Cottage holiday rentals in Three Oaks

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.

4.98 out of 5 average rating, 126 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!

4.89 out of 5 average rating, 102 reviews

Cottage in New Carlisle

Hudson lake Cottage: Notre Dame, New Buff, Amazon

Welcome to Gram's Hudson Lake cottage: The perfect retreat for Notre Dame adventures (20 MI), Michigan City beaches (21 MI), and trips to New Buffalo (15 MI) or the Indiana Dunes. Whether you’re here for a family getaway, a football weekend, or corporate travel to the AWS Data Center (7 MI), you’ll enjoy peaceful lake views, a cozy fireplace, and easy access to local attractions. Hudson Lake Beach is 2 miles away, no direct access from the home. *pontoon, kayak & paddleboard rental available!

An inviting kitchen and dining area is highlighted by a long wooden table surrounded by a mix of chairs. Natural light fills the space through large windows, illuminating the white walls and beamed ceiling. A cozy living area is visible in the background, featuring a fireplace.

4.93 out of 5 average rating, 196 reviews

The Happy Cozy-Pets Welcome, Fire Pit, Privacy

If relaxing in nature in a calm and cozy home is what you're seeking, you'll find it here! It's been designed to make you feel at peace and comfortable inside while providing several outdoor spaces for you to enjoy the sights, sounds, and smells of nature. The open floor plan and large dining table create a grand gathering space for everybody to be together and create the memories that matter most. Feel free to safely start a campfire outside or in the fireplace indoors. It's all here for you!

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, 197 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 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, 391 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, 157 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.

4.97 out of 5 average rating, 183 reviews

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.

Cottage in Harbert

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!

4.91 out of 5 average rating, 273 reviews

Cozy Sawyer Beach Cottage- Walk to Warren Dunes

Beautiful renovated beach cottage on a quiet tree-lined street. Private comfortable home perfect to stay home and chill, or centrally located to enjoy the best of Pure Michigan! 0.5 mi to Warren Dunes State Park. Plenty of outdoor space to play, skylights to soak up the natural light and central to wineries & restaurants. Grab local farm fresh produce, s’mores for the firepit and a local natural wine to sip as you watch the sun set from the huge back deck and large backyard.

4.81 out of 5 average rating, 207 reviews

Hot Tub + Sauna | Walk to Beach | Family Friendly

Escape to this unique multi-level barn retreat tucked into the woods just a short walk from the beach. Designed with two separate living and sleeping zones, Naomi’s Barn is ideal for families, couples, and friend groups looking to relax. Enjoy the year-round hot tub, indoor sauna, fireplace lounge, game area, cruiser bikes, and peaceful wooded setting. Please note: the main kitchen, primary living room, and upstairs bedroom are on the second level, accessed by stairs.

4.96 out of 5 average rating, 133 reviews

A spacious cottage is surrounded by tall trees, offering shade and a relaxing environment. A large deck extends from the back, while a fire pit area with Adirondack chairs sits on the grassy lawn, inviting outdoor gatherings.

Cottage in Dowagiac

The Wildwood Cottage, private lake access

New for summer 2023, private lake access across the street on Little Crooked Lake! Peaceful, 2-bedroom cottage in the heart of Sister Lakes, Michigan. Fully renovated in 2021, this cottage features a large deck overlooking trees and a partial view of Little Crooked Lake. Eat-in kitchen, Weber charcoal grill, Adirondack chairs, and patio dining for 6. Walking distance to The Strand and Sister Lakes Brewing Company. 17 miles to Lake Michigan and 30 miles to Notre Dame.

4.95 out of 5 average rating, 348 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!

4.89 out of 5 average rating, 609 reviews

A rustic cottage is nestled among lush greenery, featuring a stone path that leads to the entrance. The home, with blue shutters and a welcoming porch, is framed by a flowering tree and various plants, creating a peaceful setting.

Cottage in Valparaiso

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking the channel that leads to Flint Lake. - Pet free -May not be appropriate for people with mobility issues. - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Wood fireplaces (winter only!)

Popular amenities for cottage rentals in Three Oaks

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

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.

4.98 out of 5 average rating, 41 reviews

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

4.97 out of 5 average rating, 91 reviews

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.

Cottage in Miller

SYLVIA's CHARMING & RELAXING COTTAGE

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.

4.82 out of 5 average rating, 207 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, 243 reviews

Cottage near Hagar Beach Pet friendly with Hot tub

4.94 out of 5 average rating, 580 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

Cottage Escape cozy getaway for two, Clean, Quiet

4.87 out of 5 average rating, 211 reviews

Hot tub! Red Tin Cottage of Harbor Country!

4.94 out of 5 average rating, 455 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, 219 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

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.

4.98 out of 5 average rating, 86 reviews

Comfortable, charming vintage 2 bed/1 bth cottage

The exterior of the barn showcases a vibrant red facade adorned with greenery. Large overhanging vines and trees frame the entrance, creating a welcoming atmosphere. A paved area leads to the barn, with side windows visible on the left. This setting hints at a rustic charm.

4.88 out of 5 average rating, 212 reviews

Northwind Llama retreat 'Loft Cottage'

4.93 out of 5 average rating, 101 reviews

Cottage in Decatur

Lakeside Getaway

A serene sunset is captured over a calm lake, with hues of orange and pink blending in the sky. Silhouetted trees frame the view, while a hanging chair is visible in the foreground, offering a cozy perspective of the tranquil scene.

4.92 out of 5 average rating, 117 reviews

Lake Bluff cottage, Unforgettable view and sunsets

4.83 out of 5 average rating, 201 reviews

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.

Cottage in Miller

Midcentury Cottage 3bd IN Dunes Natl Park, Lake MI

4.86 out of 5 average rating, 124 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

4.98 out of 5 average rating, 224 reviews

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.

Cottage in New Buffalo

New Buffalo retreat - Perfect year-round getaway!

4.97 out of 5 average rating, 484 reviews

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.

Cottage in New Buffalo

Twin Cottage B- Walk to Beach & Town!

Private cottage rentals

4.98 out of 5 average rating, 55 reviews

Cottage in New Carlisle

Private Beach Home on Hudson Lake New Carlisle

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.

4.98 out of 5 average rating, 155 reviews

The Pines Cottage on Birchwood

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.

4.91 out of 5 average rating, 44 reviews

Cozy Cottage - Newly Renovated

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.

4.74 out of 5 average rating, 47 reviews

Australian Style Cottage Unwind / Reset Recharge

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.

4.95 out of 5 average rating, 62 reviews

Modern Michigan Cottage

4.96 out of 5 average rating, 230 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

4.93 out of 5 average rating, 91 reviews

Cottage in New Buffalo

Blue Haven Lake Cottage

A spacious screened porch features comfortable seating options arranged on a patterned rug. Ambient lighting creates a cozy atmosphere, with views of the surrounding greenery through the large windows. A ceiling fan hangs above, providing a refreshing breeze in this inviting outdoor space.