Benson Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Benson
Price found within the past 48 hours. Click for updated prices.
Emrose Luxury Cabins
€618
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
8.8/10 Excellent! (116 reviews)
The Cabins are very nice clean and cozy , love how well they were thought out to fit everything so perfectly in a small space . Full bathroom , full kitchen and nice size refrigerator and microwave .
Perfect for a romantic getaway . Plus the outdoor accommodations were great . And can’t wait for the soon to come restaurant and lounge for the guests . A++ stay .
Staff were very nice and helpful
Reviewed on 26 Aug 2026
Greenbrier Inn
€656
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (686 reviews)
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on 3 Aug 2026
The Mountain Inn at Killington
€656
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (1,020 reviews)
It was a cute hotel with a great distillery/restaurant. The food was amazing as well as the drinks!
The room was a nice size. It was very comfortable.
Reviewed on 28 Aug 2026
Top hotels in Benson
Ultimate relaxing vacation
Orwell VT
9.8/10 Exceptional! (242 reviews)
"Great remote and peaceful cabin getaway overlooking Perch Pond. The cabin is clean and had more space and amenities than expected. The host is very helpful with any questions and quick to respond. We loved our stay!"
Reviewed on 15 Aug 2026
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundable
€129
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,000 reviews)
"we have been coming here every year for 6 years now. the room had a musty smell, we brought plug in air fresheners. The guest laundry room was not working; we were told by a manager to go up the road to the laundry mat... the ice machines on the 2nd and 3rd floor were not working; you had to go to ..."
Reviewed on 26 Aug 2026
'Highlands Castle'... two suites in the castle!
Bolton NY
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 Benson attractions
Sunset Lake
Commune with nature and explore the great outdoors at Sunset Lake during your travels in Benson.
Perch Pond
Commune with nature and explore the great outdoors at Perch Pond during your travels in Benson.
Benson Public Library
After visiting Benson Public Library, make a plan to see the other sights and activities in Benson.
Strong Swamp
Commune with nature and explore the great outdoors at Strong Swamp during your travels in Benson.
Doughty Pond
Commune with nature and explore the great outdoors at Doughty Pond during your travels in Benson.
Pond Woods Wildlife Management Area
Explore the great outdoors at Pond Woods Wildlife Management Area, a lovely green space in Benson.
Frequently asked questions
How much does a Benson holiday package cost?
You'll find cheap prices from €618 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?
- 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.
- 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.
- 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.
- 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.
