Search Deals onRupert Vacation Packages
Rupert Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

The Shire Woodstock
Price was $1,128, price is now $852 per person
$852
per person
Dec 24 - Dec 28
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star 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.

Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,335, price is now $1,015 per person
$1,015
per person
Dec 24 - Dec 28
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Stay at this 3.5-star 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 Black Dog Sports are located nearby.


Mount Snow Grand Summit Resort
Price was $2,007, price is now $1,574 per person
$1,574
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Save 100% on your flight
Price was $2,685, price is now $2,162 per person
$2,162
per person
Dec 24 - Dec 28
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage I are located nearby.

The Covered Bridge Inn
Price was $1,135, price is now $963 per person
$963
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.

Deerfield Valley Inn
Price was $1,190, price is now $1,012 per person
$1,012
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

The Engel House
Price was $1,211, price is now $1,041 per person
$1,041
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Stay at this 3-star B&B in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jacksonville Pond and Honora Winery are located nearby.
Rupert Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Rupert Vacation Packages 5-7 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, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago

Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$320 Roundtrip, found 7 hours ago
$320
Roundtrip
found 7 hours ago

Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago

Sun, Dec 21 - Fri, Dec 26
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$412 Roundtrip, found 1 day ago
$412
Roundtrip
found 1 day ago
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