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.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
Great little place. Very friendly and clean.

Reviewed on Jul. 31, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Views were spectacular

Reviewed on Jul. 16, 2025

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.6/10 Excellent! (74 reviews)
Nice, clean room in prime location

Reviewed on Mar. 15, 2025

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9/10 Wonderful! (39 reviews)
The customer service was excellent!

Reviewed on Jul. 14, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
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

Ready to book your vacation to Benson?

 

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Benson Hotel Deals

Ultimate relaxing vacation

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

Ultimate relaxing vacation
Waterfront Home on Lake Champlain w/ Dock & Kayaks

Waterfront Home on Lake Champlain w/ Dock & Kayaks

2 out of 5
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

Get rates
Waterfront Home on Lake Champlain w/ Dock & Kayaks
Middlebury Inn

Middlebury Inn

3 out of 5
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

Middlebury Inn
See all 783 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Benson vacation package cost?
Offering great value package deals from CA $1,239 on Expedia, you'll be pleasantly surprised at how much a vacation to Benson costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Benson?
To pick up cheap Benson vacation packages, plan your trip outside of busy periods such as public holidays. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Benson?
With a well-organized schedule, you can easily visit the main Benson attractions in a few days. But if you want to explore off the beaten track or go on day tours, think about booking your Benson vacation for longer.
How to find the best Benson package deals?
Use Expedia's filter tool to help you find some of the best Benson package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Benson package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Benson vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Benson vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Benson?
If you have your Benson travel dates finalized, book early to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Benson?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to Benson.
  2. Set your budget: Factor in costs like food, flights and transportation when calculating how much to set aside for your trip to Benson. Then, pick a hotel that fits your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide how long to go away for: Now that you're more familiar with Benson, you can figure out the right length of your vacation. Put together a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Benson vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.