Winchester Flight + Hotel Packages

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

Jackson Gore Village, A Vail Resorts Property

$736

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) 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.

The Shire Woodstock

$851

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) 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 Weston

$1,008

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) to Springfield (VSF)

Book a stay at this luxury guesthouse in Weston. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Weston Playhouse and Mill Museum are located nearby.

Stone Hearth Inn and Eatery

$824

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) to Springfield (VSF)

Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.

Winterplace at Okemo, A Vail Resorts Property

$781

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) to Springfield (VSF)

Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.

Woodstock Inn & Resort

$1,363

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) to Springfield (VSF)

Book a stay at this 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 Quechee Gorge Bridge and Middle Covered Bridge are located nearby.

Solitude Village at Okemo by Vail Resorts

$738

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) to Springfield (VSF)

Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.

Deer Brook Inn

$844

per person

Jun 26 - Jun 29

found 6 hours ago

Roundtrip non-stop flight included

Washington (WAS) 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.

Winchester Vacation Packages 3-4 Night Stays

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