Benson Vacation Packages
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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.
Pointe at Castle Hill Resort
Price was CA $1,316, price is now CA $1,247 per person
CA $1,247
per person
Jun 24 - Jun 28
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.8/10 Excellent! (1,002 reviews)
Hotel is not near any resturants and it had no on-premisis restaurant for breakfast.
Reviewed on May 17, 2026
Golden Stage Inn B&B
Price was CA $1,760, price is now CA $1,571 per person
CA $1,571
per person
Jun 24 - Jun 28
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
10/10 Exceptional! (44 reviews)
We stayed for the weekend and went skiing at Okemo. It was a 10 min drive away. The staff was very accommodating, welcoming and friendly. The food provided was delicious. We will definitely be back!
Reviewed on Mar 8, 2026
Castle Hill Resort And Spa
Price was CA $1,733, price is now CA $1,630 per person
CA $1,630
per person
Jun 24 - Jun 28
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9/10 Wonderful! (118 reviews)
This was our second time staying here and it never disappoints! I booked this trip during our kids' spring break for a quick getaway and to use the amazing heated outdoor pool. It's a great location convenient to all the amazing sites Vermont has to offer. Would love to go back again in the fall!
Reviewed on Apr 19, 2026
The Upper Pass Lodge at Magic Mountain
Price was CA $1,615, price is now CA $1,529 per person
CA $1,529
per person
Jun 24 - Jun 28
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.2/10 Very Good! (700 reviews)
Charming rustic inn. Staff were delightful and food was great.
Reviewed on Apr 3, 2026
Benson Hotel Deals
Ultimate relaxing vacation
Orwell VT
9.8/10 Exceptional! (227 reviews)
"Great property, clean convenient and like new. We will be back!"
Reviewed on May 3, 2026
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from May 25 to May 26
CA $189
CA $208 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
"Free breakfast would be nice."
Reviewed on May 20, 2026
Middlebury Inn
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from May 25 to May 26
CA $190
CA $210 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Did not eat"
Reviewed on May 19, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
