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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

Mountain Lodge at Okemo

3 out of 5
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

Jackson Gore Village

3 out of 5
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

Mount Snow Grand Summit Resort

3 out of 5
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

Woodstock Inn & Resort

4.5 out of 5
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.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
per person
Oct 12 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)

Top Flight Deals

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

Breeze Airways
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
Select Breeze Airways flight, departing Wed, Sep 17 from Los Angeles Intl. to T.F. Green, returning Tue, Sep 23, priced at $154 found 17 hours ago
Spirit Airlines
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
Select Spirit Airlines flight, departing Wed, Aug 13 from Los Angeles Intl. to Logan Intl., returning Tue, Aug 26, priced at $178 found 14 hours ago
Breeze Airways
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
Select Breeze Airways flight, departing Thu, Sep 4 from Los Angeles Intl. to Bradley Intl., returning Sun, Sep 7, priced at $192 found 2 days ago
American Airlines
Tue, Oct 14 - Sat, Oct 25
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, found 14 hours ago
$217
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Tue, Oct 14 from Portland Intl. to Logan Intl., returning Sat, Oct 25, priced at $217 found 14 hours ago