
Holiday rentals in Rolling Prairie
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Top-rated holiday rentals in Rolling Prairie
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Cabin on Swede Hill
Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Pet friendly, lakefront home with pontoon included
Looking for a relaxing lake vacation? Our studio home is directly on the water with docks to offer for guest use during warm months. Great fishing spot with included kayaks and seasonal pontoon boat to explore on the lake. Our gas fireplace on the deck provides amazing memories and relaxation. Gas grill, outdoor furniture, clean space to swim between docks, and so on! Wifi, streaming networks, and board games provided in home! Pine Lake Airbnb is the place to be for your next vacation adventure!

Happy Acres: Modern Luxury Country Farmhouse
Happy Acres is a modern oasis that’s close to beaches, wineries, restaurants & shopping and far enough removed to watch the stars glisten from your outdoor living space. Perfect place to get away & relax. Short drive to New Buffalo restaurants and shopping, Union Pier and Warren Dunes. Enjoy beaches, hike sand dunes, visit local wineries and breweries and antique. Three Oaks is a few minutes away-- enjoy restaurants, art galleries, Journeyman Distillery and Acorn Theater. South Bend is 35’ drive

Hudson lake Cottage: Notre Dame, New Buff, Amazon
Welcome to Gram's Hudson Lake cottage: The perfect retreat for Notre Dame adventures (20 MI), Michigan City beaches (21 MI), and trips to New Buffalo (15 MI) or the Indiana Dunes. Whether you’re here for a family getaway, a football weekend, or corporate travel to the AWS Data Center (7 MI), you’ll enjoy peaceful lake views, a cozy fireplace, and easy access to local attractions. Hudson Lake Beach is 2 miles away, no direct access from the home. *pontoon, kayak & paddleboard rental available!

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.

Second Floor Apartment sitting on Pine Lake
My Airbnb is close to parks, restaurant and Sand Dunes. The apartment is in the house on beautiful Pine lake. Please note that the balcony in the picture is not part of the apartment. the pictures are to show the patio of which you have full access. Pets are welcome but there is a $15 charge per pet per night. The fee should be made in advance through the send money. We live in a area that pets must be walked to do bathroom duties. They are NOT allowed on my grass or in flower beds.

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!

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 treehouse at Warren Dunes
Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

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!

Hot tub open year round in modern/rustic cottage!
Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

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.
Popular amenities for Rolling Prairie holiday rentals
Other great holiday rentals in Rolling Prairie

Downtown Daydream - walk to shops + restaurants

Lakeview Suite

LeRoy's Market Boutique Studio

Stone Lake Lookout

Dog-Friendly Farmhouse | 1+Acre near Lake Michigan

The Hudson 14mi to New Buffalo!

Mainstay Mini

Millie's Rose Cottage
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
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- St. Louis Holiday rentals
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- Detroit Holiday rentals
- Milwaukee Holiday rentals
- Lexington Holiday rentals
- Traverse City Holiday rentals
- London Holiday rentals
- Warren Dunes State Park
- Indiana Dunes State Park
- University of Notre Dame
- Washington Park Zoo
- Silver Beach Carousel
- Beachwalk Vacation Rentals
- Potato Creek State Park
- New Buffalo Public Beach
- 12 Corners Vineyards
- Van Buren State Park
- Grand Mere State Park
- Shady Creek Winery
- Woodlands Course at Whittaker
- Weko Beach
- Jean Klock Park
- Four Winds Casino
- Silver Beach Park
- Dablon Winery and Vineyards
- Four Winds Casino
- Potawatomi Zoo
- Studebaker National Museum
- Four Winds Field
- Howard Park
- Deep River Waterpark





