Search Deals onWinchester Vacation Packages
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Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock
Price was $656, price is now $537 per person
$537
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Okemo Mountain Lodging
Save 100% on your flight
Price was $1,963, price is now $1,577 per person
$1,577
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Woodstock Inn & Resort
Price was $1,098, price is now $908 per person
$908
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Jackson Gore Village
Price was $1,148, price is now $955 per person
$955
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Book a stay at this spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Lincoln Inn & Gallery
Price was $722, price is now $634 per person
$634
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this inn in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
The Vesper
Price was $643, price is now $565 per person
$565
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum are located nearby.
Winterplace at Okemo
Price was $728, price is now $694 per person
$694
per person
Jan 13 - Jan 15
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Mountain Lodge at Okemo
Price was $595, price is now $572 per person
$572
per person
Jan 13 - Jan 15
found 13 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Winchester Vacation Packages 3-4 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.
Tue, Jan 20 - Wed, Jan 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$108 Roundtrip, found 7 hours ago
$108
Roundtrip
found 7 hours ago
Mon, Apr 20 - Tue, Apr 28
PDX
Portland Intl.
BOS
Logan Intl.
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Wed, Feb 25 - Tue, Mar 3
PDX
Portland Intl.
PVD
T.F. Green
$251 Roundtrip, found 2 days ago
$251
Roundtrip
found 2 days ago
Tue, Jan 27 - Tue, Feb 3
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$252 Roundtrip, found 6 hours ago
$252
Roundtrip
found 6 hours ago
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