Search Deals onWindsor Vacation Packages
Photo by William E Berry Jr.
Windsor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.


The Shire Woodstock
per person
Jul 30 - Aug 6
found 15 hours ago
Roundtrip non-stop 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
per person
Sep 11 - Sep 19
found 22 hours ago
Roundtrip flight included
Nairobi (NBO) 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.

Lincoln Inn & Gallery
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.

Jackson Gore Village
per person
Sep 11 - Sep 19
found 22 hours ago
Roundtrip flight included
Nairobi (NBO) 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
per person
Sep 11 - Sep 19
found 22 hours ago
Roundtrip flight included
Nairobi (NBO) 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.

Mountain Lodge at Okemo
per person
Sep 11 - Sep 19
found 22 hours ago
Roundtrip flight included
Nairobi (NBO) 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.

Woodstock Inn & Resort
per person
Aug 25 - Aug 30
found 1 day 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.
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 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$361 Roundtrip, found 1 hour ago
$361
Roundtrip
found 1 hour ago

Mon, Sep 8 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$365 Roundtrip, found 1 hour ago
$365
Roundtrip
found 1 hour ago

Mon, Sep 8 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$366 Roundtrip, found 1 hour ago
$366
Roundtrip
found 1 hour ago

Mon, Sep 8 - Mon, Sep 15
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$370 Roundtrip, found 1 hour ago
$370
Roundtrip
found 1 hour ago
Discover Other Travel Deals
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Windsor
- Car rentals in Woodstock
- Car rentals in White Mountains
- Car rentals in Killington
- Car rentals in White River Junction
- Car rentals in Hanover
- Car rentals in Rutland
- Car rentals in Lebanon
- Car rentals in Ludlow
- Car rentals in Quechee
- Car rentals in West Lebanon
- Car rentals in Newbury
- Car rentals in Appalachian Mountains