Bridgeport Vacation Packages

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Top Holiday Package Deals in Bridgeport

Price found within the past 48 hours. Click for updated prices.
Casa Clayton at Donhead - New Kingston

Casa Clayton at Donhead - New Kingston

3.5 out of 5
New Kingston
Price was CA $2,214, price is now CA $1,028 per person
CA $1,028
per person
Jun 12 - Jun 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
10/10 Exceptional! (35 reviews)
Area around the property was beautiful and quiet. The property is a fire trap bar..around the windows with only one entrance door. In addition the kitcken is at the entrance the only waytoexisttheproperty. ...... .....bars

Reviewed on Mar 9, 2025

New Kingston Guest Apt at Fairway

New Kingston Guest Apt at Fairway

3.5 out of 5
New Kingston
Price was CA $4,076, price is now CA $1,864 per person
CA $1,864
per person
Jun 12 - Jun 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
No reviews
New Kingston Corporate Apts at Donhead

New Kingston Corporate Apts at Donhead

3.5 out of 5
New Kingston
Price was CA $2,237, price is now CA $1,058 per person
CA $1,058
per person
Jun 12 - Jun 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
9.4/10 Exceptional! (32 reviews)
Very decent, true to what is shown online

Reviewed on Apr 16, 2026

Kingston Luxury Family Retreat

Kingston Luxury Family Retreat

3.5 out of 5
Jack's Hill
Price was CA $4,469, price is now CA $2,179 per person
CA $2,179
per person
Jun 12 - Jun 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
No reviews
New Kingston Guest Apartment V

New Kingston Guest Apartment V

3 out of 5
New Kingston
Price was CA $2,488, price is now CA $1,227 per person
CA $1,227
per person
Jun 12 - Jun 19
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Kingston (KIN)
2/10 (1 review)

Where to stay in Bridgeport

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

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 May 10 to May 11
CA $238
CA $301 total
May 10 - May 11
includes taxes & fees
9.4/10 Exceptional! (1,666 reviews)
As always the staff over delivers and the grounds and rooms are impeccable. Hats off to the managers who always go above and beyond to ensure an amazing stay at the S!!!

Reviewed on May 3, 2026

S 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
The price is CA $207 per night from May 29 to May 30
CA $207
CA $256 total
May 29 - May 30
includes taxes & fees
9/10 Wonderful! (1,222 reviews)
Was Great

Reviewed on May 3, 2026

ROK Hotel Kingston, Tapestry Collection by Hilton
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 $213 per night from May 12 to May 13
CA $213
CA $261 total
May 12 - May 13
includes taxes & fees
8.4/10 Very Good! (1,177 reviews)
Excellent staff. The staff has amazing customer service. The drawback was the limited amenities

Reviewed on May 3, 2026

R Hotel Kingston
See all 1,625 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.
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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 $1,028. 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.

Discover the most popular places to visit in Bridgeport

Bob Marley Museum

Bob Marley Museum

4.5/5(15 reviews)

Learn how a poor Jamaican man from Trench Town became an international pop star thanks to his thought-provoking lyrics and feel-good reggae music.

Bob Marley Museum
Devon House

Devon House

4.5/5(23 reviews)

Explore the opulent home of Jamaica’s first black millionaire, go shopping and sample the famous ice cream in the mansion’s courtyard.

Devon House
Emancipation Park

Emancipation Park

4.5/5(16 reviews)

Take a morning jog, enjoy pleasant tropical scents or admire the artwork in Kingston’s favorite park, a tribute to Jamaican residents’ journey to freedom.

Emancipation Park

Things to do

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 $112
per adult
74% of travellers recommend
Kingston Tour & Bob Marley Museum Admission
Bob Marley Museum in Kingston & Blue Mountain Coffee Tour

Bob Marley Museum in Kingston & Blue Mountain Coffee Tour

CA $237
per adult
Bob Marley Museum in Kingston & Blue Mountain Coffee Tour
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.