Holiday rentals in Rolling Prairie

-The District 5 Schoolhouse-

The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

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!

Off Grid Yurt Glamping on Permaculture Homestead

Stay in our stylish yurt for a one of a kind "glamping" experience on a 20acre homestead! The perfect location on the Southwest Michigan wine trail and just 15 minutes to Lake Michigan beaches! Awesome ammenities - off grid solar power, private outhouse, outdoor shower, fans, fridge, grill, firepit, and more. Take the tour, meet sheep, horeses, chickens, rabbits and learn permaculture. Order our delicious DIY pancake breakfast featuring homemade maple syrup, our organic eggs and pancake batter.

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!

Cabin by the Creek

This little cabin sits on the creek side with a deck overlooking the creek. You will have a woods on one side, and farm animals on the other. It is as peaceful as it gets. Enjoy the feeling and atmosphere of camping with a crackling fire in the fire pit, enjoy a s'more or 2, & a cozy queen bed to sleep in at night. It has a loft that can fit an older child or preteen to sleep. If you love camping and farm animals this is the place for you. It’s the peace you have been looking for!

"Tiny House" Guest House - Great for Couples

"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.

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.

Barn of Three Oaks near Lake Michigan/Journeyman

The Barn is a three bedroom, two and a half bath home. The primary bedroom has an en suite full bath, while the front bedroom has a half bath en suite. Bedrooms are equipped with USB charging ports for three devices as well as a white noise machine. The kitchen is thoughtfully appointed as well, including a Keurig. There are many books, games & puzzles in addition to a selection of records to enjoy. A washer and dryer are also on site as well as an iron and ironing board.