Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $716, price is now $631 per person
$631
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
New York (JFK) to Springfield (VSF)
Stay at this 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.
Beautiful property set in a fantastic town. Proprietors were super nice and the property was absolutely beautiful. Would 100% recommend staying here.
Reviewed on Oct 24, 2026
Latchis Hotel
Price was $845, price is now $755 per person
$755
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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.
1846 Inn and Tavern
Price was $1,178, price is now $1,104 per person
$1,104
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library.
Very welcoming. A ++ for hospitality and making us welcome!
Reviewed on Oct 12, 2026
Colonial Motel
Price was $773, price is now $738 per person
$738
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. 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.
Austrian Haus Lodge
Price was $911, price is now $882 per person
$882
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Stay at this hotel in West Dover. Enjoy free breakfast, free parking, and a sauna. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
I did not use it
Reviewed on Mar 20, 2026
Colonel Williams Inn
Price was $923, price is now $900 per person
$900
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Stay at this B&B in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Southern Vermont Natural History Museum and Hogback Mountain Conservation Area are located nearby.
Excellent and comfortable place to stay in beautiful location. Welcoming owners. Delicious home cooked breakfast. Recommended
Reviewed on Oct 23, 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was $929, price is now $910 per person
$910
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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 breakfast and the helpful staff in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Hampton Inn Brattleboro
Price was $820, price is now $809 per person
$809
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and 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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Nov 18 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$424 Roundtrip, found 4 days ago
$424
Roundtrip
found 4 days ago
Wed, Nov 18 - Sat, Dec 5
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$434 Roundtrip, found 3 days ago
$434
Roundtrip
found 3 days ago
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$445 Roundtrip, found 4 days ago
$445
Roundtrip
found 4 days ago
Tue, Nov 17 - Sun, Dec 6
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$455 Roundtrip, found 4 days ago
$455
Roundtrip
found 4 days ago
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