Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow
Price was $705, price is now $626 per person
$626
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
Jackson Gore Village, A Vail Resorts Property
Price was $1,154, price is now $898 per person
$898
per person
May 24 - May 31
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,290, price is now $1,020 per person
$1,020
per person
May 24 - May 31
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Okemo Mountain Lodging by Vail Resorts
Price was $1,066, price is now $865 per person
$865
per person
May 24 - May 31
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, laundry facilities, and cable TV channels. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Mountain Lodge at Okemo, A Vail Resorts Property
Price was $1,030, price is now $839 per person
$839
per person
May 24 - May 31
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 Skywalker Carpet are located nearby.
Woodstock Inn & Resort
Save 100% on your flight
Price was $3,010, price is now $2,594 per person
$2,594
per person
May 24 - May 31
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
The Hartness House
Price was $1,336, price is now $1,193 per person
$1,193
per person
May 24 - May 31
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Springfield (VSF)
Stay at this hotel in Springfield. Enjoy free WiFi, free parking, and housekeeping. Popular attractions Muckross State Park and Eureka Schoolhouse 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.
Tue, Apr 14 - Tue, Apr 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$216 Roundtrip, just found
$216
Roundtrip
just found
Sat, Apr 18 - Tue, Apr 28
PDX
Portland Intl.
BOS
Logan Intl.
$253 Roundtrip, found 10 hours ago
$253
Roundtrip
found 10 hours ago
Sat, May 9 - Tue, May 12
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$273 Roundtrip, found 1 day ago
$273
Roundtrip
found 1 day ago
Thu, May 7 - Mon, May 11
LAX
Los Angeles Intl.
PVD
T.F. Green
$274 Roundtrip, found 10 hours ago
$274
Roundtrip
found 10 hours ago
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