Search Deals onRupert Vacation Packages
Rupert Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $1,018, price is now $910 per person
$910
per person
Jul 19 - Jul 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
Woodstock Inn & Resort
Price was $2,354, price is now $2,094 per person
$2,094
per person
Jul 18 - Jul 22
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Golden Stage Inn B&B
Price was $1,801, price is now $1,605 per person
$1,605
per person
Jul 18 - Jul 22
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this B&B in Cavendish. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Lake Bomoseen Lodge
Price was $1,594, price is now $1,455 per person
$1,455
per person
Jul 18 - Jul 22
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
The Mountain Inn at Killington
Price was $1,451, price is now $1,345 per person
$1,345
per person
Jul 18 - Jul 22
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Vikings Villages Resort
Price was $1,732, price is now $1,608 per person
$1,608
per person
Jul 18 - Jul 22
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Emrose Luxury Cabins
Price was $1,611, price is now $1,510 per person
$1,510
per person
Jul 18 - Jul 22
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Stay at this hotel in Brandon. Enjoy free WiFi, free parking, and 8 hot tubs. Popular attractions Otter Valley Winery and Stephen A Douglas Birthplace are located nearby.
Align Inn Vermont
Price was $1,474, price is now $1,383 per person
$1,383
per person
Jul 18 - Jul 22
found 11 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village 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.
Sun, May 31 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$204 Roundtrip, found 19 hours ago
$204
Roundtrip
found 19 hours ago
Sun, May 31 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$204 Roundtrip, found 19 hours ago
$204
Roundtrip
found 19 hours ago
Sun, May 31 - Sun, May 31
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$208 Roundtrip, found 19 hours ago
$208
Roundtrip
found 19 hours ago
Sun, May 31 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$210 Roundtrip, found 19 hours ago
$210
Roundtrip
found 19 hours ago
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