITE

Homewood Suites by Hilton - Milwaukee Downtown

Milwaukee – One-bedroom suites provide extra space and a separate living area. Some suites are located on the higher floors with great city and river views. Splash pad-style water features

500 N Water St, Milwaukee | WEBSITE

Milwaukee Marriott West

Waukesha – Conveniently located right off I-94 and close to several area restaurants. Indoor heated pool.

W231N1600 Corporate Ct, Waukesha | WEBSITE

The Ingleside Hotel

Lake Country – Located right off I-94 in Pewaukee, local parents love the full-fledged water park inside this hotel.

*Day Passes and Party packages also available

2810 Golf Rd, Pewaukee | WEBSITE

Blue Harbor Resort

Sheboygan – Indoor Waterpark, a spa, plus an arcade and mini-golf.

725 Blue Harbor Dr, Sheboygan | WEBSITE

The Mill Creek Hotel

Lake Geneva – Boutique hotel with condominium-style suites so you can limit your time leaving the hotel. Indoor Solarium Pool and Whirlpool.

123 Center St, Lake Geneva | WEBSITE

Timber Ridge Lodge + Waterpark

Lake Geneva – Fun Family Waterpark Resort. Receive four free waterpark passes with a one-bedroom suite, and six passes with a two-bedroom suite. “Tiny Timbers” water play area for teeny guests.

7020 Grand Geneva Way | WEBSITE

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