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.
54 properties available
This dreamy 4BR/3BA getaway is tucked into a quiet spot in the Gordon Beach Association neighborhood, offering a gorgeous PRIVATE beach, peaceful community and close proximity to Union Pier and New Buffalo. Features a light-filled open living area, elegant, yet comfy furnishings, a stone fireplace and beautifully appointed kitchen (marble-top islan
Greystone Cottage
House
Union Pier
4
bedrooms
3
baths
10
guests
5
(21)
Escape to nature and this impeccable 3BR-2BA home beautifully designed w/ elegant/cozy furnishings! LR has soaring ceiling and gas fireplace. Kitchen features all high-end appliances. Each BR is stylish - the main ensuite has a King bed and private bath w/ walk-in shower. One guest BR has a King bed; the other a twin-over-full bunkbed. Smart TVs, d
Casi Cielo
House
Sawyer
3
bedrooms
2
baths
7
guests
5
(8)
Vaulted ceilings, wood floors and beams enhance this 4 BR/2.5 BA home! Stylish Great Room w/ stone fireplace. 2 enclosed patios w/ wood views. Kitchen has wraparound granite top + hi-end appliances. All 4 BRs are well-appointed + cozy. 2 twin-sink vanities, stone tile BAs + a half-bath, with 2 King beds, a Queen and 2 twin-beds. Each floor has a co
Wild Horse Run
House
New Buffalo
4
bedrooms
2
baths
1
half baths
8
guests
5
(21)
Pool is OPEN for Summer 2024! 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,
Scout's Haven
House
Rolling Prairie
5
bedrooms
3
baths
12
guests
4.6
(3)
Elegantly furnished yet comfy throughout, this gorgeous home's ample space and many amenities is a perfect fit for a large group. The 3 BR Main House has a Chef's Kitchen and 4 adjoining dining and entertaining areas, all with woodland views. Chill by the fireplace or catch a fave movie! All BRs and BAs are uber-richly appointed. The Guest Cottage
Rabbit Run
House
Sawyer
7
bedrooms
6
baths
18
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
New Buffalo
4
bedrooms
2
baths
10
guests
5
(11)
Rich design 6 BR/5 BA home near New Buffalo Harbor + beaches. Great Room w/ stone fireplace. Chef’s kitchen w/ marble-top island. 3-season sunroom. Elegant-comfy furniture. Master BR has stone fireplace + BA w/ twin sinks, tile walk-in shower + jacuzzi. Lower-level Guest BR has fireplace, full BA, game room + posh screening room. 2nd floor has loft
The Moose House
House
New Buffalo
6
bedrooms
5
baths
14
guests
4.9
(34)
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
Douglas
4
bedrooms
2
baths
1
half baths
8
guests
5
(10)
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
Stevensville
4
bedrooms
3
baths
10
guests
4.9
(21)
Welcome to Bella and Dulce's Lakehouse! This freshly remodeled retreat offers the perfect blend of modern luxury and natural beauty. Enjoy the serenity of a private wooded lot while taking a dip in the refreshing pool or roasting marshmallows by the firepit. Inside, the designer kitchen is a chef's dream, and the 3 BDs and 3 full BAs ensure comfort
Bella and Dulce's Lakehouse
House
Union Pier
3
bedrooms
3
baths
8
guests
5
(3)
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 3 - The Moss
House
Union Pier
2
bedrooms
1
baths
6
guests
Features:- Stunning and sleek 3BR/2.5BA vacation home- Accommodates up to 8 guests- Open floor plan with cozy living room- Large bar with seating for 6- Unique elevated outdoor deck with fire table- Full laundry room- Garage parking for 1 car- Steps away from Townline Beach, shops, and eateries in Union PierStunning and sleek 3BR/2.5BA vacation hom
Townline Treasure
House
Union Pier
3
bedrooms
2
baths
1
half baths
8
guests
5
(18)