Holiday rentals in Harbor Country

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Top-rated holiday rentals in Harbor Country

Guests agree: these stays are highly rated for location, cleanliness and more.

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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

4.97 out of 5 average rating, 249 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, 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!

Guest favourite

An indoor pool area features a bright, open design with vaulted wooden ceilings and intricate skylights. Surrounding the pool, large windows provide natural light, complemented by tiled flooring. Comfortable seating is positioned nearby, creating a relaxing and inviting atmosphere.

Home in Union Pier

4.85 out of 5 average rating, 108 reviews

Heated Indoor Pool & Tennis/Pickleball Court!

Fabulous Union Pier home with heated indoor pool & private combination tennis/pickleball court! Escape from the city life to Asolare, the upscale 4 bedroom, 4 bathroom vacation home located just couple blocks from lake Michigan beach. This 3800 sf villa host up to 16 lucky guests & provides a multitude of amenities to make for a trip you will never forget! Accommodations include private beach rights, indoor pool, tennis & pickleball court and supplies, sauna, billiard, screened porch & fire pit.

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

4.96 out of 5 average rating, 254 reviews

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.

Top guest favourite

An aerial view showcases a marina filled with boats, adjacent to modern waterfront homes. The calm water reflects a clear sky, while a tree-lined pathway and parking area are visible in the foreground, enhancing the serene environment.

Apartment in New Buffalo

4.93 out of 5 average rating, 102 reviews

Live the marina life in New Buffalo!

Enjoy the unique experience of living in the center of a marina and in the heart of the waterfront district walking distance to the beach, restaurants & shops in downtown New Buffalo! Our penthouse 2bed/2 bath condo w 2 large balconies is thoughtfully outfitted for everything you need to enjoy your stay with water views from any window. We ask that guests do not smoke inside the home/ first floor marina. Pets & parties are also not welcome. Follow us on IG at "themarinalifenewbuffalo"

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

5.0 out of 5 average rating, 102 reviews

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!

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

4.98 out of 5 average rating, 270 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.

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

4.99 out of 5 average rating, 165 reviews

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.

Guest favourite

A stylish living area features a blue sofa with throw pillows, situated on a patterned rug. Natural light streams through a skylight, illuminating the open layout that includes a dining space and kitchen with modern appliances. Minimalist decor enhances the inviting ambiance.

Home in New Buffalo

4.92 out of 5 average rating, 238 reviews

Steps to Beach & Starbucks! Private Yard, Firepit!

Walk to Starbucks! Walk to beach, cafes, shops, ice cream, grocery! 2 queen bed 2 bath home is perfect to enjoy fenced yard, grill, fire pit, & yard games! Take a few days to explore wineries/breweries, art galleries, antique stores, kayaking, casino and more! Live bands Fridays/Saturdays till around 2am Memorial Weekend to Fall, New Year's at Casey's (behind property). Noise machines in each bdrm. Pet fee $100, 2 dogs MAX. Exterior areas have video/audio cameras w/live feeds. Wp#bcnbwmech

Top guest favourite

A cabin exterior is presented, featuring a screened-in porch that offers comfortable seating. The structure, painted in a muted green tone, is surrounded by trees and foliage. A set of steps leads to the porch, creating easy access to the welcoming retreat.

Cabin in Union Pier

4.98 out of 5 average rating, 178 reviews

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace

Tucked away sophisticated cabin in the heart of Downtown Union Pier. Killer location that's just steps away from dining and drinks: Black Current Bakery, Neon Moon Gelato, Union Pier Market, and Union Pier Social. Townline Beach is a 10 minute walk, and the cabin is right off the bike path. Seeds Brewery is just down the road and local Wineries are 1 mile away. Back home enjoy a relaxing hot tub (available year round), wood burning fire place, spacious screened in porch & outdoor fire pit.

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

5.0 out of 5 average rating, 152 reviews

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.

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

4.97 out of 5 average rating, 204 reviews

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 .

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

4.98 out of 5 average rating, 165 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.