Vacation rentals in Rolling Prairie

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Rolling Prairie

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

0 of 0 items showing

1 of 3 pages

Superhost

Condo 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.

Superhost

Cottage in Lakeside

4.79 out of 5 average rating, 48 reviews

Fun Duplex 200Yds 2 Lake Michigan-Pool/HotTub&More

Two 4 Bedroom 2 Bath Cottages only steps to private Lake Michigan Beach. Dedicated rental Cabins each w/ Chef's Kitchen, Updated Design w/ modern amenities. Kids & adults enjoy the amazing Pool and Hot Tub (Seasonal availability). Near Lakefront, Fruit Picking Farms, Vineyards, Warren Dunes St. Park, Golfing, XC Skiing, Union Pier & Three Oaks where kids play at Timbertown. 5 min. to New Buffalo to charter fishing boats & witness amazing views of harbor & sunsets from restaurant roof-top deck.

Guest favorite

Cottage in Union Pier

4.98 out of 5 average rating, 211 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.

Superhost

Apartment 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 favorite

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 favorite

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 favorite

Home in Michigan City

5 out of 5 average rating, 11 reviews

Villa Vesta-Lake Retreat

Escape to this charming 3-bedroom,2-bathroom house to get your VIP ticket to relaxation. Step inside the house and be greeted by an open concept living room. The kitchen is fully equipped for culinary adventures. Gather around the firepit for cozy evenings under the stars. Don't forget the hot tub; your personal time machine to a stress-free dimension. Your memories are waiting to be made here-beach is minutes away. See you soon- all those 5 star ratings last summer can’t be all wrong

Guest favorite

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.

Superhost

Home in Three Rivers

5 out of 5 average rating, 7 reviews

Beautiful Family Friendly Beachfront Retreat

This three-bedroom, two-bathroom home sleeps up to 10 people and features a beautiful beachfront with a dock, hammock, and campfire area. Enjoy stunning sunsets from the deck, and dine in the screened-in porch or cook on the gas grill. The fully renovated interior includes all new appliances, a washer/dryer, TV, and Wi-Fi. Just a short drive to town for grocery stores and dining, this tranquil retreat is ideal for escaping the hustle and bustle of city life.

Guest favorite

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 favorite

Apartment 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 favorite

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.