Search Deals onWinchester Vacation Packages
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Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Mountaineer Inn
Price was $606, price is now $493 per person
$493
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.

Stone Hearth Inn and Eatery
Price was $988, price is now $762 per person
$762
per person
Nov 28 - Dec 2
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.

The Shire Woodstock
Price was $924, price is now $716 per person
$716
per person
Nov 28 - Dec 2
found 22 hours ago
Roundtrip flight included
Tampa (TPA) 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 $1,214, price is now $985 per person
$985
per person
Nov 28 - Dec 2
found 22 hours ago
Roundtrip flight included
Tampa (TPA) 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 $1,082, price is now $889 per person
$889
per person
Nov 28 - Dec 2
found 22 hours ago
Roundtrip flight included
Tampa (TPA) 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.

Jackson Gore Village
Price was $1,066, price is now $876 per person
$876
per person
Nov 28 - Dec 2
found 22 hours ago
Roundtrip flight included
Tampa (TPA) 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.

Okemo Mountain Lodging
Price was $1,027, price is now $850 per person
$850
per person
Nov 28 - Dec 2
found 22 hours ago
Roundtrip flight included
Tampa (TPA) 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.

The Vesper
Price was $715, price is now $593 per person
$593
per person
Nov 7 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum 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, Oct 20 - Sat, Oct 25
PDX
Portland Intl.
BOS
Logan Intl.
$190 Roundtrip, just found
$190
Roundtrip
just found

Thu, Oct 30 - Sat, Nov 1
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$201 Roundtrip, found 4 days ago
$201
Roundtrip
found 4 days ago

Fri, Oct 31 - Fri, Oct 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago

Tue, Nov 18 - Wed, Dec 3
PDX
Portland Intl.
PVD
T.F. Green
$288 Roundtrip, found 1 day ago
$288
Roundtrip
found 1 day ago
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