
Holiday rentals with outdoor seating in Bridgeport
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Bridgeport

Total holiday rentals
Explore 30 holiday rentals in Bridgeport

Nightly prices starting at
Bridgeport holiday rentals start at $69 NZD per night before taxes and fees

Verified guest reviews
Over 2,570 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Bridgeport holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Bridgeport rentals

4.7 Average rating
Bridgeport stays receive an average rating of 4.7 out of 5 from guests
Top-rated Holiday Houses with Outdoor Seating in Bridgeport
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Cozy Hideout in Art Filled Chicago Neighborhood
Your private guest suite is newly renovated. You will have a private room with your own keypad entrance, thermostat and bathroom, T.V. with internet access, mini fridge, serving ware, coffee maker, fruit and yogurt in the fridge! We also have a toaster oven in case you want to warm up leftovers. You will only have access to your room, which is comparable to a short term stay hotel room, but way cooler. send a text or message me and I'll respond as soon as I can The Pilsen neighborhood got voted one of the 12 coolest neighborhoods in the world in 2018, according to Forbes magazine. There’s venues, studios, and bars booming with more culture all only blocks away. Uber / Lyft is a great way to get anywhere quick - usually a 15 min ride to downtown. Public transit options are the CTA El Train (Pink Line 18th stop is 0.7 mile walk from our house) or CTA Bus (18th & Racine stop is a block away). Once you’re at the transit stop both options take about a 20 - 30 minute to downtown. There are other bus lines nearby that take you other places (i.e. McCormick Place) - feel free to ask us for help when you arrive. Street parking is free in certain areas for those who are driving. Please message us and we’ll direct you where to park. We are a 20 minute cab ride from Midway International Airport and 40 minutes from O'Hare without heavy traffic, double these estimates if traffic is heavy (rush hour, accidents, etc).

Cozy 1BR + Futon • Deck • Laundry • Private Entry
Located at the geographic center of Chicago with plenty of FREE street parking. The area is very safe and about a 10-min walk to the 35th/Archer Orange Line and just 3 blocks from the Archer bus—both take you downtown within minutes. This lower-level 1BR has a private entrance, spacious queen bedroom, living room with full futon, full kitchen, and private bath. Perfect for solo stays, couples, small families, or work trips. Enjoy your own space with access to a back patio, grill, and laundry.

Large Home | Free Parking | Near Downtown
• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood

Chicago's Bridgeport Huge 4 Story w/Garage Parking
Large and beautiful 4 story single-family home centrally located in the trendy Bridgeport community of Chicago. The house is 5 minutes from McCormick Place, 3 miles away from Magnificant Mile shopping on Michigan Ave. 2 blocks from the Bridgeport Art Center, and 5 minutes from Soldier Field! 6 blocks to catch a White Sox game! Close to beaches and Lake Shore Drive, this spacious and welcoming home will serve all your vacation needs. 5 minutes from Chinatown, Greektown, Little Italy, and Pilsen.

A space crafted for comfort and intentional stays.
A calm, light‑filled suite in the heart of Pilsen, made for comfort and staying with intention. A kitchen built for everyday cooking. Fast Wi‑Fi. A dedicated workspace built for long days of focus. The bedroom stays calm and dark. The living area holds your everyday routines. The art throughout adds warmth and character. Walkable to cafés, the Pink Line, the Medical District, and McCormick Place. Made for travel nurses, remote workers, creatives, and anyone settling in for more than a weekend.

Convenient & Spacious 3BR Condo w/Free Parking
Get cozy in this spacious 3-bedroom condo, conveniently located 3 blocks from the Halsted Orange Line overlooking Palmisano Park and only 5 minutes' drive to McCormick Place. Clean, neat, modern and comfortable, the condo offers spacious living space with an open kitchen, washer/dryer, and an outdoor balcony perfect for families and groups. Hungry? Our complex offers a few delicious high rated yelp restaurant options to fulfill your appetite. We look forward to hosting you and your guests!

Modern Getaway w/ Hot Tub, Lrg Yard, Parking
*Due to AirBnB new changes in fee disclosure, 18% of the daily rate you see goes to Airbnb* 1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (2 Queens) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. A parking space in the rear allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions. NO CHORES!

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

WF Home Sweet Home
Located in the center of the Bridgeport area, This AirBnB is clean, tidy, cozy and comfortable. It's the first choice for visitors. Two minutes walk to 8 and 31 bus stop, 15 minutes drive to downtown, McComick Place, and it close to Chinatown and White Sox Field. In addition, you can enjoy a variety of cuisines in a few minutes' walk, including Chinese, Japanese, Korean, Mexican restaurant, Starbucks,McDonald's, Dunkin Donuts, CVS. Warmly welcome friends from all over the world

The Oasis / Free street parking
Nothing beats summertime in Chicago! Explore downtown, recharge at the Oasis! Recently rehabbed 1st floor unit. Plentiful free street parking, well-stocked kitchen, lush backyard. Walk to parks, coffee shops, grocery store, restaurants, White Sox. Access to red & orange line trains to downtown and tourist attractions. Quick drive to Midway Airport & McCormick Center. No dishwasher Free washer dryer No chores at checkout =) Free early check in/late checkout *if available*

Vintage Suite Home Chicago by Sox/Park/Transit
Walkout basement studio in a ca.1890 home built for laborers in the Chicago Stockyards - Please read entire listing before booking. This quiet, tree-lined neighborhood is a respite from city buzz. Get downtown in 4 stops by train or any of 5 nearby buses. Your space has great natural light, 2 comfy beds, private bath, flexible work/dining area, super-fast WiFi, and kitchen with all the essentials. Private entry via back door Free street parking Se habla español

Quaint Comfort Studio Near Downtown/Queen Bed
Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.
Popular amenities for Bridgeport outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Vintage Designed 3BR Condo Near DePaul University

RetroModern Bungalow | free parking | pet friendly

Top Floor Escape | Modern Amenities | Lush Garden

The Ashlin House.

Floresitas Oasis, your home in Chicago

3 bed/2 bath by United Center w/ private parking

NEW! 3BR/2.5B Duplex in Noble Sq

Chicago Home (1st floor) by Midway near Downtown
Apartment rentals with outdoor seating

Spacious Bronzeville Apartment

Peaceful River West, free parking

Charming retreat w/ fireplace

Cozy guest studio, great for couples!

Great Location & Bright 2BR+2BA | Mapletree Suites

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

The Metropolitan Retreat (Fitness Center • Sauna)

Spacious 2BR on Quiet St - Free Park/Late Checkout
Condo rentals with outdoor seating

Two Bedroom w Porch in Wicker Park

Stylish 2-bedroom flat in Vibrant Bucktown.

Welcoming 2BR in Chicago's Best Neighborhood!

Grace House | Cozy, contemporary + convenient 2-BR

NEW luxury Old Town 1-Bedroom condo

Downtown Park #11 - Mich Ave PH | gym+rooftop

Chicago Oasis | Spa Bath, Patio & Fireplace

Modern Chicago Movie Themed Apt
Destinations to explore
- Family-friendly rentals Bridgeport
- Rentals with a patio Bridgeport
- Pet-friendly rentals Bridgeport
- House rentals Bridgeport
- Rentals with a washing machine and dryer Bridgeport
- Apartment rentals Bridgeport
- Rentals with outdoor seating Chicago
- Rentals with outdoor seating Cook County
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- Rentals with outdoor seating United States
- Wrigley Field
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