Ski-in/Ski-out holiday rentals in East Troy

Willow Springs Loft @ Wern Valley

Looking for that beautiful once in a lifetime opportunity to sleep in the hay loft? Look no further. No expense has been spared in the space. It is beyond beautiful with every rustic feel you can think of, yet extremely classy. Railings made from cattle stanchions, shower heads that are watering cans and sinks from wash tubs. The evening view of deer and turkeys in the valley from your 30 foot deck is priceless. Ride your ATV to Wern Valley Sportsmen’s Club for a pheasant hunt or clays shooting.

Sunset Lakefront Cottage in Fox Lake w/ Boat Pier

Come relax at this tranquil lakeside retreat. This spacious ranch-style cottage features a large, west-facing, fenced-in lawn that’s perfect for games and over-the-water sunsets. Three bedrooms make the space comfortable enough for the whole family, or even larger groups. Swim off the dock in a no-wake zone, or take the kayaks or paddleboard out for a paddle around the bay. Come see for yourself what it’s like to live the lake life! Bring Your boat and fishing poles. Enjoy our lakeside firepit.

Beachkonong gr8 sunrise n shine

The place is right on Olson's Bay w/great lake frontage sandy beach, restaurants, live music, family-friendly activities, and nightlife. My place is good for couples, solo adventurers, business travelers, families (with kids), big groups, and furry friends (pets). Singles and groups 2-16 can be accommodated, single private room with shared access to Kitchen Bathroom, living room and deck, yard and beach. If your party is greater than 16, we can open “End of the road lake house”and ad 8 more.

Founders House - view the slopes of Little Switz

Walk to the slopes of Little Switzerland Ski Area in the Founder's House located at the base of the hill. Recently renovated and designed to maximize beds, this is the perfect place for your ski weekend. Located just 12 miles from Erin Hills and seconds from the Slinger Speedway. This is an occasional use home free from any clothing and other items. This property is owned and operated by Little Switzerland. For lift tickets, rentals and lessons, book in advance and save at LittleSwitz.com

The Eastpoint Suite 2| Walk to the Lake & Town

The Eastpoint offers meticulously designed rooms that showcase a stunning mid-century modern aesthetic, blending timeless elegance with modern comforts. Located within walking distance of both the lake and downtown Lake Geneva, our boutique lodging invites you to be among the first to enjoy while we continue to build out a destination that will soon be recognized as Lake Geneva's newest and most exciting hotel experience. Room 2 features a King bed, cozy seating area and spacious bathroom.

The little Green Birdhouse-McFarland/Monona

Adorable tiny house located just 1/2 block to Lake Waubesa with public lake access. It's a 1/2 mile walk to the Yahara bike path, access to the Capital City bike path and into downtown Madison. Spacious, open living room. Open concept kitchen with butcher block countertops. One bedroom with an attached full bath. Laminate hardwood floors throughout. 2 car parking pad. Large backyard with a firepit, brand new fence, and a nice view of the lake. The neighborhood is quiet and welcoming.

End of the road Lake House/ Super Quiet.

Best sunrises west of the Atlantic. Close to Madison (30mins), Milwaukee (85mins) and Chicago (120mins) Rustic cabin feel, Vaulted ceilings, Single over Full Bunk bed, queen, full and leather couch and room for air mattresses. Perfect for 1 to 8 guests. Super large shared backyard leads to the lake with a sandy beach. (unique property comprised of a 2br/1ba cottage and a house 2br/2ba joined together by a Great Room built to seamlessly connect the two)

Country cabin, birders paradise.

Country cabin with small kitchen, SMALL BATHROOM, large porch, gardens and birds galore. Located in the country just south of Madison WI. Enjoy the country life, quiet yet close enough to the city to enjoy Madison's activities or Stoughton's Opera House. Sauna, Fire pit, hiking, ask about pets. WiFi is available but not reliable, this is a country setting with slow connections. Please communicate with me regarding pets before booking.

Aprés House - On the slopes of Little Switzerland

Walk to the slopes of Little Switzerland Ski Area in the Aprés House located near the base of the hill. Recently renovated and designed to maximize beds, this is the perfect place for your ski vacation. Located just 12 miles from Erin Hills and seconds from the Slinger Speedway. This is an occasional use home free from any clothing and other items. This property is owned and operated by Little Switzerland.

Vessel: "Freckled Fin" - East Dock 1, Slip 29

Freckled Fin Marina Boat Rental Sleeps 4 guests, perfect for couples. Spacious deck, heated pool, hot tubs, close to the beach. Cozy stateroom, private deck, perfect for a romantic getaway. Book your stay today!