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 57 properties available
A classy 3BR-2½BA home, richly designed with custom radiant heat floors and elegant/cozy furnishings! LR has great views and gas fireplace. Kitchen features all high-end appliances. Each BR is stylish - the Master suite has a King bed and chic bath w/ twin marble vanities and walk-in shower. One guest BR has a Queen bed; the other, bunkbeds (one tw
The White Owl
House Location Harbert
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 5 (16)
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
In the heart of Douglas, this fabulous, spacious loft is a true Vacay Paradise! Stylish and chic throughout, you're in the lap of elegance and comfort, with each room reflecting first-class modern metro decor. The open kitchen has wraparound counters + seating and all the essentials for making great meals. The living room's plush seating + flat-scr
Luxe Loft
Location Douglas
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (1)
Presenting The Townie Cottages, the epitome of lakeside luxury designed exclusively by Kate Marker Interiors (whose work has been recognized by Architectural Digest and Luxe Home). Nestled in the heart of Union Pier, these exquisite cottages offer a blend of rustic charm and modern elegance, ensuring an unforgettable stay. Immerse yourself in a met
Townie 1 - The Ivy
House Location Union Pier
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Filled with magical charm, this 3BR-2BA home will start your vacation right! Main living space has a playful color decor and open design with modern kitchen (stone-top island) and stylish dining and entertainment areas. All the bedrooms-incl. 1 with custom bunk bed plus Qn. bed-are super-comfy. The sleek Master BR has a walk-in shower and balcony.
Wade's Lookout
House Pet Friendly Location Michiana
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 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)
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)
Gorgeous "cabin" on 15 acres of Indiana farmland loaded with amenities: pool, spa, deck, fishing pond, pastures, barn. Spacious, luxurious interior: stainless-steel appliances, custom stonework, fireplace, huge windows. 5 BR, one is main ensuite - priv. bath and deck; 2 more full baths, all lushly styled. Sleeper sofa, Wii-TV, Bluetooth speakers, g
Scout's Haven
House Pet Friendly Location Rolling Prairie
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 12 guests
Rating 4.6 (3)
3BR/3BA lakeside home w/ Nantucket styling, wraparound deck + views galore! Walls of French windows. Vaulted ceilings. Double-sided stone (gas) fireplace. Kitchen has hi-end appliances, granite tops. Upscale-cozy furniture thruout. Main floor has 2 BRs w/ Queen beds. Large loft has 4 twins. Finished basement has King bed + common area w/ Smart TV (
Coastal Cottage
House Pet Friendly Location Stevensville
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 (21)
Welcome to Casa Azur, your ideal vacation retreat in the sought-after Gowdy Shores neighborhood of Union Pier just minutes to popular SW Michigan attractions! This exceptional 5-BD/3-BA residence offers an array of luxuries, including a private pool, hot tub, sun porch, and outdoor shower. Nestled within walking distance of the neighborhood's prist
Casa Azur
House Location Union Pier
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Sumptuous 4 BR/2.5 BA vacation home 1 block to Lake Michigan. Fully refurbished: reclaimed flooring, antique beams, custom doors and fixtures. High-end kitchen-DR-LR has entire walls of French windows. LR features stone fireplace, stylish couches, wide-screen TV. 3 BRs and BAs on ground floor w/ 2nd-flr bunkbed sleeping loft. Detached garage is a p
Black Door Bungalow
House Pet Friendly Location Lakeside
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 10 guests
Rating 5 (22)
Mile-wide Lake Michigan views and a great open floor plan make this 5BR/4BA lakefront home a vacation dream come true. A heated pool, hot tub, fire pit, balconies, decks and most rooms in the house all feature lakefront vistas that can’t be beat. Spend mornings, afternoons, and evenings outdoors on the deck enjoying the fresh air and sounds of wave
Coastal Escape
House Pet Friendly Location New Buffalo
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half Bathrooms 1 half baths
Guests 12 guests
Rating 4.8 (38)

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