Holiday houses in Little Crooked Lake

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.

-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.

Luxury Country Escape for 2, Private, Creekside,

*Escape to your private couple’s retreat. *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 to reconnect

Lakefront Boardwalk

Welcome to the Lakefront Boardwalk! Here you'll find everything to make your next visit to Sister Lakes, MI the most fun and memorable for everyone. Our home offers a completely renovated space with all the amenities needed and wanted for an amazing stay on Little Crooked Lake. Wake up to beautiful sunrises right on the water and finish the day with s'mores by the campfire. Our home is conveniently located within walking distance to the local restaurants and Driftwood Ice Cream shop.

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.

Family Lake Getaway • 3BR • Near Beach & Wineries

❄️🐟🎰🍷🍺🏖️☀️ Sister Lakes Escape Gather your people and unwind, to our 3 bedroom retreat. 3 mins walk to Cable Lake and close to wineries, breweries, and charming Dowagiac. Perfect for families, couples, or friend groups looking for an easy getaway with space to relax, explore, and reconnect. Filled with Lakehouse character! ✔ Walk to Cable Lake ✔ Close to wine trail & breweries ✔ Easy drive from Chicago, South Bend & St. Joseph ✔ Sleeps 8 comfortably Book your dates now!

Paradise Point

Experience paradise on the point of Little Crooked Lake in Sister Lakes. This cozy 3-bedroom house comfortably sleeps 7 and overlooks a 105 acre all-sports lake with 80' private beach complete with a pier, raft, and chairs. Entertain on the deck while sitting at the wrought iron patio table for 4 under the umbrella. Continue your evening enjoying the fire table while stargazing. Enjoy convenient amenities of AC, WiFi, a washer and dryer, dishwasher, coffee bar, and a smart TV.

The Wildwood Cottage, private lake access

New for summer 2023, private lake access across the street on Little Crooked Lake! Peaceful, 2-bedroom cottage in the heart of Sister Lakes, Michigan. Fully renovated in 2021, this cottage features a large deck overlooking trees and a partial view of Little Crooked Lake. Eat-in kitchen, Weber charcoal grill, Adirondack chairs, and patio dining for 6. Walking distance to The Strand and Sister Lakes Brewing Company. 17 miles to Lake Michigan and 30 miles to Notre Dame.

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.

Cabin off 39 - Peaceful, private one bedroom cabin

Kick back and relax in this calm, stylish space. Nestled among the trees, it provides a quiet getaway from the chaos of life allowing you to recharge and renew. The main residence is approximately 400 feet from the cabin. The cabin is secluded and yet close to local attractions, restaurants, biking and nature trails. The Cabin has a total of 420 sq ft living space with 280 sq ft on the ground floor and a 140 sq ft bedroom loft.

Van Auken Lake cottage rental

This cottage ambiance is quiet and relaxing. You have the option of relaxing on the deck, kayaking on the lake, or driving a short distance to Lake Michigan. You can sit by the fire and enjoy the night sounds, or relax inside with a book or play a game together. We have quiet when you want to relax and fun towns and beaches when you are ready for exploring. It offers you a comfortable visit to a great area of Michigan.