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Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TV, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.

Luxury Urban Loft w/ River View - Near Notre Dame

Welcome to your luxury loft on the 9th floor, where industrial charm meets modern comfort. High concrete ceilings and large windows fill the space with light, while the electric fireplace adds a cozy touch for evenings. A dedicated workspace makes it perfect for remote work or planning your city adventures. Step onto your private balcony for stunning views of the St Joseph River and skyline. With a bistro set, tabletop fire pit, and string lights, it’s the ideal spot to unwind after a busy day.

Cozy 2BD Lake Apt Near Downtown, McCormick & More

Enjoy your getaway in this cozy solar powered and eco-sustainable garden apartment 5 minutes walking to Lake Michigan where you can access beaches, bike paths, prairies, parks & more! We are less that 8 min away from downtown, the University of Chicago, Soldier Field, the Field Museum and more. Our home is located in the historic Oakland neighborhood, central to so much of what Chicago has to offer. We love welcoming guests to our garden apartment where making your stay relaxing is our pleasure

Couples Getaway, Jacuzzi, Sauna, Pool is Open

Couples Getaway | Private Suite w/ Jacuzzi, Sauna, Pool & Gym Indulge in a luxurious, private retreat designed for couples! This beautifully styled guesthouse suite is attached to the main house but completely private—you’ll have your own private entrance for total seclusion. Enjoy spa-like relaxation with a jacuzzi, sauna, pool access, and a fully equipped gym. Perfect for honeymoons, anniversaries, or weekend escapes, our space blends comfort, privacy, and elegance for an unforgettable stay.

Quiet Farmhouse Retreat

Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

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.

Boutique Historic Downtown Loft - Heart of Niles

Welcome to the Heart of Niles, a character-filled second-story loft adjacent to the Niles Outdoor Downtown Experience (NODE) pedestrian plaza. Walk to restaurants, coffee shops, and local venues. A comfortable home base for hiking, biking, Notre Dame/South Bend visits, or day trips to Harbor Country and Lake Michigan. Best for guests who enjoy a vibrant small-town downtown experience. Locally owned and personally hosted by a husband-and-wife Superhost team — not a corporate rental group.

Play @ The Hideaway - hot tub, sauna, gymnasium

Accommodating up to 22 guests, this expansive 5,891 sqft property is set on 22.6 acres, creating a private oasis complete with a pool, hot tub, sauna, and gymnasium. The residence features a Great Room, fireplace, fire pit, and a private trail, making it an ideal setting for relaxation and recreation. With 3 king-size beds, 4 queen-size beds, and 2 bunk beds with trundles, comfortably catering to the needs of large groups. This venue offers enjoyable experiences for guests of all ages.

Pool, Hot tub, Kayaks, Waterfront, SW Michigan

Waterfront property with a private hot tub, pool, and tennis court, making it an ideal destination for those seeking both relaxation and recreation. Visit beautiful Southwest Michigan and stay at the St. Joe Overlook. Take a swim in the pool, unwind in the hot tub, take the kayaks out for a river cruise, or sit by the fire. Enjoy this stunning location and top-notch amenities. A trip to the St Joe Overlook is the perfect place to gather & reconnect. Maximum Guest Count 16.

Hoosier Home - 5 min walk to the beach

Enjoy quiet, cozy, and spacious home just a short walk from the beach and local restaurants/bars. Located 2.1 miles from Indiana Dunes National Park (West Beach), 11 miles from Indiana Dunes State Park, and a few blocks from Marquette Park, which features a disc golf course and seasonal concessions. The Miller Beach train station, with service to Chicago, is also a short drive away. Please note: a 2-night minimum stay is required - single-night bookings not accepted.

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Clover Haven | High Rise | Down Town South Bend ND

Immerse yourself in the heart of South Bend with breathtaking views of the illuminated Saint Joseph River and the city skyline. Your perfect stay starts here! This space is within walking distance to many restaurants, bars, stores, parks, and more! Nearby attractions include: - Notre Dame Campus - Trader Joe’s - Century Center - Morris Performing Arts Center - South Bend Chocolate Factory - Eddy’s Street Commons - East Race Market - Howard Park and many more!