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Places to stay near Shady Creek Winery

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Top-rated vacation rentals near Shady Creek Winery

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Guest favorite
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!

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

4.97 out of 5 average rating, 150 reviews
Guest favorite
A clear view of Lake Michigan is presented from a wooden deck. Sandy pathways lead down to the beach, framed by lush greenery. The tranquil blue waters stretch toward the horizon under a bright blue sky.
Home in Michigan City

Lifetime Memories-Big Beachfront House 8 BR 5BA

Lakefront 8Br 5Bath (Sleeps 24). Unobstructed views of Lake Michigan & steps to beach. Firepit, WIFI, Big Weber Gas grill, fireplace, etc. Lower level (walk-out) redone with LR, 3BR, new Bath and laundry. 1st floor open plan - new kitchen, bath, and wood floors! 2nd & 3rd floors brand new - 2nd floor with 4 BR & 2 Ba - 2 BR w/doors 2 deck facing lake! Spiral stair to 3rd floor loft/Br w/6 twins, Full Bath & deck. Beach is virtually private at this, the far end of Michigan City's public beach.

4.9 out of 5 average rating, 169 reviews
Top guest favorite
A spacious living area showcases a light-colored sectional sofa adorned with plush pillows. Large windows allow natural light to fill the room, revealing wooden flooring and eye-catching artwork on the walls. A dining table is visible in the background, complemented by a minimalist plant.
Home in Michigan City

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.

4.98 out of 5 average rating, 347 reviews
Guest favorite
Home in Michigan City

Michigan City Family Friendly Beach Escape

Enjoy a relaxing stay at one of the best beaches on fresh water Lake Michigan in our century old former fisherman’s cottage updated to fit today’s lifestyle. This 3 bedroom, 2 bathroom house is perfect for large or extended families looking to relax and enjoy a few days away but still close to restaurants and other activities. Spend your days with STEP FREE access to a wide and clean sandy beach, evenings with picturesque sunsets and nights by the fire. Truly a hidden gem in Northwest Indiana.

4.96 out of 5 average rating, 109 reviews
Top guest favorite
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

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.

5.0 out of 5 average rating, 282 reviews
Top guest favorite
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
Guest favorite
A dining area showcases a long, dark wooden table paired with a bench and a stylish chair. An industrial-style light fixture hangs above, illuminating the space. A decorative plant and artwork add warmth to the setting, accented by textured wall coverings and natural light.
Home in Michigan City

Lake Michigan Farm Retreat w/ Yoga Shed & Hot Tub

Luxury farm retreat on 7 wooded acres with hot tub, yoga shed, fire pit, fully fenced yard & pond! This home is a five minute drive to the beach, blueberry picking, Burn 'Em Brewing, Shady Creek Winery, next to Tryon Farm or 10 minute drive to downtown, the casino, and the outlet mall, but our guess is that you won't want to leave the property! This designer home has super comfy beds, 800 thread count sheets, a gourmet coffee bar, screened in porch, and even a tiny library in the laundry room

4.93 out of 5 average rating, 417 reviews
Guest favorite
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 favorite
A modern house is situated amidst lush greenery. A wooden walkway leads to the entrance, framed by trees and underbrush. Large windows reflect natural light, blending the structure harmoniously with its surroundings while offering a glimpse of the cozy interior.
Cabin in Michigan City

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!

4.97 out of 5 average rating, 310 reviews
Guest favorite
The charming two-story home features a wide front porch with ample seating and decorative lighting. White railings and a wooden design enhance its appeal. Flanking trees provide some greenery, and the entryway is welcoming with its open doors and stylish decor.
Home in Michigan City

5 Bedroom Luxury Home In Heart of Beachwalk Resort

Beautiful home in the heart of Beachwalk, across the street from Lake Kai, pools, basketball & tennis courts and 2 blocks to Lake Michigan. This home is bursting with charm. Front porch runs the width of the house. Dining area opens up to family room with a lovely fireplace. Stunning master bedroom w/walk-in closet and beautiful new bathroom with all the finishes. 3 more bedrooms upstairs, one with full bathroom attached and the other 2 sharing bathroom. 5th bedroom on the lower level.

4.96 out of 5 average rating, 203 reviews
Top guest favorite
The cottage entrance features a welcoming porch with two white adirondack chairs flanking a vibrant blue door. Lush greenery surrounds the space, and potted plants add a touch of color. The steps lead up to the main entrance under a charming overhang.
Cottage in Michiana Shores

Michiana Cottage

Michiana Shores, Indiana Entire cottage - 4 guests Nestled in nature, Michiana Cottage offers a totally updated home with great amenities, including a hot tub. Quiet and peaceful,you can unwind with a book on the deck; stroll a nature trail; play pickle ball, tennis or horse shoes. A 10 minute walk finds you at the beach. Hungry? Stop 50 Pizza is just down the street. A short drive takes you to Washington Park and Zoo, outlet shopping, restaurants and casinos. Permit 2020-02

4.95 out of 5 average rating, 107 reviews
Guest favorite
A modern two-story home constructed from wood is nestled among trees in a wooded area. Large windows allow natural light to brighten the interior. A deck is visible at the back, surrounded by a carpet of fallen leaves and greenery.
Home in Michigan City

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."

4.96 out of 5 average rating, 432 reviews

Popular amenities for vacation rentals near Shady Creek Winery

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Shady Creek Winery

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

Central Beach

18 locals recommend

Condo rentals with wifi

Top guest favorite
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 favorite
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 favorite
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 favorite
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
Top guest favorite
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
Guest favorite
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

Family-friendly house rentals

Top guest favorite
A two-story house features a vibrant blue exterior with a spacious porch equipped with rocking chairs. A golf cart is parked in the foreground next to a white picket fence. Clear skies and sunlight enhance the inviting and serene atmosphere.
Home in Michigan City

Beach Nest, Sleeps 20, 5 min. to Lake Michigan.

4.97 out of 5 average rating, 106 reviews
Top guest favorite
A bright bedroom features a spacious bed adorned with white linens and decorative pillows, flanked by two nightstands. Natural light enters through two windows with woven shades. Wall art depicting foliage adds a touch of nature to the cozy space.
Home in Trail Creek

Perfect for the dunes! Summer dates available now

4.99 out of 5 average rating, 159 reviews
Superhost
A large hot tub is positioned in a well-maintained backyard, surrounded by lush trees. Nearby, a sandy firepit area is complemented by seated benches, while a swing set is visible towards the rear, all enclosed by a tall wooden fence.
Home in Michigan City

Singing Sands Trl | Hot Tub Retreat | Dogs OK

4.9 out of 5 average rating, 137 reviews
Guest favorite
Home in Michigan City

Historic Victorian Mansion

4.92 out of 5 average rating, 157 reviews
Top guest favorite
Home in La Porte

Aunt Betty's Lakeside Abode, Hot Tub Steam Shower

4.98 out of 5 average rating, 253 reviews
Top guest favorite
The spacious living area features large windows allowing natural light to illuminate the comfortable seating arrangements. A round wooden coffee table is centered on a patterned rug, while a ceiling fan enhances airflow within the open layout connecting the kitchen.
Home in Michigan City

Perfect House Steps To The Beach w/Parking!**NEW**

4.93 out of 5 average rating, 107 reviews
Guest favorite
The game area features various arcade games, including a shuffleboard table and foosball. A large projector and ping pong table are present, alongside colorful murals depicting the local scenery. The inviting space emphasizes relaxation and entertainment, supported by comfortable seating arrangements.
Home in New Buffalo

Arcade/Game Room • Private Beach Access • Fire Pit

4.89 out of 5 average rating, 150 reviews
Guest favorite
The open living area features large floor-to-ceiling windows framing views of the surrounding woods. A sleek two-tone sofa and modern armchairs are arranged near a minimal table. Warm wooden flooring complements the contemporary design, and a staircase leads to the upper level.
Home in Beverly Shores

Secluded Modern Retreat Near Beach - "Sandlot"

4.95 out of 5 average rating, 243 reviews

Apartment rentals with air conditioning

Guest favorite
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
Guest favorite
Apartment in Michigan City

King Bed Retreat, Minutes to Beach & Dunes

4.95 out of 5 average rating, 116 reviews
Top guest favorite
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
Top guest favorite
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
Top guest favorite
A studio space is designed with calming colors and patterns. A spacious bed is centered in the room, complemented by a small wooden table and cozy seating. The kitchen area features blue cabinets and essential appliances. Natural light streams through windows, enhancing the inviting ambiance.
Apartment in Michigan City

Honeymooner's Hut: Stylish/Stocked Studio for Two

4.96 out of 5 average rating, 109 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 favorite
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 favorite
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

Other great vacation rentals near Shady Creek Winery

Guest favorite
A charming two-story home features light blue siding and white exterior accents. A welcoming front porch is bordered by a white picket fence. Large windows allow natural light to fill the space, offering a glimpse of the cozy seating area within.
Home in Michigan City

The Lake Escape - 5 Mins from beach, casino, & zoo

4.87 out of 5 average rating, 200 reviews
Top guest favorite
A private backyard features a patio space with a table surrounded by four chairs. The area is paved with stones and includes a raised wooden deck, a grill on the deck, and flower beds adding a touch of greenery. The house is painted in a warm peach color.
Home in Michigan City

Midcentury marvel steps from beach! Pups

4.95 out of 5 average rating, 187 reviews
Top guest favorite
A cozy bedroom features a spacious bed adorned with layered textiles and decorative pillows. Large windows provide views of the outdoors, while natural light is enhanced by wooden ceiling beams. A small dining area with chairs and a table is positioned nearby.
Guesthouse in New Buffalo

Rainbows End 🌈 Plensa

4.96 out of 5 average rating, 705 reviews
Guest favorite
A charming cottage is surrounded by lush greenery, featuring a welcoming front porch with yellow steps. The exterior showcases a combination of stone and brick with multiple windows. A garage is visible to the right, and an American flag gently waves in the breeze.
Home in Michigan City

Cozy Cottage Near Lake Michigan

4.97 out of 5 average rating, 156 reviews
Top guest favorite
An outdoor seating area is presented, featuring a sectional sofa with blue cushions surrounding a fire pit table. The table is designed with a black wooden finish and filled with decorative stones. A fenced backyard enhances the sense of privacy, complemented by a green lawn.
Home in Michigan City

Beach Farmhouse - Lake Michigan Beach & Hot Tub

4.96 out of 5 average rating, 110 reviews
Top guest favorite
A spacious living area is presented with large windows allowing natural light to fill the room. A dark sectional sofa, accented with red pillows, faces a wooden coffee table. A light-colored armchair and a small ottoman complement the cozy setting, while a framed rug adds warmth to the wooden floor.
Home in Grand Beach

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

5.0 out of 5 average rating, 139 reviews
Top guest favorite
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

5.0 out of 5 average rating, 150 reviews
Top guest favorite
Bungalow in New Buffalo

Beautiful garden oasis w/HOT TUB & screened porch!

5.0 out of 5 average rating, 185 reviews