Bennington Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Find the Best Bennington Vacation Packages

Bennington Hotel Deals

Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
777 Belterra Drive Florence IN
Fully refundableReserve now, pay when you stay
The price is SARĀ 504 per night from Aug 5 to Aug 6
SARĀ 504
SARĀ 611 total
5 Aug - 6 Aug
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Fabulous !"

Reviewed on 20 July 2026

Belterra Casino Resort
Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

2.5 out of 5
525 Dale Drive I 71 Exit 57 Sp Sparta KY
Fully refundableReserve now, pay when you stay
The price is SARĀ 252 per night from Jul 27 to Jul 28
SARĀ 252
SARĀ 278 total
27 Jul - 28 Jul
includes taxes & fees
Ramada by Wyndham Sparta/At Speedway
Best Way Inn Madison

Best Way Inn Madison

2.5 out of 5
700 Clifty Drive Madison IN
Fully refundableReserve now, pay when you stay
The price is SARĀ 297 per night from Jul 23 to Jul 24
SARĀ 297
SARĀ 341 total
23 Jul - 24 Jul
includes taxes & fees
7/10 Good! (552 reviews)
"This was one of the few rooms left in town for Madison Regatta 2026. Pretty standard for a pet friendly hotel, we were traveling without our dog, definitely in need of a massive remodel. Front desk had a left over Covid glass in place, so communication required asking for repeats at loud volumes ..."

Reviewed on 7 July 2026

Best Way Inn Madison
See all 173 properties in Bennington
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.

Frequently asked questions

How much does a Bennington vacation package cost?
You can snap up a vacation package to this popular destination 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 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, favorite 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.