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Pirate Cove Cottages - Vacation Rentals in Bridgeport

Urban Cottage From US $153
         

5.0 (2 Reviews)
Cottage
Urban Cottage
  • Air Conditioner
  • TV
  • Bedding/Linens

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Luxury Places to Stay in Bridgeport

Over 1421+ Luxury Places to Stay in or Near Bridgeport
4 Luxury 2BRs, Stay Together in Style, For Groups From US $2,954
         

New
Apartment
4 Luxury 2BRs, Stay Together in Style, For Groups
  • Air Conditioner
  • Parking
  • Pool

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Premium Lake Views + Ideal for Group Getaways From US $2,918
         

New
Apartment
Premium Lake Views + Ideal for Group Getaways
  • Air Conditioner
  • Parking
  • Pool

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South Loop 2 Bedroom Apt From US $2,671
         

New
Apartment
South Loop 2 Bedroom Apt
  • Air Conditioner
  • Parking
  • Security/Safety

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LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking+Pool From US $2,402
         

New
Condo
LUX Dtown Penthouses 9bd/9ba Sleep 25+Parking+Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pilsen Chicago 6BR Getaway with Game Room, Gym & Paid Parking Near Soldier Field & McCormick Place From US $2,110
         

New
Apartment
Pilsen Chicago 6BR Getaway with Game Room, Gym & Paid Parking Near Soldier Field & McCormick Place
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury High-Floor Retreats + Lake Views From US $2,081
         

New
Apartment
Luxury High-Floor Retreats + Lake Views
  • Air Conditioner
  • Parking
  • Pool

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2BRs w/Lakefront Views, Sleeps Large Groups From US $2,075
         

New
Apartment
2BRs w/Lakefront Views, Sleeps Large Groups
  • Air Conditioner
  • Parking
  • Pool

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

10.0 (3 Reviews)
Condo
Downtown Mich Ave - 6 Penthouses, Sleep 25
  • Air Conditioner
  • Pet Friendly
  • TV

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Top-Rated Vacation Rentals with a Pool in Bridgeport

Over 224+ 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
Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Top Floor Views + Central Comfort From US $459
         

10.0 (8 Reviews)
Apartment
Top Floor Views + Central Comfort
  • Air Conditioner
  • Pet Friendly
  • Pool

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Lux Apts with Lake Views and Top Amenities From US $1,582
         

|
10.0 (4 Reviews)
Apartment
Lux Apts with Lake Views and Top Amenities
  • Air Conditioner
  • Parking
  • Pool

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Downtown Penthouse Lake Views #1|Gym, Parking+Pool From US $477
         

10.0 (4 Reviews)
Condo
Downtown Penthouse Lake Views #1|Gym, Parking+Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct From US $413
         

10.0 (4 Reviews)
Apartment
2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
  • Air Conditioner
  • Parking
  • Pool

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Front Row to the Lake & Skyline: Epic 60th Flr 3BR From US $1,055
         

10.0 (3 Reviews)
Apartment
Front Row to the Lake & Skyline: Epic 60th Flr 3BR
  • Air Conditioner
  • Pool
  • TV

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Relaxing Studio with Private Patio Downtown Chicago From US $507
         

10.0 (2 Reviews)
Apartment
Relaxing Studio with Private Patio Downtown Chicago
  • Air Conditioner
  • Parking
  • Pet Friendly

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Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift From US $226
         

10.0 (2 Reviews)
Apartment
Spacious 1 bd sleeps 4 quiet and near Michigan Ave. free gift
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Bridgeport

Over 599+ Pet-Friendly Vacation Rentals in or Near Bridgeport
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba From US $332
         

10.0 (26 Reviews)
Condo
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
  • Air Conditioner
  • Parking
  • Pet Friendly

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

|
9.7 (18 Reviews)
Apartment
Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Neighborhood Hotel-Little Italy From US $126
         

|
9.6 (224 Reviews)
Apartment
The Neighborhood Hotel-Little Italy
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible

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Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba From US $310
         

10.0 (10 Reviews)
Condo
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy Boho Chicago - 10 Minutes to Downtown Chicago From US $204
         

10.0 (8 Reviews)
Apartment
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area From US $792
         

10.0 (7 Reviews)
Apartment
Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
  • Air Conditioner
  • Pet Friendly
  • TV

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

10.0 (4 Reviews)
Apartment
Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
  • Air Conditioner
  • Pet Friendly
  • TV

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

10.0 (3 Reviews)
Condo
Downtown 3bd Penthouse| Lake Mich VIEWS +gym
  • Air Conditioner
  • Pet Friendly
  • TV

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Large Vacation Homes & Villas in Bridgeport

Over 181+ Large Vacation Homes & Villas in or Near Bridgeport
4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena From US $447
         

10.0 (22 Reviews)
Apartment
4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
  • Parking
  • TV
  • Security/Safety

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Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field From US $737
         

|
10.0 (3 Reviews)
Apartment
Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field
  • Air Conditioner
  • Parking
  • Pet Friendly

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Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10 From US $309
         

New
Apartment
Modern 3 BR Apt - 5 Mins to Downtown Sleeps 10
  • Air Conditioner
  • Parking
  • Pet Friendly

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1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown From US $467
         

10.0 (15 Reviews)
Condo
1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
  • Air Conditioner
  • Parking
  • TV

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Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick From US $511
         

10.0 (6 Reviews)
House
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick
  • Air Conditioner
  • Parking
  • TV

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

10.0 (6 Reviews)
Apartment
Modern West Loop Gem-City Views & Prime Location 6
  • Air Conditioner
  • TV
  • Security/Safety

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McCormick 6B/4Ba Luxury Suite for groups/12 guests From US $666
         

10.0 (3 Reviews)
Apartment
McCormick 6B/4Ba Luxury Suite for groups/12 guests
  • Air Conditioner
  • Parking
  • TV

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Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field From US $364
         

10.0 (2 Reviews)
Apartment
Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
  • Air Conditioner
  • Parking
  • TV

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Wheelchair Accessible Vacation Homes in Bridgeport

Over 629+ Wheelchair Accessible Vacation Homes in or Near Bridgeport
Downtown 3bd #7 near Park+Museums From US $407
         

10.0 (4 Reviews)
Condo
Downtown 3bd #7 near Park+Museums
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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The Polo Inn Bridgeport U.S.A. From US $360
         

|
9.4 (49 Reviews)
Bed & Breakfast
The Polo Inn Bridgeport U.S.A.
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

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HI Chicago Hostel From US $73
         

9.0 (1077 Reviews)
Hostel
HI Chicago Hostel
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility

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Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field From US $234
         

10.0 (4 Reviews)
Apartment
Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field
  • Air Conditioner
  • Parking
  • TV

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Luxéry Stay "Game of Thrones" Downtown/McCormick/WinTrust Area From US $612
         

10.0 (2 Reviews)
Apartment
Luxéry Stay "Game of Thrones" Downtown/McCormick/WinTrust Area
  • Air Conditioner
  • Pet Friendly
  • TV

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McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio From US $327
         

10.0 (2 Reviews)
Apartment
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
  • Air Conditioner
  • Parking
  • TV

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Modern West Loop Gem-City Views & Prime Location 2 From US $261
         

10.0 (2 Reviews)
Apartment
Modern West Loop Gem-City Views & Prime Location 2
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Downtown 2bd #6 +Gym near Park, Lake, Museums From US $247
         

10.0 (2 Reviews)
Condo
Downtown 2bd #6 +Gym near Park, Lake, Museums
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Bridgeport Varoom and Airbnb Places to Stay Under $200

Over 576+ 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
The Landmark; a comfy suite near McCormick Place
  • Air Conditioner
  • TV
  • View

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A Stylish & Cozy Apartment near Downtown Chicago From US $150
         

|
9.0 (1 Review)
Apartment
A Stylish & Cozy Apartment near Downtown Chicago
  • Air Conditioner
  • Parking
  • Child Friendly

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Mccormick Place Guest House From US $88
         

|
8.8 (45 Reviews)
House
Mccormick Place Guest House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Perfect for a Hip and Romantic Getaway - This Chic Studio Offers the Best of the City by AllSet Turnover From US $170
         

10.0 (3 Reviews)
Apartment
Perfect for a Hip and Romantic Getaway - This Chic Studio Offers the Best of the City by AllSet Turnover
  • Air Conditioner
  • TV
  • Security/Safety

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Stylish comfortable 3BR with tons of natural light From US $169
         

10.0 (2 Reviews)
Apartment
Stylish comfortable 3BR with tons of natural light
  • Air Conditioner
  • Parking
  • TV

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

10.0 (1 Review)
Apartment
Spacious 2BR Group Retreat Near McCormick Place
  • Air Conditioner
  • Parking
  • TV

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

10.0 (1 Review)
Apartment
Modern West Loop Gem-City Views & Prime Location 3
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10 From US $183
         

10.0 (1 Review)
Apartment
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
  • Air Conditioner
  • Parking
  • Pet Friendly

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Instantly Bookable Vacation Homes in Bridgeport

Over 844+ Instantly Bookable Vacation Homes in or Near Bridgeport
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC From US $220
         

10.0 (320 Reviews)
Apartment
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
  • Air Conditioner
  • Parking
  • TV

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Near McCormick Place 420-Friendly 3BR/2BA with Optional Parking and sleeps 8 From US $603
         

6.0 (1 Review)
Apartment
Near McCormick Place 420-Friendly 3BR/2BA with Optional Parking and sleeps 8
  • Air Conditioner
  • Parking
  • TV

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3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place From US $296
         

10.0 (269 Reviews)
Apartment
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
  • Air Conditioner
  • Parking
  • TV

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Spacious 5BR Chicago Suite Near McCormick Place & Soldier Field From US $548
         

8.0 (1 Review)
Apartment
Spacious 5BR Chicago Suite Near McCormick Place & Soldier Field
  • Air Conditioner
  • Parking
  • TV

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

10.0 (168 Reviews)
Apartment
1F Chicago's Little italy Graystone nearDowntown
  • Air Conditioner
  • Parking
  • TV

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Luxury Modern home minutes from Downtown Chicago From US $469
         

10.0 (18 Reviews)
House
Luxury Modern home minutes from Downtown Chicago
  • Air Conditioner
  • Parking
  • TV

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Penthouse, Lux stay near Downtown, McComick & Lake From US $258
         

10.0 (18 Reviews)
Apartment
Penthouse, Lux stay near Downtown, McComick & Lake
  • Air Conditioner
  • Parking
  • TV

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1 Mi to University of Chicago: Urban Escape! From US $228
         

10.0 (10 Reviews)
Apartment
1 Mi to University of Chicago: Urban Escape!
  • Air Conditioner
  • Parking
  • TV

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About Bridgeport Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Piratecovecottages 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 with prices averaging $153 a night.

Piratecovecottages 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
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Bridgeport

★ Pro Tip: Piratecovecottages makes it easy to compare the best listings on Piratecovecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Piratecovecottages 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

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