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Chester Vacation Packages

Build your package with 2 more options

Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Price was $632, price is now $559 per person
$559
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $829, price is now $645 per person
$645
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Stay at this 3-star 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 $740, price is now $627 per person
$627
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Stay At Jimmy's

Stay At Jimmy's

3 out of 5
Price was $1,391, price is now $1,194 per person
$1,194
per person
Nov 23 - Nov 28
found 19 hours ago
Roundtrip flight included
Tampa (TPA) 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 Red Wagon Toy Company are located nearby.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Price was $725, price is now $628 per person
$628
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Price was $667, price is now $585 per person
$585
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Price was $661, price is now $580 per person
$580
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $647, price is now $574 per person
$574
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Price was $667, price is now $585 per person
$585
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $829, price is now $645 per person
$645
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
The Vesper

The Vesper

3 out of 5
Price was $740, price is now $627 per person
$627
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $725, price is now $628 per person
$628
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)

Chester Vacation Packages 5-7 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 $1,135, price is now $886 per person
$886
per person
Nov 23 - Nov 28
found 19 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,586, price is now $1,260 per person
$1,260
per person
Nov 23 - Nov 28
found 19 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Price was $1,319, price is now $1,072 per person
$1,072
per person
Nov 23 - Nov 28
found 19 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,301, price is now $1,057 per person
$1,057
per person
Nov 23 - Nov 28
found 19 hours ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)

Top Flight Deals

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

JetBlue Airways
Tue, Oct 7 - Tue, Oct 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$156 Roundtrip, found 17 hours ago
$156
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Tue, Oct 7 from Logan Intl. to Lebanon Municipal, returning Tue, Oct 7, priced at $156 found 17 hours ago
Cape Air
Sun, Oct 5 - Sun, Oct 5
BOS
Logan Intl.
LEB
Lebanon Municipal
$156 Roundtrip, found 17 hours ago
$156
Roundtrip
found 17 hours ago
Select Cape Air flight, departing Sun, Oct 5 from Logan Intl. to Lebanon Municipal, returning Sun, Oct 5, priced at $156 found 17 hours ago
JetBlue Airways
Sat, Oct 18 - Tue, Oct 28
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Oct 18 from Raleigh - Durham Intl. to Lebanon Municipal, returning Tue, Oct 28, priced at $345 found 1 day ago
Delta
Tue, Oct 21 - Tue, Oct 28
SAN
San Diego Intl.
LEB
Lebanon Municipal
$448 Roundtrip, found 1 day ago
$448
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 21 from San Diego Intl. to Lebanon Municipal, returning Tue, Oct 28, priced at $448 found 1 day ago