Beachfront vacation rentals in Oakwood Beach

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Top-rated beachfront rentals in Oakwood Beach

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

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Superhost

Guest suite in Evanston

4.82 out of 5 average rating, 100 reviews

Historic Manor House Private Guest Suite Evanston

Stay in the Guest Suite of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire third floor, which includes 3 bedrooms, a private bath with claw-foot soaking tub and shower, private kitchen with full amenities, and the original ballroom which serves as a living and dining room. Air mattress for 1 extra guest. Available as separate rental, is a 2nd floor bedroom for 2 extra guests or a coach house which sleeps 2.

Superhost

Private room in Evanston

4.88 out of 5 average rating, 73 reviews

NU/Lake Evanston quiet/cozy semi private

SEMI private room divided from my bedroom by a half wall and nature tapestry: (photo from my room looking in.) NOT sound proof but visually private, with separate entrance and large desk with lovely window. Also 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 because it is against fire regulations, but all safe.

Guest favorite

Townhouse in Chicago

4.84 out of 5 average rating, 202 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also those who fancy a beach in the City!

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 229 reviews

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.

Superhost

Condo in Chicago

4.87 out of 5 average rating, 193 reviews

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Top guest favorite

Private room in Chicago

4.98 out of 5 average rating, 43 reviews

Sunny,Comfortable,CleanTop Location at Lake,Beach

Comfortable, large, sunny bedroom. Perfect for relaxation, work, study. Many amenities: wifi, desk, tv, coffee maker, small refrigerator. Private bathroom with shower/tub. Friendly hosts will welcome you. Fabulous location, fifteen minutes from downtown Chicago. Within 1/2 block of public transportation, Lake Michigan, beach, park, tennis courts. Six blocks to Loyola University. 3.5 miles to Northwestern U. Wonderful neighborhood, stores, restaurants, theaters, coffee shops, grocery.

Private room in Chicago

4.75 out of 5 average rating, 169 reviews

Basic accomodation equipped for short terms stays.

I am renting out my extra bedroom in my 2 bed condo for 1 guest only. Guests have access to their bedroom and bathroom only. No kitchen or living room access. My space is not luxury, but it's sanitized and clean, the neighborhood is cute/safe where you can feel calm/ peaceful. I have a lovely park across the street you can lounge. I am in an area where there are good restaurants within walking distance. Apartment 1W edit: Do not book my place for someone else under your profile.

Villa in Chicago

4.63 out of 5 average rating, 52 reviews

Rooftop | Villa | Parking

Meet up with group at this gorgeous designer space, a mini Villa but large throughout making it light, bright, airy with feelings of calm and tranquility. Indoor features Luminaire Chandeliers, 10 feet ceilings, Grand Piano, Music Box etc. Huge backyard offer spaces to entertain. You’re booking a private residence: 3 levels of home exclusive to your guests/party. Guest can view cameras of all entrances; Roof deck, Front, Back & Alley via Monitor (HDMI-1) 24/7 record

Guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 61 reviews

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach

FREE GARAGE PARKING! Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

Superhost

Apartment in Chicago

4.82 out of 5 average rating, 51 reviews

Woodlawn Oasis

Welcome to Woodlawn Oasis! Come and enjoy the charm and warmth of this fully remodeled and furnished apartment with original artwork! Just 5 minutes from our beautiful Chicago lakefront, the prestiges University of Chicago, and soon to be Tiger Woods golf course and President Obama library. Also, 10 minutes from Chicago museums, Soldier Field (Chicago Bears), Guaranteed Rate Field (Chicago White Sox) and the fabulous night life of Downtown Chicago!

Home in Chicago

4.84 out of 5 average rating, 32 reviews

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.