
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.





The Mountain Inn at Killington
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.2/10 Wonderful! (850 reviews)
Great place to stay, so close to the mountain, rode my bike all weekend. Clean comfortable room and the staff treated us like family.
Highly recommended.
Thanks!
Reviewed on Aug. 6, 2025
Benson Hotel Deals

Ultimate relaxing vacation
Orwell
The price is CA $206 per night from Aug 14 to Aug 15
CA $206
CA $265 total
Aug 14 - Aug 15
includes taxes & fees
9.6/10 Exceptional! (196 reviews)
Perfect family getaway
"This was the perfect family getaway. The house was very spacious and had everything we needed. My kids loved fishing in the pond, swimming to the raft and boating. We are looking forward to going back!"
Reviewed on Jul. 10, 2025

Waterfront Home on Lake Champlain w/ Dock & Kayaks
Benson
8/10 Very Good! (2 reviews)
Quiet and relaxing
"Very relaxing and a very quiet part of the lake. Enjoyed swimming every day. Great time together with my growing family: My 2 sons, daughter in law and new grandbaby, along with their very well behaved dog. The owner and Dominic were very responsive to all my questions."
Reviewed on Jul. 26, 2025

Middlebury Inn
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Aug 10 to Aug 11
CA $198
CA $217 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"This inn was great! I loved all the historical pieces that are shown around the inn. It is close enough to be able to walk to all the little shops and cafes in town. The staff were wonderful and super friendly. The food in the restaurant was amazing!"
Reviewed on Aug. 5, 2025
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.