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Rupert Vacation Packages

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Rupert Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $448, price is now $363 per person
$363
per person
Jan 3 - Jan 5
found 19 hours ago
Roundtrip flight included
New York (NYC) 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

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,107, price is now $852 per person
$852
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) 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

Mount Snow Grand Summit Resort

3 out of 5
Price was $1,621, price is now $1,355 per person
$1,355
per person
Dec 25 - Dec 28
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Price was $1,088, price is now $910 per person
$910
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
Stay at this 3.5-star B&B in Cavendish. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,653, price is now $1,392 per person
$1,392
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Save 100% on your flight
Price was $3,188, price is now $2,698 per person
$2,698
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
New York (NYC) 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.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,164, price is now $988 per person
$988
per person
Dec 25 - Dec 28
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Four Columns Inn

Four Columns Inn

3 out of 5
Price was $728, price is now $622 per person
$622
per person
Jan 9 - Jan 12
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Stay at this 3-star B&B in Newfane. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Moore Free Library and Rock River Preserve are located nearby.

Rupert Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,107, price is now $852 per person
$852
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $1,621, price is now $1,355 per person
$1,355
per person
Dec 25 - Dec 28
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,318, price is now $1,102 per person
$1,102
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
Price was $1,088, price is now $910 per person
$910
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)

Rupert Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was $980, price is now $853 per person
$853
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,483, price is now $1,105 per person
$1,105
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,653, price is now $1,392 per person
$1,392
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $2,251, price is now $1,957 per person
$1,957
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Rutland (RUT)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Dec 7 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 10, priced at $304 found 1 day ago
American Airlines
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Dec 4 from LaGuardia to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $321 found 1 day ago
United
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
Select United flight, departing Sun, Dec 7 from Newark Liberty Intl. Airport to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $344 found 1 day ago
American Airlines
Sun, Dec 21 - Fri, Dec 26
FLL
Fort Lauderdale - Hollywood Intl.
RUT
Rutland Southern Vermont Regional
$749 Roundtrip, found 2 days ago
$749
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Dec 21 from Fort Lauderdale - Hollywood Intl. to Rutland Southern Vermont Regional, returning Fri, Dec 26, priced at $749 found 2 days ago