Holiday rentals in Benton Harbor

Cozy Green Cottage with Private Beach

Cozy cottage hidden away in a quiet neighborhood 1.5 blocks from Lake Michigan, featuring a screened back porch perfect for morning coffee. Near the Benton Harbor Arts District, downtown St Joe, this cottage is surrounded by local restaurants, breweries, wineries, golf courses and shops. The beach is a year round destination, each season has its own wonders. Note: no TV, and WiFi can be spotty due to hills. Expect 90+ tiered steps to the sandy beach below. AC upstairs, original claw footed tub.

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

Farm Cottage

Sweet cottage on our farm: Fully equipped kitchen and furnished living/sleeping area 14’x15' approx., washer/dryer. Sleeps 4: queen bed and queen sofa bed. Lots of privacy and next to organic garden, fields, stable and fruit orchards. All utilities, TV and WI-FI included. Well water with new water softener and water heater. Pet friendly; no pet fee. Lots of farm paths to walk your pet. Encourage off leash if trained. Horses have moved to another farm while pasture and stable rehabbed.

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

Welcome to "Lake 2 Grapes" Bridgman is a little gem located between St. Joe and Warren Dunes. Minutes to Lake Mi. beaches, craft breweries, and wine trails. Relax in the upper level of our bi-level vacation home w/private entrance. This 3 bedroom, 2 bath includes a beautiful Master suite! Enjoy the Hot tub and fire pit in the backyard. Wine Tour? Stay with us and you'll receive a discount with "Grape & Grain Tours" plus complimentary pick up and drop off. Must be 25 or older to book.

The Candy Loft in Arts District - 1BR/1.5BA Luxury

Welcome to The Candy Loft in Benton Harbor's Arts District! This 1BR/1.5BA condo boasts exposed brick, a king bed, and an oversized river rock shower in a spa-like bathroom illuminated by a skylight. The chef’s kitchen features a luxe Kitchenaid gas range, and an air mattress adds extra sleeping space. Housed in a historic candy factory, with an office in a former elevator shaft, it’s walking distance to restaurants, a brewery, and a coffee shop. Note: on the 2nd floor, stairs required.

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

Tiny Retro Studio for One Person

TINY studio for ONE. Non-smoking inside & out. Our typical guest is a busy academic, intern, medical worker or businessperson. This TINY studio is located in an old 4-unit apartment house, so there is some in-house sound transfer. Our neighborhood is usually quiet, but not always. See the LOCATION section under the map to read a description of our neighborhood. *Winter Note: We shovel the walkways at the Airbnb, but not usually until later in the day. So mornings might be snowy.

Historic Arts District Gastro Loft

This newly renovated loft was re-created from a long-neglected space in the historic Sheffield building. A perfect getaway for two, the loft is located above the area’s hottest new restaurant, the Houndstooth. Classic urban finishes - high ceilings, exposed brick, hardwood floors...and an expansive view of City Center Park.  Houndstooth draws diners from as far away as Chicago - a visit to Benton Harbor will not be complete without experiencing the big city fare of this hot spot.

Charming 2BR St Joseph Retreat Peaceful Setting

Beautiful two bedroom apartment with private access sitting in a scenic country setting nestled in vineyards and overlooking the valley. The kitchen includes a dw, range & fridge. Bedroom 1 has a queen bed while bedroom 2 has two single beds providing sleeping space for 4. The bath includes a tub/shower. The living space provides furniture for sitting or watching TV. There is also a washer and dryer. Should also note that this is a lower level suite with stairs to access.

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

The Blue Barn - A cozy country getaway!

Welcome to “Blue Barn” vacation home, a country retreat located between beautiful St. Joseph beaches and several Baroda wineries. A welcoming, open floor plan makes it easy for your group to spend time together. Enjoy the crisp white bedding, fully stocked coffee and wine bar, and private fire pit to unwind with friends and family. Grand Mere State Park, Weko Beach, and several local breweries are all just a short drive from this ideally located property.

*Luxury condo on water in St Joseph, 2 queen beds*

Modern and beautiful condo on the river going into the mouth of Lake Michigan near Silver Beach. Immediately next door to Clementine’s restaurant and within walking distance to many shops, bars, downtown, and the beach. Right next to Pier 33 Marina and docks and water rentals. You can eat, drink, fish, shop, and enjoy the beautiful scenery all at one spot. Silver beach/the pier is literally a short walk away!