Best Family Escapes - Vacation Rentals in Bridgeport

Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown From US $299
         

1F Chicago's Little italy Graystone nearDowntown From US $243
         

10.0 (168 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba From US $332
         

10.0 (26 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Modern home minutes from Downtown Chicago From US $469
         

10.0 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Luxury Places to Stay in Bridgeport

Over 1411+ Luxury Places to Stay in or Near Bridgeport
South Loop 2 Bedroom Apt From US $2,671
         

New
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Luxury High-Floor Retreats + Lake Views From US $2,081
         

Downtown Mich Ave - 6 Penthouses, Sleep 25 From US $2,036
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV

Top-Rated Vacation Rentals with a Pool in Bridgeport

Over 225+ Top-Rated Vacation Rentals with a Pool in or Near Bridgeport
Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool From US $538
         

10.0 (12 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Top Floor Views + Central Comfort From US $459
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Lux Apts with Lake Views and Top Amenities From US $1,582
         

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10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Downtown Penthouse Lake Views #1|Gym, Parking+Pool From US $477
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Front Row to the Lake & Skyline: Epic 60th Flr 3BR From US $1,055
         

Relaxing Studio with Private Patio Downtown Chicago From US $507
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift From US $226
         

Pet-Friendly Vacation Rentals in Bridgeport

Over 596+ Pet-Friendly Vacation Rentals in or Near Bridgeport
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba From US $310
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Mccomick Place/China town getaway From US $338
         

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New
Apartment
  • Parking
  • Pet Friendly
  • Child Friendly
The Neighborhood Hotel-Little Italy From US $126
         

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9.6 (224 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Cozy Boho Chicago - 10 Minutes to Downtown Chicago From US $204
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area From US $792
         

Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area From US $543
         

Downtown 3bd Penthouse| Lake Mich VIEWS +gym From US $393
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV
Modern & Spacious Stay by Northwestern Hospital Bronzeville From US $300
         

Large Vacation Homes & Villas in Bridgeport

Over 181+ Large Vacation Homes & Villas in or Near Bridgeport
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10 From US $309
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick From US $511
         

Modern West Loop Gem-City Views & Prime Location 6 From US $309
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
McCormick 6B/4Ba Luxury Suite for groups/12 guests From US $666
         

Modern West Loop Gem-City Views & Prime Location 4 From US $360
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Wheelchair Accessible Vacation Homes in Bridgeport

Over 624+ Wheelchair Accessible Vacation Homes in or Near Bridgeport
Downtown 3bd #7 near Park+Museums From US $407
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
The Polo Inn Bridgeport U.S.A. From US $360
         

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9.4 (49 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
HI Chicago Hostel From US $73
         

9.0 (1077 Reviews)
Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Downtown 2bd #6 +Gym near Park, Lake, Museums From US $247
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Downtown 2bd #4 - Near Grant Park, Museums, Lake From US $245
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
McCormick 3B/2Ba w optional parking/Up to 8 guests From US $243
         

Bridgeport Varoom and Airbnb Places to Stay Under $200

Over 577+ Bridgeport Varoom and Airbnb Places to Stay Under $200
The Landmark; a comfy suite near McCormick Place From US $166
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • TV
  • View
A Stylish & Cozy Apartment near Downtown Chicago From US $150
         

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9.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Child Friendly
Mccormick Place Guest House From US $88
         

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8.8 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Stylish comfortable 3BR with tons of natural light From US $169
         

Spacious 2BR Group Retreat Near McCormick Place From US $194
         

Modern West Loop Gem-City Views & Prime Location 3 From US $189
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Instantly Bookable Vacation Homes in Bridgeport

Over 836+ Instantly Bookable Vacation Homes in or Near Bridgeport
1 Mi to University of Chicago: Urban Escape! From US $228
         

10.0 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Dubois Guest House Room 201 From US $292
         

7.4 (3 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Charming Cottage Home Near Little Italy & UIC From US $380
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Your Home Away from home -12 mins from Downtown From US $282
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About Bridgeport Vacation Rentals

With more than 1420 Bridgeport vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bestfamilyescapes and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Bridgeport.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bestfamilyescapes Bridgeport, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Bridgeport. Places to stay near Bridgeport are 773.16 ft² on average, with prices averaging $332 a night.

Bestfamilyescapes makes it easy and safe to find and compare vacation rentals in Bridgeport with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Bridgeport

Type Count
Holiday Apartments 1023
Vacation Homes 135
Hotels with Suites 95
B&B 19
Hostels 4
Villas 2
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Bridgeport

Pro Tip: Bestfamilyescapes makes it easy to compare the best listings on Bestfamilyescapes homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bestfamilyescapes homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Bridgeport.

Weather in Bridgeport

View the weather forecast for Bridgeport before booking your Bridgeport Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F