
Holiday rentals in Berrien County
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Top-rated holiday rentals in Berrien County
Guests agree: these stays are highly rated for location, cleanliness and more.

-The District 5 Schoolhouse-
The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

Charming Downtown Sawyer Home Close to the Dunes
Enjoy this charming home in the heart of downtown Sawyer. Venture out on foot, and you're a 2 min walk to Greenbush, Infusco, Section House and more. Hop in the car and be at Warren Dunes or Journeyman Distillery in under 10 mins. Centrally located to be close to everything Harbor Country has to offer. Inside you'll find all the comforts of home, including a full kitchen, plush queen beds, as well as a 55" Smart TV with many apps ready to go on the Apple TV. Kitchen & bathroom basics provided.

McComb's Cabin, Union Pier, MI
Giant trees welcome you down the drive back to the cabin in the woods. The cabin, along with my house and a small cottage reside on the 2 1/2 acre property. A contemporary cabin of steel and pine with vaulted ceiling and sky lights. Open living space, inviting queen size bed, luxury rain shower, full kitchen but no stove. A wood burning fireplace- fall through end of March and outside fire pit. Public beach a 5 minute drive away. Couples check out the cabin for anniversaries & special days.

Heron's Rest Hideaway, nature lovers' dream
Privacy on 11 acres of conservancy-protected land including two lakes, river access, woods. Rowboat available. Fishing on site. Nature lovers dream! 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.

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 treehouse at Warren Dunes
Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

Cozy Sawyer Beach Cottage walk to Warren Dunes
Beautiful renovated beach cottage on a quiet tree-lined street. Private comfortable home perfect for a winter weekend away! Enjoy the best of Pure Michigan, 2 mi from Sawyer & 0.5 mi to Warren Dunes State Park. Plenty of outdoor space to play, skylights to soak up the natural light and central to wineries, restaurants and the Dunes. Grab local farm fresh produce, s’mores for the firepit and a local natural wine to sip as you watch the sun set from the huge back deck and large backyard.

Idyllic A-frame in Michigan’s Harbor Wine Country
Follow a wooded path to a secluded mid-century modern cottage constructed of stone and wood reclaimed wood from a historic St Joe's rollercoaster. Retro pink ceramic tiles line an open-plan main floor surrounded by sliding doors. You will be surrounded by the great outdoors while sitting cozy inside by our electric fireplace. Located about 10 minutes south of downtown St. Joe, our Idyllic A-frame is a perfect location for the escape to SW Michigan that you've been dreaming about.

"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.

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.

Charming Apt near AU, ND, lake beaches & wineries
Welcome to this thoughtfully planned one-bedroom apartment, equipped to host up to 3 guests. It is located in a quiet countryside neighborhood and has a dedicated workspace. You'll enjoy all the tourism possibilities this well-located unit offers and the cool amenities prepared to make you feel at home. You are: 5 minutes from Andrews University 20-25 minutes from St. Joseph & fantastic beaches on Lake Michigan 30 minutes from Notre Dame, SBN, Warren Dunes & wineries
Popular amenities for Berrien County holiday rentals
Other great holiday rentals in Berrien County

Floyd's Cabin Lakeside Mich

The Cottage of Harbor Country - Close to it all!

Herons Nest Cottage - #2 Erie | Lake Access!

Randi's Blue Cabin in Grand Mere

Cozy Cabin in the Woods

Beach & Wine Retreat: Close to Lake Michigan Dunes

Great weeks still available for summer 2026!

1Bed apartment, steps from the New Buffalo beach
Destinations to explore
- Rentals with a kayak Berrien County
- Rentals with breakfast Berrien County
- House rentals Berrien County
- Rentals with a patio Berrien County
- Rentals with a hot tub Berrien County
- Waterfront rentals Berrien County
- Pet-friendly rentals Berrien County
- Tiny house rentals Berrien County
- Rentals with a firepit Berrien County
- Beachfront rentals Berrien County
- Rentals with beach access Berrien County
- Cottage rentals Berrien County
- Guest house rentals Berrien County
- Townhouse rentals Berrien County
- Rentals with a washing machine and dryer Berrien County
- Bed and breakfasts Berrien County
- Cabin rentals Berrien County
- Rentals with outdoor seating Berrien County
- Apartment rentals Berrien County
- Rentals with pools Berrien County
- Flat rentals Berrien County
- Rentals with a fireplace Berrien County
- Rentals with lake access Berrien County
- Family-friendly rentals Berrien County
- Farm stay rentals Berrien County
- Luxury rentals Berrien County
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Shedd Aquarium
- Guaranteed Rate Field
- The Field Museum
- Warren Dunes State Park
- University of Notre Dame
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Museum of Science and Industry
- Willis Tower
- Washington Park Zoo
- University of Chicago
- Silver Beach Carousel
- Potato Creek State Park
- Chicago Cultural Center
- Loyola University Chicago




