Holiday houses in West Bend

Waterfront Retreat *Gazebo*Private Deck*Fireplace

Imagine waking up to peaceful sounds of nature, stepping onto your private deck with a hot cup of coffee, & watching the morning light dance across the pond & gardens. Nestled on a charming 1880s homestead, our Waterfront Country Retreat offers 4 acres of beauty, walking paths, & wildlife. Relax by the indoor gas fireplace, enjoy the gazebo w/fireplace, or unwind in the tranquility of the countryside—just minutes from West Bend & a short drive to Cedarburg. Perfect for Romantics & Nature Lovers.

Family · Location · Condition

Perfect Balance in Cedarburg Gem

This spacious, private studio apartment offers a perfect blend of serenity and activity. Situated at the back of a 1.25 acre lot, beyond the lovely 1862 stone farmhouse it overlooks, the carriage house is a peaceful getaway -- minutes from all that bustling historic Cedarburg has to offer. Just .4 mile from the OZA Fairgrounds and .8 mile to downtown shops and restaurants, it's a quick drive or an easy walk to many amenities. Relax on the balcony before or after a day of fun sightseeing. Cheers!

Value · Family · Check-in

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

Value · Location · Bathroom

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.

Value · Family · Amenities

Local Landmark CF / Artisan Coffeehouse

Wake up to the aroma of fresh coffee, stroll downstairs for breakfast, then spend the afternoon hiking the Kettle Moraine before returning to a luxurious bed. The iconic Coffee Corner Bistro (Est 1999) is steps from the Wisconsin 9/11 Memorial & Eisenbahn Bike Trail, and is the "Gateway to the Kettle Moraine" Proudly recognized by the Fond du Lac Reporter Travel Section in its June 13, 2026 feature: "Top Airbnb Stays Near Fond du Lac" Google CBS 58 story on our historical Coffeehouse.

Family · Location · Bathroom

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Location · Family · Beach

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Value · Family · Barbecue

Family friendly farmstay just outside Milwaukee

Thanks for your interest in staying with us at the farm! We are currently closed for renovations. We'll update the calendar when we can! The Inn at Paradise Farm is an 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers. We are licensed and inspected. Paradise Farm welcomes all.

Location · Family · Barbecue

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.

Location · Value · Decor

Entire Use of Shalom House

Shalom House, a Frank Lloyd Wright style design, accommodates 1-12 guests with five bedrooms, 4 bathrooms, great room with fireplace, large kitchen, and labyrinth. NEW at Shalom House is WiFi, though the woods is a great place to connect with the world too. Wonderful drinking water and whole house water system. We have both!! *Shalom House is an experience-"a quiet place to be" *Enjoy the beauty of nature, friends, family, relaxation, celebration.

Location · Value · Comfort

2 Bed/1 Bath Condo - West Bend

Experience West Bend, WI like a local in this 2-bedroom fully furnished condo. Step into this welcoming and adorable property- the kitchen in this unit is fully equipped with everything you need, including glassware, kitchen utensils, and pots and pans. Washer & Dryer is available within the unit. One garage spot and one exterior off-street parking spot is included in rental price. Our place is equipped for both long or short stays.

Location · Nearby · Accuracy

GGG Spacious Log Cabin apartment on the IAT

With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated with new floors, paint, fixtures and more, it’s a perfect retreat from the city. Explore the adjoining 500 acres of state forest, with public lake and boat launch across the street for fishing and paddling. The adjacent trail leads right the Parnell Segment of the Ice Age trail and Mauthe Lake State Park.

Family · Value · Sleep quality