Search Deals onBenson Vacation Packages
Benson Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Brandon Inn
Price was $770, price is now $685 per person
$685
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stephen A Douglas Birthplace and Judith Reilly Gallery are located nearby.
Great place to stay in. I loved it.
Reviewed on Sep 14, 2026
Mountain Green Resort
Price was $1,547, price is now $1,249 per person
$1,249
per person
Dec 1 - Dec 5
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Lake Bomoseen Lodge
Price was $886, price is now $722 per person
$722
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
Beautiful lake, lodge was in great location, great restaurant, will definitely be back.
Reviewed on Sep 12, 2026
The Suites at Killington Center
Price was $1,252, price is now $1,035 per person
$1,035
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Greenbrier Inn
Price was $932, price is now $782 per person
$782
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington Resort and Gifford Woods State Park are located nearby.
Steve was very helpful on local things to do. Very relaxed home like atmosphere. Room was a little outdated but very clean.
Reviewed on Sep 15, 2026
The Vermont Inn
Price was $960, price is now $819 per person
$819
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this family-friendly B&B in Rutland. Enjoy free WiFi, free parking, and a conference center. Popular attractions Killington Resort and Golden Express Quad are located nearby.
The place needs a little help. The room was cute but one of the sinks needed cleaning and there was
No coffee creamer and the place needs tlc. A little disappointed but
I get it
Reviewed on Aug 8, 2026
Castle Hill Resort And Spa
Price was $961, price is now $853 per person
$853
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this luxury hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Pointe at Castle Hill Resort
Price was $884, price is now $789 per person
$789
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Benson Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Benson Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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