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Winchester Vacation Packages

Build your package with 2 more options

Winchester Flight + Hotel Packages

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

Mountain Lodge at Okemo, A Vail Resorts Property

3 out of 5
Price was $780, price is now $767 per person
$767
per person
Jul 10 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,210, price is now $1,009 per person
$1,009
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this 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.

Winchester Vacation Packages 3-4 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 $982, price is now $910 per person
$910
per person
Jul 2 - Jul 6
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $1,210, price is now $1,009 per person
$1,009
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip 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.

American Airlines
Sat, Sep 12 - Sat, Oct 3
LAX
Los Angeles Intl.
BOS
Logan Intl.
$237 Roundtrip, found 2 hours ago
$237
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Sep 12 from Los Angeles Intl. to Logan Intl., returning Sat, Oct 3, priced at $237 found 2 hours ago
American Airlines
Tue, Aug 18 - Sun, Aug 23
LAX
Los Angeles Intl.
PVD
T.F. Green
$297 Roundtrip, found 7 hours ago
$297
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to T.F. Green, returning Sun, Aug 23, priced at $297 found 7 hours ago
Bargain Flight
Sat, Jun 6 - Sat, Jun 13
PDX
Portland Intl.
BOS
Logan Intl.
$302 Roundtrip, found 7 hours ago
$302
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Sat, Jun 6 from Portland Intl. to Logan Intl., returning Sat, Jun 13, priced at $302 found 7 hours ago
Delta
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$336 Roundtrip, found 19 hours ago
$336
Roundtrip
found 19 hours ago
Select Delta flight, departing Wed, Jul 22 from Los Angeles Intl. to Bradley Intl., returning Wed, Jul 29, priced at $336 found 19 hours ago