Bennington Vacation Packages

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

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Top Bennington vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A multi-story hotel with a sign reading 'Cottonwood Airport & Expo.'
    Jan 14 - Jan 17

    Cottonwood Airport & Expo Hotel Louisville + Flight

    Shively
    3 nights
    3.5 star property
    8.8/10 - Excellent (1,002 reviews)
    Roundtrip • Buffalo (BUF) - Louisville (SDF)
    BUF - SDF • 1 stop SDF - BUF • 1 stop
    CA $791
    CA $658
    per traveller
    found 1 day ago
    Cottonwood Airport & Expo Hotel Louisville
  • A rooftop patio with a fire feature, seating, and a view of the sunset.
    Jan 14 - Jan 17

    Crowne Plaza Louisville Airport Expo Ctr by IHG + Flight

    Fairgrounds
    3 nights
    3.5 star property
    8.8/10 - Excellent (1,947 reviews)
    Roundtrip • Buffalo (BUF) - Louisville (SDF)
    BUF - SDF • 1 stop SDF - BUF • 1 stop
    CA $964
    CA $806
    per traveller
    found 1 day ago
    Crowne Plaza Louisville Airport Expo Ctr by IHG
  • A modern interior with a fireplace, bookshelves, a green sofa, and leather chairs.
    Jan 14 - Jan 17

    The Grady + Flight

    Downtown Louisville
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,006 reviews)
    "Property and location are outstanding. The wild swan restaurant is amazing and if you have the chance to meet Mark, you get the history of the hotel and get to have the service you would want. Mark was fantastic and was the highlight of the hotel for us. Everything is spotless and clean. Great service and great food!"
    Reviewed November 4, 2026
    Roundtrip • Buffalo (BUF) - Louisville (SDF)
    BUF - SDF • 1 stop SDF - BUF • 1 stop
    CA $918
    CA $772
    per traveller
    found 1 day ago
    The Grady
  • A classical gold statue in front of a multi-story building with large windows and a brick facade.
    Jan 14 - Jan 17

    21c Museum Hotel Louisville + Flight

    Downtown Louisville
    3 nights
    4.5 star property
    9.4/10 - Exceptional (1,001 reviews)
    "Nice room. It was very clean and comfortable."
    Reviewed November 4, 2026
    Roundtrip • Buffalo (BUF) - Louisville (SDF)
    BUF - SDF • 1 stop SDF - BUF • 1 stop
    CA $982
    CA $855
    per traveller
    found 1 day ago
    21c Museum Hotel Louisville
  • A modern kitchen with wooden cabinets, a long countertop, and a variety of food items displayed.
    Jan 14 - Jan 17

    SpringHill Suites by Marriott Louisville Downtown + Flight

    Downtown Louisville
    3 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "My husband had a medical appointment. We live about 3 hours away so we decided to stay the night before so that we wouldn't have to leave so early. The rooms were very nice, clean and updated. The bed and pillows were very comfortable. The lady who checked us in was so nice and helpful. The breakfast had so many options and was really delish! My husband will have surgery on November 30th so we will more than likely be staying again."
    Reviewed November 3, 2026
    Roundtrip • Buffalo (BUF) - Louisville (SDF)
    BUF - SDF • 1 stop SDF - BUF • 1 stop
    CA $838
    CA $730
    per traveller
    found 1 day ago
    SpringHill Suites by Marriott Louisville Downtown

Bennington Hotel Deals

A hotel room with a bed, two bedside lamps, a dresser, a chair, and a balcony with a view.

Hillside Inn

Hillside Inn
2.5 star property
24.1 km from Bennington
8.8 out of 10, Excellent, (1,003 reviews)
The price is CA $125
CA $143 total
includes taxes & fees
Nov 12 - Nov 13
Hillside Inn
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.
See all properties in Bennington

Frequently Asked Questions

How much does a Bennington vacation package cost?

You can snap up a vacation package to this popular destination from CA $658 on Expedia. However, how much your vacation to Bennington costs will depend on your hotel choice, length of stay and season.

What are the cheapest months to go to Bennington?

January, February and November are the best times to look for cheap Bennington vacation packages. Choosing to travel in less busy periods means you can generally find lower prices on hotels and flights.

How many days is enough for Bennington?

The ideal length for your Bennington vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to go to all the major attractions and discover some hidden treasures along the way.

How to find the best Bennington package deals?

Use Expedia's filter tool to find some great Bennington package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Bennington package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.

Is it cheaper to book a Bennington vacation as a package?

You can enjoy significant savings on your Bennington break by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.

When to book a vacation package to Bennington?

Score fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Bennington break.

How to plan a trip to Bennington?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Bennington.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and flights. Your accommodations will probably be the biggest expense during your trip to Bennington.
  3. Decide how long to go for: Now that you're up to speed on Bennington, you can figure out the ideal length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Bennington vacation package.

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