Holiday houses in Benton Harbor

Guesthouse in Benton Harbor

4.94 out of 5 average rating, 176 reviews

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.

4.99 out of 5 average rating, 153 reviews

Private Beach/Lake Michigan/Panoramic View/Hot Tub

Welcome The Windover! • Private Beach • Panoramic Lake Michigan Views • Hot Tub and Outdoor Shower •Expansive Yard /Outside Activities • 4 minutes to downtown St. Joseph, The Benton Harbor Arts District, and Harbor Shores • Centrally located Close to 6 additional Local Beaches Fine and Casual Dining World Class Golfing Wineries Breweries Nature Parks and Trails Mountain Bike Trail Park 1/4 from Property Curious Kids Museum Compass Fountain Silver Beach Carousel St. Joseph Lighthouse

5 out of 5 average rating, 201 reviews

Farm stay in Vandalia

One of a kind•HotTub•Fire Pit• Private•Lux•Charm

*Escape the ordinary and experience rural country luxury *Whether sipping coffee at sunrise or star gazing the Grain Binn is the perfect blend of rest and charm *Situated on 70 acres with flowing creek *Pickle Ball court 1 mile from Binn *Fully stocked kitchen *Fireplace *Hot tub with towels provided * Firepit with firewood *Bird feeder for Bird lovers *King size bed with quality bedding *Forgot something? Got cha *In floor heat *Snacks *Walking trails *Good WIFI *Unplug and un

4.8 out of 5 average rating, 224 reviews

Tiny home in Coloma

-Shingle Diggins Cottage-

Enjoy whimsical luxury in quaint cottage. Steeped in the History of charming Coloma once called Shingle Diggins in the early 1800's for the wooden shingles manufactured in the area. Cozy comfort with everything you need. Nestled in the heart of the stunning Great Lakes Region, Southwest Michigan Wine Trail, and the Fruit Belt. Full kitchen, 100% linen sheets, fully enclosed private backyard for fur babies, easy access to lakes, beaches, dining, wineries, breweries, outdoor adventures, and more.

4.89 out of 5 average rating, 199 reviews

Loft in Benton Harbor

Sunbay Suite At The Stewart

Central location in the middle of the Arts District with a beautiful view of it all from any window, but especially the front bay window! There is street parking right next to the door or parking lot adjacent to the building. Walk to The Livery Brewery, Harbor Shores Golf Course, Mason Jar Cafe, Hounds Tooth Restaurant, Sweenies Weenies, Forte Coffee, Piggin 'n' Grinnin BBQ and more! Wifi throughout, laundry facilities on same floor (2nd). Just minutes from St. Joe shopping, beaches, and more

Guesthouse in Sodus Township

4.78 out of 5 average rating, 257 reviews

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.

4.92 out of 5 average rating, 336 reviews

Loft in Benton Harbor

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.

Guesthouse in New Buffalo

4.98 out of 5 average rating, 840 reviews

"Tiny House" Guest House - No Cleaning Fee

"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.

4.94 out of 5 average rating, 144 reviews

Loft in Benton Harbor

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.

4.98 out of 5 average rating, 159 reviews

Lake MI views: King bed: Mins to St. Joe: Hot tub

🤩 Spectacular Lake Michigan views 🌅 Deck overlooking Lake Michigan 🔥 Year-round hot tub 📍 Minutes to downtown St. Joe ✨ Magical fire pit space 🏖️ 5 Lake Michigan beaches within 5 miles 🌞 Beach necessitates included 🍷 Close to The Lakeshore Wine Trail 🏓 Ping pong table ⭐️ Top rated home in St. Joe ⛳️ Near Harbor Shores Golf Course 🧑‍🍳 Fully stocked kitchen ☕️ Keurig Duo w/ complementary k-cups ⚡️ High speed internet 👶 Highchair & portable crib 🧺 Washer & dryer

4.93 out of 5 average rating, 181 reviews

Guesthouse in Sawyer

Heron's Rest Hideaway, nature lovers' dream

Privacy on 11 acres of conservancy-protected land including two small lakes, river access , woods. Rowboat available. 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. Kayak, bike, hike nearby. Separated from our home by a breezeway. Private entrance, quiet road, dark nights. Daytime woodworking noise possible. Limit of 4 guests.

Apartment in Benton Harbor

4.79 out of 5 average rating, 129 reviews

Lovely 2 bedroom apartment minutes from the lake

You’ll walk through your own private entrance to this spacious first floor apartment & see tall ceilings, exposed duct work, an open living room & kitchen for fun family gatherings. You can relax on the couch & watch Netflix, enjoy a warm beverage together around the table or lounge in your own Queen-sized bed. There are many options for casual & fine dining, shopping, walking trails, enjoying stunning sunsets at Lake Michigan & wine tours just minutes away.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Benton Harbor holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Benton Harbor's top sights

Silver Beach88 locals recommend

Silver Beach Carousel33 locals recommend

Harbor Shores Golf Club40 locals recommend

Other great holiday rentals in Benton Harbor

Apartment in Saint Joseph

4.94 out of 5 average rating, 72 reviews

Luxury Waterfront Condo

DianaRating, 5 stars1 day ago

This was a fabulous experience, and James was very responsive. Loved the experience. The two full baths were amazing for our needs.

4.99 out of 5 average rating, 95 reviews

Cabin in Union Pier

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace

IonitRating, 5 stars5 days ago

Thank you for hosting, Sarah! We enjoyed walking to the beach and crossing the street for coffee and pastries at the Blackcurrent Bakery.

4.86 out of 5 average rating, 71 reviews

Nestled in History

ShawnaRating, 5 stars2 days ago

My sister and I wanted a three day get away to Silver Lake and were super lucky to have picked this cute little home. It was in a convenient location to everything we wanted to do. The one thing I cannot say enough about is the cleanliness of the house; there was not a speck of dust or one thing out of place. I will definitely save this to my stays for future trips!

4.94 out of 5 average rating, 18 reviews

Home in Stevensville

Cozy Bluebird Cott. w/ Hot Tub!

RossRating, 5 stars5 days ago

This property is immaculate. We had a lovely time visiting wineries in the nearby vicinity. Make sure you buy a croissant at the nearby bakery.

Cottage in Benton Harbor

4.82 out of 5 average rating, 164 reviews

Beach Bliss | Pet Friendly Cottage Near Lake MI

AsiaRating, 5 stars5 days ago

Very accommodating host and quick to respond. Wonderful location, as it was only a 3 minute drive to the wedding venue we needed to go to.

Guest suite in Stevensville

4.95 out of 5 average rating, 60 reviews

Cozy One Bedroom Upstairs Unit, Near Beach

GayeRating, 5 stars2 weeks ago

This is our second time staying at Paula’s place. We love staying there. Paula is wonderful to work with and her place is fantastic to stay at.

4.94 out of 5 average rating, 72 reviews

Barn in Benton Harbor

Updated Pool House with Private Pickle Ball Court

ShelbyRating, 5 stars6 days ago

We had THE BEST TIME here! We loved swimming, playing pickleball, and our family favorite—watching the chickens and collecting eggs. The location was perfectly situated, close to beautiful beaches and lots of fun activities. It was a quiet, private area surrounded by nature, which made it feel like a true retreat. Amy was so kind and hospitable. We cooked all of our meals at the house throughout the week, and the kitchen had everything we needed—it was well stocked with utensils, dishes, and cookware. The beds were also very comfortable. We can’t wait to come back!