Vacation rentals in Rolling Prairie

Unique Dome Retreat by Indiana Dunes w/ Lake View

Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

South Bend, 1 Bedroom Cottage Built in 1912

South Bend historic cottage in the National Historic District of Chapin Park. Close to Notre Dame. One dog is welcome. No cats. There is a queen sized bed and a sofa, NOT sofa bed in the sitting room. This cottage built in 1912. Private and cozy, the cottage has a big screen TV, wifi and a gourmet kitchen. The owner lives almost directly behind and is available and happy to assist. Chapin Park's tree-lined, brick streets and diverse historic architecture are charming. No smoking.

Romantic-Hot Tub-Secluded-Scenic-Creek- Wildlife

*Escape to your private couple’s retreat. *Whether sipping coffee at sunrise or star gazing, The Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug to reconnect

Pure Michiana - Rustic & Cozy - near the stateline

NO EVENTS. 10 person max on property at all times. It puts too much wear on the septic/well and deck. Dining table seats 8. 3- block walk to a small shared lake and near a host of lovely spots: Breweries/Wineries, Dunes, Three Oaks, Frisbee Golf, and more. A gas fireplace for cold winter nights, an outdoor firepit, a hammock, grill, and outdoor seating/camping chairs. A short walk to the Nowhere Bar & Grill for great local food! Only 1 hour 15 minutes from Chicago. Sleeps 8 comfortably.

The Little House at Tryon Farm

The little house is located within a 170-acre modern farm community filled with open meadows, woods and dunes. Minutes to beach, 1 hour to Chicago. Relax and enjoy the property or head out to explore the lakeshore, wineries, and great area restaurants! Two bedrooms, 1.5 baths, a fully appointed kitchen, living area w/fireplace, and a large screened in porch. Large windows flood the house with natural light and will make you feel like you're living in the treetops. A perfect getaway!

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

Aunt Betty's Lakeside Abode, Hot Tub Steam Shower

Aunt Betty’s Lakeside Abode offers 3 king bedrooms, 2.5 baths, 2 twin cots, west-facing beautiful Stone Lake views, screened porch with gas fire, lakeside terrace, and year-round hot tub. Enjoy multiple gathering areas, a steam shower, ping-pong. Perfect for families, couples, or groups exploring LaPorte County, Indiana Dunes or wineries, breweries, trails surrounding Lake Michigan. Sleeps 8, or book with Uncle Larry’s Lake Place next door for larger groups and shared lakefront fun!

Tiny Retro Studio for One Person

TINY studio for ONE. Non-smoking inside & out. Our typical guest is a busy academic, intern, medical worker or businessperson. This TINY studio is located in an old 4-unit apartment house, so there is some in-house sound transfer. Our neighborhood is usually quiet, but not always. See the LOCATION section under the map to read a description of our neighborhood. *Winter Note: We shovel the walkways at the Airbnb, but not usually until later in the day. So mornings might be snowy.

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Be Our "Country" Guest

Welcome to "Be Our Country Guest". Our family has farmed for well over 100 years and have received the Hoosier Homestead Award. The property is surrounded by farm fields and woods. Enjoy the quiet of the country, but close enough to many restaurants just minutes away and many other activities. We are within 30 minutes to 3 state parks, Notre Dame, South Bend, LaPorte, Michigan City, IN and New Buffalo, Union Pier, Three Oaks, Sawyer, MI.