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.

4.99 out of 5 average rating, 117 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, 219 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

The screened-in porch is visible, surrounded by tall grasses that add a natural element. Soft ambient lighting is seen, enhancing the inviting space within. The porch features large screens, allowing views of outdoor greenery and tree silhouettes in the background.

4.98 out of 5 average rating, 298 reviews

B's Retreat: Hot Tub & 10-min walk to Beach!

B's Retreat is a 1940's 700 sq ft cottage on a quiet dead-end street. It is 1 block from downtown UP! B's is sandwiched between rentals and vacation homes, so perfect for a family of 4 or 1-2 couples/friends looking to unwind. B's best attributes are the vaulted ceilings, wide-plank pine floors, bonus kids loft, hot tub, fire pit & the 23-foot wide screened in porch! B's is a .4-mile / 10-minute walk down Townline Rd. to the public beach. Parking is available at beach for early birds!

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, 192 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!

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, 287 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.

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, 188 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, 249 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, 118 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, 378 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, 151 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, 174 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!

4.82 out of 5 average rating, 201 reviews

Hot Tub • Sauna • Billiards | Stay & Play!

Wanna Play?? You name the game & we probably have it! Outdoor fun includes Pickleball & Volleyball nets, Putting Green, corn hole and even cruiser bikes. Indoor fun incl. BILLIARDS & table tennis, complete poker set & board games galore! If you prefer to take it easy you can relax in our YEAR-ROUND hot tub, cozy up by the gas fireplace or the outdoor fire pit, unwind in the indoor SAUNA or stroll to nearby Harbert Beach. Whatever your choice, THIS is the place to STAY & PLAY!

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 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, 51 reviews

Charming Cottage - Hot Tub, Sauna, Large Yard

4.84 out of 5 average rating, 153 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!

The exterior of a modern home is framed by tall trees. A welcoming front porch features yellow chairs and an American flag. The stone pathway leads to a manicured lawn, providing an inviting approach to the entrance. A garage door is visible on the right.

5 out of 5 average rating, 43 reviews

Heated Pool & Pvt Hot Tub

4.81 out of 5 average rating, 200 reviews

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.

Cottage in Benton Harbor

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

4.94 out of 5 average rating, 567 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

4.94 out of 5 average rating, 448 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, 85 reviews

Heated Pool, Hot Tub, Walk to Beach/ Markets

4.98 out of 5 average rating, 45 reviews

Sprawling Retreat w/ Private Beach Access!

Pet-friendly cottage rentals

The exterior of the cottage is presented, showcasing a spacious screened-in porch framed by greenery. The flat roofline and large windows invite natural light, while a neatly landscaped area with a stone border enhances the tranquil setting. Lush grass complements the peaceful environment.

4.96 out of 5 average rating, 82 reviews

Rosie’s Cottage close to Warren Dunes (w pool)

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, 208 reviews

Northwind Llama retreat 'Loft Cottage'

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, 230 reviews

Bright & Warm by Warren Dunes Maple St Beach House

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, 68 reviews

Dog-Friendly Farmhouse | 1+Acre near Lake Michigan

4.93 out of 5 average rating, 101 reviews

Cottage in Decatur

Lakeside Getaway

4.93 out of 5 average rating, 115 reviews

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.

Cottage in Benton Harbor

Lake Bluff cottage, Unforgettable view and sunsets

4.87 out of 5 average rating, 117 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

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, 476 reviews

Twin Cottage B- Walk to Beach & Town!

Private cottage rentals

4.92 out of 5 average rating, 49 reviews

An inviting sleeping area features a spacious bed adorned with a patterned blanket and decorative pillows. Natural light filters through a skylight, illuminating the wooden floor and a nearby lamp, positioned next to the bed, adding subtle warmth to the room.

Cottage in Michigan City

*Charming Lake Michigan Bungalow*

4.93 out of 5 average rating, 40 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

Magnolia in bloom ~ walk to the beach

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

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, 43 reviews

Cozy Cottage - Newly Renovated

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

Cottage in Michiana Shores

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

4.52 out of 5 average rating, 33 reviews

A screened-in porch is shown, featuring a mix of wicker and wooden seating, including a cozy sofa and rocking chairs. Natural light filters through the screens, illuminating the space. A view of the spacious yard and fire pit is visible beyond the porch.

Cottage in Harbert

Harbert Cottage w/ Fire Pit: Half Mile to Beach!