Bennington Trips (flight + hotel)

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Top hotels in Bennington

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is P5,754 per night from Aug 17 to Aug 18
P5,754
P6,272 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
Quiet, relaxing hotel
"Room was spacious. Bed was comfortable. Building was quiet. Wifi was fast and stable. Very relaxing environment. I would definitely come back to see what future improvements are made to the property as I was told by the front desk staff that they're making a constant effort to upgrade the ..."

Reviewed on Aug 5, 2025

Hotel Vervana, Trademark Collection by Wyndham
The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street, Bennington, VT
The price is P5,106 per night from Aug 11 to Aug 12
P5,106
P5,565 total
Aug 11 - Aug 12
includes taxes & fees
7.6/10 Good! (592 reviews)
good bed
"Have stayed here before overall conditions were good convenient for my visit biggest determining factor for me was the availability of a king size bed which as it turned out was quite comfortable"

Reviewed on Aug 4, 2025

The Autumn Inn
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is P6,606 per night from Aug 12 to Aug 13
P6,606
P7,201 total
Aug 12 - Aug 13
includes taxes & fees
7.6/10 Good! (868 reviews)
"Great customer service. Perfect spot for a berkshires getaway"

Reviewed on Jul 20, 2025

Best Western Bennington
See all 738 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.

What to do in Bennington

Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway

Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway

P963
per traveler
Self-Guided Audio Driving Tour of Vermont, RT100 Scenic Byway
Vermont RT 100 Self Guided Driving Audio Tour

Vermont RT 100 Self Guided Driving Audio Tour

P963
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Bennington

Frequently asked questions

How much does a Bennington vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Bennington costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Bennington?
You can generally find lower prices and greater availability in January, March and November. Browse our cheap Bennington vacation packages and you could land some great off-season discounts.
How many days is enough for Bennington?
With about 2 days, you'll have plenty of time to experience popular neighborhoods like Old Bennington and South Shaftsbury during your Bennington vacation. Remember to also add Norman Rockwell Exhibition and Robert Frost Stone House Museum to your list of must-sees. Looking for more adventures? Consider venturing outside of Bennington on day trips and tours.
Is it worth booking a vacation package to Bennington?
Bennington is a good vacation destination with attractions like Bennington Battle Monument among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Bennington vacation promises a good time for everyone.
How to find the best Bennington package deals?
Finding a cheap Bennington package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Bennington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Bennington vacation as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat 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 amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Bennington adventure.
How to plan a trip to Bennington?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to escape to Bennington.
  2. Plan your budget wisely: As well as the price of your stay, you should factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that may arise during your trip to Bennington.
  3. Decide how long to go for: Now that you're more familiar with Bennington, you can figure out the right length of your break. Create a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the ideal Bennington vacation package for you.

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