Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.


The Shire Woodstock
Save 100% on your flight
per person
Oct 29 - Nov 3
just found
Roundtrip flight included
Dallas (DFW) 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.

Mountaineer Inn
per person
Oct 29 - Nov 3
just found
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.

Woodstock Inn & Resort
Save 100% on your flight
per person
Oct 29 - Nov 3
just found
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 4.5-star 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.


Latchis Hotel
per person
Oct 29 - Nov 3
just found
Roundtrip flight included
Dallas (DFW) 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.

Farm Road Estate
per person
Oct 29 - Nov 3
just found
Roundtrip flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star 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.

Mount Snow Lodging
per person
Sep 20 - Sep 24
found 20 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Springfield (VSF)
Stay at this 3-star ski hotel in West Dover. Enjoy free WiFi, free parking, and ski-in/ski-out access. Popular attractions Mount Snow and Ego Alley Ski Lift 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.

Thu, Sep 4 - Sat, Sep 13
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$363 Roundtrip, found 23 hours ago
$363
Roundtrip
found 23 hours ago

Thu, Sep 4 - Wed, Sep 10
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$366 Roundtrip, found 23 hours ago
$366
Roundtrip
found 23 hours ago

Tue, Sep 2 - Sat, Sep 13
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$369 Roundtrip, found 10 hours ago
$369
Roundtrip
found 10 hours ago

Thu, Sep 4 - Thu, Sep 11
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$370 Roundtrip, found 23 hours ago
$370
Roundtrip
found 23 hours ago
Discover Other Travel Deals
- DaVallia Art & Accents Vacations
- Bonnie's Bundles Dolls Vacations
- Killington Resort Vacations
- Okemo Mountain Resort Vacations
- Stratton Mountain Resort Vacations
- Mount Snow Vacations
- Green Mountain National Forest Vacations
- Bromley Mountain Ski Resort Vacations
- Magic Mountain Ski Resort Vacations
- Keene State College Vacations
- Golf Club at Equinox Vacations
- Vermont Country Store Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Chester
- Car rentals in Woodstock
- Car rentals in Killington
- Car rentals in White Mountains
- Car rentals in Manchester
- Car rentals in Brattleboro
- Car rentals in Keene
- Car rentals in Rutland
- Car rentals in White River Junction
- Car rentals in Ludlow
- Car rentals in West Lebanon
- Car rentals in Quechee
- Car rentals in Manchester Center