Holiday rentals in Rolling Prairie

The Walnut House, Michigan Woods Retreat

Beautifully designed home, surrounded by trees. 5 minutes drive from the white sandy beaches of Lake Michigan, and conveniently close to historic Three Oaks downtown: Journeyman whiskey distillery, Acorn Theater, Froehlich's bakery and deli, Patellie's pizza and more. The home has beautiful large windows in every room and bedroom. It is well stocked with books, thoughtfully appointed rooms that are perfect for a quiet escape, family retreat, and home base for exploring the areas activities.

La Casita De Lago

Welcome to LaCasita De Lago! Charming lakefront home north of Laporte. Enjoy the serene lake view and sunsets from the spacious back yard and unwind by the firepit overlooking the water. Natures beauty at your door steps. LaCasita is located at a perfect half way point to all the NW Indiana attractions. House is located 35min from Notre Dame, 20min to Michigan Wineries and 20 min from the Dunes. Relax in this comfy Casita which comes with modern amenities, high speed wifi & so much more!

Luxury Country Retreat for Romantic Escape, Creek

*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

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country

Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

Steps to the Beach! Screened in Porch & Firepit!

Experience the ultimate Harbor Country getaway! Just a 90-second stroll to a public beach access and under 5 minutes to another, this location is unbeatable. Spend your day soaking up the sun, kayaking, paddle-boarding, antiquing, golfing, or climbing majestic dunes. Discover endless local breweries, wineries, and top-rated restaurants. Unwind in the evening on the spacious screened-in porch or by the cozy firepit. Your perfect retreat awaits - adventure and relaxation all in one!

Pure Michiana - Rustic & Cozy - near the stateline

Ideal for a peaceful, low-key getaway. Sleeps 8 and is close to breweries, wineries, Indiana Dunes, Three Oaks and over an hour from downtown Chicago. Outdoor amenities include a firepit, hammock, grill, and seating. Max 10 people on property at all times (includes visitors). No parties or events. Unauthorized gatherings will result in immediate cancellation without refund. Not a party house — perfect for respectful guests seeking a relaxing lake-area retreat.

Welcome to Blue Buff! Pet Friendly/Firepit/Fenced!

Enjoy this nicely appointed 3 bed/2 bath. Spacious kitchen open to comfy living room. Basement houses a comfy rumpus room. Have fun playing board games, watching tv, & games like Jenga, checkers. Enjoy the fenced yard, playing bags & putting green, grill, & firepit after you come home from a day of touring wineries/breweries, shopping in the local stores, galleries, antique stores, & casinos. Noise machines provided. Pet fee $150 flat, 2 pet max. License # Cr230049

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!

Dog Friendly Downtown Three Oaks Cottage! Fenced!

Just a short walk to charming downtown Three Oaks, home of the famous Journeyman’s Distillery and all the shops and eateries Three Oaks has to offer. It is also a quick drive to the beautiful beaches at Warren Dunes State Park and New Buffalo. This cheerful home has queen beds and a fully stocked kitchen. Plus a huge fenced-in back yard, so bring the kids or the dogs and know they are safe while you relax in the three-season room or on the outdoor deck!

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.

Renovated french country lake home. 6bedroom/4bath

6 bedroom/4 bath renovated country french home on private Horseshoe Lake. 5 min to historic La Porte and Pine Lake. 20 min to South Bend, 15 to New Buffalo/Lake MI. 1 min to public golf course. Perfect location to access water, towns, beaches, state parks/hiking and gorgeous wildlife. Lawn games, outdoor decks, grill, game room and more. Ideal for family getaway, or week-long stay. Beautiful large private lake (no boating/swimming).

Your SW Michigan Modern Farmhouse Cottage Awaits

Located in Sawyer, you can bike or drive to countless beaches, breweries, wineries, distilleries, and outdoor adventures. Afterward come home to this stylish modern farmhouse cottage that looks out onto 14 acres of scenic barn, pasture. and woods. Your home away from home has a well appointed kitchen for foodies who like to cook or great local dining options for those who don't.