Search Deals onBenson Vacation Packages
Benson Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Emrose Luxury Cabins
Price was $631, price is now $601 per person
$601
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Book a stay at this family-friendly hotel in Brandon. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
The property is beautiful loved the heated pool and outdoor activities .
Reviewed on Aug 19, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was $1,154, price is now $973 per person
$973
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Knoxville (TYS) to Rutland (RUT)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Brandon Inn
Price was $963, price is now $953 per person
$953
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Knoxville (TYS) 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.
The Mountain Inn at Killington
Price was $740, price is now $664 per person
$664
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Didn’t stay
Reviewed on Aug 20, 2026
The Landgrove
Price was $664, price is now $619 per person
$619
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Book a stay at this family-friendly inn in Londonderry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hapgood Pond and Wild Wings Ski Touring Center are located nearby.
Comfort Inn Rutland - Killington
Price was $982, price is now $919 per person
$919
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Sacramento (SMF) to Rutland (RUT)
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
North Star Lodge and Resort
Price was $742, price is now $699 per person
$699
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
San Diego (SAN) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Killington School for Tennis are located nearby.
Castle Hill Resort And Spa
Price was $1,025, price is now $981 per person
$981
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Sacramento (SMF) 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.
The castle is an historic treasure. From the intricate designs of the plaster ceilings to the woodwork and tiles surrounding the fireplace in the library, every nook offered some unique detail. Our dinner was outstanding as well. Then there was the heated pool, hot tub, and sauna to experience. Our stay was relaxing and just what we wanted.
Reviewed on Aug 17, 2026
Benson Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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