Cottage vacation rentals in Three Oaks

4.93 out of 5 average rating, 201 reviews

A cozy living room is featured with a soft beige sofa and an armchair in navy blue. A light rug with earthy tones is placed under a white coffee table, which holds magazines. A fireplace is surrounded by decorative mirrors, enhancing the welcoming environment.

Cottage in Stevensville

Cheerful Stevensville cottage, GREAT LOCATION!

Right in the prettiest area of Stevensville, Glenlord Cottage is an ideal location for your Southwest Michigan stay. Down the road you will find Glenlord Beach Park, a beautiful Lake Michigan overlook. Around the corner, an award-winning bakery. In Stevensville with its variety of restaurants, beaches, and shops, Glenlord Cottage is also within easy reach of many SW Michigan attractions and is well placed for visits to wineries, golf courses, and downtown St. Joseph with its shops and festivals.

A spacious living area features large French doors that open to a deck. A neutral-toned sofa is adorned with decorative pillows, while a wooden coffee table sits in front. An inviting armchair and framed artwork complement the warm, natural lighting filtering in.

4.99 out of 5 average rating, 109 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, 194 reviews

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.

4.89 out of 5 average rating, 176 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, 246 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.

Cottage in Michiana Shores

A charming cottage is nestled among tall pine trees, partially obscured by greenery. The natural surroundings create a tranquil setting, while the rustic stone chimney adds character to the cozy structure.

4.98 out of 5 average rating, 115 reviews

1930’s Cozy Cottage in the Woods.Walk to the beach

Come fall in love with Michiana Shores, we promise you'll love the peace and quiet. Our charming cottage sits back tucked away, nestled among pine trees and twinkle lights. Roast marshmallows while sitting around the fire with 6 modern adirondack chairs, take a stroll to the beach, ride bikes, BBQ, watch the sunset along lakeshore drive. Play tennis or pickle at the local park. 10 minute walk to the beach. Far away enough to relax yet close enough to new Buffalo, Union Pier or Long Beach

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 hot tub is visible in the foreground, with steam rising gently from the water. In the background, a rustic barn with a blue roof is framed by trees, and snow covers the surrounding area. Outdoor seating is arranged nearby, enhancing the tranquil winter setting.

4.97 out of 5 average rating, 169 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!

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, 229 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

Escape to the Windjammer, Designer Cottage, Pool & Spa Relaxation in Lakeshore Cottages Union Pier. Enjoy 4 bedrooms, 3 bathrooms, community pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax and unwind in this luxurious updated getaway with plenty of sun filled space for all to enjoy year-round. Professional Wolf stove for the chefs. Book your stay today! Create lasting memories!

A cozy living area features a fabric sectional sofa with colorful cushions and a knit throw. Natural light streams through large windows with gray curtains, complementing the soft carpet flooring. A vintage wooden coat rack stands nearby, adding functional charm.

4.84 out of 5 average rating, 157 reviews

Wineries Breweries Warren Dunes Lake Michigan WOW!

Located just outside of Bridgman, this Lake Township home is clean, quaint and accessible to so many great things that are offered in Southwest Michigan—-15 wineries within a ten mile radius, many breweries including Transient and Haymarket in Bridgman, great restaurants, Weko Beach and Warren Dunes State Park! The home offers a perfect place to wind down after a day on the beach or at the wineries—with countless options for amazing food for any meal—or you can cook at home

A spacious wooden deck includes a hot tub surrounded by lush greenery, providing a serene outdoor setting. A white dining table with chairs allows for meals outside, while a large blue umbrella offers shade. The scene is complemented by a simple decorative plant centerpiece.

4.99 out of 5 average rating, 118 reviews

The Dacha • Hot Tub, Family-and-Dog-Friendly House

A four-minute walk to town and a quick drive to everything Harbor Country has to offer! "Dacha" is the Ukrainian word for a country house where the whole family gathers. Relax in a hot tub facing the woods, watch your kids play from the deck, enjoy coffee and sunrise on the front porch, have a glass of wine on the screened-in back porch, roast s’mores at the fire pit, read quietly in one of our reading nooks - these are only some of your options when you stay at The Dacha.

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!

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 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, 43 reviews

Charming Cottage - Hot Tub, Sauna, Large Yard

A modern white home is pictured, featuring a welcoming front porch supported by wooden posts. Multicolored stones create a path leading to the doorway, surrounded by neatly landscaped greenery on a newly mulched yard. Natural light reflects off large windows, inviting a peaceful ambiance.

4.97 out of 5 average rating, 116 reviews

Casa Playa - Union Pier Home w/ Pool & Private Spa

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, 169 reviews

The Lemonade Cottage, New Buffalo. Walk to beach!

4.84 out of 5 average rating, 151 reviews

A hot tub filled with bubbling water is positioned in the foreground. Nearby, four bright red chairs are arranged on a grassy area, offering a space for relaxation. The background features a wooden fence and a clear sky.

Cottage in Benton Harbor

Hot tub! Blue Bird Cottage of Harbor Country!

4.87 out of 5 average rating, 54 reviews

A charming blue exterior of a home is framed by lush greenery and a well-maintained pathway. The inviting front porch features bright red chairs under a pergola, with large glass doors providing a glimpse into the interior.

Cottage in Lakeside

Private Hot Tub and Association Beach!

A recently renovated cottage is framed by lush greenery, featuring a welcoming front porch with multiple large windows. The dark exterior contrasts against light-colored trim, while natural stone pathways lead through vibrant foliage to the entrance.

4.95 out of 5 average rating, 85 reviews

MLK & Pres idents Union Pier, 3 BR+loft, hot tub,

4.98 out of 5 average rating, 44 reviews

Sprawling Retreat w/ Private Beach Access!

Pet-friendly cottage rentals

4.98 out of 5 average rating, 86 reviews

A quaint front porch is featured, highlighted by rocking chairs and decorative elements. An American flag gently waves, with colorful flowers and greenery framing the steps, creating a welcoming entryway to the vintage cottage.

Cottage in Three Oaks

Comfortable, charming vintage 2 bed/1 bth cottage

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, 267 reviews

Northwind Llama retreat “Chicken coop”

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

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!

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, 213 reviews

New Buffalo retreat - Perfect year-round getaway!

4.87 out of 5 average rating, 113 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

4.86 out of 5 average rating, 86 reviews

A fire pit area is arranged with red Adirondack chairs surrounding it, set on a gravel surface. Logs serve as natural seating. The backyard shows a mix of grass and landscaped patches, with a glimpse of the cottage and patio area in the background.

Cottage in Lakeside

The Rail House, Lakeside MI

Private cottage rentals

4.98 out of 5 average rating, 55 reviews

Cottage in New Carlisle

30+ day off season Lake Home New Carlisle

A comfortable living area features a large sectional sofa facing a stone fireplace. Light streams through curtain-draped windows, illuminating the wooden floor. A dining table is positioned nearby, surrounded by six upholstered chairs, while wall decor adds subtle detail to the space.

5 out of 5 average rating, 5 reviews

2 updated Cottages for one price close to beach

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

4.97 out of 5 average rating, 39 reviews

A comfortable living area is featured, showcasing two sofas adorned with blue and gray cushions. A sleek wall-mounted TV is positioned above a white brick fireplace, while natural light filters through multiple windows, illuminating the space. Decorative items are neatly arranged on a nearby shelf.

Cottage in Grand Beach

Cozy 2 bedroom cottage steps from Lake Michigan

5 out of 5 average rating, 28 reviews

Cottage in Eau Claire

Channel House on Indian Lake

4.87 out of 5 average rating, 92 reviews

The lodge features a spacious lakefront view with multiple decks and patio seating for outdoor relaxation. A sandy beach is visible in front, leading to calm waters. Surrounding greenery adds to the serene environment, while nearby recreational equipment hints at available activities.

Cottage in Decatur

Lakefront A-Frame - Beach, Fire Pit, SUP/Kayaks

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

The cottage's exterior showcases a large deck with a dining table and a hot tub, surrounded by greenery. Large windows provide views of the forested area. The structure features a combination of white and dark siding, contributing to the vintage charm.