Holiday rentals in Rolling Prairie

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Top-rated holiday rentals in Rolling Prairie

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Top guest favourite
A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.
Farm stay in La Porte
4.99 out of 5 average rating, 533 reviews

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.

Top guest favourite
A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.
Guest house in Valparaiso
4.99 out of 5 average rating, 160 reviews

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!

Top guest favourite
A spacious luxury home is surrounded by lush trees, showcasing a multi-level design with large windows. Soft exterior lighting illuminates the deck and pathways, creating a warm ambiance. The stone perimeter adds a natural touch to the inviting outdoor space.
Holiday home in Buchanan
5 out of 5 average rating, 87 reviews

Luxury Waterfront Home w/hot tub in Harbor Country

Kick back & relax at Lost Lodge, a spacious, very private luxury home on 10 acres of woods, groomed trails, & a 5-acre peaceful lake. Slip into the hot tub with a glass of wine & enjoy lakeviews from the expansive deck. When the sun sinks low, gather at the firepit to relive your memories of the day. You'll be near wineries & U-pick farms, minutes from Lake Michigan's finest beaches & quaint lake towns full of boutiques & restaurants. Notre Dame is 30 mins away & Redbud Motocross is 5 mins away.

Guest favourite
The exterior of the cottage is surrounded by lush greenery, featuring a stone chimney and warm-toned siding. A small seating area with a lounge chair and table is positioned on the well-maintained lawn, creating a welcoming outdoor space.
Cottage in New Carlisle
4.89 out of 5 average rating, 102 reviews

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!

Top guest favourite
A welcoming entrance features a bright yellow door against a mint green facade. Brick steps lead to a patio area, adorned with potted plants and a vintage cooler. The sun casts a warm glow over the peaceful lakeside view.
Home in La Porte
5 out of 5 average rating, 169 reviews

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.

Top guest favourite
An outdoor patio area is surrounded by tall trees, featuring a fire table at the center. Several cushioned chairs are arranged around the table. String lights hang above, illuminating the space, while a grill is positioned nearby, contributing to a relaxed environment.
Cottage in New Buffalo
4.96 out of 5 average rating, 71 reviews

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***

Top guest favourite
The cabin exterior features a wooden facade with a sloped roof and a welcoming front porch. A bench sits on the porch, surrounded by potted flowers. Warm light from string lights enhances the inviting entryway, set against a backdrop of open grass and distant trees.
Tiny home in New Carlisle
4.99 out of 5 average rating, 210 reviews

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.

Top guest favourite
A modern house is situated amidst lush greenery. A wooden walkway leads to the entrance, framed by trees and underbrush. Large windows reflect natural light, blending the structure harmoniously with its surroundings while offering a glimpse of the cozy interior.
Cabin in Michigan City
4.97 out of 5 average rating, 296 reviews

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!

Top guest favourite
A welcoming entrance is showcased, featuring a wooden door with large glass panels and modern light fixtures. The covered porch offers a spacious wooden deck, surrounded by greenery, providing a serene setting for relaxation.
Home in New Carlisle
5 out of 5 average rating, 49 reviews

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!

Top guest favourite
A rustic cabin exterior is framed by dark wood siding and features a welcoming porch. Two rocking chairs are positioned beside the entrance, adorned with potted flowers. Sunlight streams onto the porch, enhancing the inviting atmosphere.
Cabin in Walkerton
4.99 out of 5 average rating, 103 reviews

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!

Guest favourite
The exterior of a modern tiny house is seen surrounded by trees. Soft lighting strings hang above a fire pit with four Adirondack chairs arranged around it. Smoke rises from a fire, creating a cozy outdoor space.
Tiny home in Sawyer
4.92 out of 5 average rating, 147 reviews

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.

Top guest favourite
A unique gazebo with a rusted metal roof is surrounded by lush trees, providing a sheltered space for relaxation. Four chairs are arranged around a fire pit in the center, and flower baskets hang from the sides, adding color to the peaceful outdoor setting.
Barn in New Carlisle
4.97 out of 5 average rating, 159 reviews

Be Our "Country" Guest

Welcome to "Be Our Country Guest". Our family has farmed for well over 100 years and have received the Hoosier Homestead Award. The property is surrounded by farm fields and woods. Enjoy the quiet of the country, but close enough to many restaurants just minutes away and many other activities. We are within 30 minutes to 3 state parks, Notre Dame, South Bend, LaPorte, Michigan City, IN and New Buffalo, Union Pier, Three Oaks, Sawyer, MI.

Popular amenities for Rolling Prairie holiday rentals