Cottage vacation rentals in Three Oaks

4.93 out of 5 average rating, 228 reviews

Bright & Warm by Warren Dunes Maple St Beach House

Beautiful renovated house on wooded lot, half mile to the Warren Dunes! Home completely designed for the ultimate vacation rental getaway! SS kitchen, memory foam mattresses, marble bathrooms w/walk-in shower on main floor & full bath w/tub up, hardwood floors, gas fireplace in sitting area and great room that connects the living/dining and kitchen. Roast s’mores, grill steaks & sip local brews in the private backyard w/ fire pit. Central to everything in Harbor Country. Come enjoy winter w/us!

4.99 out of 5 average rating, 113 reviews

The Cottage of Harbor Country - Close to it all!

Welcome to your very own Cottage in Harbor Country! The perfect weekend getaway from Chicago, our cottage is close to Warren Dunes and just a 15-20 minute walk to Lake Michigan. Renovated and beautifully appointed, it blends vintage charm with modern updates! Enjoy morning coffee on the new deck or screened-in porch, take a dip in the new hot tub, or cozy up next to the wood-burning fireplace. Enjoy the perfect place to relax, hike, go antiquing, wine-tasting, and make memories with loved ones!

4.82 out of 5 average rating, 200 reviews

An indoor sauna features warm wooden paneling and multiple seating levels. A wooden bucket and two glasses are placed on the upper bench, while a pair of blue flip-flops and neatly folded towels rest on the lower bench, inviting relaxation.

Cottage in Three Oaks

Hot Tub • Sauna • Fireplace | Cozy Winter Retreat

Wanna Play?? You name the game & we most likely have it! Outdoor fun includes YEAR-ROUND hot tub, Pickleball & Volleyball nets, Soccer goals, Putting Green, corn hole and even cruiser bikes. Indoor fun incl. complete poker table/set & a ton of board games! If you prefer to take it easy you can relax by our indoor fireplace or the outdoor fire pit, recharge in the YEAR-ROUND indoor sauna or stroll to nearby Harbert Beach. Whatever your choice, THIS is the place to experience Harbor Country

The exterior of the cottage is showcased, featuring a welcoming dark grey facade. The front yard contains well-maintained greenery and small trees. Two large picture windows allow natural light into the interior, while a small patio leads to the entrance.

4.9 out of 5 average rating, 182 reviews

Camp Wanderlust-Cozy lodge-20 minute walk to beach

A place to wander with the ones whose company you enjoy. Enjoy a cozy getaway, in our quiet cottage. 10 minute walk from shops and brewery and restaurants of Union Pier. 10 minute walk to Winery Tasting. 20 minute walk to Townline Beach. Union Pier is the perfect beach town in the heart of harbor country, enjoy exploring this magical region or maybe just kick back and build a fire and enjoy the space. 1914 a colony of Chicago bohemians, vacationed at the "Camp's Cottages" at Union Pier.

A cabin-style home is nestled among tall pine trees, featuring a large facade with distinctive tall windows that allow natural light to flood the interior. Colorful chairs are positioned on the screened porch, surrounded by well-maintained greenery and flower beds.

4.98 out of 5 average rating, 248 reviews

"The Pines" in Union Pier: Year-round getaway

Under towering pine trees that feel more like the Northwoods, you're in the heart of Harbor Country. About 1.25 miles from the shore, minutes from New Buffalo & Three Oaks. Updated cabin-style home offers rustic feel with luxury comforts & highspeed WiFi, and great indoor & outdoor space. Garage plus additional parking. Enjoy the area's beaches, restaurants, outdoor activities, breweries & wineries. Southwest Michigan at it's best! Please see policies for pets & children in house rules.

A cozy fire pit is situated in a gravel area, surrounded by four wooden chairs. The background features a quaint cottage with soft lighting glowing from the windows, framed by large trees, creating a peaceful outdoor setting.

4.94 out of 5 average rating, 374 reviews

Steps to the Beach! Screened in Porch & Firepit!

Experience the ultimate Harbor Country getaway! Just a 90-second stroll to a public beach access and under 5 minutes to another, this location is unbeatable. Spend your day soaking up the sun, kayaking, paddle-boarding, antiquing, golfing, or climbing majestic dunes. Discover endless local breweries, wineries, and top-rated restaurants. Unwind in the evening on the spacious screened-in porch or by the cozy firepit. Your perfect retreat awaits - adventure and relaxation all in one!

The exterior of Twin Cottage A is shown, featuring a light blue front door framed by white columns. A white bench is positioned beside the entrance on a wood deck. Lush greenery and sunlight illuminate the area, contributing to a welcoming atmosphere.

4.95 out of 5 average rating, 420 reviews

Twin Cottage A- Walk to Beach & Town!

Twin Cottage A is your home for convenience & comfort! 2 blocks from town shopping & restaurants, Church Brewing Co. around the corner, an artisanal cocktail lounge up the block and only 3700 feet to the beach! You'll have a private, fenced in backyard for the kids and/or dogs. gas grill, outdoor dining & a fire pit stocked with wood. Check out Cottage B as well for a complete look at our reviews. *Stays 28 days or longer require weekly cleaning fee added after inquiry or request

The exterior of the cottage is surrounded by trees, with a designated seating area featuring two blue Adirondack chairs and a wooden table. A firepit sits in the gravel yard, offering a natural gathering space among green foliage.

4.97 out of 5 average rating, 150 reviews

Beach Bird Cottage- 5min walk to the lake! 3BR/1BA

Dear friends, Welcome to Beach Bird Cottage, situated on a quiet street with other vintage cottages in the heart of Union Pier. It is an easy 5-minute walk to an association beach. The cottage has many updates, including a new kitchen, bathroom, washer/dryer, outdoor shower and a wood stove. The master and second bedroom each have queen-size beds and the children's bedroom has two twin beds. Enjoy an early swim before breakfast or have an evening beach picnic under the sunset.

A spacious screened-in porch is adorned with comfortable seating and decorative pillows. Large windows allow natural light to fill the area, while a decorative table at the center holds a selection of refreshments. The serene view of the surrounding landscape enhances the inviting ambiance.

4.97 out of 5 average rating, 172 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!

An inviting cottage exterior features a wooden fence and a screened porch. Surrounding greenery showcases tall grasses and autumn foliage, creating an appealing atmosphere. A chimney and part of the roof can be seen, indicating the cozy interior space.

4.95 out of 5 average rating, 332 reviews

J’s Beach House: Hot Tub & short walk to beach!

J's Beach House is < a 5 minute walk to the beach! My cottage is equipped with a private hot tub and fireplace. Enjoy the walkable town or jump in your car for a quick drive to any Harbor Country activity! Potential for rental with adjacent cottage "Riley's Retreat". *Please inquire about our other Airbnb cottage near downtown Union Pier. This cottage is a 2-bedroom plus kids loft, screen porch, hot tub, fire pit, plus walking distance to Townline Beach!

A charming farmhouse is surrounded by blooming pink magnolia trees, creating a serene setting. Two large windows are visible on the upper level, complemented by decorative latticework on the side. A vintage wheel and garden furniture hint at the inviting outdoor space.

4.93 out of 5 average rating, 269 reviews

Northwind Llama retreat “Chicken coop”

Tucked away on a peaceful working llama retreat—voted the #3 stay in the state of Michigan—this charming efficiency suite offers a cozy retreat surrounded by nature. The thoughtfully designed space features ample seating for relaxing after a day outdoors with a convenient kitchenette. Step outside to not one, but two private gardens. A truly unique and tranquil getaway that blends comfort with award-winning countryside charm.

4.92 out of 5 average rating, 124 reviews

A circle of Adirondack chairs surrounds a central fire pit, positioned on gravel. Potted plants and flowers add greenery, while a backdrop of trees and a storage shed enhance the natural setting of the outdoor space.

Cottage in Three Oaks

Private, Sun-filled Union Pier Cottage

Sunny, private cottage set on a half-acre facing woodlands. Quick drive to everything - beaches, hiking, restaurants, wineries, breweries, etc. High-speed internet available and desk with two monitors. Please be advised: reservation requests from first-time AIRBNB renters will be declined. You must have rented through AIRBNB in the past and received a high rating.

Popular amenities for Three Oaks cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.88 out of 5 average rating, 132 reviews

The exterior of the cottage is shown, featuring a yellow siding with large windows that provide ample natural light. A small wooden deck is visible in front, furnished with a grill and seating. Well-maintained green shrubs and grass surround the property.

Cottage in Decatur

Charming Cottage on the Lake

A spacious living area features wooden ceilings and large windows, allowing natural light to fill the room. Comfortable sofas surround a sleek coffee table, complemented by accent chairs. An open layout connects to the kitchen, creating a seamless flow between spaces.

4.97 out of 5 average rating, 36 reviews

Hot Tub, Fire Pit | Jungle Gym | Near Warren Dunes

A spacious outdoor area is depicted, featuring multiple wooden lounge chairs arranged around a stone fire pit. Potted plants add greenery, while the house's large windows provide a glimpse of the interior. Trees surround the patio, enhancing the privacy of this inviting outdoor space.

5 out of 5 average rating, 45 reviews

Charming Cottage - Hot Tub, Sauna, Large Yard

A charming yellow cottage is framed by a white picket fence and greenery. An American flag decorates the front, while a welcoming pathway leads to the entrance. Large windows with shutters provide light to the interior, complemented by a modest porch and seating.

4.95 out of 5 average rating, 171 reviews

The Lemonade Cottage, New Buffalo. Walk to beach!

The exterior of Claddagh Cottage is showcased, featuring a blue siding home surrounded by trees. A circular fire pit is surrounded by various chairs in playful colors, with an outdoor hot tub visible to the side. The yard is spacious and filled with fallen leaves.

4.73 out of 5 average rating, 66 reviews

Union Pier Home With Hot Tub

4.81 out of 5 average rating, 196 reviews

An open kitchen and dining area is visible, featuring a dark wooden table with three matching stools. The kitchen is equipped with white appliances and blue cabinetry, illuminated by natural light from a nearby window. The flooring is a mix of dark wood and light tiles.

Cottage in Benton Harbor

Beach Bliss | Pet Friendly W/Hot Tub Near Lake MI

4.86 out of 5 average rating, 199 reviews

An outdoor area is shown featuring a hot tub positioned on a wooden deck. The red exterior of the cottage contrasts with the surrounding green grass and wooden fencing. A glass door leads into the main structure, enhancing the inviting rural charm.

Cottage in Benton Harbor

Hot tub! Red Tin Cottage of Harbor Country!

A bright living room features high ceilings with a chandelier above a central wooden coffee table. Comfortable dark gray sofas are positioned around the table, complemented by decorative cushions. Large windows allow natural light to fill the space, and a stone fireplace adds a cozy focal point.

4.97 out of 5 average rating, 231 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

Pet-friendly cottage rentals

The exterior of the cottage is presented, showcasing a spacious screened-in porch framed by greenery. The flat roofline and large windows invite natural light, while a neatly landscaped area with a stone border enhances the tranquil setting. Lush grass complements the peaceful environment.

4.96 out of 5 average rating, 82 reviews

Rosie’s Cottage close to Warren Dunes (w pool)

4.94 out of 5 average rating, 16 reviews

A charming waterfront property is showcased, featuring a spacious deck with two red umbrellas providing shade. A small red shed is visible, along with seating options, and colorful paddle boats are moored nearby. Lush green trees surround the area, complementing the serene setting.

Cottage in Dowagiac

Pontoon Included *5/1/26-10/12/26* MI Getaway

4.91 out of 5 average rating, 43 reviews

The entrance features a bright pink door with an oval design and decorative detailing. A black doorknob and a keypad lock are visible, providing easy access. Light-colored walls and a natural woven mat contribute to the welcoming appearance of the entryway.

Cottage in Three Oaks

Cozy Cottage - Newly Renovated

A charming farmhouse is seen at dusk, featuring a well-maintained exterior with a welcoming front porch lit softly. An American flag gently flutters above, while the property is surrounded by greenery and trees. Warm light spills from the windows, adding to the serene evening ambiance.

4.96 out of 5 average rating, 68 reviews

Dog-Friendly Farmhouse | 1+Acre near Lake Michigan

4.93 out of 5 average rating, 101 reviews

Cottage in Decatur

Lakeside Getaway

The exterior of the cottage is shown, featuring a mix of siding in varying shades of gray. Two potted plants in black containers frame the entrance, while a porch with a railing adds a welcoming touch. Lush greenery surrounds the property, enhancing the inviting appearance.

4.81 out of 5 average rating, 242 reviews

The Koi Cottage - Union Pier- Dog Friendly!

4.87 out of 5 average rating, 115 reviews

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

Vintage Romance Finds Cozy Charm at Depot Cottage

A spacious wooden deck is adorned with soft string lights overhead, creating a cozy ambiance. Two comfortable chairs and a small table are positioned for relaxation. A potted plant with bright yellow flowers adds a touch of color to the inviting outdoor space.

4.98 out of 5 average rating, 215 reviews

New Buffalo retreat - Perfect year-round getaway!

Private cottage rentals

4.98 out of 5 average rating, 55 reviews

A private sandy beach area offers six Adirondack chairs in a circle, facing a tranquil lake. In the distance, a dock holds two boats, while a kayak and paddleboard rest nearby. Lush green grass frames the scene, enhancing the serene lakeside setting.

Cottage in New Carlisle

30+ day off season Lake Home New Carlisle

4.96 out of 5 average rating, 24 reviews

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

Family Lake Getaway • 3BR • Near Beach & Wineries

4.95 out of 5 average rating, 66 reviews

A comfortable living area features dark wicker furniture and a glass coffee table. Large sliding glass doors provide a view of the lake and outdoor seating on the deck. Natural light fills the room, while the serene water and boats are visible through the windows.

Cottage in Niles

Barron Lake front Cottage. Notre Dame Nearby!

4.97 out of 5 average rating, 39 reviews

Cottage in Grand Beach

Cozy 2 bedroom cottage steps from Lake Michigan

A charming white cottage is framed by lush greenery, featuring a welcoming pathway lined with diverse plants. The entrance is accentuated by a screened door, and large windows invite natural light, creating a bright and airy atmosphere.

4.85 out of 5 average rating, 52 reviews

Elephant Walk- Cottage 5

A modern cottage exterior is framed by tall white columns, offering a welcoming porch area. Comfortable seating arrangements face the lush green yard, while a large tent adds a cozy outdoor element. The home is surrounded by mature trees, providing a private ambiance.

4.76 out of 5 average rating, 46 reviews

Australian Style Cottage Unwind / Reset Recharge

4.86 out of 5 average rating, 88 reviews

Cottage in Coloma

Farmhouse Retreat Near Lake Michigan and Wineries

An outdoor patio area features a covered seating arrangement with wooden tables and chairs. Lush greenery surrounds the space, providing a serene atmosphere. A hot tub is conveniently located nearby, inviting relaxation under the covered breezeway.