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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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
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

Stone Hearth Inn and Eatery

3 out of 5
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

The Shire Woodstock

3 out of 5
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

Winterplace at Okemo

4 out of 5
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

Solitude Village at Okemo

4 out of 5
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

Jackson Gore Village

3 out of 5
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

Okemo Mountain Lodging

3.5 out of 5
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

The Vesper

3 out of 5
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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $757, price is now $582 per person
$582
per person
Nov 7 - Nov 10
found 20 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
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)
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
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)
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
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)

Winchester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,229, price is now $1,190 per person
$1,190
per person
Dec 21 - Dec 26
found 22 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)

Top Flight Deals

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

Delta
Mon, Oct 20 - Sat, Oct 25
PDX
Portland Intl.
BOS
Logan Intl.
$190 Roundtrip, just found
$190
Roundtrip
just found
Select Delta flight, departing Mon, Oct 20 from Portland Intl. to Logan Intl., returning Sat, Oct 25, priced at $190 just found
Breeze Airways
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
Select Breeze Airways flight, departing Thu, Oct 30 from Los Angeles Intl. to Bradley Intl., returning Sat, Nov 1, priced at $201 found 4 days ago
JetBlue Airways
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
Select JetBlue Airways flight, departing Fri, Oct 31 from Los Angeles Intl. to Logan Intl., returning Fri, Oct 31, priced at $210 found 2 days ago
Delta
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
Select Delta flight, departing Tue, Nov 18 from Portland Intl. to T.F. Green, returning Wed, Dec 3, priced at $288 found 1 day ago