Airbnb your place

Places to stay near Four Winds Casino

Book unique holiday rentals, homes and more on Airbnb

Top-rated holiday rentals near Four Winds Casino

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

1 of 1 pages1 / 1
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
A spacious wooden deck is adorned with soft string lights overhead, creating a cozy ambiance. Two comfortable chairs and a small table are positioned for relaxation. A potted plant with bright yellow flowers adds a touch of color to the inviting outdoor space.
Cottage in New Buffalo

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

4.98 out of 5 average rating, 239 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
Top Guest favourite
A screened-in porch features a cozy seating arrangement with two navy blue chairs and a matching sofa set around a narrow coffee table. Skylights and large windows create a bright space with views of the surrounding wooded area.
Cottage in New Buffalo

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.

4.99 out of 5 average rating, 309 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
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
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
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
The entrance features a solid gray exterior enhanced by a bright turquoise door. White trim outlines the windows, while a covered porch is adorned with a white bench. Clean lines and a welcoming atmosphere characterize the overall design.
Cottage in New Buffalo

Twin Cottage B- Walk to Beach & Town!

Twin Cottage B is your home for convenience & comfort! 2 blocks from town shopping & restaurants, Church Brewing Co. around the corner, an artisanal cocktail lounge up the block and only 3700 feet to the beach! You'll have a private, fenced in backyard for the kids and/or dogs. Gas grill, outdoor dining & a fire pit stocked with wood. Check out Cottage A as well for a complete look at our reviews. *Stays 28 days or longer require weekly cleaning fee included in monthly price

4.97 out of 5 average rating, 504 reviews
Guest favourite
Home in New Buffalo

New buffalo Farmstead main home pool hot tub

5 bedroom 2 bath 2200 sq ft modern farmstead , 2 minutes to new buffalo and beach and all its offerings , 18x36 new heated shared pool open 5/20 to 10/ 20 and hot tub open year round maintained at 104 f . Property on 3 acres with plenty of room for kids to play , 26 apple trees and woods , ride host bikes to new buffalo .. Best of both worlds in country , close to town .There’s 1 other home on 3 acre property, this home and 1 guest home ( rented separately) .

4.94 out of 5 average rating, 142 reviews

Popular amenities for holiday rentals near Four Winds Casino

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Four Winds Casino

Washington Park Beach

114 locals recommend

Warren Dunes State Park

488 locals recommend

Silver Beach

271 locals recommend

Washington Park Zoo

190 locals recommend

Harbor Shores Golf Club

94 locals recommend

Blossom Trails Golf Club, Inc

14 locals recommend

Condo rentals with Wi-Fi

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.
Condo in New Buffalo

Live the marina life in New Buffalo!

4.93 out of 5 average rating, 101 reviews
Superhost
Condo in New Buffalo

Updated Cottage Downtown, walk to Beach

4.84 out of 5 average rating, 127 reviews
Guest favourite
A modern living room features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while two lamps provide soft lighting. Artwork adorns the wall above, accompanied by a round mirror reflecting the space.
Condo in New Buffalo

Nightingale Dunes - Modern beach town retreat

4.93 out of 5 average rating, 105 reviews
Superhost
A dining area features a wooden table surrounded by six chairs, creating a space for gathering. A spiral staircase leads to an upper level, while nautical-themed decor adorns the walls. An adjacent open doorway reveals additional kitchen space, enhancing the home's inviting layout.
Condo in New Buffalo

New Buffalo Getaway Condo

4.9 out of 5 average rating, 100 reviews
Top Guest favourite
A spacious living area is featured, showcasing a modern dark sectional sofa and a unique round chair. A glass coffee table sits at the center, complemented by decorative wall art and mirrors. Natural light fills the room through large windows with blinds.
Condo in St. Joseph

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

4.92 out of 5 average rating, 247 reviews
Guest favourite
A bright living area showcases a comfortable blue sofa with decorative pillows and a matching ottoman. Two white armchairs are positioned nearby, with a patterned area rug beneath. The space is infused with natural light from large windows leading to a private patio. An open kitchen area is visible in the background.
Condo in Bridgman

Premium Dunes Villa: Family Luxury Near Beaches

4.94 out of 5 average rating, 32 reviews
Guest favourite
An outdoor pool is surrounded by lounge chairs, providing a relaxing area for guests. The three-story building features balconies on the upper floors. Clear blue skies add to the inviting atmosphere, enhancing the setting for relaxation and leisure.
Condo in New Buffalo

Perfect Location Condo Pools Walk to all Beach 1.5

5.0 out of 5 average rating, 7 reviews
Top Guest favourite
An open-concept living area is presented, featuring a large dining table surrounded by wicker chairs. A modern kitchen with stainless steel appliances is visible in the background, and a comfortable leather couch is positioned near a wall-mounted television and ceiling fan.
Condo in St. Joseph

Beautiful top floor condo- river view- near beach

4.97 out of 5 average rating, 86 reviews

Family-friendly house rentals

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

4.99 out of 5 average rating, 165 reviews
Top Guest favourite
A charming cottage exterior is shown with large windows allowing ample natural light. Lush landscaping surrounds the entrance, featuring ornamental grasses and rocky accents. The inviting covered porch provides a welcoming entry point to the home.
Home in New Buffalo

Modern Farmhouse - Walk to Downtown, beach & pool!

4.96 out of 5 average rating, 107 reviews
Top Guest favourite
Home in Sawyer

Luxe Cabin Minutes to Lake Michigan

4.98 out of 5 average rating, 175 reviews
Superhost
Home in Michigan City

Home near the lake with an inground pool

4.9 out of 5 average rating, 102 reviews
Guest favourite
A cozy reading nook features a daybed with beach-themed cushions and soft throw pillows, framed by large windows. Two chairs are positioned nearby on polished hardwood floors, creating an inviting space for relaxation. Soft lighting from wall sconces complements the natural light.
Home in New Buffalo

White Corner Cottage

4.88 out of 5 average rating, 120 reviews
Guest favourite
A comfortable living area showcases a sectional sofa adorned with decorative pillows. The space is complemented by a light-colored area rug and wall decor featuring framed images. A bright kitchen area is visible in the background, enhancing the open layout.
Home in New Buffalo

Eagle's Beach Nest: Pet-Friendly*Fenced*Walk2Beach

4.9 out of 5 average rating, 497 reviews
Guest favourite
The dining area features a large wooden table surrounded by comfortable seating, illuminated by a modern pendant light. Nearby, the hot tub area is visible through large glass doors, nestled among lush greenery, providing a tranquil outdoor experience.
Home in Michigan City

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

4.97 out of 5 average rating, 150 reviews
Top Guest favourite
The exterior of the cottage features vibrant blue siding and a covered porch with white railings. Lush greenery and landscaped beds surround the entrance, creating a serene and welcoming façade. A pathway leads to the front door, inviting guests into the home.
Home in New Buffalo

Designer Cottage - walking distance to downtown

5.0 out of 5 average rating, 216 reviews

Apartment rentals with air conditioning

Top Guest favourite
A retro living area features a curved beige sofa paired with a rust-colored armchair. A floor lamp provides lighting, and a framed wall art piece is displayed nearby. A wooden table holds colorful items, while a soft area rug adds comfort to the space.
Apartment in New Buffalo

Peach by the Beach! Retro Apt Close to Downtown

4.95 out of 5 average rating, 399 reviews
Superhost
A spacious dining area features a wooden table surrounded by chairs, illuminated by natural light from large windows. Artwork is displayed on the wall, and comfortable seating is available in a cozy corner. Exposed brick and wooden flooring add to the industrial-chic ambiance.
Apartment in Three Oaks

The Loft at the Acorn Theater

4.82 out of 5 average rating, 110 reviews
Top Guest favourite
Two white Adirondack chairs are positioned adjacent to a circular fire pit. The ground is covered with colorful fallen leaves, and trees with yellow foliage provide a natural backdrop. The scene reflects a serene outdoor space ideal for relaxation.
Apartment in Sawyer

Morton's Retreat Cozy 1 Bedroom Apartment

4.9 out of 5 average rating, 132 reviews
Top Guest favourite
A sunroom is filled with natural light, featuring large picture windows offering leafy views. Two rattan chairs, adorned with cushions, face a wooden table. A decorative lamp stands nearby, with vintage touches enhancing the relaxed ambiance of the space.
Apartment in Sawyer

Cozy Chalet by Lake MI&Dunes with Fire Pit

4.94 out of 5 average rating, 586 reviews
Top Guest favourite
A circular stone fire pit is situated on a stone patio overlooking the lake. Flames flicker from the center, providing a warm glow against the twilight sky. The serene water reflects the evening colors, creating a peaceful waterfront setting.
Apartment in La Porte

Second Floor Apartment sitting on Pine Lake

4.93 out of 5 average rating, 543 reviews
Guest favourite
Apartment in Michigan City

King Bed Retreat, Minutes to Beach & Dunes

4.95 out of 5 average rating, 116 reviews
Guest favourite
A seating area features a white sofa adorned with a richly patterned throw and cushions. Natural light filters through large windows, illuminating the surrounding greenery visible outside. A small lamp and a side table enhance the cozy atmosphere.
Apartment in Trail Creek

Country feel near beaches and Dunes!

4.76 out of 5 average rating, 123 reviews
Top Guest favourite
A garden pathway leads from the house to the beach, surrounded by lush trees and colorful blooms. A charcoal grill is visible on the patio, and gray steps ascend towards the entrance. The tranquil Lake Michigan is seen in the background through the foliage.
Apartment in Stevensville

Quiet Grand Mere Coach House on Lake Michigan

4.92 out of 5 average rating, 897 reviews

Other great holiday rentals near Four Winds Casino

Top Guest favourite
A charming two-bedroom house presents a welcoming exterior, featuring a white facade and arched windows. The front porch is lined with steps leading to a yellow door. A well-maintained lawn and surrounding trees enhance the property's inviting appearance.
Tiny home in New Buffalo

SoulShine Inn • Pets Welcome•Fully fenced backyard

4.96 out of 5 average rating, 614 reviews
Guest favourite
The exterior of a charming barn-style home is showcased, featuring a distinctive arched roof, large double doors, and black shutters. Two potted plants frame the entrance, with a welcome sign visible above the door. A grassy area and gravel pathway lead to the entrance.
Barn in Three Oaks

Barn of Three Oaks near Lake Michigan/Journeyman

4.88 out of 5 average rating, 146 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

4.98 out of 5 average rating, 268 reviews
Top Guest favourite
The open main living area features a stone fireplace underneath a wooden mantel. A circular dining table is set near large windows, while a plush sectional sofa and unique coffee table enhance the cozy atmosphere. Natural light floods the space, accentuating earthy tones.
Cabin in Michiana

Romantic Getaway in the Dunes for a Couple—Hüüsli

5.0 out of 5 average rating, 282 reviews
Guest favourite
The spacious screened-in porch features a mix of seating options including a wicker chair and multiple cushioned chairs arranged around a central gas fire pit. Natural light filters through the screens, revealing a serene outdoor view and wooden flooring that enhances the inviting space.
Townhouse in New Buffalo

PumpHouse- Walk Everywhere! Private porch firepit!

4.92 out of 5 average rating, 291 reviews
Guest favourite
The cottage features a natural facade, partially covered by green foliage. Surrounding vegetation creates a serene outdoor setting, with a wraparound screen porch visible. Mature trees and lush grass contribute to the peaceful atmosphere, providing a secluded retreat.
Cottage in Lakeside

Floyd's Cottage in Lakeside, Michi

4.89 out of 5 average rating, 611 reviews
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

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

4.99 out of 5 average rating, 176 reviews
Top Guest favourite
A cozy living area features a comfortable couch adorned with soft pillows. A modern coffee table sits in front, complemented by a small potted plant. A fireplace is surrounded by a white stone wall, with flickering flames providing a warm glow, and large windows allow natural light to enter.
Home in Michiana

House of Lotus- Chicago getaway

4.97 out of 5 average rating, 150 reviews