
Places to stay near Four Winds Casino
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Top-rated holiday rentals near Four Winds Casino
Guests agree: these stays are highly rated for location, cleanliness and more.

Couples alert! PVT beach access, hot tub, firepit!
ADORABLE LAKESIDE COTTAGE W/YEAR-ROUND HOT TUB AND A GUEST FAVORITE - ACCESS TO SEMI-PRIVATE LAKE MICHIGAN BEACH SHARED BY JUST 10 HOMES SO IT'S NEVER CROWDED! BEACH ACCESS GATE IS 7 MIN WALK FROM COTTAGE. LOFT LIKE HOME IS SUPER CLEAN WITH VERY COMFY KING SIZE BED AND ONE PULL-OUT COUCH FOR 4 GUEST (MAX). FIREPIT SUPPLIED WITH WOOD, AN OUTDOOR PATIO AND WEBER GRILL - YOU WILL LOVE IT! Bike/walking path out front and just 10 mins to New Buffalo, Whistle Stop, coffee - just steps away!! HURRY!

-The District 5 Schoolhouse-
The District 5 Schoolhouse was historically built "with not a single nail in the structure" in the 1800's. It still stands as a symbol of dedication to craftsmanship and community. Lovingly restored, preserving as much of the original soul as possible, it promises to be a luxury stay in understated sophistication with 100% linen sheets, beautiful kitchen/dining, lovely private outdoor space, tranquil idyllic work/recharge areas, and enough space to make your own history. You won't want to leave.

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.

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

Cozy Cabin 2.0 Mins from Michigan’s Harbor Country
Immerse yourself in nature inside this charming cabin featuring all of the necessary amenities, including a queen-sized bed, kitchen basics, fire pit, grill, and deck. Surrounded by 40 acres of woodlands, this cabin offers a quiet retreat while being only twenty minutes from Michigan's Harbor Country. Relax inside with a book or head out to enjoy golden sand dunes, art and antiques, locally-sourced food, hiking trails, and over twenty wineries along the windy, tree-lined Red Arrow Highway.

Peach by the Beach! 1 Bdrm Apt close to downtown
The Peach by the Beach is a one-bedroom private apartment that sleeps two people. It's a two-minute walk to downtown New Buffalo and a ten-minute walk to the beach! This chic apartment is close to the beach, restaurants, shopping, and all kinds of fun! This location is perfect for couples, singles, and business travelers. It is the perfect getaway from the hustle and bustle of daily life. This location includes free wifi, coffee and tea, beach towels and chairs, and a full-service kitchen.

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!

"Tiny House" Guest House - Great for Couples
"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.

Modern Minimalist Tiny House | Firepit | Nature
Welcome to our modern minimalist tiny house located a half mile from Warren Dunes State Park beach and 1.5 miles from all that Sawyer Michigan area has to offer. Tiny is the second dwelling on this property and is technically a mobile tiny house. While we do have electricity and water, much like an RV the drains run to holding tanks. This means VERY LIMITED WATER USE for showers and toilet flushing. It features a fully stocked kitchen, bathroom, and a queen bed in the small loft.

Dunefarmhouse Modern Country Escape
Experience nature and design in an unforgettable way! This thoughtfully curated home is located within a unique green community surrounded by 200+ acres of woods, prairies and meadows - yet minutes to the beach, great restaurants, wineries and activities in harbor country. A unique and immerse art experience awaits every guest. Dunefarmhouse was featured in TimeOut magazine in 2019-2020, as a "Top 10 Airbnb rental in the Midwest" and part of "Perfect Midwest Getaways."

Rainbows End 🌈 Plensa
Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Eagle's Beach Nest: Pet-Friendly*Fenced*Walk2Beach
Nestled in New Buffalo's heart, this cozy retreat is a stone's throw from key attractions. The beach, Marina, and esteemed Bentwood Tavern lie within a mile. Venture a tad further to Stray Dog or the town center. Four Winds Casino is a quick 10-min drive, with Blue Chip Casino just 15 mins away. Ideally positioned amidst Harbor Country, nearby renowned wineries beckon. Perfect for girls' getaways, family trips, or group gatherings, and pet-friendly to boot!
Popular amenities for holiday rentals near Four Winds Casino
Apartment rentals with wifi

Beautiful top floor condo- river view- near beach

*Luxury condo on water in St Joseph, 2 queen beds*

Updated Cottage Downtown, walk to Beach

Spacious Riverfront Condo | Marina Views

Perfect Location Condo Pools Walk to all Beach 1.5

Sunset Dunes Villa D8

Nightingale Dunes - Modern beach town retreat

Live the marina life in New Buffalo!
Family-friendly house rentals

The Heartwood House<3 : DT Three Oaks w/Game Room

Lux home, sauna, hot tub, firepit, 5 min to beach

Cozy Vintage Cottage Near the Lake

Lakeside Retreat Nestled Among the Trees

UncleLarrysLakePlace HotTubKayaksPingPong

The treehouse at Warren Dunes

2027 dates Luxe Cabin Minutes to Lake Michigan

Perfect for the dunes! Summer dates available now
Apartment rentals with air conditioning

Cozy Chalet by Lake MI&Dunes with Fire Pit

Historic Studebaker Carriage House- Lower Level

Morton's Retreat Cozy 1 Bedroom Apartment

King Bed Retreat, Minutes to Beach & Dunes

Lake Breeze Suite - Beaches, Dunes, Golf, Wine Tr

The Loft at the Acorn Theater

Second Floor Apartment sitting on Pine Lake

Ozzie’s Hideaway-Smack between Three Oaks & Sawyer
Other great holiday rentals near Four Winds Casino

PumpHouse- Walk Everywhere! Private porch firepit!

SoulShine Inn • Pets Welcome•Fully fenced backyard

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

Dog Friendly Downtown Three Oaks Cottage! Fenced!

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

The Lemonade Cottage, New Buffalo. Walk to beach!

Lakeside Dome Retreat w Hot Tub Near Indiana Dunes

New Buffalo retreat - Perfect year-round getaway!
Destinations to explore
- Soldier Field
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- Warren Dunes State Park
- Indiana Dunes State Park
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Shedd Aquarium
- Chicago River Walk
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Washington Park Zoo
- Beachwalk Vacation Rentals
- Museum of Science and Industry
- Oak Street Beach
- Silver Beach Carousel
- University of Illinois At Chicago
- Potato Creek State Park
- Chicago Theatre





