Old Bennington Holidays

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Top hotels in Old Bennington

The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
21 West Road Bennington VT
The price is S$359 per night from 4 Aug to 5 Aug
S$359
4 Aug - 5 Aug
includes taxes & fees
9.4/10 Exceptional! (289 reviews)
"We enjoyed our stay."

Reviewed on 11 Jul, 2026

The Four Chimneys Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is S$232 per night from 17 Aug to 18 Aug
S$232
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Every one was very helpful and friendly"

Reviewed on 15 Jul, 2026

Hotel Downstreet, an Ascend Collection Hotel
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$166 per night from 3 Aug to 4 Aug
S$166
3 Aug - 4 Aug
includes taxes & fees
Hotel Vervana, Trademark Collection by Wyndham
See all 1,016 properties in Old 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.

Stay near popular Old Bennington attractions

Bennington Battle Monument

9.0/10 (202 reviews)
After visiting Bennington Battle Monument, make a plan to see the other sights and activities in Old Bennington. Discover the cafes and its art scene while you're in the area.
See properties

What to do in Old 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 Old Bennington

Frequently asked questions

How much does an Old Bennington holiday package cost?
You'll find cheap prices on Expedia for your Old Bennington escape. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your holiday to Old Bennington costs.
What are the cheapest months to go to Old Bennington?
January, March and August are great times to look for cheap Old Bennington holiday packages. Opting to travel in quieter periods means you can generally find better prices on flights and hotels.
How many days is enough for Old Bennington?
Typically, a handful of days is enough to visit the main sights during your Old Bennington holiday. However, if you prefer to have time to relax or go on day tours, consider extending your itinerary.
How to find the best Old Bennington package deals?
Use Expedia's filter tool to find some great Old Bennington package deals. When you begin 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 adventure for midweek, or search for Old Bennington package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book an Old Bennington holiday as a package?
An Expedia holiday package could land you considerable savings when compared to arranging hotels and flights separately. Better still, you can tailor your Old Bennington escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Old Bennington?
Land amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Old Bennington adventure.
How to plan a trip to Old Bennington?

  1. Pick your dates: What you want to do in Old Bennington and your favourite season will help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will likely be the biggest expense during your trip to Old Bennington.
  3. Work out your trip length: Consider how long you'd like to spend discovering Old Bennington. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick an Old Bennington holiday package that brings all your bookings together.

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. 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.