Holiday rentals in Rolling Prairie

Hudson lake Cottage: Notre Dame, New Buff, Amazon

Welcome to Gram's Hudson Lake cottage: The perfect retreat for Notre Dame adventures (20 MI), Michigan City beaches (21 MI), and trips to New Buffalo (15 MI) or the Indiana Dunes. Whether you’re here for a family getaway, a football weekend, or corporate travel to the AWS Data Center (7 MI), you’ll enjoy peaceful lake views, a cozy fireplace, and easy access to local attractions. Hudson Lake Beach is 2 miles away, no direct access from the home. *pontoon, kayak & paddleboard rental available!

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.

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!

Mainstay Mini

This apartment was my home for 2 years. It's got all of the essentials on a budget. Offstreet parking steps from your door in centrally located unit walkable distance to bars/ restaurants. Front door opens to your living/sleeping space, continue through to laundry, kitchen and bath with a very small shower further inside. Light sleepers take notice: this unit shares a wall with 2 units and a stairwell. You will hear the wall mounted heat and air unit and other tenants occasionally.

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!

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.

Millie's Rose Cottage

Welcome to Millie’s Rose Cottage, a quaint two-story home, built in 1880, that is included on the National Historic Register in New Carlisle. An old building it may be, but the home offers modern amenities, including Wi-Fi and high-speed Internet. Simplicity is the name of the game. This charming home offers a family-friendly, comfortable place to stay while you enjoy your time in northern Indiana. We are just a few miles from Lake Michigan and the University of Notre Dame.

Relaxing Glamping Experience in a Tiny Cabin

Experience a serene and relaxing getaway in our tiny cabin on our farm. Created with the intention of slowing down (no tv, no wifi and no refrigerator), enjoy wandering the fields relaxing in one of the hammocks, cooking on the outdoor fire pit, sipping coffee on the front deck and generally taking a break from modern life. If you'd like to explore the area, we are nearby popular trails and bike routes, U-pick farms, breweries & restaurants and beaches along Lake Michigan.

LeRoy's Market Boutique One Bedroom

Enjoy a stylish experience at this centrally-located one bedroom apartment. Newly remodeled and furnished in vintage mid-century and modern finds. Located in downtown LaPorte, you are walking distance to shops, restaurants, farmer's market and city events, concerts, trails, lakes and the Dunes volleyball center. The LeRoy's building was built in 1860 and housed a neighborhood grocery for much of it's lifetime and will transition into a boutique hotel in 2025.