Bennington Holidays

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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 S$141 per night from 17 Aug to 18 Aug
S$141
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Room key issue
"Upgrades done are good. Rooms are clean and comfortable. They have a MAJOR issue with room key reader that needs to be addressed immediately. We had group of 36 guys stay for mid week golf trip. They were very accommodating but I had to have my key re-programmed 8 times in 3 days and several others ..."

Reviewed on 1 Aug, 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 S$125 per night from 7 Aug to 8 Aug
S$125
7 Aug - 8 Aug
includes taxes & fees
7.6/10 Good! (589 reviews)
"The room was comfortable. The carpets were very dirty but the rest of the room was ok."

Reviewed on 31 Jul, 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 S$162 per night from 11 Aug to 12 Aug
S$162
11 Aug - 12 Aug
includes taxes & fees
7.6/10 Good! (868 reviews)
"Great customer service. Perfect spot for a berkshires getaway"

Reviewed on 20 Jul, 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

Vermont RT 100: Self-Guided Driving Audio Tour

Vermont RT 100: Self-Guided Driving Audio Tour

S$22
per traveller
Vermont RT 100: Self-Guided Driving Audio Tour
See all activities in Bennington

Frequently asked questions

How much does a Bennington holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday 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 neighbourhoods like Old Bennington and South Shaftsbury during your Bennington holiday. 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 holiday package to Bennington?
Bennington is a good holiday 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 holiday 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," "Traveller 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 holiday as a package?
You can enjoy significant savings on your Bennington getaway by booking a personalised holiday 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 holiday 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 accommodation and airfare: After you've nailed down your travel dates and duration, book the ideal Bennington holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.