Bennington Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Bennington

Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is S$187 per night from 22 Jun to 23 Jun
S$187
22 Jun - 23 Jun
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Breakfast"

Reviewed on 8 Jun, 2025

Best Western Plus Keene Hotel
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3 out of 5
75 Railroad St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is S$206 per night from 1 Jul to 2 Jul
S$206
1 Jul - 2 Jul
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The check-in girl was excellent. The room smelled a little like dog in the rain"

Reviewed on 7 Jun, 2025

Courtyard by Marriott Keene Downtown
Keene Elm City Hotel, Ascend Hotel Collection
Keene Elm City Hotel, Ascend Hotel Collection
2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 18 Jun to 19 Jun
S$155
18 Jun - 19 Jun
includes taxes & fees
8.2/10 Very Good! (839 reviews)
"Clean but bare minimum Mattress was terrible Window with shade that allowed light in Woke up on Sat at 6 am due to it"

Reviewed on 8 Jun, 2025

Keene Elm City Hotel, Ascend Hotel Collection
See all 306 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.

Frequently asked questions

How much does a Bennington holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday to Bennington costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Bennington?
To pick up cheap Bennington holiday packages, plan your getaway outside of busy periods such as school holidays. You’ll typically find better availability and lower prices for flights and hotels.
How many days is enough for Bennington?
With a well-planned itinerary, you can easily hit the top Bennington sights in a handful of days. But if you want to discover lesser-known spots or take day trips, think about booking your Bennington holiday for longer.
How to find the best Bennington package deals?
Use Expedia’s filters to help you find some tempting Bennington package deals. When you start your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your trip for midweek, or search for Bennington package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it’s usually best to lock in your holiday package well in advance.
Is it cheaper to book a Bennington holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You’ll typically land a better deal than booking each component separately. And you’ll still get the freedom to create a tailored Bennington holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Bennington?
If you’re planning a spontaneous Bennington trip, browse our last-minute deals that can be booked up to a week before you take off. Don’t want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Bennington?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the type of activities available will also help you decide when to escape to Bennington.
  2. Budget wisely: Besides the price of your accommodation, you’ll need to consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Bennington.
  3. Work out your trip length: Consider how long you want to spend exploring Bennington. Plan your itinerary so you can get to all the attractions and activities you’re interested in at a comfortable pace.
  4. Bundle your accommodation and airfare: After you’ve nailed down your trip dates and duration, lock in the right 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.