Bridgeport Vacations from $786

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Bridgeport Vacation

Our Bridgeport vacation packages are a simple and practical way to arrange and book your next escape. Experience the magic of this unique neighborhood without the fuss of organizing it all yourself. If you're eager to sightsee during your trip to Bridgeport, head straight for nearby attractions such as Sovereign Village Mall. Stop dreaming and start doing. When it's time to book your ideal vacation to Bridgeport, Expedia will help get you there.

The Latest Bridgeport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Casa Clayton at Donhead - New Kingston
New Kingston Guest Apt at Fairway
New Kingston Guest Apartment VII
New Kingston Guest Apartment at Westbury
Millsborough Guest Apartments

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport

Bridgeport Hotel Deals

S Hotel Kingston

S Hotel Kingston

4.5 out of 5
1 St Lucia Avenue Kingston Saint Andrew
Fully refundableReserve now, pay when you stay
$196 nightly
The price is $219 total per night from Nov 20 to Nov 21
$219 total
Nov 20 - Nov 21
Total with taxes and fees
9.4/10 Exceptional! (1,816 reviews)
"The room was very clean. The staff was pleasant and welcoming. The bar staff were open to suggestions and even made a drink that they never made before based on my request. Breakfast was diverse with Jamaican and international options."

Reviewed on Nov 10, 2026

S Hotel Kingston
R Hotel Kingston

R Hotel Kingston

4 out of 5
2 Renfrew Road , Kingston 10, Jamaica Kingston Jamaica
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $183 total per night from Nov 17 to Nov 18
$183 total
Nov 17 - Nov 18
Total with taxes and fees
8.4/10 Very Good! (1,185 reviews)
"Room is clean, update, sir condition works perfect. Jamaican breakfast with plantain porridge. Continual breakfast is good."

Reviewed on Nov 10, 2026

R Hotel Kingston
ROK Hotel Kingston, Tapestry Collection by Hilton

ROK Hotel Kingston, Tapestry Collection by Hilton

4 out of 5
2-4 King Street Kingston
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $198 total per night from Nov 28 to Nov 29
$198 total
Nov 28 - Nov 29
Total with taxes and fees
ROK Hotel Kingston, Tapestry Collection by Hilton
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.

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.