Holiday rentals in Rolling Prairie

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

UncleLarrysLakePlace HotTubKayaksPingPong

A tribute to our favorite world traveler-he's the first to stay at our properties and give us the good, bad and ugly so we can fine-tune the ultimate experience for YOU. This newly remodeled lake home boasts 4 sleeping areas, year-round hot tub, game room with a ping pong table and large screen TV, large gathering spaces in and out, new kitchen and your own kayaks to explore the area. Enjoy sunsets and lake views from the hot tub on the expansive deck or while grilling on the Weber gas grill.

Stay on State 2 bed

This main floor 2 bedroom unit is a great spot for on-the-road professionals. 2 bedrooms with king-size memory foam beds flank a kitchen/living area and one bathroom. Its 1 unit in a 3 unit building so you may hear other guests occasionally. -Shared onsite laundy in the unfinished basement - Ample off street parking can accommodate large vehicles. -Walking distance to several bars and restaurants. Laporte hospital 3 min Dunes Volleyball Club 2 min Amazon Warehouse job-site. 15-20 min

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!

Dog-Friendly Farmhouse | 1+Acre near Lake Michigan

Family friendly farmhouse located just minutes from beautiful New Buffalo beach, golf course, and popular Four Winds casino! Enjoy your own slice of pure Michigan scenery surrounded by tall oaks and beautiful pines. After a day at the beach, fire up the grill and kick your feet up on the fully furnished patio equipped with firetable. Try your luck at the casino or enjoy some smores around the campfire at night. Come enjoy everything the "Acre off the Lake" has to offer! ***Dog friendly***

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!

The Hudson 14mi to New Buffalo!

Escape to The Hudson—a charming retreat near New Buffalo, MI! Enjoy a huge deck, chef’s kitchen, and 11.5-ft ceilings. Just minutes from New Buffalo Beach, local wineries, breweries, and Warren Dunes. Located in the Lake Hudson community, convenient for relaxing or exploring. Fully renovated and being stylishly furnished by July 2025. Please note: landscaping is still in progress as part of our full renovation—thanks for your understanding. Book now to enjoy this new summer experience!

"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.

Modern Minimalist Tiny House | Firepit | Nature

Welcome to our modern minimalist tiny house located a half mile from Warren Dunes State Park beach and 1.5 miles from all that Sawyer Michigan area has to offer. Tiny is the second dwelling on this property and is technically a mobile tiny house. While we do have electricity and water, much like an RV the drains run to holding tanks. This means VERY LIMITED WATER USE for showers and toilet flushing. It features a fully stocked kitchen, bathroom, and a queen bed in the small loft.

Lakeview Suite

Welcome to the "Lakeview Suite" on Hudson Lake! This private first-floor retreat offers two cozy bedrooms with queen beds, a fully equipped kitchen, modern bathroom, and a private entrance. Enjoy your own small outdoor space with a lake view, grill, and firepit. Potentially meet our "neighbors" - the eagle and swans, and potentially rent a pontoon boat for lake adventures. Perfect for a little retreat or a fun getaway. Book today and experience lakeside fun and rest!

Capt Whittaker’s Place! In Downtown New Buffalo!

Escape to Prime Downtown New Buffalo – Just 70 Miles from Chicago! Nestled one street off the main strip with easy parking.Walk to beaches, marina, Amtrak. Chill on prporch with gas fire pit. Rent bikes, boats, kayaks.Grab bites at Stray Dog, Ghost Isle Brewery, Oink's ice cream, Casey's—Shop boutiques, sip local wines, catch harbor sunsets! Stroll Galien River Park's boardwalk or hit Four Winds Casino. Tee off at Warren Golf Course or Whittaker Woods, minutes away.