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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.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
per person
Sep 15 - Sep 19
found 18 hours 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Sep 15 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
per person
Sep 15 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Sep 15 - Sep 19
found 18 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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
per person
Sep 15 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Sep 15 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Sep 15 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Sep 15 - Sep 19
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)

Top Flight Deals

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

American Airlines
Mon, Sep 8 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$361 Roundtrip, just found
$361
Roundtrip
just found
Select American Airlines flight, departing Mon, Sep 8 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Sep 15, priced at $361 just found
JetBlue Airways
Mon, Sep 8 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$365 Roundtrip, just found
$365
Roundtrip
just found
Select JetBlue Airways flight, departing Mon, Sep 8 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Sep 15, priced at $365 just found
Delta
Mon, Sep 8 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$366 Roundtrip, just found
$366
Roundtrip
just found
Select Delta flight, departing Mon, Sep 8 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Sep 15, priced at $366 just found
American Airlines
Thu, Sep 11 - Sat, Sep 13
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$368 Roundtrip, just found
$368
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 11 from Ronald Reagan Washington National to Lebanon Municipal, returning Sat, Sep 13, priced at $368 just found