Search Deals onWinchester Vacation Packages
Winchester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn
Price was $519, price is now $422 per person
$422
per person
Dec 3 - Dec 6
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 United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Good location. About what one might expect in a budget motel.
Reviewed on Oct 20, 2026
The Shire Woodstock
Price was $1,761, price is now $1,427 per person
$1,427
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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 Quechee Gorge Bridge and Billings Park and Trail are located nearby.
The manager and owners do not help with any situation. My room was not clean. Pubic hairs in the shower. Hairs all over the floor, spiders, crumbs all over the valet. Baseboards were covered in filth. No one would return my calls, emails or text messages.
Reviewed on Oct 30, 2026
Latchis Hotel
Price was $753, price is now $610 per person
$610
per person
Dec 3 - Dec 6
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.
Vikings Villages Resort
Price was $862, price is now $734 per person
$734
per person
Dec 3 - Dec 6
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 a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Keets Brook Road Conservation Area are located nearby.
The Vesper
Price was $1,397, price is now $1,211 per person
$1,211
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Charming bed-and-breakfast close to downtown. We enjoyed our stay and the breakfast was wonderful. Jessica was very hospitable and had great recommendations! Felt like family.
Reviewed on Oct 29, 2026
Sinclair Inn Bed and Breakfast
Price was $616, price is now $535 per person
$535
per person
Jan 20 - Jan 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Jackson Gore Village, A Vail Resorts Property
Price was $1,205, price is now $1,061 per person
$1,061
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Deer Brook Inn
Price was $3,951, price is now $3,635 per person
$3,635
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and climate control. Popular attractions Ottaquechee River and Union Arena Community Center are located nearby.
I highly recommend Deer Brook Inn. The photos don’t do it justice. It’s beautiful, cozy, well-kept and everything you’d want for a Vermont getaway. The innkeepers may be some of my favorite humans I’ve ever met. Their energy is bright and peaceful which reflects into the energy of the inn. They have cookies, coffee, teas and other drinks at night and a delicious custom breakfast in the morning. They have chickens out back, a fire pit and a sauna. It’s about a 7min drive from downtown Woodstock. Don't hesitate to book!
Reviewed on Oct 17, 2026
Winchester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winchester 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, Nov 26 - Wed, Dec 2
LAX
Los Angeles Intl.
BOS
Logan Intl.
$288 Roundtrip, found 3 hours ago
$288
Roundtrip
found 3 hours ago
Fri, Nov 13 - Tue, Nov 17
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$314 Roundtrip, found 10 hours ago
$314
Roundtrip
found 10 hours ago
Thu, Nov 19 - Wed, Dec 2
PDX
Portland Intl.
ALB
Albany Intl.
$327 Roundtrip, found 3 days ago
$327
Roundtrip
found 3 days ago
Sat, Nov 14 - Tue, Nov 17
LAX
Los Angeles Intl.
PVD
T.F. Green
$336 Roundtrip, found 8 hours ago
$336
Roundtrip
found 8 hours ago
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