Family-friendly holiday rentals in Grand Beach

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

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

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.

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.

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.

2026 Dates Now Open @ The Birchwood Cottage!

Time is now to hurry & book your 2026 dates @ THE ONE & ONLY BIRCHWOOD COTTAGE IN MICHIANA SHORES...where only good things happen & memories are made! Reviews tell our story & we are constantly upgrading to enhance your experience. It is a slice of heaven just 75 minutes from downtown Chicago be it for glorious summer beach days, long walks or napping on the screen potch. Once settled in this cozy cottage, you have everything you need on the property and in the area for a perfect vacation!

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

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!

Superhost, hot tub, golf cart, fire pit, large!

Newly renovated 5 bed, 2 bath home in the quaint village of Grand Beach. Golf cart included with rental (in season - May thru mid-Nov). Home is situated on a large lot, high on a sand dune that overlooks the 6th fairway and park area. Enjoy two large decks and year-round eight person hot tub. The property is very private, on secluded street and fully stocked for a great stay. It's a great place to enjoy some down time in an idyllic village in the heart of Michigan's "Harbor Country."

"Tiny House" Guest House - No Cleaning Fee

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

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.