Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow
Price was $705, price is now $626 per person
$626
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
Jackson Gore Village, A Vail Resorts Property
Price was $1,154, price is now $898 per person
$898
per person
May 24 - May 31
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Winterplace at Okemo, A Vail Resorts Property
Price was $1,290, price is now $1,020 per person
$1,020
per person
May 24 - May 31
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Okemo Mountain Lodging by Vail Resorts
Price was $1,066, price is now $865 per person
$865
per person
May 24 - May 31
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Mountain Lodge at Okemo, A Vail Resorts Property
Price was $1,030, price is now $839 per person
$839
per person
May 24 - May 31
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Treehouse Home in Ludlow
Price was $2,632, price is now $2,203 per person
$2,203
per person
May 22 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Woodstock Inn & Resort
Save 100% on your flight
Price was $3,010, price is now $2,594 per person
$2,594
per person
May 24 - May 31
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Chester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chester Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
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