Benson Vacations from $687
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
The Latest Benson Vacation Packages
- Days Inn by Wyndham Rutland/Killington Area
Sep 10 - Sep 13Days Inn by Wyndham Rutland/Killington Area + Flight
Rutland3 nights2.5 star property6.8/10 - (1,001 reviews)"It was clean and quiet. But the breakfast was horrible the coffee was like water and the syrup was well I don’t know what it was? Plus people were standing by the outside door smoking . We saw a girl climb out her window to smoke !"Reviewed July 18, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - RUT • 1 stop RUT - LGA • 1 stop$780$687found 10 hours agoper traveler - Chateau Rooms
Aug 28 - Sep 2Chateau Rooms + Flight
Bolton Landing5 nights4.5 star property9.2/10 - Wonderful (72 reviews)"The property is certainly unique, but you have to know certain things before booking. It’s run more like an Air abnb than a hotel. There’s no formal check-in or check-out process. If you arrive before 5 PM the restaurant will be closed and there will be no one to assist you or answer any questions. There are only three rooms total and they’re all located upstairs above the restaurant. If you can’t get your own bags up the outdoor staircase this may not be the place for you. An access code gets..."Reviewed July 12, 2026Roundtrip • New York (EWR) - Rutland (RUT)EWR - ALB • 1 stop ALB - EWR • 1 stop$1,500$1,251found 10 hours agoper traveler - The Landgrove
Aug 28 - Aug 31The Landgrove + Flight
Londonderry3 nights3.5 star property10/10 - Exceptional (1 review)"Tammy, the assistant inn keeper and restaurant manager was fantastic. She was attentive to every need. The restaurant staff was phenomenal as well highly recommend, it’s a little hidden gem off the beaten path. I will definitely return. Had a fabulous time."Reviewed June 27, 2026Roundtrip • Dallas (DFW) - Rutland (RUT)DFW - ALB • Nonstop ALB - DFW • 1 stop$843$723found 1 day agoper traveler - Four Columns Inn
Aug 23 - Aug 29Four Columns Inn + Flight
Newfane6 nights4.0 star property9.8/10 - Exceptional (47 reviews)"Can’t go wrong with this place."Reviewed July 13, 2026Roundtrip • Dallas (DFW) - Rutland (RUT)DFW - ALB • Nonstop ALB - DFW • Nonstop$1,293$1,129found 4 hours agoper traveler - Greenbrier Inn
Aug 20 - Aug 25Greenbrier Inn + Flight
Killington5 nights2.0 star property9.4/10 - Exceptional (685 reviews)"Nice, clean rooms with comfortable beds and plenty of room. The balconies are comfortable and private, sitting outside in the evening to unwind was nice. Breakfast was just right, plenty of choices and hot fresh coffee"Reviewed July 12, 2026Roundtrip • Dallas (DFW) - Rutland (RUT)DFW - RUT • 1 stop RUT - DFW • 1 stop$1,253$1,125found 10 hours agoper traveler
Discover the most popular places to visit in Benson
Benson Hotel Deals
Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
Days Inn by Wyndham Rutland/Killington Area
Days Inn by Wyndham Rutland/Killington Area
Best Western Plus Ticonderoga Inn & Suites
Best Western Plus Ticonderoga Inn & SuitesFrequently Asked Questions
How much does a Benson vacation package cost?
You'll find cheap prices from $687 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 vacation to Benson costs.
What are the cheapest months to go to Benson?
If you're hoping to snag a cheap Benson vacation package, consider planning a trip in October, November and December. You'll typically find lower rates on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Benson?
Typically, a handful of days is enough to visit the main sights during your Benson vacation. However, if you prefer to have some time to rest or take day trips, consider extending your itinerary.
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 vacation package well in advance.
Is it cheaper to book a Benson vacation as a package?
Expedia vacation 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 vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Benson vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Benson vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
Book with confidence
Things to do near Benson
Benson, Vermont, offers a delightful escape for outdoor enthusiasts and couples seeking romance. Visitors can enjoy recreational areas perfect for picnics and relaxation, as well as explore local shopping centers and malls. Whether you're planning a beach vacation or looking for the best activities and itineraries, Benson provides a charming backdrop for memorable experiences amidst its scenic beauty.
Shopping
Benson offers unique shopping at Bulwagga Books & Gallery, a charming store 12 miles away. If you're up for a drive, check out Diamond Run Mall, 19 miles away, for a lively shopping experience, or head to the Outlets at Lake George, located 31 miles away, for great deals and entertainment.
Recreation
At Prospect Bay Country Club, enjoy a day of golfing surrounded by lush landscapes, only 7 miles from Benson. For a unique experience, head to Brandon Music, 14 miles away, where you can indulge in live performances that blend relaxation and entertainment. Neshobe Golf Club, also 14 miles from Benson, offers another excellent golfing opportunity with scenic views.
Adventure
Experience thrilling ziplining at Adirondack Extreme Adventure Course, located 20 miles from Benson. Engage in family-friendly fun at the Green Mountain Rock Climbing Center, 19 miles away. For a serene outdoor escape, camp at Little Gourd Island, situated 17 miles from town.
Nightlife
Benson, Vermont, offers a quaint nightlife with cozy spots like The Benson Village Inn for relaxed dining and drinks. For a more lively atmosphere, check out local taverns where you can enjoy live music and friendly conversations with locals, making for an unforgettable evening.
Find the best attractions near Benson
Benson, Vermont, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore scenic lakes, historic forts, and nearby state parks, offering eco-friendly and adventurous experiences. With beachfront convenience and the charm of a Bahamas vacation in mind, Benson provides a delightful escape into nature and history for all types of travelers.
- Fort Ticonderoga: Immerse yourself in history at Fort Ticonderoga, a meticulously restored 18th-century fort that offers a glimpse into America's past. Located 10 miles from Benson, visitors can explore historic reenactments, exhibits, and breathtaking views of Lake Champlain, making it a cultural treasure.
- Lake Bomoseen: Enjoy a romantic escape at Lake Bomoseen, just 6 miles away. This picturesque lake features sandy beaches and stunning scenery, perfect for sunbathing, picnicking, or taking a leisurely stroll along the shore, offering a serene outdoor experience.
- Bomoseen State Park: Adventure awaits at Bomoseen State Park, located 4 miles from Benson. With hiking trails, fishing spots, and vibrant wildlife, this national park is perfect for outdoor enthusiasts looking to explore nature's beauty and enjoy recreational activities.
Best time to go to Benson
The best time to visit Benson can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Benson falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Benson falls in January, visitor numbers are average and weather is mostly cloudy with light rain.
Tips to save on your trip to Benson
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling during the off-peak season (typically March to April and November) for more affordable package holidays to Benson.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.