Holiday rentals with a home theatre in Wisconsin

Schoolhouse Straight Inn-three level school

Welcome back to school! This rustic remodel of 1925 schoolhouse has two full apartments, rented together or separately. Located on Elkhart's original road track just off the Ice age trail. Great for family reunions, special occasions, golf outings, team building or racing teams! Upper garage deck with Hot tub running year round. Large whirlpool tub with bath salts in upper bath. Keep your eyes out for cool cars still driving the track! There are country views through out the 3,000 sq ft space.

Castle Vineyard | Luxe Spa • Golf Sim • Theater

Stay at one of the most Wishlisted Airbnbs in the world. Featured in Men’s Health and on the cover of Haven magazine, The Castle Vineyard is a world-class destination 🍇 20-acre estate w/ vineyard, spa, & sauna 🎬 Private theater, arcade, PS5 & golf simulator 🍽️ Chef’s kitchen w/ Viking appliances 🔥 Fire pit, patio, hot tub, wildlife views 🏰 "Felt like royalty... every detail was magical" 🎉 Entire property is yours — guests may inquire about our exclusive Tasting Room for special events

New Modern Chalet(19 people)Theater. Sauna.Games

Sleeps 19! New home! Sauna, Movie Theater, games, Free Standing tub. Thought out for relaxation/family memories! You will not want to leave! Set in a beautiful vacation rental community 5-10 minutes from everything...downtown dells, America's largest waterpark, and all resorts! Spacious driveway to fit all of your cars. This is a wonderful place for family and group get togethers! Dells Trolley tours/ Golf/Land of Natura waterpark/theme park/ available at a discounted rate! in home chef $

Frontier Hideaway - 5 acres!

Come relax at our peaceful home nestled on 5 acres with no neighbors in sight. Space is clean and cozy, and offers guests' 4 bedrooms, 2 full bathrooms, and boasts an amazing 3 car detached garage converted into a Bar/Rec Room/Game Room with arcade games, ping pong, and activities for the whole family to enjoy. We are smoke free, with Wi-Fi, TVs, Firepit, Heat, A/C provided. Children of all ages welcome! Pets welcome for an additional fee. 9 min to Sister Bay, 15 min to Washington Island Ferry.

The Retreat: 5 Acre Log Cabin

Escape to this beautiful 5-acre country retreat, located a short drive from Lauderdale Lakes, Alpine Valley, and Lake Geneva. The cabin features two kitchens, two family rooms, a year around hot tub, a game room, an arcade, and five bedrooms with comfortable king-sized beds. The master suite also includes a steam room for added luxury. Spend your days enjoying the great outdoors with a game of beach volleyball or roasting marshmallows around a bonfire, while taking in the fresh midwestern air.

Spacious Milwaukee Duplex with AC and Parking

Ideal for Families & Business Travelers! Find solace & peace in this Sunny Multi Family; a Historic Milwaukee Duplex. Conveniently located to entertainment, transportation & local attractions. Easy access to I-43 & I-94. Flexible stays, as low as one night! Fully equipped & furnished. Fast wi-fi, whole house water filtration (Aquasauna), ceiling fans in high ceilings, central air-conditioning, secure parking, free laundry, garage, private fenced patio with fire pit & covered grand balcony!

We Call It "The Farmhouse"

Relax and recharge with the whole family at our beautiful country estate! This unique and peaceful property is just minutes from shopping and restaurants, yet maintains the quiet charm and rural feel that is quintessential Wisconsin! Enjoy the tranquil view of a sunrise while horses pasture out back or deer browsing at the forest edge in the waning hours of daylight. Your children or pets will appreciate the fresh air, freedom to roam and safety provided by our fenced in back yard.

Secluded Spread Eagle Sanctuary

Executive home lower level nestled in a private sanctuary of unique trees and shrubs. Right off ATV trail, river access with public boat launch. Extra parking for a boat, trailer, etc. Private entrance into furnished 14x24 bedroom with full bath, great room w/ 52" tv wifi, second split king size bed, fully stocked kitchen with dishes, pans, keurig, etc. dining table for 4, full stove, micro, fridge & dishwasher. Light & Airy patio doors onto lighted, covered patio with fire pit.

HOT TUB~KingBed~PoolTable~PokerTable~BatmanMovieRm

Gather with loved ones in a small neighborhood just beyond Manitowoc city edge. Convenient access to Manitowoc and nearby towns. Just minutes to I-43, making trips to Whistling Straits or Green Bay (20–30 mins) a breeze. Enjoy the perfect blend of privacy and ease. The home’s layout is ideal for traveling professionals & families, with three bedrooms each paired with a full bath. Everyone gets their own space. Infant and toddler gear is available upon request for added comfort.