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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this 3-star 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
per person
Jul 18 - Jul 26
found 1 day ago
Roundtrip flight included
Tallahassee (TLH) 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

Winterplace at Okemo

4 out of 5
per person
Jul 18 - Jul 26
found 1 day ago
Roundtrip flight included
Tallahassee (TLH) 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
per person
Jul 18 - Jul 26
found 1 day ago
Roundtrip flight included
Tallahassee (TLH) 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.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
per person
Jul 18 - Jul 26
found 1 day ago
Roundtrip flight included
Tallahassee (TLH) 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

Okemo Mountain Lodging

3.5 out of 5
per person
Jul 18 - Jul 26
found 1 day ago
Roundtrip flight included
Tallahassee (TLH) 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.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
per person
Jul 18 - Jul 26
found 1 day ago
Roundtrip flight included
Tallahassee (TLH) 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)