
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.

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, 254 reviews
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, 314 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"
4.93 out of 5 average rating, 105 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.
4.98 out of 5 average rating, 272 reviews
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.
4.94 out of 5 average rating, 413 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
4.92 out of 5 average rating, 239 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.
5.0 out of 5 average rating, 153 reviews
"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 an umbrella. Convenient charger for electric cars. Never a cleaning fee.
4.98 out of 5 average rating, 970 reviews
Twin Cottage A- Walk to Beach & Town!
Twin Cottage A 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 B as well for a complete look at our reviews. *Stays 28 days or longer require weekly cleaning fee added after inquiry or request
4.95 out of 5 average rating, 460 reviews
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, 197 reviews
Barn of Three Oaks near Lake Michigan/Journeyman
The Barn is a three bedroom, two and a half bath home. The primary bedroom has an en suite full bath, while the front bedroom has a half bath en suite. Bedrooms are equipped with USB charging ports for three devices as well as a white noise machine. The kitchen is thoughtfully appointed as well, including a Keurig. There are many books, games & puzzles in addition to a selection of records to enjoy. A washer and dryer are also on site as well as an iron and ironing board.
4.89 out of 5 average rating, 151 reviews
PumpHouse- Walk Everywhere! Private porch firepit!
Escape to Prime Downtown New Buffalo – Just 70 Miles from Chicago! Nestled one street off the main strip with easy parking. Walk to beaches, marina, Amtrak. Chill on private screened porch with gas fire pit. Rent bikes, boats, kayaks. Grab bites at Stray Dog, Ghost Isle Brewery, Oink's ice cream and Casey’s. Shop boutiques, sip local wines, catch harbor sunsets! Stroll Galien River Park's boardwalk or hit Four Winds Casino. Tee off at Whittaker Woods golf, minutes away.
4.92 out of 5 average rating, 298 reviewsPopular amenities for holiday rentals near Four Winds Casino
Condo rentals with Wi-Fi

Updated Cottage Downtown, walk to Beach
4.81 out of 5 average rating, 130 reviews
Nightingale Dunes - Modern beach town retreat
4.93 out of 5 average rating, 105 reviews
New Buffalo Getaway Condo
4.9 out of 5 average rating, 101 reviews
*Luxury condo on water in St Joseph, 2 queen beds*
4.92 out of 5 average rating, 253 reviews
Premium Dunes Villa: Family Luxury Near Beaches
4.94 out of 5 average rating, 33 reviews
Beautiful top floor condo- river view- near beach
4.97 out of 5 average rating, 90 reviews
(3 Nt Min!) New Buffalo Condo With Association
4.85 out of 5 average rating, 33 reviews
Perfect Location Condo Pools Walk to all Beach 1.5
5.0 out of 5 average rating, 7 reviewsFamily-friendly house rentals

Lakeside Retreat Nestled Among the Trees
4.99 out of 5 average rating, 168 reviews
Designer Cottage - walking distance to downtown
5.0 out of 5 average rating, 219 reviews
Landmark Home 1 Blk from Lake MI Game Rm & EV Chgr
4.93 out of 5 average rating, 120 reviews
Luxe Cabin Minutes to Lake Michigan
4.98 out of 5 average rating, 177 reviews
5BR on 5 Acres w/ Hot Tub, Pickleball, Arcade
4.96 out of 5 average rating, 101 reviews
Eagle's Beach Nest: Pet-Friendly*Fenced*Walk2Beach
4.89 out of 5 average rating, 503 reviews
Lux home, sauna, hot tub, firepit, 5 min to town
4.95 out of 5 average rating, 140 reviews
Dunefarmhouse Modern Country Escape
4.96 out of 5 average rating, 435 reviewsApartment rentals with air conditioning

The Loft at the Acorn Theater
4.82 out of 5 average rating, 113 reviews
Second Floor Apartment sitting on Pine Lake
4.93 out of 5 average rating, 545 reviews
Cozy Chalet by Lake MI&Dunes with Fire Pit
4.94 out of 5 average rating, 591 reviews
Morton's Retreat Cozy 1 Bedroom Apartment
4.9 out of 5 average rating, 134 reviews
Quiet Grand Mere Coach House on Lake Michigan
4.92 out of 5 average rating, 901 reviews
The Sunshine House: Breezy Beach Unit!
4.95 out of 5 average rating, 128 reviews
Ozzie’s Hideaway-Smack between Three Oaks & Sawyer
4.97 out of 5 average rating, 346 reviews
King Bed Retreat, Minutes to Beach & Dunes
4.95 out of 5 average rating, 119 reviewsOther great holiday rentals near Four Winds Casino

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace
4.98 out of 5 average rating, 180 reviews
TRYON FARM MID-MODERN SPA IN THE WOODS
4.95 out of 5 average rating, 333 reviews
The Little House at Tryon Farm
4.97 out of 5 average rating, 314 reviews
Beach Bird Cottage- 5min walk to the lake! 3BR/1BA
4.98 out of 5 average rating, 166 reviews
New Buffalo retreat - Perfect year-round getaway!
4.98 out of 5 average rating, 241 reviews
SoulShine Inn • Pets Welcome•Fully fenced backyard
4.96 out of 5 average rating, 616 reviews
Designer Cottage Relax Pool Beach & Spa—Windjammer
4.97 out of 5 average rating, 250 reviews
Blue Haven Lake Cottage
4.94 out of 5 average rating, 105 reviewsDestinations to explore
- Soldier Field
- Lincoln Park
- Grant Park
- Warren Dunes State Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- 875 North Michigan Avenue
- University of Chicago
- The Field Museum
- Shedd Aquarium
- University of Notre Dame
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Beachwalk Vacation Rentals
- Washington Park Zoo
- Chicago Theatre
- University of Illinois At Chicago
- Oak Street Beach
- Museum of Science and Industry
- Silver Beach Carousel
- Wintrust Arena
- Potato Creek State Park





