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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.
Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

3.5 out of 5
Price was $752, price is now $685 per person
$685
per person
May 22 - May 25
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,448, price is now $1,143 per person
$1,143
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) to Springfield (VSF)
Stay at this 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.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,173, price is now $1,023 per person
$1,023
per person
Jun 12 - Jun 15
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Stay at this 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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $3,111, price is now $2,730 per person
$2,730
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) 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 Vesper

The Vesper

3 out of 5
Price was $1,558, price is now $1,379 per person
$1,379
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) to Springfield (VSF)
Stay at this 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.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Price was $846, price is now $757 per person
$757
per person
May 22 - May 25
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Price was $1,383, price is now $1,243 per person
$1,243
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) to Springfield (VSF)
Stay at this inn in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $1,067, price is now $966 per person
$966
per person
Jun 12 - Jun 15
found 8 hours 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.

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $846, price is now $757 per person
$757
per person
May 22 - May 25
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $962, price is now $793 per person
$793
per person
May 22 - May 25
found 9 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,173, price is now $1,023 per person
$1,023
per person
Jun 12 - Jun 15
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,067, price is now $966 per person
$966
per person
Jun 12 - Jun 15
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)

Winchester Vacation Packages 5-7 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 $1,448, price is now $1,143 per person
$1,143
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) to Springfield (VSF)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $3,111, price is now $2,730 per person
$2,730
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) to Springfield (VSF)
The Vesper

The Vesper

3 out of 5
Price was $1,558, price is now $1,379 per person
$1,379
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) to Springfield (VSF)
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
Price was $1,383, price is now $1,243 per person
$1,243
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Roanoke (ROA) to Springfield (VSF)

Top Flight Deals

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

Frontier Airlines
Tue, Apr 28 - Sat, May 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Los Angeles Intl. to Logan Intl., returning Sat, May 2, priced at $187 found 1 hour ago
American Airlines
Fri, May 8 - Sat, May 9
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select American Airlines flight, departing Fri, May 8 from Portland Intl. to Logan Intl., returning Sat, May 9, priced at $217 just found
Breeze Airways
Tue, Aug 18 - Sun, Aug 23
LAX
Los Angeles Intl.
PVD
T.F. Green
$232 Roundtrip, found 5 hours ago
$232
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Tue, Aug 18 from Los Angeles Intl. to T.F. Green, returning Sun, Aug 23, priced at $232 found 5 hours ago
Frontier Airlines
Wed, Apr 22 - Mon, Apr 27
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$265 Roundtrip, found 5 hours ago
$265
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Los Angeles Intl. to Bradley Intl., returning Mon, Apr 27, priced at $265 found 5 hours ago