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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 out of 5
Price was $899, price is now $804 per person
$804
per person
Jan 31 - Feb 4
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Price was $2,294, price is now $1,967 per person
$1,967
per person
Jan 1 - Jan 5
found 1 hour ago
Roundtrip flight included
San Juan (SJU) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $984, price is now $851 per person
$851
per person
Jan 31 - Feb 4
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,969, price is now $1,744 per person
$1,744
per person
Jan 1 - Jan 5
found 1 hour ago
Roundtrip flight included
San Juan (SJU) 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.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Price was $9,973, price is now $8,873 per person
$8,873
per person
Jan 31 - Feb 4
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Snow Stars Carpet are located nearby.
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Price was $2,605, price is now $2,359 per person
$2,359
per person
Jan 31 - Feb 4
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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 Vesper

The Vesper

3 out of 5
Price was $900, price is now $818 per person
$818
per person
Jan 31 - Feb 4
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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

Winterplace at Okemo

4 out of 5
Price was $1,451, price is now $1,330 per person
$1,330
per person
Jan 5 - Jan 9
found 1 day 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 daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.

Chester 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 $984, price is now $851 per person
$851
per person
Jan 31 - Feb 4
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $2,294, price is now $1,967 per person
$1,967
per person
Jan 1 - Jan 5
found 1 hour ago
Roundtrip flight included
San Juan (SJU) to Springfield (VSF)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,969, price is now $1,744 per person
$1,744
per person
Jan 1 - Jan 5
found 1 hour ago
Roundtrip flight included
San Juan (SJU) to Springfield (VSF)
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Price was $9,973, price is now $8,873 per person
$8,873
per person
Jan 31 - Feb 4
found 3 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Vesper

The Vesper

3 out of 5
Price was $1,508, price is now $1,355 per person
$1,355
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $2,597, price is now $2,134 per person
$2,134
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,125, price is now $1,791 per person
$1,791
per person
Dec 20 - Dec 27
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $2,279, price is now $2,107 per person
$2,107
per person
Jan 2 - Jan 8
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Springfield (VSF)

Top Flight Deals

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

American Airlines
Tue, Feb 10 - Tue, Feb 10
JFK
John F. Kennedy Intl.
LEB
Lebanon Municipal
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Feb 10 from John F. Kennedy Intl. to Lebanon Municipal, returning Tue, Feb 10, priced at $294 found 2 days ago
JetBlue Airways
Sat, Dec 13 - Wed, Dec 17
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Dec 13 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 17, priced at $309 found 3 days ago
American Airlines
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$340 Roundtrip, found 4 days ago
$340
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Dec 4 from LaGuardia to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $340 found 4 days ago
United
Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select United flight, departing Sun, Dec 7 from Newark Liberty Intl. Airport to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $344 found 1 day ago