Deals on vacations and trips to Benson

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Benson flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $738, price is now $673 per person
$673
per person
Feb 26 - Mar 1
found 19 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Rutland (RUT)
This bed & breakfast features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the sauna and free perks like continental breakfast and free self parking.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,855, price is now $1,585 per person
$1,585
per person
Feb 26 - Mar 1
found 19 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,665, price is now $1,448 per person
$1,448
per person
Feb 26 - Mar 1
found 19 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services and a virtual front desk are also provided.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,223, price is now $1,112 per person
$1,112
per person
Feb 26 - Mar 1
found 19 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Rutland (RUT)
This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.
Mt Green 3-f04 in Killington

Mt Green 3-f04 in Killington

2 out of 5
Price was $1,569, price is now $1,451 per person
$1,451
per person
Feb 26 - Mar 1
found 19 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Rutland (RUT)
A full-service spa and a gym are featured at this apartment. Enjoy the sauna and perks like free self parking and free WiFi. Laundry facilities and barbecue grills are also provided.

Top Benson hotels deals

Ultimate relaxing vacation

Ultimate relaxing vacation

Orwell VT
$160 nightly
The price is $179 total per night
$179 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This cabin features barbecue grills.
Kitchen
Outdoor Space
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $158 total per night
$158 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Hot Tub
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
19 Skyline Drive Bolton Landing NY
$1,221 nightly
The price is $1,356 total per night
$1,356 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
This castle doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace is also provided.
Parking included
Free WiFi
Waterfront Home on Lake George w/ Boat Dock!

Waterfront Home on Lake George w/ Boat Dock!

3 out of 5
Queensbury NY
Get rates
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
Kitchen
Parking included
Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
$144 nightly
The price is $158 total per night
$158 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A business center, a terrace, and a lobby fireplace are also on offer.
Spa
Parking included
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place Rutland VT
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $197 total per night
$197 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This hotel features a 24-hour gym and an outdoor tennis court. Enjoy the free ski shuttle and onsite ski storage. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
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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.

Popular places to visit

Bomoseen State Park

You can take time to visit Bomoseen State Park during your travels to Fair Haven. Amble around the area's parks or visit its shops.

Bomoseen State Park

Perch Pond

Commune with nature and explore the great outdoors at Perch Pond during your travels in Benson.

Perch Pond

Halfmoon Pond State Park

You can take time to visit Halfmoon Pond State Park during your travels to Hubbardton. Wander the parks or discover the area's mountain views.

Halfmoon Pond State Park

Frequently asked questions

How much are vacation packages to Benson?
With vacation packages on offer for only $673, it's not necessary to max out the credit card to travel to Benson. Travelocity is here to help. Bundle up experiences, flights and hotels into a convenient package and land some excellent discounts. The more you book, the bigger the savings.
Where can I get the best vacation package deals for Benson?
Your dream vacation can be booked through Travelocity. With access to 400 airlines and at least 1,000,000 hotels around the world, selecting the ultimate Benson package deal couldn't be easier.
Why should I purchase my Benson vacation package with Travelocity?
You'll not only save lots, but you'll also have access to our round-the-clock support, quality service and a Price Match Guarantee. Explore every nook-and-cranny across the world, discover hidden gems and make unforgettable memories — we'll take care of the important details.
Can I save on my Benson car rental if I combine it with hotels and flights?
With a Benson vacation package, you can bundle your car, hotel and flight bookings and save tons. If you're in the mood to discover the best of this awesome city, why not check out The Egg? This top sight is 75 mi from Benson. With a rental car, you'll be there soon enough.
Which airport is best for Benson?
Burlington Intl. Airport (BTV) is one of the most popular airports in Benson. It's roughly 55 mi north of the downtown area. Your other choices are Lebanon Municipal Airport (LEB) (50 mi away from central Benson) and Rutland Southern Vermont Regional Airport (RUT) (20 mi away from central Benson).
Where should I stay when visiting Benson?
The Ultimate relaxing vacation is popular with many visitors. Book as soon as possible to avoid missing out.

Photos of local treasures

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