Holiday houses in Washington Park

4.9 out of 5 average rating, 30 reviews

Home in South Side

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

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A spacious living area features high ceilings with a skylight and large windows, offering ample natural light. A comfortable green sofa and a black armchair are positioned near a coffee table. A fireplace and a television are visible, with scenic views seen through the glass doors.

4.96 out of 5 average rating, 71 reviews

Sunny Penthouse - Oakwood Beach

Bright top-floor 2-bedroom, 2-bath condo in the heart of Bronzeville with soaring ceilings and abundant natural light. Relax in the in-unit jacuzzi jetted tub after a day exploring Chicago. The fully equipped kitchen has everything you need to cook at home, or enjoy nearby restaurants. 🌊 Just a 18-minute walk to Oakwood Beach & the lakefront. Within a 20-minute drive of Downtown, Soldier Field, Guaranteed Rate Field, the Field Museum, the Art Institute, Chinatown, Hyde Park, Pilsen & more!

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A spacious living room is displayed, featuring a large sectional sofa adorned with decorative pillows. A glass coffee table rests on a patterned rug, while creative wall art and a wooden sculpture enhance the atmosphere. Soft lighting from a ceiling fan provides a warm ambiance.

4.94 out of 5 average rating, 68 reviews

Private Theater Duplex • 15 Min to Downtown

Enjoy our spacious 2-level home this fall and winter, perfect for families and groups. The lower level is your entertainment hub with a 120" projector, retro arcade, ping pong, board games, reclining sectional, 1 bedroom, and 1 bath. Upstairs features 2 bedrooms, a full bath, an electric fireplace for cozy nights, a fully stocked kitchen, and a furnished patio. Kids and young adults especially love the fun setup, making it a memorable Chicago stay for all. We welcome last minute bookings!

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4.87 out of 5 average rating, 15 reviews

Near UChicago, 3BR Apt, Parking, W/D, 2 Workspaces

Work-ready 3BR, 2BA apartment located just minutes from UChicago and several major hospitals. Once inside, everything is on one floor. Sleep well with a king, queen, and full bed, plus two full tub/shower baths. Set up at 2 dedicated workspaces with fast WiFi. Cook in a stocked kitchen with full-size stainless appliances, a dishwasher, a coffeemaker, kettle, and other basics. Private in-unit stackable washer/dryer. Free street parking usually nearby. Great for professionals and longer stays.

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5 out of 5 average rating, 4 reviews

Stylish Flat near Downtown,Obama Library, UChicago

Stylish Luxury Retreat in Woodlawn | Near the Obama Presidential Center, Downtown & UChicago. Experience modern comfort and style in this beautifully space nestled in the vibrant community of Chicago. Features two beautifully designed bedrooms , luxurious bathroom, and an open living and dining area perfect for relaxing. Prepare your favorite meals in the upscale, fully equipped kitchen, then unwind on the private balcony with your morning coffee or evening glass of wine.

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4.94 out of 5 average rating, 67 reviews

An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.

Condo in South Side

UChicago Condo | 2 Baths, Private Parking & Entry

Enjoy the convenience of a dedicated private parking space with direct access to your own private entrance. This upgraded and spacious 1-bedroom, 2-bathroom condo near the University of Chicago features hardwood floors, stainless steel appliances, in-unit laundry, two Smart TVs, a cozy reading nook, and a large outdoor patio. Conveniently located near Hyde Park, Lake Michigan, Jackson Park, and the Obama Presidential Center. Perfect for extended stays and remote work.

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A modern kitchen features white cabinetry and stainless steel appliances, including a refrigerator and microwave. A marble countertop extends to a bar area with three red stools. Decorative elements, including a vase of flowers, enhance the inviting atmosphere.

4.88 out of 5 average rating, 86 reviews

Washington Estate minutes from University of CHI

Kick back and relax in this calm, stylish space. The Washington Estate is the professional escape. We provide a 1-bed/2-bath to accommodate a maximum of two guests. Everything you need, full kitchen, WIFI, exercise room, in unit laundry and exterior patio seating for your enjoyment. Gated parking available upon request. Near the historic Hyde Park, the University of Chicago and 8 minutes away from Lake Shore Drive. Walking distance from public transportation.

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5 out of 5 average rating, 26 reviews

Stylish Hyde Park/Kenwood Brownstone Garden Apt

Enjoy a stylish experience in Chicago's historic Hyde Park/Kenwood neighborhood in this updated brownstone garden apartment. You'll have an entire tastefully designed speakeasy chic 2-bedroom/1.5-bathroom unit with a separate entrance to yourself. Great location off South DuSable Lakeshore Drive- you're minutes away from Lake Michigan's scenic lakefront, the University of Chicago, McCormick Place and downtown Chicago.

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4.98 out of 5 average rating, 48 reviews

Modern Eco Stay • UChicago • Parking • Backyard

Relax in this eco-friendly South Side retreat designed for comfort, style, and convenience. Located minutes from UChicago, Hyde Park, Jackson Park, the Museum of Science & Industry, and the lakefront, this unit is perfect for families, medical visits, students, and anyone exploring Chicago. With a private entrance, free parking, and a large fenced backyard, this modern space gives you privacy and peace in the city.

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4.86 out of 5 average rating, 79 reviews

The exterior of a two-story condo building is presented, featuring dark brick and a light-colored stone facade. A decorative wreath is hung on the front door, and colorful pumpkins are arranged on steps alongside a ghost figure. Beside the entrance, a small yellow table and chairs contribute to the outdoor ambiance.

Condo in South Side

WoodlawnLUXE 4 Bedrooms

5 minutes to Obama Center and University of Chicago! WEEKLY AND MONTHLY DISCOUNTS!!! Enjoy this newly renovated LUXE 4 bedroom 1 bathroom condo on the entire second floor of a two flat building! All 4 bedrooms have LG Smart TV'S! A 30 minute drive to Midway airport 45 minute to Ohare. Chicago’s downtown, McCormick Place, and museums 30 minute drive. Located 4 blocks to Greenline Line

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5 out of 5 average rating, 25 reviews

Spacious 3BDR Luxury Penthouse

Stylish 3BD/2BA penthouse with high ceilings, oversized windows, stainless steel appliances, quartz countertops, in-unit laundry, and parking. Located in Bronzeville, just 10 mins to downtown, 8 mins to the University of Chicago, 18 mins to Soldier Field, and 25 mins to Midway Airport. Perfect for families or groups seeking comfort, convenience, and a premium city stay.

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