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Benson Vacation Packages

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Benson Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $862, price is now $807 per person
$807
per person
Sep 24 - Sep 28
found 1 hour ago
Roundtrip flight included
Dallas (DFW) 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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
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.
Laundry room in the building, get beds.

Reviewed on Aug 16, 2026

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,271, price is now $1,122 per person
$1,122
per person
Sep 29 - Oct 3
just found
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,354, price is now $1,230 per person
$1,230
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Only suggestion is to provide a coffee maker.

Reviewed on Aug 18, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,089, price is now $995 per person
$995
per person
Sep 24 - Sep 28
found 1 hour ago
Roundtrip flight included
Dallas (DFW) 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.
Lake Bomoseen Lodge and Taproom was an absolute delight! From the breathtaking lake view to the kayaks and ice cream shack, there was so much to enjoy. We stayed in the cozy and well-organized Maple Cottage, which was perfect for families. The food at the Taproom was simply delicious, and I thoroughly enjoyed my stay. I highly recommend this place and would definitely return! (I also got a fishing day pass and was allowed to fish off the dock!!)

Reviewed on Aug 19, 2026

Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home

Forest Mountain Escape: Beautiful Mountaintop Escape In Mendon, Vt. 20 Min To Killington/14 To Pico. 4 Bedroom Home

3 out of 5
Price was $2,311, price is now $2,278 per person
$2,278
per person
Sep 24 - Sep 28
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
Book a stay at this golf vacation home in Rutland. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions McLaughlin Falls and Green Mountain Rock Climbing Center are located nearby.

Brandon Inn

Brandon Inn

3 out of 5
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.

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
Price was $1,371, price is now $1,364 per person
$1,364
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Stay at this hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Green Mountain Rock Climbing Center and Hathaway Farm are located nearby.
room 211, the carpet floors were damp

Reviewed on Aug 17, 2026

Benson Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $862, price is now $807 per person
$807
per person
Sep 24 - Sep 28
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,271, price is now $1,122 per person
$1,122
per person
Sep 29 - Oct 3
just found
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,354, price is now $1,230 per person
$1,230
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,089, price is now $995 per person
$995
per person
Sep 24 - Sep 28
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)