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.

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

Welcome to Valparaiso Lakeside Retreat a private getaway on Long Lake featuring a one-of-a-kind outdoor geodesic dome (11 feet), hot tub, fire pit, & kayaks. 20 minutes from Indiana Dunes National Park. Perfect for couples, remote workers & nature lovers seeking a tranquil escape. Enjoy stunning Long Lake views from your private backyard & dome. Long Lake public beach access is just around the corner. Perfect for kayaking, swimming, or a morning walk to the water. Book this unique stay today!

-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!

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.

1 Block to Journeyman | Pets | Dunes & Beaches

Our newly built (2022) home is located just 1 block to Journeyman Distillery and the quaint downtown of 3 Oaks. Our home has been thoughtfully designed to create a serene and memorable stay for our guests. Eclectic shops, restaurants, and galleries are a short walk away. Drive to local beaches in less than 15 minutes. Spend your day exploring Harbor Country - wineries, breweries, hiking, biking, golf, beaches, blueberry picking, antiquing, and so much more. 3 Oaks is at the center of it all!

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 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!

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!

Private Beach Home on Hudson Lake New Carlisle

Relax Disconnect Serene Family Privacy VERY unique destination. Enjoy the amenities of your own private beach & dock , bonfires. Perfect for your intimate getwaway or small family retreat on one of Indiana's cleanest all sports lakes: Swim, kayak, paddle board, fish w/Pontoon Rental availability 3rd party. Historic New Carlise, IN is a small hometown destination with eateries, brewery, shops but close to everything Sunrise/Sunset views are spectacular! Serene neighborhood.

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!