Benson Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
Your Benson Vacation
Food, history, entertainment and more … There's so much to experience with a Benson vacation package. And with the ability to easily customize your city getaway, you know it'll be one you won't forget. Like to explore? Bomoseen State Park, Halfmoon Pond State Park and Half Moon State Park are just a few of the top places to visit during your trip to Benson. A few quick clicks is all it takes to craft the ideal Benson vacation on Expedia.
Top Benson Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Killington Mountain Lodge, Tapestry Collection by Hilton
Price was CA $1,790, price is now CA $1,538 per person
CA $1,538
per person
Mar 19 - Mar 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Staff great, shower pressure soft. Extra noise due to room being right next to elevator, heard it going up and down all night.
Reviewed on Jan 29, 2026
Benson Hotel Deals
Ultimate relaxing vacation
Orwell VT
The price is CA $191 per night from Feb 9 to Feb 10
CA $191
CA $245 total
Feb 9 - Feb 10
includes taxes & fees
9.6/10 Exceptional! (218 reviews)
We had a great time!! I can't wait to go back in the summer!!
Reviewed on Jan 21, 2026
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Feb 8 to Feb 9
CA $208
CA $229 total
Feb 8 - Feb 9
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Everything was great! The staff were very nice and the free breakfast is legit!
Reviewed on Feb 3, 2026
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
19 Skyline Drive Bolton Landing NY
The price is CA $1,381 per night from Mar 9 to Mar 10
CA $1,381
CA $1,845 total
Mar 9 - Mar 10
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
We loved our visit here. John and Yvonne were wonderful. The space was clean, quiet, and truly magical. The views were second to none and the castle and other buildings are truly worth experiencing. We loved learning about the history of this place and we will certainly be back.
Reviewed on Jan 18, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
