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Vacation rentals in Rolling Prairie

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Top-rated vacation rentals in Rolling Prairie

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Cabin in Rolling Prairie

4.87 out of 5 average rating, 135 reviews

3+ acres of Privacy, Pup heaven!7 minutes 3~Oaks!

Hello! we are 10 minutes to Three Oaks, Mi. This town is divine and very fun~ restaurants, galleries, Journeyman Distillery, Antiquing & Warren Dunes (epic hiking, dog-beaching-as private or social as you like). My artsy, sunny and cozy home welcomes you! We back up to over 3 + acres of private woods, a fresh spring fed brook and seconds from some of the best biking roads in the midwest! My place is VERY private yet 10 minutes to 3 Oaks for an evening of fun, live music & shows @ The Acorn! .

Nov 20 – 27

G$31,587 GYD per night

Farm stay in New Carlisle

4.94 out of 5 average rating, 154 reviews

Glamping Off Grid in a Tiny Cabin on a Farm

Experience a serene and relaxing getaway in our off-grid tiny cabin on our farm. Created with the intention of slowing down (no tv, no wifi and limited electricity), 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.

Oct 28 – Nov 4

G$26,446 GYD per night

Barn in Michigan City

4.96 out of 5 average rating, 342 reviews

The Black Pearl Great Escape Spa & Art Shop

Check out our website! thegreatescapespah.com The Black 🖤 Pearl is perfect for a Special Occasion for the Evening. Book a Couples Massage @ 3p.m. & Check into your Spa Suite @ 4 p.m. Kick your feet Up & Order in.... Or Dine Out~ This quaint property is located in a woodsy setting 5 minutes from Lake Michigan. The keyless entry door to The Black Pearl is located on the East wall of The Great Escape. Upon entry the Black Pearl door will be directly in front of you. Mini Luxury awaits!

Feb 15 – 22

G$25,922 GYD per night

Cabin in New Carlisle

4.94 out of 5 average rating, 172 reviews

Cozy Cabin Minutes 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.

May 19 – 26

G$29,312 GYD per night

Villa in Michigan City

4.9 out of 5 average rating, 127 reviews

Steps from the beach. Entire beach villa renovated

Private, ~800 sq ft, ground-level renovated beach villa with close trail access to the beach. Includes 1 BR with queen bed, 1 BR with futon & extra folding guest bed, kitchen, bathroom, & living room with small couch that converts to sleeping space if needed. Amenities: washer/dryer, free wi-fi/streaming services, 2 free parking spaces, AC/heating, self check-in, laptop friendly workspace, games, complimentary coffee/tea, beach chairs, towels, umbrella & toys, & cleaning/laundry supplies.

Mar 8 – 15

G$26,130 GYD per night

Guesthouse in Chesterton

4.96 out of 5 average rating, 114 reviews

Bro’s Place

Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

Dec 26 – Jan 2

G$21,514 GYD per night

Guesthouse in New Buffalo

4.98 out of 5 average rating, 692 reviews

"Tiny House" Guest House Under the Oak Trees

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

Apr 30 – May 7

G$21,760 GYD per night

Tiny home in South Bend

4.98 out of 5 average rating, 245 reviews

The Cottage @ Portage Lion - Treat Yourself!

Cozy cottage fully renovated tucked into a beautiful park-like surrounding. Near to Notre Dame, South Bend, Lake Michigan Beaches, and wine trails. Relax here on your own patio. Luxuriate in the huge new shower. This darling two-room tiny house with a kitchenette has the conveniences and comfort you want for a short stay. The queen bed sleeps two while the couch in the main room is deep and can sleep another. Wifi and Roku enabled. Perfect little getaway!

Oct 29 – Nov 5

G$20,389 GYD per night

Guesthouse in Sawyer

4.92 out of 5 average rating, 148 reviews

Heron's Rest hideaway close to beaches, breweries

Privacy on 11 acres of conservancy-protected land including woods, two ponds, and a river. Minutes from Michigan’s most popular beach, breweries, wineries, antique malls, farm-to-table restaurants. Fully equipped kitchen, gas fireplace. Private fire pit, deck, and gas grill. Fish on site. Kayak, bike, hike nearby. Ideal for nature lovers. Separated from our home by breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible.

May 3 – 10

G$21,954 GYD per night

Guesthouse in New Buffalo

4.95 out of 5 average rating, 352 reviews

Rainbows End 🌈 Puryear

Discover the tranquility of a charming cottage nestled on a 20-acre farm, surrounded by nature with walking trails that end up at the South Branch of the Galien River. Unwind on the patio with a cozy fire pit and enjoy all the amenities you'll need for a perfect getaway. Just 10 minutes away from the beautiful shores of Lake Michigan and only 3 miles from Four Winds Casino. Experience the peaceful countryside retreat—book now!

May 3 – 10

G$26,909 GYD per night

Home in Rolling Prairie

4.96 out of 5 average rating, 173 reviews

Rustic Elegance in the Michiana area

NO EVENTS. 10 person max at all times. 3- block walk to a small shared lake and near a host of lovely spots: Breweries/Wineries, Dunes, Three Oaks, Frisbee Golf, and more. A gas fireplace for cold winter nights, an outdoor firepit, a hammock, grill, and outdoor seating/camping chairs. A short walk to the Nowhere Bar & Grill for great local food! Only 1 hour 15 minutes from Chicago. Sleeps 8 comfortably.

Aug 14 – 21

G$52,395 GYD per night

Home in La Porte

4.94 out of 5 average rating, 208 reviews

Camp Knotty Pine

Secluded country getaway! Home set on 13 private wooded acres in the beautiful Hesston Corridor. Remote location but just minutes from Three Oaks, New Buffalo, Four Winds Casino, Hesston Steam Museum, Heston Supper Club, Spicer Lake Nature Preserve, Williams Apple Orchard, blueberry farms, bike routes and more.

Sep 9 – 16

G$50,351 GYD per night

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Popular amenities for Rolling Prairie vacation rentals

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Other great vacation rentals in Rolling Prairie

Apartment in La Porte

4.93 out of 5 average rating, 452 reviews

Second Floor Apartment sitting on Pine Lake

Nov 3 – 10

G$38,514 GYD per night

Chalet in La Porte

4.93 out of 5 average rating, 336 reviews

Cozy, pet friendly, private home on Pine Lake

Oct 17 – 24

G$54,613 GYD per night

Guest suite in Berrien Springs

4.98 out of 5 average rating, 259 reviews

BrightWood House

Oct 7 – 14

G$22,815 GYD per night

Cabin in Michigan City

4.95 out of 5 average rating, 398 reviews

Little Copper Cabin

Jan 28 – Feb 4

G$36,008 GYD per night

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Mar 5 – 12

G$17,596 GYD per night

Cabin in Goshen

4.92 out of 5 average rating, 145 reviews

Tiny home log cabin at the pines

Aug 2 – 9

G$22,542 GYD per night

Guest suite in Three Oaks

4.91 out of 5 average rating, 305 reviews

Maddie’s Place - Deluxe Guest Suite

Oct 12 – 19

G$30,499 GYD per night

Farm stay in Sawyer

4.98 out of 5 average rating, 339 reviews

Your SW Michigan Modern Farmhouse Cottage Awaits

Nov 14 – 21

G$39,958 GYD per night

Destinations to explore