Bridgeport Vacation Packages

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Your Bridgeport Vacation

Put together a custom vacation package to Bridgeport and get ready for your next epic adventure. Consider basing yourself in the neighborhood of Elm Grove, which is good for walking and history, for a true taste of this exciting city. Imperial Glass Museum and Toy and Plastic Brick Museum are just two of the key attractions to visit during a trip to Bridgeport. Whoever you're taking a break with and whether your budget is big or small, your dream Bridgeport vacation is just clicks away with Expedia.

Top Bridgeport Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was CA $963, price is now CA $896 per person
CA $896
per person
Aug 27 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,005 reviews)
We have stayed here on several visits to Pittsburgh. Front desk and breakfast staff always friendly. Rooms are always clean and the breakfast is good. We definitely recommend staying here..

Reviewed on Jul 5, 2026

The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
Oakland
Price was CA $1,367, price is now CA $1,268 per person
CA $1,268
per person
Aug 17 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9.2/10 Wonderful! (789 reviews)
I found the property to be excellent in all phases, from cleanliness to staff. A wonderful experience and I will definately stay again when in Pittsburgh.

Reviewed on Jul 1, 2026

Courtyard by Marriott Pittsburgh Downtown

Courtyard by Marriott Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
Price was CA $1,146, price is now CA $1,072 per person
CA $1,072
per person
Aug 17 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,003 reviews)
We arrived unexpectedly early and Joshua and John were very accommodating to get us to our room as soon as we arrived. I loved the lobby music and evening nibbles. The housekeeping and front desk were both attentive to any needs (like an extra pillow for a sore back). Great location, especially for PNC Park and the Warhol Museum!

Reviewed on Jul 3, 2026

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was CA $1,334, price is now CA $1,250 per person
CA $1,250
per person
Aug 27 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,310 reviews)
Great stay. The hotel honored our Expedia VIP benefits . We will stay again.

Reviewed on Jun 28, 2026

Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
Price was CA $1,130, price is now CA $1,060 per person
CA $1,060
per person
Aug 27 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9/10 Wonderful! (1,377 reviews)
The hotel was in a perfect location for walking to the PNC Park

Reviewed on Jul 4, 2026

Ready to book your vacation to Bridgeport?

 

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Bridgeport Hotel Deals

Wingate by Wyndham St. Clairsville/Wheeling

Wingate by Wyndham St. Clairsville/Wheeling

3 out of 5
51130 National Road E St. Clairsville OH
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jul 12 to Jul 13
CA $112
CA $127 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Anytime I go to saint clearsville, Ohio I stay here. It's clean. The staff is nice. The property is always clean and well tookn.Care of and breakfast is always good"

Reviewed on Jul 5, 2026

Wingate by Wyndham St. Clairsville/Wheeling
Microtel Inn & Suites by Wyndham Wheeling at Highlands

Microtel Inn & Suites by Wyndham Wheeling at Highlands

2 out of 5
85 Fort Henry Rd Triadelphia WV
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Jul 12 to Jul 13
CA $105
CA $117 total
Jul 12 - Jul 13
includes taxes & fees
9.2/10 Wonderful! (1,103 reviews)
"Was clean and very well kept up. Staff was wonderful. Would highly recommend."

Reviewed on Jul 5, 2026

Microtel Inn & Suites by Wyndham Wheeling at Highlands
Comfort Inn & Suites Triadelphia - Wheeling

Comfort Inn & Suites Triadelphia - Wheeling

2.5 out of 5
675 Fort Henry Rd Triadelphia WV
Fully refundable
The price is CA $99 per night from Aug 4 to Aug 5
CA $99
CA $111 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very good! (1,005 reviews)
"Great place good location clean and very friendly"

Reviewed on Jul 5, 2026

Comfort Inn & Suites Triadelphia - Wheeling
See all 122 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
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Beach Vacations
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Frequently asked questions

How much does a Bridgeport vacation package cost?
You'll find cheap prices from CA $896 on Expedia for your Bridgeport break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Bridgeport costs.
What are the cheapest months to go to Bridgeport?
To pick up cheap Bridgeport vacation packages, plan your getaway outside of peak times like public holidays and major festivals. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Bridgeport?
With a well-organized itinerary, you can easily hit the main Bridgeport attractions in a handful of days. But if you prefer to explore off the beaten track or take day trips, consider booking your Bridgeport vacation for longer.
How to find the best Bridgeport package deals?
Use Expedia's filter tool to find some great Bridgeport package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Bridgeport package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Bridgeport vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Bridgeport vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Bridgeport?
If you've got your Bridgeport travel dates confirmed, book as early as you can to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Bridgeport?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Bridgeport.
  2. Set your budget: Factor in costs such as flights, food and transportation when calculating how much to save for your trip to Bridgeport. Then, pick a hotel that works with your budget, whether that's an affordable option or a high-end getaway.
  3. Decide how long to go away for: Now that you know more about Bridgeport, you can figure out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Bridgeport vacation package.

Explore a world of travel with Expedia

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