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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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
The Vesper

The Vesper

3 out of 5
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this 3-star ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
per person
Aug 15 - Aug 17
found 14 hours ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
Stay at this 4-star 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.
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 out of 5
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions State Fish and Wildlife Management Area and Baltimore Covered Bridge are located nearby.

Winchester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
The Vesper

The Vesper

3 out of 5
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
per person
Jul 20 - Jul 23
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)

Top Flight Deals

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

Spirit Airlines
Tue, Aug 26 - Sun, Aug 31
LAX
Los Angeles Intl.
BOS
Logan Intl.
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to Logan Intl., returning Sun, Aug 31, priced at $187 found 1 hour ago
Breeze Airways
Wed, Sep 17 - Tue, Sep 23
LAX
Los Angeles Intl.
PVD
T.F. Green
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Sep 17 from Los Angeles Intl. to T.F. Green, returning Tue, Sep 23, priced at $199 just found
American Airlines
Wed, Aug 13 - Tue, Aug 19
PDX
Portland Intl.
BOS
Logan Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select American Airlines flight, departing Wed, Aug 13 from Portland Intl. to Logan Intl., returning Tue, Aug 19, priced at $217 just found
Bargain Flight
Fri, Oct 24 - Sat, Oct 25
LAX
Los Angeles Intl.
MHT
Manchester-Boston Regional
$296 Roundtrip, just found
$296
Roundtrip
just found
Select Bargain Flight flight, departing Fri, Oct 24 from Los Angeles Intl. to Manchester-Boston Regional, returning Sat, Oct 25, priced at $296 just found