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
9.6/10 Exceptional! (219 reviews)
Lovely Inn - Delicious Food - A Pleasant Surprise
"This is a lovely Inn that is as charming as its setting. An unexpected pleasure was the delicious food. I loved that you pick your breakfast time and food choice the day before. My only regret was not staying long enough to have each of the breakfast offerings. An added delight was dinner at the ..."

Reviewed on 3 Aug, 2025

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The Four Chimneys Inn
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is S$304 per night from 7 Sept to 8 Sept
S$304
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (481 reviews)
"The property was spacious but still had a cozy feel."

Reviewed on 29 Jul, 2025

The Williams Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is S$206 per night from 7 Sept to 8 Sept
S$206
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (999 reviews)
"Great location! Large comfortable room."

Reviewed on 5 Aug, 2025

Hotel Downstreet, Ascend Hotel Collection
See all 945 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.

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.

* 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.