Book Holiday Homes in Bridgeport

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Featured Holiday Homes in Bridgeport

Cozy Ocean Front Retreat with Private Beach!

Cozy Ocean Front Retreat with Private Beach!

Milford
Located in Milford, this vacation home is by the ocean, within a 5-minute drive of Silver Sands State Park and The Coastal Center at Milford Point.
Opens in a new windowCozy Ocean Front Retreat with Private Beach!
Business or Weekend escape

Business or Weekend escape

Stratford
The price is AU$220 per night from 16 Nov to 17 Nov
AU$220
16 Nov - 17 Nov
includes taxes & fees
Located in Stratford, this vacation home is within a 15-minute drive of Fairfield University and Sacred Heart University.
Opens in a new windowBusiness or Weekend escape
McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale

West Haven
The price is AU$820 per night from 11 Nov to 12 Nov
AU$820
11 Nov - 12 Nov
includes taxes & fees
With a stay at this vacation home in West Haven, you'll be within a 5-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowMcAngel Haven: 5 mins from Yale
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Newly renovated Private bedroom near Stony Brook University

Newly renovated Private bedroom near Stony Brook University

2 out of 5
Stony Brook, NY
The price is AU$523 per night from 11 Nov to 12 Nov
AU$523
11 Nov - 12 Nov
includes taxes & fees
With a stay at this vacation home in Stony Brook, you'll be steps from Stony Brook University and a 4-minute drive from Long Island Museum of American Art, History, ...
Opens in a new windowNewly renovated Private bedroom near Stony Brook University
Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach

West Haven
When you stay at this vacation home in West Haven, you'll be near the beach, within a 5-minute drive of Yale University and Yale-New Haven Hospital.
Opens in a new windowCozy 3 bedroom minutes from Yale and the beach
Stay at Black Rock Harbor

Stay at Black Rock Harbor

Bridgeport
With a stay at this vacation home in Bridgeport (Black Rock Historic District), you'll be a 4-minute drive from Fairfield University and 9 minutes from Sacred ...
Opens in a new windowStay at Black Rock Harbor
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Stamford
The price is AU$517 per night from 17 Nov to 18 Nov
AU$517
17 Nov - 18 Nov
includes taxes & fees
With a stay at this vacation home in Stamford (Waterside), you'll be within a 5-minute drive of Mill River Park and Stamford Town Center.
Opens in a new windowGem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Charming Colonial for Events and Getaways! – Perfect for Family Retreat!

Bridgeport
The price is AU$2,153 per night from 11 Nov to 12 Nov
AU$2,153
11 Nov - 12 Nov
includes taxes & fees
When you stay at this vacation home in Bridgeport, you'll be near the airport, a 4-minute drive from Sacred Heart University and 8 minutes from Fairfield ...
Opens in a new windowCharming Colonial for Events and Getaways! – Perfect for Family Retreat!
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

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

Milford
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.
Opens in a new windowBeach Front Arts & Crafts House With Gorgeous Views Of The Sound
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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.

Bridgeport Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Bridgeport vacation homes are the perfect way for you to wing it.

Holiday houses in Bridgeport let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Bridgeport in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Bridgeport adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Bridgeport with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Bridgeport vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Bridgeport Holiday Homes essential information

Accommodation
424 Holiday Homes
Lowest Price
AU$159
Highest Price
AU$2,153
Popular accommodation
Cozy Ocean Front Retreat with Private Beach!, Business or Weekend escape, McAngel Haven: 5 mins from Yale, Newly renovated Private bedroom near Stony Brook University, Cozy 3 bedroom minutes from Yale and the beach, Stay at Black Rock Harbor, Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi, Charming Colonial for Events and Getaways! – Perfect for Family Retreat!, Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Top trending hotels in Bridgeport

DoubleTree by Hilton Stamford

DoubleTree by Hilton Stamford

3.5 out of 5
1 First Stamford Pl, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is AU$275 per night from 21 Nov to 22 Nov
AU$275
21 Nov - 22 Nov
includes taxes & fees
Located in Stamford (Waterside), DoubleTree by Hilton Stamford is within a 5-minute drive of Mill River Park and University of Connecticut Stamford Campus.
Opens in a new windowDoubleTree by Hilton Stamford
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 30 Nov to 1 Dec
AU$159
30 Nov - 1 Dec
includes taxes & fees
With a stay at La Quinta Inn & Suites by Wyndham Stamford / New York City in Stamford (Waterside), you'll be within a 5-minute drive of Mill River Park and E. ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Stamford / New York City
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
Located in Stamford (Downtown Stamford), Amsterdam Hotel is within a 15-minute walk of Stamford Town Center and Stamford Center for the Arts.
Opens in a new windowAmsterdam Hotel
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Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

4 out of 5
99 East Avenue, Norwalk, CT
Fully refundableReserve now, pay when you stay
A stay at Norwalk Inn & Conference Center places you in the heart of Norwalk, within a 5-minute drive of Historic South Norwalk and The SoNo Collection.
Opens in a new windowNorwalk Inn & Conference Center
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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.

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^Subject to availability and chosen travel dates.