Holiday houses in Little Crooked Lake

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Little Crooked Lake

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Superhost
Home in Dowagiac
5 out of 5 average rating, 3 reviews

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.

Top Guest favourite
A hot tub invites relaxation on a stone patio overlooking the serene lake. Nearby, a shaded umbrella provides comfort for lounging chairs arranged by the water. The scene includes a private dock and boats moored in the distance, framed by lush greenery along the lakeshore.
Cottage in Benton Harbor
4.98 out of 5 average rating, 102 reviews

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

Guest favourite
Home in Buchanan
4.97 out of 5 average rating, 120 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.

Guest favourite
Guesthouse in Berrien Springs
4.96 out of 5 average rating, 138 reviews

Secluded Country Cabin

Spring is just around the corner, schedule your getaway and start planning for the summer now and enjoy your stay in this 400 sf newly renovated cabin that has knotty pine interior walls throughout along with new carpet and vinyl flooring. Enjoy the peace & quiet as you sit around the fire pit or relax on the outdoor patio that's fully furnished with furniture and a charcoal grill. Come enjoy your stay as you take advantage of the local wine tours, nearby Lake MI. beaches and the county parks.

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, 283 reviews

Couples country stay, Private, Hot Tub, Creek,

*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

Guest favourite
Home in Coloma
4.98 out of 5 average rating, 163 reviews

Hot tub & sauna, pet friendly, 1/2m to Hagar Beach

Peaceful, newly renovated 1930’s cabin walkable (1/2 mile) to Hagar Beach in the heart of SWMI. This pet-friendly home has a cozy feel with an outdoor hot tub, sauna, & fully-furnished spaces perfect for a relaxing getaway, remote work, or staycation home base while you explore the lake, bike trails, breweries, & eateries. Enjoy a quiet, off-the-beaten path stay close to everything Lake Michigan offers featuring a stocked kitchen, cozy reading nook & desk, and outdoor dining & fire pit.

Guest favourite
A modern tiny house made of wood and metal is nestled among trees, featuring large picture windows that provide a view of the interior. An outdoor fire ring with two Adirondack chairs sits nearby, surrounded by mulched ground and illuminated by string lights.
Tiny home in Sawyer
4.92 out of 5 average rating, 142 reviews

Modern Minimalist Tiny House | Firepit | Nature

Welcome to our modern minimalist tiny house located a half mile from Warren Dunes State Park beach and 1.5 miles from all that Sawyer Michigan area has to offer. Tiny is the second dwelling on this property and is technically a mobile tiny house. While we do have electricity and water, much like an RV the drains run to holding tanks. This means VERY LIMITED WATER USE for showers and toilet flushing. It features a fully stocked kitchen, bathroom, and a queen bed in the small loft.

Guest favourite
Cottage in Harbert
4.97 out of 5 average rating, 182 reviews

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

Top Guest favourite
A serene view of Little Crooked Lake is captured, showcasing calm waters reflecting a cloudy sky. A small dock is visible extending into the lake, along with lush greenery framing the scene. The shoreline is gently sloped, enhancing the tranquil atmosphere.
Home in Dowagiac
5 out of 5 average rating, 14 reviews

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.

Guest favourite
Cottage in Benton Harbor
4.87 out of 5 average rating, 211 reviews

Hot tub! Red Tin Cottage of Harbor Country!

Welcome to The Red Tin Cottage of Harbor Country! Nestled in a quiet, rural setting Red Tin is a character-filled, country-chic escape in beautiful Southwest Michigan. Within minutes of award winning beaches, golf courses, wineries, breweries, and restaurants you can be close to it all and retreat back to peace. Take a dip in the hot tub on a starry night, relax in the claw foot tub after a day of play, or enjoy stories around the firepit with family and friends. Come gather!

Top Guest favourite
Holiday home in Berrien Springs
4.9 out of 5 average rating, 105 reviews

Charming Apt near AU, ND, lake beaches & wineries

Welcome to this thoughtfully planned one-bedroom apartment, equipped to host up to 3 guests. It is located in a quiet countryside neighborhood and has a dedicated workspace. You'll enjoy all the tourism possibilities this well-located unit offers and the cool amenities prepared to make you feel at home. You are: 5 minutes from Andrews University 20-25 minutes from St. Joseph & fantastic beaches on Lake Michigan 30 minutes from Notre Dame, SBN, Warren Dunes & wineries

Top 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.

Popular amenities for Little Crooked Lake holiday rentals