Holiday rentals in Little Crooked Lake

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Top-rated holiday rentals in Little Crooked Lake

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Top guest favourite
Four wooden chairs are positioned on a deck overlooking Lake Michigan. The sun is rising in the sky, creating a shimmering reflection on the water's surface. Trees frame the scene, adding a touch of greenery to the picturesque view.
Home in Benton Harbor
4.97 out of 5 average rating, 199 reviews

Lake Michigan Views | Mins. to St. Joe | Hot tub

🌊 Spectacular Lake Michigan views 🌅 Deck overlooking Lake Michigan 🔥 Year-round, private hot tub 🌞 Beach necessitates included 📍 Minutes to downtown St. Joe & Silver Beach 🏖️ 5 Lake Michigan beaches within 5 miles 🌳 Private, quiet setting with outdoor seating ✨ Magical fire pit space ⛳️ Near Harbor Shores Golf Course 🛏️ King bed ♾️ Infinity gaming table ⭐️ Top rated home in St. Joe ☕️ Complimentary coffee & tea- Keurig duo 🧑‍🍳 Fully stocked kitchen ⚡️ High speed internet 🧺 Washer

Top guest favourite
A charming, rustic cabin is nestled among vibrant autumn foliage, showcasing a wooden exterior and a sloped metal roof. The cabin is partially obscured by trees, with golden leaves creating a warm frame around the structure, signaling a serene woodland retreat.
Farm stay in La Porte
4.99 out of 5 average rating, 523 reviews

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Guest favourite
Home in Buchanan
4.96 out of 5 average rating, 113 reviews

-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.

Top guest favourite
The exterior of a circular, dark-hued building is illuminated by warm string lights during twilight. A private hot tub and a fire pit with chairs are visible, while the surrounding natural landscape emphasizes the peaceful setting.
Farm stay in Vandalia
5 out of 5 average rating, 278 reviews

Lux, Couples Hideout, Creek, Private Hot Tub,

*Imagine soaking in your private hot tub under the stars while a gentle creek flows just steps away. You are surrounded by trees and natural beauty. *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

Top guest favourite
The cabin exterior features a wooden facade with a sloped roof and a welcoming front porch. A bench sits on the porch, surrounded by potted flowers. Warm light from string lights enhances the inviting entryway, set against a backdrop of open grass and distant trees.
Tiny home in New Carlisle
4.99 out of 5 average rating, 199 reviews

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country

Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

Top guest favourite
A lakefront home is depicted, featuring a modern two-story design with a dark roof and white siding. Soft light from string lights illuminates the outdoor space. Reflection on the calm water captures the structure and surrounding trees, creating a serene atmosphere.
Home in Dowagiac
5 out of 5 average rating, 23 reviews

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.

Guest favourite
The A-frame cottage is nestled among tall trees, featuring a blend of stone and wood in its design. Large glass windows create a connection with nature, inviting natural light into the living spaces. A pathway leads toward the entrance, surrounded by lush greenery.
Cabin in Stevensville
4.95 out of 5 average rating, 108 reviews

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.

Top guest favourite
The exterior of the house features a light-colored facade surrounded by greenery. A deck extends from the house, furnished with a red umbrella over a patio table and chairs. An American flag is displayed near the entrance, contributing to a welcoming outdoor space.
Home in Dowagiac
5 out of 5 average rating, 14 reviews

Paradise Point - Lake front fun

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.

Guest favourite
Cottage in Dowagiac
4.96 out of 5 average rating, 133 reviews

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.

Top guest favourite
A charming log cabin features a welcoming facade with large windows framed by wooden accents. The entrance is accessed via a stone pathway lined with landscaped garden beds, showcasing lush greenery and colorful plants. Surrounding trees provide a serene, natural setting.
Cabin in Middlebury
4.99 out of 5 average rating, 417 reviews

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.

Guest favourite
Cottage in Dowagiac
4.83 out of 5 average rating, 77 reviews

Home Away From Home

Home across from Round Lake, in the heart of Sister Lakes. Walking distance to two breweries, multiple restaurants, roller rink, public beach, shopping and public boat launch. Plenty of room in the driveway for boat and trailer. In close proximity to many other breweries and South West Michigan Wine Trail. Located on the snowmobile trail. Perfect for all ages and all seasons get away!

Top guest favourite
A comfortable living area features two blue sofas adorned with patterned cushions. A dark wooden coffee table is centered on a spacious tan carpet. Colorful wall art adds visual interest, while a ceiling fan provides airflow. Barstools are positioned by a breakfast counter in the background.
Home in Benton Harbor
4.97 out of 5 average rating, 152 reviews

Country home near 6 beaches and Harbor Shores Golf

Convenient and close to the following attractions: Harbor Shores Golf Club - 4.9 mi Silver Beach County Park - 7.2 mi Tiscornia Park Beach - 7.0 mi Roadside Park Beach - 5.5 mi Rocky Gap Beach - 4.9 mi Hagar Park Beach - 3.0 mi Riverside Kayak Park - 2.0 mi Third Coast Paddling - Kayak Rental, Paw Paw River - 5.9 mi Whirlpool Corporation Headquarters - 3.5 mi

Popular amenities for Little Crooked Lake holiday rentals