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Winchester 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
Jackson Gore Village
Mount Snow Grand Summit Resort
Woodstock Inn & Resort

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo
Jackson Gore Village
Mount Snow Grand Summit Resort
Woodstock Inn & Resort

Top Flight Deals

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

Breeze Airways
Spirit Airlines
Breeze Airways
American Airlines