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

Mountaineer Inn
Price was $851, price is now $630 per person
$630
per person
Dec 12 - Dec 16
found 14 hours ago
Roundtrip non-stop 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.

The Shire Woodstock
Price was $1,358, price is now $991 per person
$991
per person
Dec 19 - Dec 25
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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.

Mount Snow Grand Summit Resort
Price was $1,076, price is now $861 per person
$861
per person
Dec 12 - Dec 16
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.

The Covered Bridge Inn
Price was $776, price is now $642 per person
$642
per person
Dec 12 - Dec 16
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Latchis Hotel
Price was $754, price is now $644 per person
$644
per person
Dec 12 - Dec 16
found 14 hours ago
Roundtrip non-stop 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.

Solitude Village at Okemo
Price was $1,124, price is now $976 per person
$976
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.

Winterplace at Okemo
Price was $1,122, price is now $975 per person
$975
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.

Mountain Lodge at Okemo
Price was $931, price is now $812 per person
$812
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this 3-star ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Windsor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Windsor 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.

Tue, Oct 21 - Wed, Oct 29
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$325 Roundtrip, found 3 days ago
$325
Roundtrip
found 3 days ago

Mon, Oct 20 - Wed, Oct 29
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$330 Roundtrip, found 3 days ago
$330
Roundtrip
found 3 days ago

Mon, Oct 20 - Mon, Oct 27
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$335 Roundtrip, found 3 days ago
$335
Roundtrip
found 3 days ago

Sat, Oct 18 - Tue, Oct 28
RDU
Raleigh - Durham Intl.
LEB
Lebanon Municipal
$345 Roundtrip, found 3 days ago
$345
Roundtrip
found 3 days ago
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