Search Deals onWindsor Vacation Packages
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Windsor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village
Save 100% on your flight
Price was $945, price is now $687 per person
$687
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
The Shire Woodstock
Save 100% on your flight
Price was $2,583, price is now $1,849 per person
$1,849
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
Winterplace at Okemo
Price was $1,091, price is now $973 per person
$973
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
Solitude Village at Okemo
Price was $1,010, price is now $910 per person
$910
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
Okemo Mountain Lodging
Price was $962, price is now $873 per person
$873
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this 3.5-star vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Woodstock Inn & Resort
Price was $3,777, price is now $3,430 per person
$3,430
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) 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.
The Hartness House
Price was $1,283, price is now $1,173 per person
$1,173
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this 3-star hotel in Springfield. Enjoy free WiFi, free parking, and housekeeping. Popular attractions Muckross State Park and Eureka Schoolhouse are located nearby.
Luxury 6br Solitude Ge- Indoor Bball Court, Private Tub 6 Bedroom Home by RedAwning
Price was $5,387, price is now $4,948 per person
$4,948
per person
Oct 3 - Oct 7
found 7 hours ago
Roundtrip flight included
Minneapolis (MSP) to Springfield (VSF)
Stay at this 3.5-star ski vacation home in Ludlow. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Okemo Mountain Resort and Solitude Express Ski Lift 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.
Mon, Sep 8 - Wed, Sep 17
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
Mon, Sep 8 - Fri, Sep 12
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Wed, Sep 10 - Sun, Sep 21
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$300 Roundtrip, found 2 days ago
$300
Roundtrip
found 2 days ago
Sat, Sep 6 - Wed, Sep 17
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$331 Roundtrip, found 1 day ago
$331
Roundtrip
found 1 day ago
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