Lake house holiday rentals in Pewaukee

Bark Lake, Entire Home, Private Lake Frontage 50ft

A 1,700 sqft home with 3 bedrooms, 2 baths, sofa bed and couch, large outdoor deck, hot tub, grill, 50 feet of lake access. Enjoy the morning sunrise from the East and relax by the waterfront and watch the sunset on the West. Bring the family and enjoy some lake life where the days linger on longer. During the Summer months we have a pier available to fish off of. There are two fire pits, one by the lake and another tucked away near the house. You will love it here, it is very calm and relaxing.

Lakefront Views, Walk to Dining | Kayaks + Firepit

Wake up to sparkling water views, spend your days enjoying the amenities, and end the evening with dinner, drinks, and music—all just steps from your door. Welcome to Water’s Edge Cottage! Our lakefront home offers unbeatable views, lake amenities, and one of the best locations in Lake Country—perfect for guests who want to relax and enjoy everything the area has to offer. Whether you're here for summer lake days, fall sunsets, or a cozy winter reset, this is memorable lake living at its best.

Close to Lake with Great Ammenities & Breakfast!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

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.

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.

Cozy Modern Lake Cottage 3 baths and Pet Friendly

Our modern farmhouse-style cottage on Lake Tichigan is fully renovated. RARE, featuring two en-suite bathrooms - say goodbye to waiting times! Our cottage offers an idyllic escape with stunning lake views from every room.. Sleeps 8, pet-friendly, fully stocked kitchen. Enjoy shared lakefront, pier, and pontoon rental (May-Sept). Perfect for groups—check our profile to rent both cottages on the same premise! 30 mins fr. Alpine Valley & Rock Snow Park 30 mins fr. Mke 1 hr fr. Chicago

Lakefront Cabin in the Woods (fully fenced yard)

Unwind at this peaceful hilltop getaway overlooking Lake Wandawega. Sip your morning coffee on the enclosed porch surrounded by fresh air and birdsong, a perfect anticdote to city hustle. Bring your furry friend along, the securely fenced yard makes this spot stress-free. Adventure awaits: explore the rolling Kettle Moraine landscape or discover nearby towns like East Troy, Burlington, Whitewater, and Lake Geneva. Whether you’re here to relax or roam, this is your ideal escape!

Beautiful home with amazing Lake Michigan views

Historic home with modern upgrades that has gorgeous views of Lake Michigan. The home was recently upgraded with amazing features including two gas fireplaces, high end kitchen finishes, and a spa style primary bathroom with heated floors. The house is located in the Southside Historic District, steps from the lake, and a short walk to downtown Racine. You can enjoy the local restaurants and shopping, explore the lakefront, or stay in and relax in the peaceful home.

LakeLife is Dam Good! 4 Bedroom Waterfront Home

Fun for the whole family at this stylish lakeside home in the heart of Beaver Dam. The house as everything a group needs and wants for the perfect weekend, week, or overnight adventure. From the open floor plan living room to the exposed game room basement that leads right out to the lakeside yard. We've filled this home with all the touches needed to guarantee lake life living. The backyard overlooks thousands of acres of lake with endless lake views.

Bright 3BR w/ Garage in Bayview (The Owl House)

Sunny upper duplex with AC in the heart of Bay View, just blocks from South Shore Park. Enjoy the entire top unit with 3 bedrooms (queen in master, 2 rooms with twin-to-king beds), a spacious living room, fully stocked kitchen, and washer/dryer. One-car garage included. Walk to restaurants, bars, coffee shops, and public transit. Perfect for families, no parties. Not handicap accessible (one flight of stairs).

Quiet Lake Country Retreat

Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Pabst farms, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open and 2025 US Women's Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison.

Okauchee Lakefront Cabin Escape

The perfect lake house for a family or a group of friends: kayaks, fire pit, gas grill, bags, jukebox, darts, bumper pool and sunsets on the deck. Near Erin Hills for golfers (15 minutes). Down the road from the Kettle Moraine hiking trails (10 minutes) and the Nashotah dog park (5 minutes). Several bars and restaurants within 5 minutes. The very best in lake life, outdoor life and night life.