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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.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
Price was $718, price is now $659 per person
$659
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
Stay at this 3-star inn in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,141, price is now $870 per person
$870
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip 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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $794, price is now $760 per person
$760
per person
Dec 11 - Dec 15
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
Stay at this 4-star 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.

Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
Price was $718, price is now $659 per person
$659
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,141, price is now $870 per person
$870
per person
Dec 4 - Dec 7
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $794, price is now $760 per person
$760
per person
Dec 11 - Dec 15
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)

Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,016, price is now $913 per person
$913
per person
Dec 30 - Jan 4
found 3 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Tue, Nov 4 - Sun, Nov 9
BOS
Logan Intl.
LEB
Lebanon Municipal
$181 Roundtrip, found 15 hours ago
$181
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Tue, Nov 4 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 9, priced at $181 found 15 hours ago
JetBlue Airways
Sun, Dec 7 - Wed, Dec 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sun, Dec 7 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Wed, Dec 10, priced at $304 found 2 days ago
American Airlines
Thu, Dec 4 - Mon, Dec 8
LGA
LaGuardia
RUT
Rutland Southern Vermont Regional
$320 Roundtrip, found 1 day ago
$320
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Dec 4 from LaGuardia to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $320 found 1 day ago
United
Sun, Dec 7 - Mon, Dec 8
EWR
Newark Liberty Intl. Airport
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 1 day ago
$344
Roundtrip
found 1 day ago
Select United flight, departing Sun, Dec 7 from Newark Liberty Intl. Airport to Rutland Southern Vermont Regional, returning Mon, Dec 8, priced at $344 found 1 day ago