Old Bennington Trips (flight + hotel)

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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! (217 reviews)
"The owners are there everyday. The staff is friendly and very custimer focused. The standards are high and the inn has a great history and is lovely. It felt more like being a house guest than a customer. The restaurant was an outstanding choice for dinner and accommodation for vegetarians and allergies ..."

Reviewed on Mar 27, 2025

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The Four Chimneys 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 P8,124 per night from Jul 27 to Jul 28
P8,124
P9,075 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Friendly and clean"

Reviewed on Jun 27, 2025

Hotel Downstreet, Ascend Hotel Collection
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 P13,981 per night from Jul 9 to Jul 10
P13,981
P15,617 total
Jul 9 - Jul 10
includes taxes & fees
9.6/10 Exceptional! (457 reviews)
"great!"

Reviewed on Jun 20, 2025

The Williams Inn
See all 949 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.

Frequently asked questions

How much does an Old Bennington vacation 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 vacation 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 vacation 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 vacation. 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 vacation package as soon as possible.
Is it cheaper to book an Old Bennington vacation as a package?
An Expedia vacation 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 vacation 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 favorite 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 accommodations 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 vacation package that brings all your bookings together.

What to do in Old Bennington

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

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

P955
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

P955
per traveler
Vermont RT 100 Self Guided Driving Audio Tour
See all activities in Old Bennington
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.