Holiday rentals in Rolling Prairie

Romantic Getaway in the Dunes for a Couple—Hüüsli

Cozy, charming, romantic and modern. Huusli is the perfect place for a couple to getaway, not too big, not too small. Soaring ceiling with wood burning fireplace greets you in the main living area with an updated kitchen, remodeled bathroom and two adorable bedrooms. Bonus is the four-season room where you can have all your meals or enjoy your morning coffee surrounded by nature, but without the fear of bugs. Make new memories, celebrate an anniversary or just relax in this magical place.

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.

Second Floor Apartment sitting on Pine Lake

My Airbnb is close to parks, restaurant and Sand Dunes. The apartment is in the house on beautiful Pine lake. Please note that the balcony in the picture is not part of the apartment. the pictures are to show the patio of which you have full access. Pets are welcome but there is a $15 charge per pet per night. The fee should be made in advance through the send money. We live in a area that pets must be walked to do bathroom duties. They are NOT allowed on my grass or in flower beds.

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!

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.

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!

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 House" Guest House - No Cleaning Fee

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

Beach Bird Cottage- 5min walk to the lake! 3BR/1BA

Dear friends, Welcome to Beach Bird Cottage, situated on a quiet street with other vintage cottages in the heart of Union Pier. It is an easy 5-minute walk to an association beach. The cottage has many updates, including a new kitchen, bathroom, washer/dryer, outdoor shower and a wood stove. The master and second bedroom each have queen-size beds and the children's bedroom has two twin beds. Enjoy an early swim before breakfast or have an evening beach picnic under the sunset.

Rustic & Cozy House in the Woods - Sleeps 10

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.

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.