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, 220 reviews

One of a kind Grain Binn | Hot Tub | Private,

*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

Top guest favorite

A welcoming entrance to the log home is framed by manicured grass and landscaped flower beds. The wooden porch offers a spacious area for relaxation, while the surrounding trees provide a natural, serene backdrop. Colorful flowers dot the garden, enhancing the outdoor appeal.

Guest suite in Cassopolis

4.99 out of 5 average rating, 378 reviews

The Hideaway on Mitchellii Lane

A completely furnished apartment in the basement of our log home (our main residence) on 5 acres of woods above beautiful Shavehead Lake. Entrance into the apartment through a screened in porch and double French doors provides privacy and space to relax and enjoy the beautiful outdoor landscape. A large egress window allows natural sunlight into the bedroom on the opposite side of the wall from the kitchen/dining room/living room. High speed internet & YouTubeTV provide entertainment options.

Top guest favorite

An interior view of the studio apartment showcases a small kitchenette with a refrigerator, stove, and sink. A door leads outside, and a window with turquoise curtains allows natural light to enter. A cozy bed with a patterned quilt is positioned nearby, creating a functional yet inviting space.

Apartment in South Bend

4.97 out of 5 average rating, 265 reviews

Tiny Retro Studio for One Person

TINY studio for one non-smoker. Our usual guest is a busy academic, intern, medical worker or businessperson. This TINY studio is located in an old 4-unit apartment house, so there is some in-house sound transfer. Our neighborhood is usually quiet, but not always. See the LOCATION section under the map to check if our neighborhood is suitable for you. No smoking indoors or out. Memorial Hospital 3 blocks, Notre Dame 2.5 miles, downtown 1/2 mile. 8 minutes to SB Airport and 80/90 Toll Road.

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, 270 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, 12 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.

Top guest favorite

A serene riverside view captures vibrant autumn foliage reflected in calm waters. Comfortable seating is arranged on a stone patio, overlooking the river, enhancing the tranquil outdoor experience. Sunlight dances on the water's surface, inviting relaxation and connection with nature.

Apartment in Mishawaka

4.96 out of 5 average rating, 521 reviews

Private Entrance Guest Suite on the River

Stay in our studio apartment suite with private exterior door entrance. Hosts live in the rest of the house. From the backyard you can fish, kayak/canoe, paddle board, enjoy a bonfire, grill, and relax by the river. There's a king memory foam bed, sleeper sofa, and 49" TV. Remote work friendly with spacious workspace desk, fast WIFI, and coffee. The closet has a mini food prep area with mini fridge and microwave, and grill out on back patio. It's a quick 15 min drive to Notre Dame.

Top guest favorite

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, 22 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 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, 126 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 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, 368 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 the cottage showcases a spacious deck adorned with colorful Adirondack chairs. Large glass doors reflect the surrounding greenery, while landscaped flower beds provide a vibrant touch. A gas grill is visible near the deck, enhancing the outdoor gathering space.

Cottage in Bangor

4.95 out of 5 average rating, 227 reviews

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.

Top guest favorite

A charming brown exterior of the home is framed by tall trees and bushes, creating a serene and private setting. Large windows provide a glimpse of the inviting spaces inside, while stone features at the base enhance the natural landscape.

Guest suite in Benton Harbor

4.97 out of 5 average rating, 290 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

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, 21 reviews

Beach front 4bd 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!