Search Deals onRupert Vacation Packages
Rupert Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge
Price was $596, price is now $510 per person
$510
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,015, price is now $798 per person
$798
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Book a stay at this ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
The Suites at Killington Center
Price was $1,164, price is now $938 per person
$938
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Stay at this condo in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Woodstock Inn & Resort
Price was $1,055, price is now $870 per person
$870
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was $1,363, price is now $1,136 per person
$1,136
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Book a stay at this ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Mountain Green Resort
Price was $1,016, price is now $848 per person
$848
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) 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 Pico Mountain at Killington Ski Resort are located nearby.
North Star Lodge and Resort
Price was $661, price is now $555 per person
$555
per person
Jan 7 - Jan 10
found 15 hours ago
Roundtrip non-stop flight included
New York (JFK) 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 Pico Mountain at Killington Ski Resort are located nearby.
The Shire Woodstock
Price was $610, price is now $525 per person
$525
per person
Jan 16 - Jan 18
found 9 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Rupert Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Dec 16 - Wed, Dec 24
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$295 Roundtrip, found 20 hours ago
$295
Roundtrip
found 20 hours ago
Tue, Dec 9 - Tue, Dec 16
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 14 hours ago
$344
Roundtrip
found 14 hours ago
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$361 Roundtrip, found 4 days ago
$361
Roundtrip
found 4 days ago
Sun, Dec 21 - Fri, Dec 26
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$829 Roundtrip, found 4 days ago
$829
Roundtrip
found 4 days ago
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