Search Deals onWoodstock Vacation Packages
Woodstock Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Vesper
Price was $819, price is now $695 per person
$695
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Springfield (VSF)
Stay at this B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum are located nearby.
Such a wonderful experience and it was magical. Beautiful rooms and property and the location was prime.
Reviewed on Sep 29, 2026
Vikings Villages Resort
Price was $1,022, price is now $788 per person
$788
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Sinclair Inn Bed and Breakfast
Price was $1,296, price is now $1,056 per person
$1,056
per person
Dec 14 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) 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 Veterans' Park and Mills Riverside Park are located nearby.
Friendly owners and the property was amazing Beautiful garden, even in the fall Breakfast was delicious
Reviewed on Sep 25, 2026
Inn At Mount Snow
Price was $1,760, price is now $1,441 per person
$1,441
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Snow Lake are located nearby.
The property was beautifully done, with very inviting public spaces/game rooms and sophisticated decor in the room. The driveway was not obvious from the road and appeared to be a drop-down, so was easily missed. The bathroom was small but well organized. Overall really liked the property.
Reviewed on Oct 5, 2026
Grand Summit Resort, A Vail Resorts Property
Price was $1,168, price is now $973 per person
$973
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Allen in the restaurant is great.
Reviewed on Oct 6, 2026
1846 Inn and Tavern
Price was $1,019, price is now $850 per person
$850
per person
Dec 20 - Dec 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
We went for a girls trip for one night! Everything was amazing from check in to check out! We felt like we were greeting and taking care of our stay. The food is amazing the atmosphere is fantastic and can’t wait till next year!!!!
Reviewed on Sep 21, 2026
Latchis Hotel
Price was $1,017, price is now $851 per person
$851
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Salt Lake City (SLC) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Jackson Gore Village, A Vail Resorts Property
Price was $3,272, price is now $2,765 per person
$2,765
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
El Paso (ELP) 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.
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.
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$474 Roundtrip, found 10 hours ago
$474
Roundtrip
found 10 hours ago
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$484 Roundtrip, found 10 hours ago
$484
Roundtrip
found 10 hours ago
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$495 Roundtrip, found 10 hours ago
$495
Roundtrip
found 10 hours ago
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$495 Roundtrip, found 10 hours ago
$495
Roundtrip
found 10 hours ago
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