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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.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $693, price is now $647 per person
$647
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $842, price is now $702 per person
$702
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Price was $939, price is now $798 per person
$798
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
Price was $782, price is now $675 per person
$675
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
Book a stay at this spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
The Hartness House

The Hartness House

3 out of 5
Price was $924, price is now $852 per person
$852
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
Stay at this hotel in Springfield. Enjoy free WiFi, free parking, and housekeeping. Popular attractions Muckross State Park and Eureka Schoolhouse are located nearby.
Farm Road Estate

Farm Road Estate

3 out of 5
Price was $1,144, price is now $1,065 per person
$1,065
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
Book a stay at this golf hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 out of 5
Price was $776, price is now $736 per person
$736
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was $946, price is now $901 per person
$901
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
Price was $782, price is now $675 per person
$675
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $842, price is now $702 per person
$702
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $939, price is now $798 per person
$798
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
The Hartness House

The Hartness House

3 out of 5
Price was $924, price is now $852 per person
$852
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)

Top Flight Deals

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

JetBlue Airways
Wed, Apr 22 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, just found
$178
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Apr 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $178 just found
Cape Air
Wed, Apr 22 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Cape Air flight, departing Wed, Apr 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $179 just found
Cape Air
Sat, May 30 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, just found
$180
Roundtrip
just found
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $180 just found
JetBlue Airways
Wed, Apr 22 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, just found
$183
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Apr 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $183 just found