Beachfront holiday rentals in Oakwood Beach

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

NU/Lake Evanston quiet/cozy/greatview!

This room features a large desk with lovely window and very comfy single bed. It is separated from my room by a tapestry and half wall, but I can sleep elsewhere when requested. It's a block from Whole Foods and the library. Four blocks from Davis street train station, Trader Joe’s, numerous restaurants, shops and landmarks very near. Bike, divvys available. Free breakfast!! Room CANNOT be locked from the outside, just inside because it's against fire regulations, but all's safe. Charming!

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

Modern 4BR Gold Coast Duplex w/ Jacuzzi & Balcony

Welcome to the Bellevue Penthouse Suite, your luxurious retreat in the heart of Chicago’s iconic Gold Coast. This beautifully designed 4-bedroom, 2-bathroom duplex spans two levels of modern comfort and elevated style. Enjoy the private Jacuzzi tub inside the master suite, a balcony with outdoor furniture, and two spacious living areas—perfect for families, business travelers, and groups looking for a true city escape. 📲 Message us directly for special discounts or long-term stay rates

1 Room for up to 3, Near NU & Old Orchard Mall

Near bus, trains, Old Orchard Mall, NU, beaches. Avoid the traffic! Walk, or jump on public transport. Can host 1 couple or up to 3 people in one room; 2nd room available for 2 more guests. Charming art-filled Tudor home, beautiful garden setting. Large private room, queen bed + twin, updated bathroom. Free street parking. Perfect spot for visiting NU, many North Shore sights, local retirement communities. Easy access to trains to city. Great restaurants! Discounts on longer stays.

A Sunny, Well-Kept & Comfy Studio in Gold Coast

Stay in a cozy, clean, and bright Gold Coast studio right in Chicago’s most iconic neighborhood. Rest comfortably in the well-furnished space, complete with a seating area and a full kitchen for convenient cooking. The bathroom is stocked with fresh towels and essential toiletries. With Oak Street Beach, Michigan Avenue shops, dining, nightlife, and public transit only moments away, getting around is effortless. Perfect whether you’re here for a quick trip or an extended visit.

Golden Suite on State|Steps to Oak Beach & MagMile

Wake up in the heart of Chicago’s glamorous Gold Coast on iconic State Street. Just a short walk from Oak St Beach and Lake Michigan, this stylish high-rise retreat places you steps from the city’s best dining, boutiques, and famous attractions. Spend the day exploring tree-lined streets and lakefront paths, then return to a bright, modern space perfectly positioned to experience Chicago like a local. A central stay where convenience, charm, and city energy meet.

Guest Favorite Escape Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Explore nearby beaches, stroll along the lakefront, and discover vibrant downtown shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable Evanston getaway!

Gold Coast 1BR – Easy Downtown Access

Settle into Chicago’s Gold Coast, a distinguished and charming neighborhood just a short walk from downtown. Steps away, you’ll find Oak Street Beach, the lively restaurants of Rush Street, high-end shopping along Michigan Avenue, and an inviting mix of cafes, boutiques, and nightlife. With public transit nearby, exploring the city and surrounding areas is effortless. Inside, enjoy a cozy and well-appointed space crafted for both comfort and convenience.

Cannabis Condo 4BR

Beautiful, spacious apartment is located 10 min from Beach. 10 mins to Hyde Park, (Tiger Woods) Golf Course. 10 mins from Obama Library (coming soon). 10 mins from Museum of Science and Industry. 20 mins from downtown/Soldiers Field (Bears Stadium), Northernly Island concerts, Field Museum, and Shedd Aquarium (beautiful drive down Lakeshore, Metra Electric Line train, or Bus). 15 min from Indiana casino. Ideal for Summer time Chi or Winter snow Chicago!

Only Urban Beach House in Chicago

Why stay in a hotel or dorm when you can have your own house! The Urban Beach House of Rogers Park, Chicago’s only urban beach house, has 4 bedrooms, 3 full baths, and is loaded with features that make it the perfect place for vacationers, students, faculty, family and gatherings of all kinds. Steps from the sandy beaches of Lake Michigan, walking distance from dozens of restaurants and shops, and minutes from 3 train stations and a Divvy bike station.