Benson Holidays

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

Top hotels in Benson

Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 1 Jul to 2 Jul
S$227
1 Jul - 2 Jul
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Great location to walk around the old parts of town, shops and dining. Also close to the river and waterfalls. Very quiet and quality for such an old inn."

Reviewed on 10 Jun, 2025

Middlebury Inn
Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is S$164 per night from 15 Jun to 16 Jun
S$164
15 Jun - 16 Jun
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Solid, clean, basic accommodation. Easy access from Rt. 4. Would use again when in the area."

Reviewed on 9 Jun, 2025

Comfort Inn Rutland - Killington
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3 out of 5
19 Skyline Drive, PO Box 269, Bolton Landing, NY
"John and Yvonne were the perfect hosts hosts...Tvicolorfulsunse"

Reviewed on 15 Aug, 2022

Get rates
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
See all 777 properties in Benson
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 Benson holiday package cost?
You’ll find cheap prices on Expedia for your Benson escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Benson costs.
What are the cheapest months to go to Benson?
Plan your trip for the off-peak season and you’re likely to get cheap Benson holiday packages. Remember that public holidays and local festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Benson?
Typically, a handful of days is enough to explore the major attractions during your Benson holiday. However, if you’d like to have more time to chill out or go on day tours, think about extending your trip.
How to find the best Benson package deals?
Use Expedia’s filters to help you find some of the best Benson package deals. When you start your search, simply set your maximum budget and then sort the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or browse for Benson package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it’s usually best to book your holiday package well in advance.
Is it cheaper to book a Benson holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You’ll generally get a better deal than booking each component individually. And you’ll still enjoy the freedom to create a tailored Benson holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Benson?
If you’re planning a spur-of-the-moment Benson adventure, browse our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Benson?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Benson.
  2. Budget wisely: As well as the price of your hotel, you should factor in other expenses too. These include transportation, flights and food. Also, set aside a little extra for unexpected costs that could arise during your trip to Benson.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you’d like to get to in Benson. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your airfare and accommodation: After you’ve settled on your trip dates and duration, book the ideal Benson 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.