Holiday rentals in Rolling Prairie

FARM 10 acres, pond, Hot tub, king bed 30 min ND

Come to the farm for peace, quiet, nature walks, bird watching, and fishing in the spring-fed 3-acre pond and find a new sense of calm. All you need is to build a fire, then sit back and relax. Winter or summer, the farm offers 10 acres of space to run around with your pups or bags, frisbee, and even a bit of golf. Kayak or canoe, too! So many wineries, bike trails, and parks are close by. End your day with a relaxing, stargazing hot tub overlooking the pond. Enjoy! 10 min east of Three Oaks.

McComb's Cabin, Union Pier, MI

Giant trees welcome you down the drive back to the cabin in the woods. The cabin, along with my house and a small cottage reside on the 2 1/2 acre property. A contemporary cabin of steel and pine with vaulted ceiling and sky lights. Open living space, inviting queen size bed, luxury rain shower, full kitchen but no stove. A wood burning fireplace- fall through end of March and outside fire pit. Public beach a 5 minute drive away. Couples check out the cabin for anniversaries & special days.

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

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.

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!

Lux, Hot Tub, Restore, Calm, Creekside, Escape

*Escape to your private couple’s retreat. *Whether sipping coffee at sunrise or star gazing, The Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug to reconnect

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!

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.

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.

Dog Friendly Downtown Three Oaks Cottage! Fenced!

Just a short walk to charming downtown Three Oaks, home of the famous Journeyman’s Distillery and all the shops and eateries Three Oaks has to offer. It is also a quick drive to the beautiful beaches at Warren Dunes State Park and New Buffalo. This cheerful home has queen beds and a fully stocked kitchen. Plus a huge fenced-in back yard, so bring the kids or the dogs and know they are safe while you relax in the three-season room or on the outdoor deck!