Search Deals onWoodstock Vacation Packages
Woodstock Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Brattleboro VT
Price was $652, price is now $604 per person
$604
per person
Oct 9 - Oct 12
just found
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
Stay at this motel in Brattleboro. Enjoy free WiFi, free parking, and room service. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Jackson Gore Village, A Vail Resorts Property
Price was $759, price is now $641 per person
$641
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) 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.
Pool was nice with dry and steam sonna. Restaraunt and bar was good not a big food selection but food was good quality. Lift base was very near the facility with a lot of trails nearby
Reviewed on Aug 9, 2026
Latchis Hotel
Price was $901, price is now $771 per person
$771
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Fort Myers (RSW) 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.
BAD, Did not stay after seeing the room. No refund.
Reviewed on Aug 12, 2026
Deerfield Valley Inn
Price was $805, price is now $694 per person
$694
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Inn is beautiful and Oz the owner made us feel very welcome. I would definitely like to return
Reviewed on Aug 11, 2026
Stone Hearth Inn and Eatery
Price was $1,022, price is now $907 per person
$907
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.
1846 Inn and Tavern
Price was $927, price is now $824 per person
$824
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Fort Myers (RSW) 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.
Chalet 239
Price was $798, price is now $713 per person
$713
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Beautifully renovated, and well designed property unlike anything I’ve ever seen!
Reviewed on Aug 7, 2026
Mount Snow Lodging by Vail Resorts
Price was $860, price is now $783 per person
$783
per person
Oct 9 - Oct 12
found 1 hour ago
Roundtrip non-stop flight included
Fort Myers (RSW) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and ski-in/ski-out access. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
The bar tender in the lounge on Saturday 10/18 was not friendly. Seemed like he didn’t like his job. He was the only one working and there were not many customers at the bar. Dining room had no one in it. He just was not attentive to me party of 3 who just wanted to order a drink. Fitness center at the Season was very nice but hours were not very accommodating
Reviewed on Oct 20, 2025
Woodstock Vacation Packages 3-4 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 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$495 Roundtrip, found 1 day ago
$495
Roundtrip
found 1 day ago
Tue, Sep 15 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$501 Roundtrip, found 16 hours ago
$501
Roundtrip
found 16 hours ago
Sat, Sep 12 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 16 hours ago
$504
Roundtrip
found 16 hours ago
Sun, Sep 13 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$660 Roundtrip, found 4 days ago
$660
Roundtrip
found 4 days ago
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