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
Affectionately nicknamed, “The Douglas Darling,” this classy 4 BR-2.5BA vacation home directly across from Lake Kalamazoo (and 2 miles from Lake Michigan) is a 2-block walk from downtown Douglas’s excellent art galleries, scrumptious restaurants and trendy boutiques. Spacious, modern and loaded with amenities, it features everything you need for a
Douglas Darling
House Pet Friendly Location Douglas
Bedrooms 4 bedrooms
Bathrooms 2 baths
Half Bathrooms 1 half baths
Guests 8 guests
Rating 5 (10)
Fully renovated 3BR/2BA home. Stylish, elegant-comfy furniture, bamboo floors. Chef's kitchen has quartzite counters, hi-end appliances, breakfast nook. Apple TV/theater-style screen in posh LR. Great window views! Plush Master BR has King, deluxe BA: soaker tub, walk-in shower, twin marble vanity. Two guest BRs - 1 Queen, the other has full bunk b
The Birdcage
House Pet Friendly Location Douglas
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 5 (14)
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)
Just a few minutes from a gorgeous Lake Michigan beach, The Cape Cottage invites you to relax in style! The open design LR-DR-Kitchen is elegantly furnished and includes a chic fireplace, flat-screen TV and spacious high-end kitchen for cooking up great vacay meals. The Master BR has an Ensuite BA and the 2nd BA has a soaker tub and walk-in shower.
The Cape Cottage
House Location Union Pier
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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
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)
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
Hot HOT 230
Townie 3 - The Moss
House Location Union Pier
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
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
Premier 3BR-2BA home on 1.5 acres w/ private drive. Oak flrs, stylish furnishings thruout, cathedral ceilings and statement fireplace. Kitchen has hi-end cabinets, double-wd fridg, gas stove. Master BR has King, Smart TV; washer-dryer and upgraded bathrm. Other 2 BRs are bright and comfy: 1 w/ a Queen and Smart TV; the other w/ bunks and twin pull-
The Coyote
House Location Saugatuck
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 5 (22)
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)
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)
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)

Tell us what you're looking for and someone will contact you with available options.

I agree