Holiday rentals in Michiana

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.

Beach! Hot Tub! New Buffalo! Firepit! King Bed!

Highlights: ✔ 8-person Hot Tub ✔ Sleeps 12 (10 in main house + 2 in guest cabin) ✔ 1 mile to beach ✔ 6 min to Shady Creek Winery ✔ 10 min to New Buffalo + Michigan City ✔ Outdoor firepit & picnic table ✔ Gas BBQ grill ✔ Smart TVs & board games ✔ King bed in main bedroom ✔ Luxury custom-designed home ✔ Private wooded lot ✔ 2 Adult & 2 kids' bikes ✔ Beach chairs, toys, wagon and towels ✔ Pickleball paddles & nearby courts ✔ 4 vehicle parking ✔ 2-person workstation ✔ High speed wifi ✔ Fully stocked

Romantic Getaway in the Dunes for a Couple—Hüüsli

Cozy, charming, romantic and modern. Huusli is the perfect place for a couple to getaway, not too big, not too small. Soaring ceiling with wood burning fireplace greets you in the main living area with an updated kitchen, remodeled bathroom and two adorable bedrooms. Bonus is the four-season room where you can have all your meals or enjoy your morning coffee surrounded by nature, but without the fear of bugs. Make new memories, celebrate an anniversary or just relax in this magical place.

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, and close to Indiana Dunes National Park, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum stay during summer, but open up 2 night stays 1-2 weeks before if possible.

Quiet Walk to Lake Michigan Beach - Seaside Smores

So close to Chicago and yet in a world of its own! Adorable two bedroom cottage is located on a quiet wooded lane about a half-mile walking distance to the world class beach on Lake Michigan. Enjoy nearby park with playground, basketball, volleyball, and tennis courts, performing arts theatre, horseback riding stables, golf course, and more - all within a block or two of the cottage. See our other nearby listings, too! Relax in simple comfort — you made a great choice to stay at the cottage.

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.

Beautiful Wooded Cabin short walk to Lake Michigan

Escape to a beautifully updated 1930s cabin nestled on a wooded acre in Southwest Michigan's Harbor Country - an hour from Chicago. Thoughtfully curated amenities & little extras ensure an unforgettable stay. Absorb natures beauty viewing wildlife or enjoying the stunning private neighborhood beaches (5-10 minute walk). A new park with sports courts & playground just 3 blocks, or take a short drive to Indiana Dunes National Park or Harbor Country's amazing wineries, breweries & restaurants.

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.

The Little House at Tryon Farm

The little house is located within a 170-acre modern farm community filled with open meadows, woods and dunes. Minutes to beach, 1 hour to Chicago. Relax and enjoy the property or head out to explore the lakeshore, wineries, and great area restaurants! Two bedrooms, 1.5 baths, a fully appointed kitchen, living area w/fireplace, and a large screened in porch. Large windows flood the house with natural light and will make you feel like you're living in the treetops. A perfect getaway!

Cozy 2 bedroom cottage steps from Lake Michigan

Located 3 houses from Lake Michigan and a 5 minute drive to downtown New Buffalo, this cozy 2 bedroom cottage is perfect for a peaceful getaway. Spend the day at the beach, explore local wineries, play some of Michigan’s best golf courses, or just relax on the deck and make s’mores at sundown. There is a golf course and playground with tennis/pickle ball courts within walking distance. This cottage has it all for a perfect getaway for a couple or small family!

Lake Michigan Cottage Retreat

This completely renovated cottage is a cozy retreat just 90 minutes from Chicago. The bright, open concept home features a fully stocked kitchen, comfortable seating for ultimate relaxation, and three beautiful and private bedrooms. All bedrooms have a king or queen! The location is walkable to Lake Michigan (less than 10 minutes, 0.5 miles). All amenities you could want, including towels and beach gear. Near New Buffalo, Union Pier, Sawyer and more!

Charlie's on Comanche

Enjoy vintage charm and modern comfort at this cozy Michiana cottage, just a short walk to Lake Michigan beaches. Relax on the new deck with outdoor dining, unwind in the screened porch, or gather at the backyard fire pit. Inside, enjoy an updated kitchen and baths, a main-floor double bedroom, and a lofted king bedroom up a spiral staircase. Peaceful mornings, beach days, and twinkle-lit evenings make this an easy, memorable getaway.