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!
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.
Aloft Hotel - MIlwaukee
Milwaukee – Downtown hotel on the Riverwalk. Pet-friendly.
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.
The Pfister Hotel
Milwaukee – Gorgeous, iconic Milwaukee hotel! The pool is on the top floor and overlooks the city. Pet-friendly.
Holiday Inn Milwaukee Riverfront
Milwaukee – North Shore. Check out the Kids Stay + Eat Free program. Indoor pool area has been recently renovated.
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.
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.
Hyatt Place Milwaukee Airport
Milwaukee – Located near the MKE airport. Pet-friendly. Pool with large windows for the whole family to enjoy.
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
Milwaukee Marriott West
Waukesha – Conveniently located right off I-94 and close to several area restaurants. Indoor heated pool.
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
Blue Harbor Resort
Sheboygan – Indoor Waterpark, a spa, plus an arcade and mini-golf.
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.
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.
