Cottage holiday rentals in Michigan City

4.99 out of 5 average rating, 149 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, 110 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!

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, 214 reviews

New Buffalo retreat - Perfect year-round getaway!

Located in the heart of New Buffalo and walking distance to everything, this recently remodeled cottage is the perfect place for an escape. With an open kitchen/porch concept, leading out to a massive natural wood deck, your entry to a huge fenced in corner lot, there is no shortage of space for any summer activity or just to get back to a quieter, more relaxing pace. In winter months New Buffalo is just as charming with fewer visitors and plenty of opportunities to explore the area. CR23-0048

4.96 out of 5 average rating, 223 reviews

An inviting living space is showcased, featuring a light-colored sectional sofa with colorful throw pillows. A wooden coffee table sits in front, while a dining area with white chairs is visible. The kitchen is equipped with modern appliances, and a ceiling fan adds a touch of comfort.

Cottage in Michigan City

The White Cottage Home

This cottage home was built less than 5 years ago. The space is modern and open. It’s located less than 10 mins walk to Lake Michigan beach access. Guests can walk a few minutes to enjoy nearby restaurants such as Dune Billies for breakfast and Cool Runnings Jamaican restaurant. There’s a nearby park and a small dune for short hikes. Other nearby attractions include the Washington park and zoo (5-10 min walk), Blue Chip casino (2 min drive), the Indiana Dunes National Park (20 min drive)

4.99 out of 5 average rating, 280 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.

An outdoor fire pit area is surrounded by six teal chairs, arranged in a circular formation on a stone patio. The backdrop features a cozy brown cottage partially shaded by tall trees, with a gas grill visible nearby.

4.96 out of 5 average rating, 184 reviews

2026 Dates Now Open @ The Birchwood Cottage!

Time is now to hurry & book your 2026 dates @ THE ONE & ONLY BIRCHWOOD COTTAGE IN MICHIANA SHORES...where only good things happen & memories are made! Reviews tell our story & we are constantly upgrading to enhance your experience. It is a slice of heaven just 75 minutes from downtown Chicago be it for glorious summer beach days, long walks or napping on the screen potch. Once settled in this cozy cottage, you have everything you need on the property and in the area for a perfect vacation!

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, 178 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 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, 116 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 charming cottage is surrounded by lush green landscaping and vibrant flowers. A screened-in porch is adorned with lights, leading to an inviting entryway. A separate storage garage is visible in the background, complementing the colorful exterior of the cottage.

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 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.

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!

4.93 out of 5 average rating, 439 reviews

The tranquil surface of Flint Lake reflects a colorful sunset, with soft hues of pink and orange blending into the serene blue sky. The surrounding tree line is silhouetted against the fading light, creating a peaceful and calming atmosphere.

Cottage in Valparaiso

The Lake Escape -Cozy Lakefront Cottage Valparaiso

Escape the everyday with a relaxing stay at this cozy cottage located on Flint Lake! Hot tub, pontoon boat, fire pit, gas fireplace, tv, lake front, canoe, kayak, sauna, grill and more. This charming property is lake front with a small 50ft beach area and dock. Use of 2018 Sylvan pontoon boat, canoe, and kayak are included. You will love the lake life. Please note the pontoon boat is only available in season from May 1st to October 1st.

Popular amenities for cottage rentals in Michigan City

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Superhost

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

4.88 out of 5 average rating, 132 reviews

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 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, 170 reviews

The Lemonade Cottage, New Buffalo. Walk to beach!

4.94 out of 5 average rating, 559 reviews

The charming cottage is nestled among trees, featuring a metal roof and wooden exterior. A small covered porch with sheer curtains surrounds the hot tub, while a pergola with string lights stands nearby, accompanied by adirondack chairs and a neatly arranged firewood stack.

Cottage in Goshen

Quaint Cottage: guests rave clean; cozy; quality

A spacious living area is highlighted by wooden beams and natural light. A comfortable sofa and armchairs arrange around a round coffee table. A striking wall art piece features a deer, while large glass doors provide views of the outdoors.

4.97 out of 5 average rating, 170 reviews

Hot tub open year round in modern/rustic cottage!

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, 230 reviews

Designer Cottage Relax Pool Beach & Spa—Windjammer

Pet-friendly cottage rentals

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, 268 reviews

Northwind Llama retreat “Chicken coop”

A cozy living area features a gray sofa adorned with patterned cushions, complemented by a pair of leather chairs. Natural light floods through large windows, illuminating the hardwood floor. A coffee table sits at the center, while a flat-screen TV is mounted on the wall.

4.93 out of 5 average rating, 228 reviews

Bright & Warm by Warren Dunes Maple St Beach House

4.93 out of 5 average rating, 101 reviews

Cottage in Decatur

Lakeside Getaway

Superhost

The exterior of Miller Cottage features a striking red facade with modern midcentury architecture. A stone chimney adds character to the entrance, partially shaded by lush greenery. A manicured lawn and a paved driveway enhance the inviting atmosphere of the home.

4.82 out of 5 average rating, 197 reviews

Midcentury Cottage 3bd IN Dunes Natl Park, Lake MI

Superhost

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, 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

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

4.82 out of 5 average rating, 187 reviews

The living room features a white couch adorned with bright cushions, a mint green coffee table, and a standing lamp. Natural light fills the space through large windows dressed with sheer curtains. A welcoming entryway is visible, complemented by decorative wall accents.

Cottage in Elkhart

Peach Beach Cottage at Simonton Lake! 2 Bed/1 Bath

Private cottage rentals

5 out of 5 average rating, 20 reviews

The exterior of a renovated cottage features a blend of dark blue and gray siding, with a welcoming covered porch. Tall trees and well-maintained landscaping surround the property, while large windows invite natural light. A chimney is visible, adding character to the home.

Cottage in La Porte

Lake Shore Cottage at Stone Lake-Serenity

4.91 out of 5 average rating, 32 reviews

A charming cottage features a wooden shingle exterior and a welcoming covered porch. Two blue chairs and a small table are positioned on a spacious deck, surrounded by greenery. Large windows provide natural light, enhancing the inviting facade of the home.

Cottage in Michigan City

Artsy & convenient family cottage steps from beach

A charming cottage is situated on a well-maintained lawn, bordered by a white picket fence. A stone pathway leads to the front door, which is flanked by two planters. Lush trees and greenery surround the home, offering a serene outdoor setting.

5 out of 5 average rating, 22 reviews

Charming Cottage in Miller Beach

A modern living area features a dark sectional sofa adorned with a textured throw pillow and a decorative cushion. A colorful abstract artwork hangs above, complemented by a tall plant in a patterned pot. Soft lighting is provided by a standing lamp.

4.94 out of 5 average rating, 66 reviews

Miller Beach Cozy Cottage with indoor fireplace

A private wooden deck features a spacious hot tub with steps for easy access. Soft outdoor lighting creates a cozy ambiance, illuminating nearby trees and the charming cottage structure visible in the background. Green foliage enhances the serene setting.

4.96 out of 5 average rating, 84 reviews

SYLVIA's CHARMING & RELAXING COTTAGE

4.95 out of 5 average rating, 62 reviews

An aerial view captures a spacious property featuring a newly updated home surrounded by lush greenery. The yard is marked by winding paths and open grassy areas. Several seating spots are visible, alongside native prairie landscaping under a canopy of trees.

Cottage in Three Oaks

Modern Michigan Cottage

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.

4.93 out of 5 average rating, 27 reviews

Charming Union Pier cottage in the woods

The open-concept living and dining area features a comfortable couch and a wooden dining table surrounded by chairs. Large windows provide natural light, while a neutral-colored rug grounds the space. A wall-mounted cabinet adds functional storage, enhancing the inviting ambiance.