Search Deals onWinchester Vacation Packages
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Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $667, price is now $572 per person
$572
per person
Nov 10 - Nov 13
found 5 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 4-star B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
The Shire Woodstock
Save 100% on your flight
Price was $1,941, price is now $1,319 per person
$1,319
per person
Oct 9 - Oct 12
just found
Roundtrip flight included
Los Angeles (LAX) to Springfield (VSF)
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Winterplace at Okemo
Price was $916, price is now $755 per person
$755
per person
Oct 1 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Solitude Village at Okemo
Price was $817, price is now $681 per person
$681
per person
Oct 1 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Okemo Mountain Lodging
Price was $758, price is now $637 per person
$637
per person
Oct 1 - Oct 6
found 16 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Lincoln Inn & Gallery
Price was $3,455, price is now $3,137 per person
$3,137
per person
Oct 14 - Oct 22
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star inn in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
Jackson Gore Village
Price was $1,063, price is now $981 per person
$981
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
Mountain Lodge at Okemo
Price was $958, price is now $894 per person
$894
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
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.
Wed, Sep 24 - Tue, Oct 7
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$184 Roundtrip, found 3 days ago
$184
Roundtrip
found 3 days ago
Fri, Oct 31 - Mon, Nov 3
LAX
Los Angeles Intl.
BOS
Logan Intl.
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Tue, Oct 7 - Tue, Oct 14
LAX
Los Angeles Intl.
PVD
T.F. Green
$200 Roundtrip, found 3 days ago
$200
Roundtrip
found 3 days ago
Tue, Oct 14 - Sat, Oct 25
PDX
Portland Intl.
BOS
Logan Intl.
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
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