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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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $595, price is now $521 per person
$521
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
The Vesper

The Vesper

3 out of 5
Price was $654, price is now $586 per person
$586
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,136, price is now $1,045 per person
$1,045
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Price was $1,064, price is now $984 per person
$984
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Book a stay at this 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 $928, price is now $860 per person
$860
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
The Hartness House

The Hartness House

3 out of 5
Price was $676, price is now $637 per person
$637
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Treehouse Home in Ludlow

Treehouse Home in Ludlow

2 out of 5
Price was $3,740, price is now $3,660 per person
$3,660
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking and laundry facilities. Popular attractions Okemo Mountain Resort and General Parking are located nearby.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

2 out of 5
Price was $708, price is now $706 per person
$706
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.

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 $595, price is now $521 per person
$521
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
The Vesper

The Vesper

3 out of 5
Price was $654, price is now $586 per person
$586
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,136, price is now $1,045 per person
$1,045
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,064, price is now $984 per person
$984
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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, Jan 20 - Wed, Jan 28
LAX
Los Angeles Intl.
BOS
Logan Intl.
$108 Roundtrip, just found
$108
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jan 20 from Los Angeles Intl. to Logan Intl., returning Wed, Jan 28, priced at $108 just found
Delta
Mon, Apr 20 - Tue, Apr 28
PDX
Portland Intl.
BOS
Logan Intl.
$188 Roundtrip, found 9 hours ago
$188
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Apr 20 from Portland Intl. to Logan Intl., returning Tue, Apr 28, priced at $188 found 9 hours ago
American Airlines
Wed, Feb 25 - Tue, Mar 3
PDX
Portland Intl.
PVD
T.F. Green
$251 Roundtrip, found 4 days ago
$251
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Feb 25 from Portland Intl. to T.F. Green, returning Tue, Mar 3, priced at $251 found 4 days ago
American Airlines
Tue, Jan 27 - Tue, Feb 3
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$252 Roundtrip, found 2 days ago
$252
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jan 27 from Los Angeles Intl. to Bradley Intl., returning Tue, Feb 3, priced at $252 found 2 days ago