Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Windham Hill Inn
Price was $554, price is now $459 per person
$459
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this B&B in West Townshend. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hot Glass Works and Ball Mountain State Park are located nearby.
Sinclair Inn Bed and Breakfast
Price was $986, price is now $845 per person
$845
per person
Aug 22 - Aug 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Mills Riverside Park and Waters Memorial Library are located nearby.
Jackson Gore Village, A Vail Resorts Property
Price was $705, price is now $607 per person
$607
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.
Winterplace at Okemo, A Vail Resorts Property
Price was $599, price is now $535 per person
$535
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Solitude Village at Okemo by Vail Resorts
Price was $547, price is now $491 per person
$491
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Chalet 239
Price was $616, price is now $564 per person
$564
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Woodstock Inn & Resort
Price was $1,102, price is now $1,016 per person
$1,016
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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 Quechee Gorge Bridge and Middle Covered Bridge are located nearby.
Grand Summit Resort, A Vail Resorts Property
Price was $672, price is now $622 per person
$622
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Winchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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.
Mon, Aug 10 - Fri, Aug 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Tue, Aug 11 - Fri, Aug 28
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$260 Roundtrip, found 2 days ago
$260
Roundtrip
found 2 days ago
Tue, Aug 11 - Wed, Aug 26
PDX
Portland Intl.
BOS
Logan Intl.
$278 Roundtrip, found 23 hours ago
$278
Roundtrip
found 23 hours ago
Tue, Aug 18 - Sun, Aug 23
LAX
Los Angeles Intl.
PVD
T.F. Green
$294 Roundtrip, found 15 hours ago
$294
Roundtrip
found 15 hours ago
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