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 Pinto Guest Apartments

Casa Pinto Guest Apartments

3 out of 5
Price was CA $1,767, price is now CA $988 per person
CA $988
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Kingston (KIN)
9.8/10 Exceptional! (56 reviews)
Nice clean and comfortable spot definitely one of my favorite spots to just relax and enjoy Kingston at.

Reviewed on May 9, 2023

New Kingston Guest Apartment at Westbury

New Kingston Guest Apartment at Westbury

3.5 out of 5
New Kingston
Price was CA $2,479, price is now CA $1,332 per person
CA $1,332
per person
May 8 - May 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Kingston (KIN)
9.6/10 Exceptional! (23 reviews)
The property is well kept, the atmosphere relaxing, but most of all I felt very safe. The communication level however at first could've been better. The agent that I spoke with was very apologetic and very professional and courteous. Overall my stay was excellent. I'll recommend it to anyone seeking a quiet place away from home for a couple of days

Reviewed on Nov 13, 2022

Eclipse Suite Guest Apartments

Eclipse Suite Guest Apartments

3.5 out of 5
Havendale
Price was CA $1,880, price is now CA $1,068 per person
CA $1,068
per person
May 26 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
9.2/10 Wonderful! (21 reviews)
My biggest problem with the property was the water . And may i suggest that the owners consider putting in another ac unit in the living area or even ceiling fans. Other than these the unit in good location very private secure quite. Will stay again

Reviewed on Jul 12, 2019

Kingsway New Kingston Guest Apartment II

Kingsway New Kingston Guest Apartment II

3.5 out of 5
Half Way Tree
Price was CA $2,235, price is now CA $1,305 per person
CA $1,305
per person
May 26 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kingston (KIN)
9.8/10 Exceptional! (18 reviews)
Apartment was comfortable , good size but very close to good dining options being Devon house.

Reviewed on Apr 15, 2025

The Guest Apartments at Border Crossings

The Guest Apartments at Border Crossings

4.5 out of 5
Havendale
Price was CA $2,008, price is now CA $1,173 per person
CA $1,173
per person
May 26 - Jun 2
found 22 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Kingston (KIN)
No reviews

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
Devon House featuring a house and a garden

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 $273 per night from Mar 29 to Mar 30
CA $273
CA $352 total
Mar 29 - Mar 30
includes taxes & fees
9.4/10 Exceptional! (1,647 reviews)
Staff was amazing and hotel was great.

Reviewed on Mar 18, 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 $215 per night from Apr 5 to Apr 6
CA $215
CA $265 total
Apr 5 - Apr 6
includes taxes & fees
8.8/10 Excellent! (1,192 reviews)
I didn't take the shuttle, and the work space was exactly what I needed.

Reviewed on Mar 17, 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 $215 per night from Apr 3 to Apr 4
CA $215
CA $263 total
Apr 3 - Apr 4
includes taxes & fees
8.4/10 Very Good! (1,158 reviews)
ok

Reviewed on Mar 19, 2026

R Hotel Kingston
See all 1,617 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 $988. 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 which includes a house

Bob Marley Museum

5/5(14 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 featuring a house and a garden

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
#Reflections of my trip to Jamaica. This water area is in Emancipation Park which is lit up in the evening hours. Nice area to walk around and relax on a warm day.

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 $111
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 $236
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.