Cottage vacation rentals in Grand Beach

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 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

4.99 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.

Superhost

Cottage in Three Oaks

4.82 out of 5 average rating, 194 reviews

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

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.

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 you 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!

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 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.

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, 475 reviews

Twin Cottage B- Walk to Beach & Town!

Twin Cottage B 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 A as well for a complete look at our reviews. *Stays 28 days or longer require weekly cleaning fee included in monthly price

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!

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 Grand Beach cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.99 out of 5 average rating, 109 reviews

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.

Cottage in Sawyer

The Cottage of Harbor Country - Close to it all!

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!

Superhost

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.

4.8 out of 5 average rating, 191 reviews

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

A well-maintained single-story home is seen alongside a spacious driveway leading to a two-car garage. The home features a charming front porch and neatly landscaped yard, with green grass surrounding the property and trees lining the background.

4.9 out of 5 average rating, 230 reviews

Cottage near Hagar Beach Pet friendly with Hot tub

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.

4.86 out of 5 average rating, 197 reviews

Hot tub! Red Tin Cottage of Harbor Country!

4.97 out of 5 average rating, 169 reviews

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.

Cottage in Sawyer

Hot tub open year round in modern/rustic cottage!

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

4.95 out of 5 average rating, 209 reviews

A charming cottage is positioned near the water, with a gentle sunset illuminating the scene. The exterior features light-colored siding and large windows. Adjacent greenery provides a serene backdrop, while the pathway leads toward the lake, enhancing accessibility and scenic views.

Cottage in Coloma

Lake View Cottage

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

4.93 out of 5 average rating, 267 reviews

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.

Cottage in Sawyer

Northwind Llama retreat “Chicken coop”

4.76 out of 5 average rating, 106 reviews

A wooden deck features a seating area with four wicker chairs and a central glass-top table. Bright blue cushions add a pop of color, while a nearby bench complements the setting. The surrounding greenery provides a serene backdrop, enhancing the outdoor space.

Cottage in Coloma

3 min to Beach on Lake Michigan Wine Trail

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 cozy living area features two gray sofas adorned with decorative cushions. A coffee table sits in the center, complemented by a shelf displaying various decorative items. Natural light enters through two windows, flanked by soft gray curtains.

4.95 out of 5 average rating, 42 reviews

Nauti Cottage-Minutes from St Joe-Dog Friendly

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.

4.94 out of 5 average rating, 53 reviews

Lake Michigan Cottage Retreat

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

4.98 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

4.92 out of 5 average rating, 90 reviews

A picnic table is shaded by a bright red umbrella, surrounded by vibrant flowers and lush greenery. The cottage, featuring a welcoming entrance, is partially visible in the background. Sunlight filters through the trees, creating a peaceful outdoor dining space.

Cottage in Coloma

Cozy. Clean. Close to the beach.

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

4.89 out of 5 average rating, 102 reviews

The exterior of the cottage is surrounded by lush greenery, featuring a stone chimney and warm-toned siding. A small seating area with a lounge chair and table is positioned on the well-maintained lawn, creating a welcoming outdoor space.

Cottage in New Carlisle

Gram's cottage: Near Amazon Data Center & Notre D.