Cottage holiday rentals in Three Oaks

Cottage in Michiana Shores

A cozy cottage is nestled among lush green ferns and trees, with vibrant flowering shrubs nearby. The structure features a gabled roof and large windows, providing a glimpse of the welcoming interior. A picket fence frames the scene, adding charm to the natural surroundings.

4.99 out of 5 average rating, 148 reviews

The Pines Cottage on Birchwood

The Pines Cottage on Birchwood is a cozy 2 bedroom 1 bathroom cottage with separate TV room perfect for a relaxing visit in Michiana Shores, IN. Walk to the private beaches at Stop 38 and Stop 41. Rear deck and front porch for quiet mornings with coffee or evening beverage. Situated .7 mile (10 min walk) from the lake & beach at Stop 38 and Stop 41, 6 minute drive to New Buffalo and Michigan City-it's perfect for a getaway to Harbor Country. Visit local breweries, wineries, and so much more.

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, 102 reviews

The Cottage of Harbor Country - Close to it all!

Welcome to your very own Cottage in Harbor Country! Renovated and beautifully appointed, our cottage has a mix of vintage charm with modern updates! Enjoy morning coffee on the brand new deck or screened-in porch, take a dip in the new hot tub or cozy up next to the wood-burning fireplace. This is the perfect place to relax and make memories with loved ones! We are a short drive to everything in the area (see location notes for distances) and we’re an easy walk to the beach (approx. 15-20 min)

A screened-in porch features a cozy seating arrangement with two navy blue chairs and a matching sofa set around a narrow coffee table. Skylights and large windows create a bright space with views of the surrounding wooded area.

4.99 out of 5 average rating, 275 reviews

The Birdhouse – quiet luxury, walk everywhere

The Birdhouse is on a quiet wooded ravine steps from restaurants, shopping and a lovely 0.7 mile walk to the beach. This home hosts 4 guests only, including infants. Enjoy a screened-in porch with views to the woods, an outdoor eating area with grill, lovely terrace with firepit and laundry room. Bedrooms are cozy and comfortable. The bathroom features a luxurious rain shower with hand shower for junior guests. To allow our cleaning crew time to prepare, we're unable to offer early check-ins.

4.83 out of 5 average rating, 191 reviews

A private hot tub is visible, featuring a clear water surface and multiple jets. The tub is surrounded by a wooden deck, providing a relaxing outdoor space for guests to unwind.

Cottage in Three Oaks

It’s Sauna & Fireplace Season | Hot Tub| Sleeps 9

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

4.86 out of 5 average rating, 110 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

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.

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, 170 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, 240 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

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, 164 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.

4.96 out of 5 average rating, 226 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!

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, 331 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!

An inviting living area features a plush blue sectional sofa with light-colored cushions. Natural light fills the space, highlighting a cozy rug beneath. In the background, an open layout leads to a bright dining area and a well-equipped kitchen, adorned with vintage decor.

4.9 out of 5 average rating, 453 reviews

Fall into Winter at Sawyer Cottage, Harbor Country

Doze off in a rainbow hammock in a breezy screened porch. There's a timeless cottage feel among the timber floors, whitewashed rafters, and homespun throws. Books and music galore, including a record collection and vintage Dylan poster. ALSO: please see Cottage Coronavirus Protocol for guest peace of mind. AND: 300 mbps WIFI.

Popular amenities for Three Oaks cottage rentals

Kitchen

Wi-Fi

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

The Sawyer Cottage 3 bdrm 2 bath with hot tub

A spacious wooden deck is lined with sturdy, light-colored Adirondack chairs facing the lush green backyard. Tall windows allow ample natural light, while an American flag adds a touch of character. Planters with greenery enhance the inviting outdoor space.

5 out of 5 average rating, 40 reviews

Charming Cottage - Hot Tub, Sauna, Large Yard

A private heated pool is surrounded by a spacious deck shaded by lush trees. A hot tub is positioned nearby on the deck, complementing a rustic cabin with a blue metal roof. Outdoor furniture provides a comfortable space for relaxation.

5 out of 5 average rating, 11 reviews

Harbert Home With Private Pool and Hot Tub

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, 149 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!

4.98 out of 5 average rating, 92 reviews

The exterior of the lake house features a multi-level design with a spacious patio area, highlighted by a fire pit surrounded by stone borders. A hot tub sits nearby, and comfortable seating is arranged under a covered balcony. Lush greenery provides a serene backdrop.

Cottage in Benton Harbor

Cheerful Sister Lakes 4 BDR Lake Hse w/ Hot tub.

Pet-friendly cottage rentals

5 out of 5 average rating, 27 reviews

The cottage exterior showcases a welcoming entrance with a stone staircase leading up to a covered porch. Large windows allow natural light to fill the space. Lush greenery and flower beds surround the frontage, providing a serene setting.

Cottage in Michigan City

Autumn getaway: Cozy cottage on private woodsy lot

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

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, 67 reviews

Dog-Friendly Farmhouse | 1+Acre near Lake Michigan

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, 212 reviews

New Buffalo retreat - Perfect year-round getaway!

The entrance features a solid gray exterior enhanced by a bright turquoise door. White trim outlines the windows, while a covered porch is adorned with a white bench. Clean lines and a welcoming atmosphere characterize the overall design.

4.97 out of 5 average rating, 469 reviews

Twin Cottage B- Walk to Beach & Town!

A spacious living room is featured, showcasing a light blue sofa facing a wooden coffee table. A vibrant area rug covers the hardwood floor, while an armchair in deep red adds a pop of color. Artwork adorns the walls, and soft lighting creates a relaxed ambiance.

5 out of 5 average rating, 15 reviews

Steps from Private Beach & Downtown Union Pier

Private cottage rentals

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

Newly renovated Sister Lakes 3BR Cottage

4.95 out of 5 average rating, 66 reviews

The cottage exterior features a spacious deck with outdoor seating, complemented by colorful umbrellas. A gas grill is situated beside the deck, and several water sports equipment items are arranged on the grass, indicating activities available for guests.

Cottage in Niles

Barron Lake front Cottage. Notre Dame Nearby!

4.92 out of 5 average rating, 37 reviews

A cozy living area features two gray sofas positioned to face a large window, allowing natural light to illuminate the space. A wooden side table holds decorative items. Bookshelves line the wall, filled with various books, creating a welcoming atmosphere.

Cottage in Michigan City

Cozy on Blueberry Hill

4.87 out of 5 average rating, 87 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

4.94 out of 5 average rating, 16 reviews

A quaint modern cottage is depicted, with a well-maintained lawn and a pink flowering tree in the foreground. The entrance features a spacious deck, and the evening sky showcases a subtle gradient of colors as the sun sets behind the structure.

Cottage in Buchanan

Clear Lake Cottage

4.92 out of 5 average rating, 72 reviews

The two-story cottage features a dark blue exterior accentuated by a prominent white star and porch. The front steps lead up to a welcoming entrance door framed in soft pink. Large windows allow natural light to fill the space, surrounded by lush green trees.

Cottage in Michigan City

Beachwalk’s Cozy Cottage - Farmhouse decor

An outdoor seating area is surrounded by lush greenery, featuring a covered patio with comfortable chairs and vibrant flower pots. A grill is positioned nearby on a concrete slab, offering a space for outdoor cooking and dining amidst nature.

5 out of 5 average rating, 33 reviews

Cottage Getaway near Dunes & Lake MI w/Fire Pit

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.