Holiday rentals in Little Crooked Lake

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Top-rated holiday rentals in Little Crooked Lake

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Guest favourite
A welcoming porch is featured, showcasing a comfortable seating area with a navy blue cushion sofa and two matching chairs. Lush greenery surrounds the entrance, and natural light illuminates the space through large windows.
Home in Saint Joseph
4.83 out of 5 average rating, 113 reviews

Silver Beach 2bd -1 block to downtown State Street

The historic McNeil House is located on State Street just one block from Downtown restaurants, shops, and the Bluff. You won't find a better or more convenient location when visiting this beautiful city! We're offering smaller groups an opportunity to stay in our historic home by renting the main floor that sleeps up to five guests. The upstairs will not be rented during your stay, so you'll have the house to yourself but won't have access to the upstairs. Only available during the off season.

Top guest favourite
Cabin in Coloma
4.99 out of 5 average rating, 100 reviews

Cozy Cabin in the Woods

Just under two hours from Chicago and only 1/2 mile from Hagar Beach, this beautifully updated 100-year-old cabin offers a peaceful retreat in the woods. Surrounded by tranquil landscapes and towering trees, you’ll enjoy the perfect blend of rustic charm and modern comfort. Tucked along a quiet dirt road, the cabin is ideally located 15 minutes from South Haven and 10 minutes from St. Joseph making it close enough for dining, shopping, and activities, yet far enough to unwind in nature’s calm.

Top guest favourite
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, 387 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 favourite
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.
Guest house in Sodus Township
4.8 out of 5 average rating, 304 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.

Guest favourite
A cozy sleeping area features a spacious bed with a soft, textured throw blanket draped over it. An antique world map hangs above the bed, complemented by warm pendant lights. A decorative pillow adds an inviting touch to the arrangement.
Cottage in Dowagiac
4.87 out of 5 average rating, 113 reviews

Vintage Romance Finds Cozy Charm at Depot Cottage

Convenience and luxury combine in this imaginative and engaging Cottage just steps away from the Historic Train Station in this Charming All-American town. Our Vintage Travel/Train themed Cottage has family friendly features, like a children's train playroom, working model trains, stocked kitchen, and a spacious enclosed backyard for four legged babies. With romantic features like a beautiful vintage soaking tub and 100% linen bedsheets we fit any vacation requirement. Walkable to all needs.

Top guest favourite
Farm stay in Vandalia
5 out of 5 average rating, 256 reviews

Secluded, Hot Tub, Lux, Couples, Nature, Creekside

*Escape to your private couple’s retreat. *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 to reconnect

Top guest favourite
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.
Flat in South Bend
4.97 out of 5 average rating, 273 reviews

Tiny Retro Studio for One Person

TINY studio for ONE. Non-smoking inside & out. Our typical 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 read a description of our neighborhood. *Winter Note: We shovel the walkways at the Airbnb, but not usually until later in the day. So mornings might be snowy.

Top guest favourite
A modern kitchen and living space are shown, featuring a blue sofa and two light-colored chairs. A dining table set for four is positioned in the center, with a vase of flowers as the centerpiece. Appliances include a stainless-steel refrigerator and a double sink, with natural light illuminating the room.
Holiday home in Berrien Springs
4.89 out of 5 average rating, 102 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

Guest favourite
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, 131 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.

Guest favourite
A spacious living area is featured, showcasing a modern dark sectional sofa and a unique round chair. A glass coffee table sits at the center, complemented by decorative wall art and mirrors. Natural light fills the room through large windows with blinds.
Apartment in Saint Joseph
4.91 out of 5 average rating, 202 reviews

*Luxury condo on water in St Joseph, 2 queen beds*

Modern and beautiful condo on the river going into the mouth of Lake Michigan near Silver Beach. Immediately next door to Clementine’s restaurant and within walking distance to many shops, bars, downtown, and the beach. Right next to Pier 33 Marina and docks and water rentals. You can eat, drink, fish, shop, and enjoy the beautiful scenery all at one spot. Silver beach/the pier is literally a short walk away!

Top guest favourite
An inviting kitchen features wooden cabinetry and granite countertops. A black 'welcome' sign is placed on the countertop next to a vase of fresh flowers. Kitchen appliances, including a coffee maker, are neatly arranged, creating a functional and welcoming space.
Guest house in Stevensville
4.99 out of 5 average rating, 237 reviews

The Shire

Nestled on five secluded, tree-lined acres, with a pond, waterfall, fire pit, tree swing, basketball court and walking trails, The Shire feels a million miles away from it all - but isn't! We are only minutes away from wineries, breweries, amazing beaches, restaurants and shopping. (Notre Dame is an easy 30 minute drive). Southwest Michigan is a beautiful place to live! We'd LOVE to share it with you.

Guest favourite
A single-story house is presented with a gray exterior and white trim. A welcoming front porch features seating and flower arrangements. The surrounding property is characterized by a large grassy area and trees, creating a peaceful setting.
Home in Benton Harbor
4.92 out of 5 average rating, 232 reviews

The QT

Cozy country retreat. Whether you are visiting to explore Lake Michigan beaches (15 minutes away), the Lake Michigan Shore Wine Trail, the Makers Trail, or if you are invited to a wedding at the Blue Dress Barn (5 minute walk) or Sundance Studios (1 mile) this is the place for you! Fall asleep under the stars (skylight) in our brand new king size bed and wake up to a cup of coffee in a cheerful kitchen.

Popular amenities for Little Crooked Lake holiday rentals