Search Deals onWoodstock Vacation Packages
Woodstock Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
Price was $852, price is now $764 per person
$764
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Mills Riverside Park and Waters Memorial Library are located nearby.
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!
Reviewed on Jun 19, 2026
The Shire Woodstock
Price was $1,782, price is now $1,451 per person
$1,451
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Stay at this 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 Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Very nice property. Would be great to have coffee in the rooms. Also very limited hot water. Ran out a few times even after a quick shower.
Reviewed on Jul 12, 2026
The Vesper
Price was $1,014, price is now $886 per person
$886
per person
Aug 23 - Aug 28
found 7 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Charming, clean and friendly place!
Reviewed on Jul 1, 2026
Jackson Gore Village, A Vail Resorts Property
Price was $978, price is now $888 per person
$888
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Great family friendly location!
Reviewed on Jul 11, 2026
Winterplace at Okemo, A Vail Resorts Property
Price was $1,149, price is now $1,051 per person
$1,051
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Solitude Village at Okemo by Vail Resorts
Price was $1,050, price is now $967 per person
$967
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and 2 hot tubs. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
The Hartness House
Price was $986, price is now $914 per person
$914
per person
Aug 23 - Aug 28
found 7 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
Stay at this hotel in Springfield. Enjoy free WiFi, free parking, and housekeeping. Popular attractions Muckross State Park and Eureka Schoolhouse are located nearby.
Mountain Lodge at Okemo, A Vail Resorts Property
Price was $954, price is now $886 per person
$886
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Staff very helpful especially when we had a housecleaning issue when we checked into our room. Skye fixed the issue immediately. Very pleasant staff in the restaurant. Pool and adventure area was fun.
Reviewed on Jun 25, 2026
Woodstock Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Woodstock 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.
Tue, Oct 6 - Tue, Oct 13
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$330 Roundtrip, found 2 days ago
$330
Roundtrip
found 2 days ago
Tue, Oct 6 - Wed, Oct 14
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$340 Roundtrip, found 2 days ago
$340
Roundtrip
found 2 days ago
Sat, Oct 10 - Mon, Oct 12
IAD
Washington Dulles Intl.
LEB
Lebanon Municipal
$412 Roundtrip, found 2 days ago
$412
Roundtrip
found 2 days ago
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 1 day ago
$513
Roundtrip
found 1 day ago
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