Vacation rentals in Waukesha County

Exhale, rest

Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Private Guest Apt - .4 miles to Downtown Delafield

Welcome to your peaceful retreat in Delafield! This new-construction, 600 sq ft private apartment offers a perfect balance of comfort, privacy, and convenience. Although attached to our single-family home, the apartment is completely separate with its own private entrance, dedicated parking spot, & quiet setting just steps from the lake. Located within walking distance to downtown Delafield, you’re close to fantastic restaurants, boutique shops, coffee spots, and scenic walking & biking paths.

The Cozy Coop | Private Upstairs Retreat | Sleep 8

Wake up to sunrise over a peaceful backyard and enjoy your morning coffee off the balcony. Evenings are perfect by the fire pit under a starry sky. Just 5 minutes from Pewaukee Lake This private upper level comes with a large fenced in yard - ideal for relaxing and spending time together. Open-concept living, kitchen, and dining area creates a warm, inviting space to gather. Sleeps up to 8 and is best suited for small families or close-knit groups who prefer a more cozy, intimate layout.

Black Squirrel Farmhouse - (Downtown Oconomowoc)

Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

Beautiful home on Okauchee Lake, WI

I have a beautiful home on a fun lake. It is just 25 mins from Milwaukee and 50 mins from Madison. There are several bars and restaurants on&off the water; you can either walk, drive or boat to. I have a boat slip available if you want to bring your own 18' or smaller boat. There is a fire-table on the patio for those quiet nights sitting out under the stars. Winter is spectacular here too. Nearby is the Nashotah Park, with a dog park and hiking trails. Lions park has an area for parties.

Beautiful Home in Waukesha

What a wonderful location with a view from the front porch and a park in your back yard. Beautiful Brazilian Tiger wood floors in dining, living, and family room. Spacious family living area has an attractive gas fireplace as it's center point that is open to kitchen area. Off the dinette the three pane patio door has private woods view and patio area. Workout equipment in rec room. Minutes from lakes and hiking paths, Old Town Waukesha boutiques, and restaurants. Quick access to I-94

Lake Country Retreat| Shared Pier Access|Lake View

Just steps from the shores of Lake Nagawicka, this cozy home offers the perfect blend of relaxation and adventure. Enjoy a shared pier for kayaking, paddleboarding, or lakeside lounging. Minutes from downtown Delafield and endless activities. Rent from our preferred boat partner or bring your own, boat slip available for minimal cost. Ideal for couples or small families. Whether you’re looking to unwind, explore, or make lasting memories by the water, this inviting getaway has it all.

The Loft @ The Butler Place. 1846 homestead.

The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

2-acre retreat steps from Nagawicka Lake

Private Lake Country Retreat on 2 Acres | Pool, Park & Prime Location Relax at this private Lake Country retreat on 2 secluded acres surrounded by mature trees. Enjoy a private outdoor pool, spacious yard, and peaceful setting just steps from a county park with trails and a public beach. A nearby boat launch makes lake days easy, while shopping, restaurants, and coffee spots are only minutes away. Perfect for families, couples, or extended stays seeking privacy with convenience.

Garden Retreat in law Suite

Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Historic Luxury |Walk to Downtown| King bed |Shops

✨ 1870s Elegance Meets Modern Comfort | Steps from Dining & Shopping ✨ Welcome to Downtown Delafield’s most charming and highly-rated historic stay! This stunningly restored 1870s apartment offers a luxury experience with vintage charm, all within walking distance to top-rated restaurants, boutique shops, and lakeside trails. Whether you’re visiting for a romantic escape, work trip, or weekend getaway, this unique property is designed to make your stay unforgettable.

Historic Downtown Gem| Walk to Dining, Shops, Lake

✨ 1870s Elegance Meets Modern Luxury ✨ Welcome to Downtown Delafield’s most sought-after Airbnb stay! This beautifully restored historic apartment offers a 5-star luxury experience with original 19th-century charm and modern amenities—all within walking distance to the best dining, shopping, and nature spots in the area. Bonus perk: this cozy gem is perched just above one of downtown’s favorite restaurants—so you’re literally steps away from an unforgettable meal.