Bridgeport Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Holiday Package Deals in Bridgeport

Price found within the past 48 hours. Click for updated prices.
City Ridge Luxury Penthouse

City Ridge Luxury Penthouse

3.5 out of 5
Price was CA $1,714, price is now CA $1,039 per person
CA $1,039
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Kingston (KIN)
No reviews

Eclipse Suite Guest Apartments

Eclipse Suite Guest Apartments

3.5 out of 5
Havendale
Price was CA $2,156, price is now CA $1,249 per person
CA $1,249
per person
Dec 9 - Dec 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
9.2/10 Wonderful! (21 reviews)
Nice location

Reviewed on Jun 3, 2024

New Kingston Corporate Apts at Donhead

New Kingston Corporate Apts at Donhead

3.5 out of 5
New Kingston
Price was CA $2,645, price is now CA $1,586 per person
CA $1,586
per person
Jan 11 - Jan 18
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
9.8/10 Exceptional! (31 reviews)
Very decent, true to what is shown online

Reviewed on Apr 16, 2026

Sunrise Villa On The Beach

Sunrise Villa On The Beach

3 out of 5
Price was CA $2,188, price is now CA $1,314 per person
CA $1,314
per person
Jan 20 - Jan 27
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Kingston (KIN)
8.6/10 Excellent! (10 reviews)
Quite environment great staff would definitely come again

Reviewed on Aug 25, 2019

The Country Club Villa I

The Country Club Villa I

3.5 out of 5
Price was CA $2,222, price is now CA $1,343 per person
CA $1,343
per person
Jan 20 - Jan 27
found 4 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Kingston (KIN)
9/10 Wonderful! (10 reviews)
The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it.

Reviewed on Sep 8, 2022

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
A large, two-story building with a symmetrical facade, a central entrance with steps, and a formal garden with trimmed hedges and flowering plants.

New Kingston

3 out of top 10 points of interest in this area

Discover urban parks like Emancipation Park and Hope Gardens, or explore landmarks such as the Bob Marley Museum. Enjoy the redeveloped waterfront area with hotels, shops, and cultural centers, while easily navigating via buses and taxis.

Find hotels in New Kingston

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
The price is CA $238 per night from Nov 29 to Nov 30
CA $238
CA $306 total
Nov 29 - Nov 30
includes taxes & fees
9.4/10 Exceptional! (1,811 reviews)
"Love S hotels will always return"

Reviewed on Nov 4, 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
The price is CA $208 per night from Dec 4 to Dec 5
CA $208
CA $255 total
Dec 4 - Dec 5
includes taxes & fees
8.4/10 Very good! (1,187 reviews)
"clean room, great staff, breakfast and laundry"

Reviewed on Nov 4, 2026

R Hotel Kingston
AC Hotel by Marriott Kingston, Jamaica

AC Hotel by Marriott Kingston, Jamaica

4.5 out of 5
38 Lady Musgrave Rd Kingston St. Andrew Parish
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Dec 5 to Dec 6
CA $343
CA $431 total
Dec 5 - Dec 6
includes taxes & fees
AC Hotel by Marriott Kingston, Jamaica
See all 1,767 properties in Bridgeport
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Bridgeport vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Bridgeport from just CA $1,039. And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Bridgeport?
Our Bridgeport vacation packages promise plenty of savings for the savvy globetrotter. For the best deals, simply combine your flights, hotels and tours into a convenient package. But bargain prices are just the beginning of your next memorable adventure. When you book with Expedia, and you'll have over 550 air carriers and 1,000,000 properties globally to select from. No matter your budget, there's a vacation package with your name on it.
Where should I stay in Bridgeport?
A vacation in Bridgeport isn't complete without paying a visit to Sovereign Village Mall. Why not book a hotel close to this interesting tourist attraction?
How far in advance should I book my Bridgeport vacation?
It's difficult to pick the ideal time for airfares, but we normally say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to a year in advance. If you can't book early, don't worry. Budget prices occasionally appear just weeks before departure dates.
What does an Expedia Bridgeport travel package include?
Expedia has everything you need to organize your Bridgeport getaway, but how you structure your package depends on you. Pick from any combination of rental cars, hotels and flights. Searching for some activities or tours to keep you on the move? Once you've made your booking, you can add them too. No matter your budget, there's a deal to suit your needs.
What should I know before booking a Bridgeport travel package?
Whether it's relaxation or adventure you're after, a Bridgeport vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Bridgeport Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from worldwide. With such a big range of choice, finding the ideal carrier to whisk you off to Bridgeport won't be hard.
If I'm not able to travel, can I cancel my Bridgeport vacation package?
Certainly, and we're here to help. You may be able to cancel and rebook your Bridgeport vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If your circumstances suddenly change, take a look at our Customer Service Portal for further information.

Things to do

Kingston Blue Mountains Tour with Coffee Tasting

Kingston Blue Mountains Tour with Coffee Tasting

CA $115
per adult
100% of travellers recommend
Kingston Blue Mountains Tour with Coffee Tasting
Kingston Dub Club Sundays

Kingston Dub Club Sundays

CA $89
per adult
Kingston Dub Club Sundays
displays at the bob marley museum in Jamaica

Kingston Tour & Bob Marley Museum Admission

CA $114
per adult
74% of travellers recommend
Kingston Tour & Bob Marley Museum Admission
See all activities in Kingston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.