Search Deals onWinchester Vacation Packages
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Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Mountain Lodge at Okemo
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star 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.

Jackson Gore Village
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star 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.

Mount Snow Grand Summit Resort
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Woodstock Inn & Resort
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 4.5-star 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.
Winchester Vacation Packages 5-7 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.

Wed, Sep 17 - Tue, Sep 23
LAX
Los Angeles Intl.
PVD
T.F. Green
$154 Roundtrip, found 17 hours ago
$154
Roundtrip
found 17 hours ago

Wed, Aug 13 - Tue, Aug 26
LAX
Los Angeles Intl.
BOS
Logan Intl.
$178 Roundtrip, found 14 hours ago
$178
Roundtrip
found 14 hours ago

Thu, Sep 4 - Sun, Sep 7
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago

Tue, Oct 14 - Sat, Oct 25
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, found 14 hours ago
$217
Roundtrip
found 14 hours ago
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