Vacation rentals in Little Crooked Lake

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Top-rated vacation rentals in Little Crooked Lake

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Top guest favorite

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, 216 reviews

One of a kind Grain Binn | Hot Tub | Creek View

*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

Guest favorite

A yurt is set amidst a green landscape, with a wooden deck leading up to its entrance. A small private outhouse is positioned nearby, adorned with flowers. Overhead, a dramatic sky features varied cloud formations, enhancing the peaceful rural setting.

Yurt in Buchanan

4.97 out of 5 average rating, 175 reviews

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.

Guest favorite

A spacious outdoor view is presented from a deck, overlooking expansive green fields and wooden fencing. In the distance, a large barn is visible, along with a few horses grazing nearby. A tree branch frames the scene, creating a peaceful country atmosphere.

Guesthouse in Sodus Township

4.79 out of 5 average rating, 267 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.

Top guest favorite

A spacious lakeside home with multiple decks overlooks the water. The property features lush landscaping, a sandy beach area, and a variety of outdoor seating options, including lounge chairs and tables under umbrellas. An American flag gently flutters nearby, enhancing the serene setting.

Home in Dowagiac

5 out of 5 average rating, 11 reviews

The Cove on Round Lake

This tranquil Round Lake home includes luxurious and custom amenities. Enjoy a lush lawn, meticulously maintained interior, three deck levels and 120-feet of lake frontage. Featuring 4-bedroom suites and 4-full bathrooms that accommodates 11 guests. Local produce stands, breweries, wine tours and great golf courses are just around the corner. With unbeatable outdoor enjoyment and optional pontoon rental, there is something for everyone in your group to enjoy. Welcome to The Cove.

Guest favorite

A spacious cottage is surrounded by tall trees, offering shade and a relaxing environment. A large deck extends from the back, while a fire pit area with Adirondack chairs sits on the grassy lawn, inviting outdoor gatherings.

Cottage in Dowagiac

4.96 out of 5 average rating, 124 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 favorite

A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.

Guesthouse in New Buffalo

4.97 out of 5 average rating, 612 reviews

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!

Top guest favorite

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, 352 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.

Top guest favorite

The exterior of a charming, two-story house is framed by tall trees, showcasing its rustic architecture and large windows. A tire swing hangs from one of the trees, and a seating area with chairs and a fire pit is visible on the grassy lawn.

Guest suite in Benton Harbor

4.97 out of 5 average rating, 277 reviews

The Gingerbread House, respite in the woods.

If you are looking for a zen like place to get away for a few days, the Gingerbread House is perfect. Guests have separate and private apartment (with Smart Lock) on bottom floor of (occupied) home with private patio overlooking huge ravine. Our home is surrounded by over 20 acres of woods, yet we are only minutes from grocery, restaurants, golfing and beaches.

Top guest favorite

A modern cottage exterior is presented with a sloped roof and large windows, surrounded by lush greenery. A wide pathway leads to the entrance, where sunlight filters through the trees, casting delicate shadows on the manicured lawn.

Cottage in Dowagiac

4.96 out of 5 average rating, 23 reviews

Newly renovated Sister Lakes 3BR Cottage

Relaxing 3 bedroom 1 bath cottage in Sister Lakes, MI with a 3 minute walk from the calm, Cable Lake. This sought after location is 30 minutes from Lake Michigan, 40 minutes from Notre Dame/South Bend and has quick access to breweries, wineries, shopping, and all that is necessary for a relaxing vacation. Filled with Lakehouse character!

Top guest favorite

The exterior of a lakefront retreat is showcased at sunset, with a wooden dock leading to a sandy beach. The two-story house is surrounded by trees and neighboring homes, reflecting warm colors in the sky. Outdoor seating is visible on the deck, inviting relaxation.

Home in Dowagiac

5 out of 5 average rating, 16 reviews

New Beach front 5bd in Sister Lakes w/ Hot tub

Enjoy with family and friends. 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!

Guest favorite

A fire pit surrounded by two chairs is positioned on a grassy area near the lake. A wooden dock extends into the calm water, with colorful trees lining the shore visible in the background under a clear blue sky. The scene reflects a serene lakeside atmosphere.

Cottage in Dowagiac

4.89 out of 5 average rating, 54 reviews

Stylish Lakehouse, Sandy Beach Includes lux Boat!

Two contemporary cottages on Big Crooked, Sister's Lakes. Property rents together with both houses to sleep 12 AND includes new pontoon boat! Perfect for multiple families or large friend groups. Private sandy beach front and clear water, flat land perfect to hang out and swim.

Guest favorite

A small entrance area features a floral-patterned sofa against a light wall. A door leads to a connecting room, while natural light filters in through nearby windows. A textured rug lies beneath, complementing the wooden floor.

Guest suite in Berrien Springs

4.85 out of 5 average rating, 102 reviews

Green Place

Do not expect a luxurious and spacious suite! It’s small, simple , quiet and clean place. Ideal for a relaxing and peaceful stay! Close to an enjoyable atmosphere and apart from rebellious thoughts. It’s a safe stay in a peaceful place! About a 10 to 15 minute walk to Lake Chapin.