Vacation 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!

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

Luxury meets nature: forest cabin steps from the beach, 1 hour from Chicago. Book your escape to our designer log cabin on Lake Michigan just steps from the beach and nestled in a peaceful forest, it’s the perfect retreat. Built in 1932, our charming cabin sleeps 8 in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit, games, puzzles & books. Featured in Country Living and the NYT, it’s perfect for families, friends, or retreats. Book now and create lasting memories in Michiana.

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.

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***

Private Nature Retreat Abutting MI Harbor Country

Relax and unwind at this peaceful and centrally-located nature retreat. The Ripple 'Loft' is a modern, spacious 2 bedroom, 3 bathroom home tucked away on private acreage in the storied 1000 North corridor of Hesston, Indiana just south of the Michigan border. Perfectly positioned to enjoy all of the vast amenities that SW Michigan Harbor Country and NW Indiana have to offer. Reconnect and create new memories with your family and closest friends. This is the upper, main level ONLY.

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!

Luxury home with pool.

Plan your next family gathering, winery tour, football weekend, or simply hang by the pool (seasonal) in this spacious and well-appointed home. Perfectly located in the charming town of New Carlisle, approx 16 miles to New Buffalo, Michigan, and approx 17 miles to Notre Dame. This spacious, tastefully decorated home features a gourmet kitchen, private office, large family room with gas fireplace. The outdoors boasts a heated in-ground pool (seasonal), bbq, and wood-burning fireplace.

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!

The Bank- Historic Charm | Modern Stay

Step into a unique short-term rental experience at this newly renovated mid-century modern property, originally a bank. With 3 spacious bedrooms and 2.5 bathrooms, the home features an open-concept layout perfect for entertaining. Outdoor entertaining is a breeze in the covered gathering area, formerly the bank's drive-thru. The property also offers abundant parking, making it easy to accommodate larger groups, and includes an EV charger for guests driving electric vehicles.

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.

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.