Holiday rentals in Little Crooked Lake

Peaceful Cable Lake Getaway w/ Dock & Views

Escape to easygoing lake life at this cozy 2-bedroom, 2-bath cabin on beautiful Cable Lake. Perfect for families or friends, this well-equipped retreat offers peaceful views year-round, plus direct lake access for fishing, boating, or simply relaxing by the water. Spend your mornings on the screened porch, your afternoons on the lake, and your evenings by the fireplace or grill. Local wineries are just a short drive away, and St. Joseph makes a fun day trip. Why you’ll love it: - Private backyard with lake access & stunning views - Open, modern living space with fireplace & lake-facing windows - Fully stocked kitchen + wine/beverage cooler - Deck, patio furniture, Adirondack chairs & life vests - Sleeps up to 6 with a loft for extra space - Easy parking for up to 3 vehicles Whether you’re here to unwind or explore Southwest Michigan, this lakefront cabin is the perfect place to slow down and enjoy it all.

Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.

Welcome to the our Lake Retreat "The Toasted Marshmallow" and B&P Getaways where we have 5 unique lake homes in the Sister Lakes area. Please click on my profile picture twice to check them out. We have them in all sizes. Inquire about our private chefs, boat captains, wine tours, yoga instructor, massage therapist, boat rental and concierge services. We will help you make a fun, memorable and enjoyable trip. from a Family trip to your bachelorette party. book today! Inquire before booking

-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.

Off Grid Yurt Glamping on Permaculture Homestead

Stay in our stylish yurt for a one of a kind "glamping" experience on a 20acre homestead! The perfect location on the Southwest Michigan wine trail and just 15 minutes to Lake Michigan beaches! Awesome ammenities - off grid solar power, private outhouse, outdoor shower, fans, fridge, grill, firepit, and more. Take the tour, meet sheep, horeses, chickens, rabbits and learn permaculture. Order our delicious DIY pancake breakfast featuring homemade maple syrup, our organic eggs and pancake batter.

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.

Paradise Point - Perfect for Families

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 Tiny House on the River

Perfect Couples getaway guest house on the Dowagiac River! Located just a short drive away from popularly visited destinations; Saint Joseph, New Buffalo, South Bend and the renowned University of Notre Dame. Oversize queen pull out couch, table and chairs, loft seating, kitchenette: with refrigerator, microwave, toaster, and coffee bar! Full private bath, linens, toiletries, Wi-Fi, cable TV, Sonos. Outside grill, gas fireplace, deck and patio seating and hammock!

Sister Lakes A-Frame: Private Beach, Dock & Kayaks

Welcome to Keeler Lake Lodge! This classic 1960s A-frame sits on 100 ft of private sandy beach on all-sports Keeler Lake - just 2 hours from Chicago. Sleeps 10 across 3 bedrooms, a loft & sleeper sofa. Floor-to-ceiling lake views, a private dock, kayaks, paddleboards, fire pit, grill & pontoon rental available May–Oct. Updated with modern comfort while keeping the charm that makes a cabin feel like a cabin, this is the kind of place people come back to year after year.

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.

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.

Fairview Cottage

Welcome to Fairview Cottage, a charming two-story cottage tucked in a quiet corner of Berrien Springs. Enjoy cozy, cottage-style décor and unwind after a day at the Berrien County Youth Fair, just a 5-minute drive away. Perfect for fair season, winery tours, or a peaceful getaway, Fairview Cottage blends small-town charm with easy access to the area’s best attractions.

Sister Lakes - Wonder Woods "Glamping" Cabin #1

Located just 2 hours from Chicago and nestled in the epicenter of Sister Lakes, Michigan, Wonder Woods is a one-of-a-kind hospitality experience. Enjoy exclusive access to this private 4 acre gated campground featuring a game room barn and is also steps from the areas most popular attractions.