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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.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $596, price is now $510 per person
$510
per person
Jan 7 - Jan 10
found 17 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

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,015, price is now $798 per person
$798
per person
Jan 7 - Jan 10
found 17 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

The Suites at Killington Center

3.5 out of 5
Price was $1,164, price is now $938 per person
$938
per person
Jan 7 - Jan 10
found 17 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

Woodstock Inn & Resort

4.5 out of 5
Price was $1,055, price is now $870 per person
$870
per person
Jan 7 - Jan 10
found 17 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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $1,363, price is now $1,136 per person
$1,136
per person
Jan 7 - Jan 10
found 17 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

Mountain Green Resort

4 out of 5
Price was $1,016, price is now $848 per person
$848
per person
Jan 7 - Jan 10
found 17 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

North Star Lodge and Resort

2 out of 5
Price was $661, price is now $555 per person
$555
per person
Jan 7 - Jan 10
found 17 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

The Shire Woodstock

3 out of 5
Price was $610, price is now $525 per person
$525
per person
Jan 16 - Jan 18
found 12 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.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,015, price is now $798 per person
$798
per person
Jan 7 - Jan 10
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,164, price is now $938 per person
$938
per person
Jan 7 - Jan 10
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,055, price is now $870 per person
$870
per person
Jan 7 - Jan 10
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,552, price is now $1,284 per person
$1,284
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)

Rupert Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,368, price is now $1,197 per person
$1,197
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,492, price is now $1,287 per person
$1,287
per person
Jan 2 - Jan 8
found 2 hours ago
Roundtrip flight included
San Juan (SJU) to Springfield (VSF)
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $2,295, price is now $2,013 per person
$2,013
per person
Jan 2 - Jan 8
found 2 hours ago
Roundtrip flight included
San Juan (SJU) to Rutland (RUT)
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,180, price is now $1,931 per person
$1,931
per person
Jan 2 - Jan 8
found 2 hours ago
Roundtrip flight included
San Juan (SJU) to Rutland (RUT)

Top Flight Deals

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

JetBlue Airways
Tue, Dec 16 - Wed, Dec 24
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$295 Roundtrip, found 23 hours ago
$295
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Tue, Dec 16 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 24, priced at $295 found 23 hours ago
United
Tue, Dec 9 - Tue, Dec 16
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 2 hours ago
$344
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Dec 9 from Newark Liberty Intl. Airport to Rutland Southern Vermont Regional, returning Tue, Dec 16, priced at $344 found 2 hours ago
American Airlines
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
Select American Airlines flight, departing Thu, Dec 4 from LaGuardia to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $361 found 4 days ago
JetBlue Airways
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
Select JetBlue Airways flight, departing Sun, Dec 21 from Fort Lauderdale - Hollywood Intl. to Rutland Southern Vermont Regional, returning Fri, Dec 26, priced at $829 found 4 days ago