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South Woodstock Vacation Packages

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South Woodstock Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $562, price is now $491 per person
$491
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $709, price is now $598 per person
$598
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Lebanon (LEB)
Stay at this resort in Brownsville. Enjoy a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $638, price is now $539 per person
$539
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $627, price is now $544 per person
$544
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $671, price is now $583 per person
$583
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $984, price is now $862 per person
$862
per person
Jul 1 - Jul 6
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) 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.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $574, price is now $510 per person
$510
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Lebanon (LEB)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was $668, price is now $599 per person
$599
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. 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.

South Woodstock 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 $638, price is now $539 per person
$539
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $709, price is now $598 per person
$598
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Lebanon (LEB)
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $627, price is now $544 per person
$544
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $671, price is now $583 per person
$583
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)

South Woodstock 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 $984, price is now $862 per person
$862
per person
Jul 1 - Jul 6
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,043, price is now $943 per person
$943
per person
Jul 2 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,029, price is now $951 per person
$951
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 $6,454, price is now $6,062 per person
$6,062
per person
Jun 13 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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, May 31 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 13 hours ago
$183
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 8, priced at $183 found 13 hours ago
Cape Air
Sun, May 31 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 13 hours ago
$184
Roundtrip
found 13 hours ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 8, priced at $184 found 13 hours ago
JetBlue Airways
Sat, May 23 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$185 Roundtrip, found 5 hours ago
$185
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, May 28, priced at $185 found 5 hours ago
Delta
Tue, Oct 13 - Tue, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$334 Roundtrip, found 4 hours ago
$334
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Oct 13 from Baltimore Washington Intl. Thurgood Marshall to Rutland Southern Vermont Regional, returning Tue, Oct 20, priced at $334 found 4 hours ago