Bridgeport Vacation Rentals

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Vacation Rentals in Bridgeport

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Bridgeport CT

$1,403 nightly

$1,587 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Bridgeport (North End), you'll be within a 15-minute walk of Svihra Park and St. Vincent's Medical Center.

Kitchen

Washer

Peaceful Vintage Home with Private Lake in Redding, CT.

Redding CT

$570 nightly

$646 total

Dec 15 - Dec 16

Total with taxes and fees

Located in Redding, this vacation home is on a lake, a 1-minute drive from Putnam Memorial State Park and 6 minutes from Bethel Plaza Shopping Center.

Kitchen

Washer

Charming Home in Seaside

Bridgeport CT

With a stay at this vacation home in Bridgeport (South End), you'll be steps from University of Bridgeport and Seaside Park.

Washer

Dryer

Stareway to Heaven Su

Fairfield CT

With a stay at this vacation home in Fairfield, you'll be by the sea, just a 2-minute walk from South Pine Creek Beach and 8 minutes by foot from Pine Creek Par 3 Golf Course.

Kitchen

Washer

Westport Gem - walk to shops, dining, town center, pet-friendly

Westport CT

Located in Westport, this vacation home is within a 5-minute drive of Levitt Pavilion and Westport Country Playhouse.

Kitchen

Washer

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Fairfield CT

With a stay at this vacation home in Fairfield, you'll be by the sea, just a 4-minute walk from South Benson Marina and 11 minutes by foot from Fairfield Museum and History Center.

Kitchen

Washer

Business or Weekend escape

Stratford CT

$130 nightly

$147 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.

Pool

Air conditioning

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford CT

When you stay at this vacation home in Milford, you'll be on the beach, within a 15-minute drive of Yale University and Yale-New Haven Hospital.

Kitchen

Washer

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Northport NY

When you a stay at this vacation home in Northport, you'll be on the beach, within a 5-minute walk of Cow Harbor Park and Northport Village Park.

Hot Tub

Kitchen

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Branford CT

With a stay at this vacation home in Branford (Branford Center), you'll be within a 15-minute drive of Yale University and Yale-New Haven Hospital.

Kitchen

Washer

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

Sound Beach NY

Located in Sound Beach, this vacation home is by the sea, a 3-minute drive from Cedar Beach and 5 minutes from Clifton H. Lee Memorial Park.

Kitchen

Washer

Stylish Beach Home near Stamford Downtown/Beach

Stamford CT

A stay at this vacation home places you in the heart of Stamford, within a 5-minute drive of Cove Island Park and Chelsea Piers.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.