Holiday rentals in Washington Park

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Top-rated holiday rentals in Washington Park

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Guest favourite
A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.
Flat in South Side
4.92 out of 5 average rating, 143 reviews

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 TVs, 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 to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

A modern living area features a plush area rug over hardwood flooring. An arrangement of seating is complemented by a sleek ceiling fan and a large television mounted above a fireplace. Bright windows provide natural light, with greenery visible outside.
Flat in South Side
4.77 out of 5 average rating, 53 reviews

Spacious Haven Near Green Line, 20mins to Downtown

Nestled in the charming, tree-lined streets of West Woodlawn, this cozy spot invites you to explore the best of Chicago! Just steps away from the serene Washington Park, complete with playgrounds, serene hiking trails, and a lovely pond that’s perfect for a morning walk or some quiet reflection. Craving a taste of Hyde Park’s vibrant culinary scene? You’re just minutes from its top restaurants. With the Green Line train just a quick 7-minute walk away, you can be downtown in no time!

A modern living area features a comfortable dark sofa positioned in front of a sleek TV stand with a television. A low coffee table sits on a soft rug, while wall-mounted planters add greenery. Natural light filters through the window covered with blinds.
Flat in Hyde Park
4.79 out of 5 average rating, 19 reviews

Charming 1BR/1BA Apt in Chicago

Welcome to this charming 1-bedroom, 1-bath apartment nestled in one of Chicago’s most desirable neighborhoods. This cozy unit blends classic character with modern updates, featuring hardwood floors, large windows, and a bright, functional layout. The kitchen offers updated appliances and plenty of cabinet space, while the bedroom provides a quiet, comfortable retreat. Enjoy easy access to local cafes, parks, shopping, and public transit—perfect for city living with a touch of charm.

Top guest favourite
A cozy living area features two large windows allowing natural light to fill the space. A fold-out futon sofa and a black armchair are positioned around a wooden coffee table. An adjacent kitchenette with a two-seat dining table is visible, along with various plants enhancing the atmosphere.
Flat in Hyde Park
4.92 out of 5 average rating, 132 reviews

Spacious 1BR Garden Apt & Parking

Welcome to our tranquil garden apartment on a quiet residential street near the university and all Hyde Park attractions. Enjoy morning light through picture windows in the spacious living room and adjacent kitchenette. Breakfast on the patio or garden bench on a sunny morning. Stroll to one of 20+ eateries within four blocks. This is our home, so we are mostly upstairs or nearby if needed. Access is private via back gate just off the parking lot with reserved parking space.

Superhost
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.
Flat in Washington Park
4.98 out of 5 average rating, 51 reviews

Private Duplex w/ Games + Theater | Near UChicago

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 two bedrooms, a full bath, an electric fireplace for cozy nights, a fully stocked kitchen with coffee, and a furnished patio. Kids and young adults especially love the fun setup, making it a memorable Chicago stay for all.

Top guest favourite
A modern living space features a light-colored sofa with decorative pillows and a woven throw. A warm-toned wooden accent wall complements a sleek electric fireplace below a mounted television. A patterned area rug anchors the room, while shelves in the background display decorative items.
Loft in South Side
4.99 out of 5 average rating, 132 reviews

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.

Guest favourite
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.
Serviced apartment in Washington Park
4.88 out of 5 average rating, 77 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.

Guest favourite
A private room features a spacious bed with crisp white bedding. A wall-mounted television is situated opposite, with a small table and chair nearby. A fan is positioned to the side, and a compact refrigerator is visible next to the table. Natural light filters through sheer curtains.
Private room in Hyde Park
4.92 out of 5 average rating, 287 reviews

HydePark002, UC, NavyPier, Chinatown, freeparking

Feel free to check us other listings: https://www.airbnb.com/h/hydepark001 https://www.airbnb.com/h/zengarden333 https://www.airbnb.com/h/zengarden332 https://www.airbnb.com/h/zengarden001 Hyde Park luxury private room with a keypad lock on each room door. Shared full bathroom only for 2 rooms. Step to UChicago, Chicago loop, McCormick, Chinatown(hundreds of delicious food). Perfect for everyone in Chicago! Free street parking.

Superhost
Flat in Hyde Park
4.75 out of 5 average rating, 20 reviews

Bright & Cozy Studio in the Heart of Hyde Park

Cozy, sunlit Hyde Park studio just blocks from UChicago. Enjoy a comfy queen bed, private bath, fast Wi-Fi, and a fully stocked kitchen with all essentials. Nestled on a quiet, tree-lined street in a safe, walkable neighborhood near cafés, restaurants, parks, and museums. Easy CTA and Metra access for downtown trips. Perfect for solo travelers, couples, and visiting academics seeking comfort, convenience, and a welcoming, homey atmosphere.

Superhost
A modern living area features a gray couch adorned with vibrant yellow 'ICONIC' cushions. Two bright yellow chairs flank a glass coffee table central to the space, which is complemented by decorative houseplants and a minimalist wall art piece above.
Flat in Washington Park
4.81 out of 5 average rating, 62 reviews

W3N NexttoUniversity/Train 15minDowntown WorkDesk

☞ 1 Smart TV ☞ Fully equipped + stocked kitchen ☞ Self check-in ✭“Everything I needed to have a great vacation thank you ” ☞ Luggage storage available ☞ Onsite washer + dryer in basement ☞ Air conditioning 》30 mins to airports 》15 mins to Downtown Chicago 》 Walking distance to University of Chicago, L train, Park 》15 mins to McCormick Place convention, Millennium Park, museum campus 》Sleeps 6 》2 bedroom 》1 bathroom

A cozy studio space is captured, featuring a queen bed with neutral bedding and accent pillows. A small dining table with blue chairs sits next to a kitchenette, equipped with wooden cabinets and modern appliances. A flat-screen TV is mounted on the wall, enhancing the functional layout.
Flat in Hyde Park
4.68 out of 5 average rating, 50 reviews

Trendy Studio Apartment in Chicago

This warm and inviting studio is perfect for couples or solo travelers craving comfort and charm. Snuggle into a comfy queen bed, unwind with a home-cooked meal, and enjoy peaceful vibes all around. Just minutes from the lake, the Museum of Science & Industry, and scenic parks for romantic walks or chill days out. Whether you're here to explore or just cozy up and relax, this sweet little space feels like home.

A spacious sleeping area features a large bed adorned with a geometric patterned blanket. Black and white artwork decorates the walls, complemented by a standing lamp. A cozy seating area is included, showcasing patterned cushions and throws for added comfort.
Guest suite in South Side
4.81 out of 5 average rating, 326 reviews

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!

Popular amenities for Washington Park holiday rentals

When is the best time to visit Washington Park?

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Avg. price$162 SGD$174 SGD$156 SGD$184 SGD$204 SGD$207 SGD$209 SGD$207 SGD$193 SGD$194 SGD$194 SGD$179 SGD
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Quick stats about holiday rentals in Washington Park

  • Total holiday rentals

    Explore 70 holiday rentals in Washington Park

  • Nightly prices starting at

    Washington Park holiday rentals start at $52 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    70 of Washington Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Washington Park rentals

  • 4.8 Average rating

    Washington Park stays are highly rated by guests – averaging 4.8 out of 5!

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