Rolling Prairie Vacation Rentals

Rolling Prairie is an ideal vacation destination with plenty of outdoor activities, cultural attractions, and stunning scenery to enjoy. Our homes and cabins are designed to accommodate families or couples looking for a luxury experience in a unique destination with exceptional service. Join us, and stay in one of our exclusively selected Rolling Prairie Indiana rentals.

Properties Available 55 properties available
Whether you need a staycation, workcation, or a getaway, Deer Haus awaits your next adventure. The tranquil cottage is nestled in the woods and yet strikingly close to the heart of New Buffalo. Deer Haus is only half a mile from downtown New Buffalo’s restaurants and breweries, great for a bike ride. Pack up your car or continue to pedal another mi
Deer Haus
House Pet Friendly Location New Buffalo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 6 guests
Picture perfect cottage walking distance to ND Stadium! Our 3-Bed/2-Bath home that sleeps 6 is great for ND visits: Commencement, Parent’s Weekends, Graduation and Fighting Irish games. Fully renovated with stylish furnishings, LVT + tile floors, big Smart TVs on both levels, basement foosball table, and beautiful kitchen has stainless appliances +
Colonel’s Fighting Irish
House Location South Bend
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
This elegant vacation home is a true delight - vaulted ceilings and a stacked stone fireplace make for a heavenly living room, adjacent a 3-Season room-den with flat-screen TV + great views of the wooded property. All 3 spacious BRs are richly styled and comfy, plus chic tiled BAs feature walk-in showers, a soaking tub or dual vanity sinks. The Che
Pete's Place
House Pet Friendly Location Sawyer
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 6 guests
Spacious New Buffalo 4BR/4BA vacation home w/ OMG Lake MI views! Just a few blks from downtown shops, cafes + beach! 3 floors, 2 kitchens, lush social areas + lg backyard. Kitchen on main floor opens to DR w/ fireplace, leading to huge screened porch. 3 well-appointed BRs + 2 full BAs on this level. Upstairs is a Great Room, stone fireplace, wet ba
Sunset Dream
House Location New Buffalo
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 4.8 (50)
Panoramic views of Lake MI from floor-to-ceiling windows are only the beginning! A mixture of Midcentury Modern design and warm wood tones create an inviting lakefront enclave for families and friends. Large grassy backyard, sun deck leading to private beach, outdoor shower! Interior open social spaces overlook Lake MI. Main ensuite has queen bed +
Keck Hill
House Location New Buffalo
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (3)
Located just a 2-min. walk from Lake Michigan’s majestic shores, this pair of gorgeous vacation homes-Wade’s Cabin and Wade’s Lookout-are surrounded by woods and feature spacious open designs, superb styling and furnishings throughout, beautifully appointed and comfy bedrooms (with premium-quality beds and linens) and fabulous outdoor amenities. Wh
Wade’s Lookout and Cabin
Multi-Unit Pet Friendly Location Michiana
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
This luxurious vacation home 2 mins from Lake Michigan beaches has 4 levels of richly designed living space, gorgeous furnishings + so much more! You + your guests can cozy up to a fireplace or watch a flat-screen TV, relax in either of 2 comfy screened porches or dip into the pool or hot tub. Lay out or dine on the spacious deck, chill around a fi
Green Light
House Pet Friendly Location Harbert
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 10 guests
Exquisite 4BR/2BA vacation home in wooded area 1 blk from Lake MI private beach. Richly designed w/ cathedral ceilings, skylights, Great Room + fireplace, hardwood floors, curated furnishings. Hi-end pro kitchen has porcelain counters, prep island, leads to elegant dining space. All 4 BRs are chic-comfy: 3 downstairs (1 King + 2 Qn) + 1 loft-style
The Songbird
House Pet Friendly Location New Buffalo
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 5 (11)
A mixture of modern design, an inviting color palette, and curated furnishings create a sophisticated Harbor Country enclave that will impress even the most seasoned traveler. Owlwood boasts 4 ensuite bedrooms, open social areas, high-end appliances, and indoor/outdoor living brilliantly built around a large private courtyard. Pet friendly w/ a ni
Owlwood
House Pet Friendly Location Harbert
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 9 guests
Rating 5 (1)
This spacious, captivating 6BR/3.5BA home in a golf-cart friendly area has a huge back yard and pool, hardwood floors and a 2-story great room, plus a stone fireplace flanked by huge windows! The gourmet kitchen has a granite-top island and hi-end appliances. The upper-level Master suite features a gas fireplace and private balcony with Lake Michig
Main Destination
House Pet Friendly Location Grand Beach
Bedrooms 6 bedrooms
Bathrooms 3 baths
Half Bathrooms 1 half baths
Guests 12 guests
Rating 5 (23)
This newly renovated vacay home sits on 1.3 acres with a stunning Lake Michigan beach. The gorgeously designed interior, amazing lake views + superb detailing will make you + your guests feel like Heaven on Earth! Its open design features a spacious Great Room, fireplace, flat-screen TV, a wine room, Chef's Kitchen + fab 3-Season dining room. Top-q
Gasthaus Fox
House Pet Friendly Location Bridgman
Bedrooms 6 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half baths
Guests 11 guests
Escape to White Sands, a serene 3-BD/2-BA getaway retreat nestled in picturesque Grand Beach w/ terrific indoor/outdoor living space. The bright main level offers a stylish kitchen-family room-dining area. Treasure mornings and evenings relaxing in the adjacent airy screened porch. A 2nd living room with wood burning fireplace offers addl flex spac
White Sands
House Location Grand Beach
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (4)

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