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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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $532, price is now $459 per person
$459
per person
Jun 10 - Jun 13
just found
Roundtrip flight included
New York (NYC) 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.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $799, price is now $651 per person
$651
per person
Jun 10 - Jun 13
just found
Roundtrip flight included
New York (NYC) 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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $557, price is now $459 per person
$459
per person
Jun 10 - Jun 13
just found
Roundtrip flight included
New York (NYC) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Chalet 239

Chalet 239

2 out of 5
Price was $571, price is now $473 per person
$473
per person
Jun 10 - Jun 13
just found
Roundtrip flight included
New York (NYC) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,811, price is now $1,508 per person
$1,508
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) 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 Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $793, price is now $669 per person
$669
per person
Jun 15 - Jun 18
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Book a stay at this golf hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Quechee Gorge Bridge and Wilderness Trails are located nearby.
Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $917, price is now $782 per person
$782
per person
Jun 19 - Jun 22
found 6 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this luxury guesthouse in Bolton Landing. Enjoy free WiFi, a full-service spa, and room service. Popular attractions Lake George and Adirondack Extreme Adventure Course are located nearby.
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
Price was $722, price is now $621 per person
$621
per person
Jun 19 - Jun 22
found 6 hours ago
Roundtrip flight included
New York (NYC) to Glens Falls (GFL)
Book a stay at this business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Six Flags Great Escape and Charles R. Wood Theater are located nearby.

Rupert Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $557, price is now $459 per person
$459
per person
Jun 10 - Jun 13
just found
Roundtrip flight included
New York (NYC) to Springfield (VSF)
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $799, price is now $651 per person
$651
per person
Jun 10 - Jun 13
just found
Roundtrip flight included
New York (NYC) to Springfield (VSF)
Chalet 239

Chalet 239

2 out of 5
Price was $571, price is now $473 per person
$473
per person
Jun 10 - Jun 13
just found
Roundtrip flight included
New York (NYC) to Springfield (VSF)
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was $793, price is now $669 per person
$669
per person
Jun 15 - Jun 18
found 22 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)

Rupert Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $979, price is now $858 per person
$858
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,811, price is now $1,508 per person
$1,508
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Rutland (RUT)
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
Price was $6,464, price is now $5,980 per person
$5,980
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,046, price is now $968 per person
$968
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)

Top Flight Deals

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

Cape Air
Sun, May 31 - Sun, May 31
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 5 hours ago
$189
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, May 31, priced at $189 found 5 hours ago
Cape Air
Tue, May 12 - Tue, Jun 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 2 days ago
$189
Roundtrip
found 2 days ago
Select Cape Air flight, departing Tue, May 12 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 2, priced at $189 found 2 days ago
Cape Air
Sat, May 23 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Cape Air flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, May 28, priced at $190 found 2 days ago
JetBlue Airways
Sun, May 31 - Sun, May 31
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 5 hours ago
$194
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, May 31, priced at $194 found 5 hours ago