Holiday rentals in Harbor Country

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Top-rated holiday rentals in Harbor Country

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Top guest favourite

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.

Cottage in Union Pier

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, private resort-style neighborhood pool, private hot tub, fire pit, indoor fireplace, and loft for the kids! Take advantage of the beach and explore beautiful Harbor Country. Relax & 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!

4.97 out of 5 average rating, 247 reviews

Top guest favourite

The cabin's exterior is framed by colorful autumn foliage, with vibrant red leaves and dappled sunlight filtering through the surrounding trees. Stone steps lead to the entrance, enhancing the rustic charm of the well-maintained landscape.

Cabin in Michiana

Luxury Cabin Getaway •2 min to Beach• 1hr Chicago

Luxury meets nature: forest cabin steps from the beach, 1 hour from Chicago. Book your escape to our designer log cabin on Lake Michigan just steps from the beach and nestled in a peaceful forest, it’s the perfect retreat. Built in 1932, our charming cabin sleeps 8 in 4 bedrooms. Enjoy 2 living areas, a stone fireplace, fire pit, games, puzzles & books. Featured in Country Living and the NYT, it’s perfect for families, friends, or retreats. Book now and create lasting memories in Michiana.

4.96 out of 5 average rating, 251 reviews

Luxe

An open entryway reveals a modern kitchen with a large island and four high stools. Natural light flows through multiple windows, highlighting the sleek countertops and rich cabinetry. A tasteful artwork adorns the wall beside the entrance, adding character to the space.

Home in Lakeside

Landmark Home 1 Blk from Lake MI Game Rm & EV Chgr

Sumptuous 4 BR/2.5 BA vacation home, just 1 block from Lake Michigan. Fully refurbished with reclaimed flooring, antique beams, custom doors, and fixtures. High-end kitchen, dining, and living areas with French windows. Living room features a stone fireplace, stylish couches, and a wide-screen TV. Three ground-floor bedrooms and baths with a second-floor bunk bed loft. Detached garage is a posh game room with high-end tables and a big TV. Covered patio, 4-seat dining, and bluestone courtyard.

4.92 out of 5 average rating, 119 reviews

Top guest favourite

The exterior of the home features a charming design with a welcoming front porch and a peaked roof. Soft lighting highlights the entrance, surrounded by lush greenery and well-placed flower pots. The stone accents and wooden details contribute to a cozy cottage aesthetic.

Home in Lakeside

Hot tub! Starlight cottage in Lakeside!

Feel relaxed, refreshed, & recharged! Our home is the perfect blend of comfort & cottage charm!Home is 2450 sq. ft., 3 bdrm,3 bth (2 BR, 2 BA in main home),updated & features a full kitchen, laundry room,6 TV’s,WiFi, & 2 eating areas.Attached guest apt. has 1 bdrm,1 bth upstairs w/ full kitchen,w/d,king bed, kids cubby w/ queen size gel mattress, & 2 TV’s.Guest apt. is attached & is perfect for people in your party requiring privacy!Close to everything but “socially distanced” in Lakeside!

5.0 out of 5 average rating, 101 reviews

Top guest favourite

The exterior of the cozy Tree House is highlighted, featuring a spacious deck with rocking chairs. Mature trees surround the cottage, which showcases a warm exterior design. A well-maintained garden with shrubs and decorative plants enhances the inviting atmosphere.

Home in Lakeside

Lakeside Retreat Nestled Among the Trees

Please note: Summer stays are 7 night minimums from Friday to Friday. Welcome to our cozy 'Tree House,' nestled among the trees in Lakeside, Michigan! Our renovated cottage is 90 minutes from Chicago in the heart of Harbor Country. Our bright, open home features high end finishes and luxury mattresses. Nature-inspired hues invite you in, making relaxation a top priority! Generous outdoor spaces include a deck with dining area, rocking chairs, and two fire pits for s'mores under the stars.

4.99 out of 5 average rating, 165 reviews

Top guest favourite

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.

Cottage in Union Pier

"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.

4.98 out of 5 average rating, 268 reviews

Guest favourite

A spacious backyard is enclosed by wooden fencing, featuring a green lawn, a sandbox for children, and a colorful outdoor mural on the shed. A seating area with patio furniture is visible, complemented by landscaped flower beds. The sky is bright with scattered clouds.

Home in New Buffalo

In-town Lovely Home! Steps to Starbucks & Beach!

Spacious 3 bed/1.5 bath home in-town! Walk to beach, Starbucks, Stray Dog, grocery! Enjoy the fully fenced yard playing outdoor games from the shed, and a sand box for the kids! Grill and enjoy fire pit after a day of wineries, shopping in the local shops, galleries, antiquing, and casino. Outdoor live music starts Memorial Weekend on weekends to Fall until around 2 am at Casey's behind property as well as New Year's. Noise machines in each bedroom. Pet fee $150, 2 dogs MAX. Wp#acnbwmech22

4.97 out of 5 average rating, 211 reviews

Guest favourite

The modern tree-house structure is illuminated by warm lighting, showcasing large windows that reflect the surrounding trees. A screened porch with seating is visible, extending from the main building, creating a connection with nature.

Home in Michigan City

TRYON FARM MID-MODERN SPA IN THE WOODS

Come, enjoy our Tryon Farm modern spa. A Sustainable luxurious open concept tree-house in the woods. Minutes from the beach with an outdoor sauna, Hottub, shower, and Mr. Steam. Perfect for two or a family/group adventure. A true destination with Yoga studio, Mirror by LuLu lemon and wellness elements. The house is a perfect balance of art and nature and luxury and spiritual. Treat yourself to a farm to table, hand made, locally sourced chef services for an extra special experience.

4.95 out of 5 average rating, 330 reviews

Top guest favourite

A bright living area features a comfortable gray sofa adorned with decorative pillows, paired with a light brown armchair. Large windows provide views of lush greenery, while a striped rug anchors the space. A coffee table with a bowl sits at the center, enhancing the cozy atmosphere.

Home in Sawyer

The treehouse at Warren Dunes

Looking for the perfect Harbor Country getaway? We've got you covered! Just 90 miles from Chicago and adjacent to Warren Dunes State Park, this beautifully remodeled home hidden in the trees is the perfect escape. With accommodations up to 6 on four levels of living space, you'll enjoy an indoor/outdoor living experience like no other. Conveniently just 200 yards from the beach with walking path access at the end of the street and easy access to all the activities this area has to offer.

5.0 out of 5 average rating, 150 reviews

Guest favourite

The exterior view showcases a modern lodge-style home with dark wood paneling and large windows. A pathway leads toward the entrance, bordered by greenery. Soft lights illuminate the building, creating a warm ambiance against a backdrop of trees.

Home in Union Pier

luxe new buffalo lodge, hot tub, 12m walk to beach

Relax with family or friends at our peaceful place to stay. Located in the heart of Union Pier , walking distance to Beach and lots of attractions. Easily will sleep 16 , chill modern lodge vibe to it , high ceilings, heated concrete floors , 2500 sq ft , new construction , 5 bedroom/ 2.5 bath .Set on front porch overlooking forest year round , stroll to patio and enjoy your private hot tub . Home is spacious, 70 ft long so plenty of room to spread out and or host a large gatherings .

4.97 out of 5 average rating, 202 reviews

Top guest favourite

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.

Cottage in Union Pier

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.

4.98 out of 5 average rating, 164 reviews

Top guest favourite

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 3 bikes! So close to boutiques, coffee shops and cute restaurants!

4.97 out of 5 average rating, 194 reviews