
Holiday houses in Bridgeport
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Bridgeport

Total holiday rentals
Explore 160 holiday rentals in Bridgeport

Nightly prices starting at
Bridgeport holiday rentals start at $35 NZD per night before taxes and fees

Verified guest reviews
Over 7,720 verified reviews to help you choose

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

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

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

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Bridgeport rentals

4.6 Average rating
Bridgeport stays receive an average rating of 4.6 out of 5 from guests
Top-rated holiday rentals in Bridgeport
Guests agree: these stays are highly rated for location, cleanliness and more.

Chicago's Bridgeport Brownstone 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.
4.76 out of 5 average rating, 152 reviews
Prime Bridgeport – McGuane Park
Located by Halsted Orange Line in Bridgeport, our Airbnb has is CENTERED around all the action in the neighborhood; surrounded by Grocery Stores, Fast Food, Drug Stores, Restaurants, and Iconic Parks. With a short commute to the Loop, UIC, Chinatown, we are especially sustainable for longer-term tenants! Enjoy the luxury of firm memory-foam mattresses and pillows and High-speed Internet, Central Heat and A/C and unlimited complimentary coffee for an amazing stay! 1 Queen Bed 1 Full Bed
4.93 out of 5 average rating, 143 reviews
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!
4.9 out of 5 average rating, 162 reviews
Elegant 3/BR w/Balcony by Downtown, Chinatown
Newly developed condo with 3 spacious bedrooms and 2 full baths. Brand new appliances and spacious living room and kitchen. Environment is warm, comforting and modern. Public transportation just steps away. Orange line takes you directly to Midway airport. Buses will take you to major event locations such as McCormick, US Cellular & Soldier Field. Chinatown is just blocks away w/ day and night food & entertainment. Eateries are on the 1st floor for a quick bite. Private, designated parking.
4.81 out of 5 average rating, 197 reviews
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
Make yourself at home in Chicago — a beautiful minimal duplex where every detail is intentional. Two levels, free private parking, and six of Chicago's best neighborhoods within minutes. 10 min drive to the Chicago Bears at Soldier Field 5 min drive to the White Sox at Rate Field With 3 bedrooms, 2 bathrooms, a full kitchen, in-unit laundry. This duplex is ideal for families, groups, and professionals looking for more than just a place to sleep. Every detail was put together with care.
5.0 out of 5 average rating, 26 reviews
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!
4.96 out of 5 average rating, 187 reviews
The Oasis / Free street parking
Nothing beats summertime in Chicago! Explore downtown, recharge at the Oasis! Bright, well-appointed, 1st floor unit on quiet block. Plentiful free street parking, chef’s 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*
5.0 out of 5 average rating, 130 reviews
Bright & Cozy 2 Bedroom Apt - 15 Min to downtown!
Welcome to our cozy Chicago apartment in the historic Bridgeport neighborhood. This comfortable 2 bedroom, air mattress upon request, 1 bath unit is on the first floor of a classic two flat, offering easy access and a relaxing stay. Steps from a bus stop and just a 5 minute drive to the CTA Orange Line, getting downtown and around the city is simple. Close to Pilsen and Chinatown. For safety, four exterior Ring cameras monitor outside areas only. ID required for all primary guests.
4.84 out of 5 average rating, 151 reviews
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
4.87 out of 5 average rating, 132 reviews
2-King Bed Bridgeport Apartment w/Backyard Patio
Two bedrooms with king sized beds and ample closet space. Smart TV with streaming capability, breakfast bar, and dining area with expandable table. Kitchen has microwave, coffeepot, dishwasher, and all cooking and dining essentials. Central heat and a/c, in-unit laundry, and access to private backyard patio. Close to Sox Park, Soldier Field, McCormick Place, and many other downtown attractions. Easy access to multiple major highways and ride shares, as well as Orange Line.
4.98 out of 5 average rating, 105 reviews
Blue Brick Apartment in Bridgeport - Park for Free
• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)
4.93 out of 5 average rating, 249 reviews
Peaceful Modern Full House in Trendy Bridgeport
Kick back & relax in your home away from home in our modern & peaceful space in the heart of the Bridgeport neighborhood. Featuring incredible natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on popular Morgan Street, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.
4.95 out of 5 average rating, 318 reviewsPopular amenities for Bridgeport holiday rentals
Other great holiday rentals in Bridgeport

Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 76 reviews
Cozy Chicago Stay | Private Entry + Free Parking
4.99 out of 5 average rating, 69 reviews
Stay Above Chicago's Post-Punk Museum - 4BR Loft
5.0 out of 5 average rating, 32 reviews
Modern 2BR | Free Parking | McCormick & Chinatown
5.0 out of 5 average rating, 20 reviews
Al Capone Era Speakeasy 3 BRs
4.99 out of 5 average rating, 71 reviews
Bridgeport Garden Studio
4.94 out of 5 average rating, 54 reviews
PRIME 2BD Designer Retreat & Pool |Parking| Patio
4.89 out of 5 average rating, 35 reviews
Bridgeport Boho Chic Vibes
4.85 out of 5 average rating, 73 reviewsDestinations to explore
- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- Indiana Dunes State Park
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Frank Lloyd Wright Home and Studio
- Beachwalk Vacation Rentals
- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo





