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Holiday rentals in Rolling Prairie

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Top-rated holiday rentals in Rolling Prairie

Guests agree: these stays are highly rated for location, cleanliness and more.

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Apartment in St. Joseph

4.86 out of 5 average rating, 7 reviews

Surf Loft – Vacay Dwntn nr Beach, Park, Amenities

Surf Loft in St. Joseph, MI - the best of all vacation worlds. A gorgeous living space. Fireplace, flat-screen TVs, pro Foosball. Huge posh deck with gas grill. Walk to the beach, park, harbor, arboretum or thru downtown's boutiques, shops, eateries, art museum and more! Featuring spacious open design LR-DR-Kitchen, fabulous natural light, elegant-comfy bedrooms and deluxe bathrooms. Your and your guests' R-and-R levels will be off the charts. Morning coffee of the finest kind, anyone? Oh, yeah.

Guest favourite

Home in Michigan City

4.9 out of 5 average rating, 362 reviews

Best Deal In Michigan City 1.3 miles to Beach

Quiet for a well deserved nights rest. Plenty of space for 4-8 guests indoors and out. Short drive to the Washington Park beach & zoo Walking distance to south shore train for a quick ride into the heart of Chicago. Less than a mile from uptown arts center and district Short drive to The National Lakeshore, that has great beaches, hiking, and biking trails! Have a day in the sun, and come back to relax, in a quiet backyard patio area equipped with grill & night lighting... Must be 24 to book

Guest favourite

Cottage in Union Pier

4.98 out of 5 average rating, 210 reviews

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Newly updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus add'l parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

Flat in New Buffalo

4.9 out of 5 average rating, 21 reviews

Charming 2BR/2BA Cottage with Full Kitchen & Patio

The cottages, or townhouses, are situated steps away from the main inn, providing an added sense of privacy while still feeling the vibe of the community. This cottage has two bedrooms (one with a queen bed in the downstairs bedroom + another with 2 twin beds in the upstairs bedroom). Two bathrooms (one upstairs, one downstairs) keep things fresh with a queen sleeper sofa. The upstairs loft space provides extra room for rest. An in-unit washer/dryer and high speed WiFi makes things easy.

Guest favourite

Home in Sawyer

4.96 out of 5 average rating, 78 reviews

Here and Now

Newly renovated home that has been featured in magazines on Interior Design. One of a kind home right next to the Warren Dunes and walking distance to the lake. Beautiful landscaping from every window. Professionally designed home features an upscale interior with a fun twist. Brand new large screened in porch. The perfect spot to enjoy a getaway in style , look no further. 2 separate buildings on the acre property , this rental is for the front building. Wi fi included but can be weak.

Guest favourite

Home in Three Oaks

4.82 out of 5 average rating, 96 reviews

Three Oaks Creek House Perfect

3BR, 2 bath contemporary house on Spring Creek--a spawning waterway and spectacular architectural screenhouse (4th BR) at water's edge. Open floorplan, stone fireplace, gourmet kitchen and 4000CDs for spontaneous entertaining. Tempur-Pedic King master BR/office suite with lots of storage and large desk Queen 2nd BR w/standing desk, dresser, books. Full 3d BR w/ 3/4ba en-suite. Wi-fi throughout, Roku, DirecTV with HBO. Spectacular privacy, quiet and tons of specialty ameneties!

Guest favourite

Home in Lakeside

5 out of 5 average rating, 57 reviews

Beautiful New Retreat in Lakeside - Walk to Beach

Our sunny Harbor Country home is surrounded by woods at the end of a private street and is walkable to Lake Michigan. 7-day Saturday to Saturday rental only, please. We are a 15-min walk from the Union Pier/Berrien public beach, 5-min drive from New Buffalo & Sawyer, 10-min drive from Three Oaks. There is even a pickleball court outside the front door! Occasional trains only add to the atmosphere. Owners stay on premises in their separate, upstairs studio from time to time.

Guest favourite

Home in Michigan City

4.89 out of 5 average rating, 112 reviews

Roomy and Private Getaway for Families & Friends

Perfect for Gatherings, Families, Birthdays, Group Outings: Enjoyment & Tranquility in Nature. Nestled on two acres of picturesque land, the property boasts a fully-equipped six-bedroom house. Conveniently located within a 5-minute drive to popular attractions such as the beach, casino, and outlet mall. Formerly a church, the house has been transformed into an inviting Airbnb rental, featuring a renovated interior, fire pit, gazebo, and many amenities.

Guest favourite

Flat in Michigan City

4.94 out of 5 average rating, 136 reviews

Charming apartment in Arts District

Walk to outlet mall, art galleries, parks, restaurants, and Lake Michigan beach. Walk or drive to casino. This is a 2nd-story apartment in Michigan City's historic district. A full 1,400 sq ft of space! Fully appointed, clean and beautifully decorated. Newly renovated kitchen and bath. WIFI. Access to beautiful back yard patio and deck. Great proximity to attractions. Great for couples, solo adventurers, and families with children.

Guest favourite

Cabin in Benton Harbor

4.99 out of 5 average rating, 267 reviews

Charming Cabin-Private Beach & Golf

Why the rave reviews? This cabin is a unique and charming 2 bedroom retreat that sits atop a hill and is surrounded by elegantly sculpted terrain of Harbor Shores golf course and walking trails. The private beach on Lake Michigan is steps away. It is located in a quiet neighborhood and is close to family fun activities in St. Joe/Benton Harbor, fantastic restaurants, wine tasting, art galleries and quaint shops.

Guest favourite

Cottage in Three Oaks

4.91 out of 5 average rating, 112 reviews

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

Guest favourite

Townhouse in New Buffalo

4.92 out of 5 average rating, 85 reviews

Downtown NB! Walk Everywhere! Huge screened porch

If you want to be in middle of everything with ample off street parking walking distance to everything you’ve found it! This is a two story two bedroom two bathroom recently remodeled unit. Perfect for 2-6 Primary has a Queen Twin over twin guest Twin over full guest Full size pull out couch in main level. Recently remodeled 2 Large flat screen tv

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Popular amenities for Rolling Prairie holiday rentals

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Air conditioning

Other great holiday rentals in Rolling Prairie

Home in Michigan City

5 out of 5 average rating, 4 reviews

Lake Life Livin’- Beach House

Guest favourite

Home in Michigan City

5 out of 5 average rating, 5 reviews

Home for Christmas! A walk to Festival of Lights

Guest favourite

Home in Berrien Springs

4.95 out of 5 average rating, 120 reviews

Great Living Too

Guest favourite

Home in Michigan City

4.95 out of 5 average rating, 62 reviews

Home near the lake with an inground pool

Guest favourite

Cottage in Vandalia

4.9 out of 5 average rating, 21 reviews

Private Vandalia Beach Front Cottage

Guest favourite

Holiday home in Baroda

4.94 out of 5 average rating, 16 reviews

Location location

Guest favourite

Home in Chesterton

4.94 out of 5 average rating, 49 reviews

4 Season House

Home in Benton Harbor

4.75 out of 5 average rating, 12 reviews

Family Getaway

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