Woodstock Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Woodstock Vacation
Book a Woodstock vacation package and get ready for a thrilling adventure. Known for its artistic creativity and lively atmosphere, there's plenty to keep you on the move in this city. A trip to Woodstock is a superb opportunity to sightsee. Check out renowned attractions like Saskadena Six Ski Area, Billings Farm and Museum and Sugarbush Farm. Stop dreaming and start adventuring. Explore the multitude of options on Expedia today and finally put your Woodstock vacation plans in motion!
Top Woodstock Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Latchis Hotel
Price was CA $1,036, price is now CA $934 per person
CA $934
per person
May 28 - May 31
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (853 reviews)
Great location, great staff really cool old building with lots of character
Reviewed on Mar 8, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,127, price is now CA $1,042 per person
CA $1,042
per person
May 28 - May 31
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (847 reviews)
No inflatable mattress offered anymore.
Reviewed on Mar 18, 2026
Grand Summit Resort, A Vail Resorts Property
Price was CA $1,045, price is now CA $990 per person
CA $990
per person
May 28 - May 31
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (262 reviews)
Great place to stay for ski trip
Reviewed on Mar 14, 2026
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Price was CA $1,398, price is now CA $1,380 per person
CA $1,380
per person
May 28 - May 31
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (1,002 reviews)
Staff was very courteous. The hot soup in the lobby was a nice touch! Loved the breakfast selections.
Reviewed on Mar 1, 2026
Woodstock Hotel Deals
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is CA $424 per night from Mar 22 to Mar 23
CA $424
CA $527 total
Mar 22 - Mar 23
includes taxes & fees
9.2/10 Wonderful! (569 reviews)
Excellent!!
Reviewed on Mar 18, 2026
On The River Inn
1653 West Woodstock Road Woodstock VT
The price is CA $191 per night from Apr 8 to Apr 9
CA $191
CA $261 total
Apr 8 - Apr 9
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
Just a great property all around. For going a few minutes down the road from downtown you get a very well appointed, updated hotel. Breakfast was excellent, pool and Sauna are is nicely updated. Amazingly kid friendly, will be back soon!
Reviewed on Mar 18, 2026
The Shire Woodstock
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Apr 12 to Apr 13
CA $168
CA $199 total
Apr 12 - Apr 13
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Woodstock
Billings Farm and Museum
5/5(1 review)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Explore a world of travel with Expedia
- Hotels near Billings Farm and Museum
- B&B in Bridgewater
- Inns in Bridgewater
- Motels in Bridgewater
- Beach Hotel Hotels in Windsor County
- Business Hotels in Windsor County
- Cheap Hotels in Windsor County
- Hotels & Resorts for Couples in Windsor County
- Family Hotels in Windsor County
- Golf Hotels in Windsor County
- Historic Hotels in Windsor County
- Hotels with a Pool in Windsor County
- Hotels with Hot Tubs in Windsor County
- Hotels with an Indoor Pool in Windsor County
- Luxury Hotels in Windsor County
- Pet-Friendly Hotels in Windsor County
- Romantic Hotels in Windsor County
- Ski Hotels in Windsor County
- Spa Hotels in Windsor County
- Windsor County Hotels
- Hotels near Marsh-Billings-Rockefeller National Historical Park
- Farmstay in Quechee
- B&B in Quechee
- Hotels near Quechee Gorge Bridge
- Cheap Hotels in Quechee
- Family Hotels in Quechee
- Hotels with Wifi in Quechee
- Luxury Hotels in Quechee
- Mountain Hotels in Quechee
- Pet-Friendly Hotels in Quechee
- Spa Hotels in Quechee
- Quechee Hotels
- Inns in Quechee
- Lodges in Quechee
- Resorts in Quechee
- Hotels near Simon Pearce Mill
- South Pomfret Hotels
- Treehouses in South Pomfret
- Boutique Hotels in South Woodstock
- Hotels with a Pool in South Woodstock
- Luxury Hotels in South Woodstock
- Pet-Friendly Hotels in South Woodstock
- South Woodstock Hotels
- Treehouses in South Woodstock
- Hotels near Sugarbush Farm
- Cheap Hotels in Taftsville
- Taftsville Hotels
- Adults Only Resorts & in West Woodstock
- Cheap Hotels in West Woodstock
- Hotels with Hot Tubs in West Woodstock
- Hotels with Waterslides in West Woodstock
- Pet-Friendly Hotels in West Woodstock
- Romantic Hotels in West Woodstock
- Spa Hotels in West Woodstock
- Waterpark Hotels in West Woodstock
- West Woodstock Hotels
- Farmstay in Windsor County
- B&B in Windsor County
- Chalets in Windsor County
- Guest Houses in Windsor County
- Inns in Windsor County
- Lodges in Windsor County
- Resorts in Windsor County
- Treehouses in Windsor County
- Hotels near Woodstock Country Club
- Andover Vacations
- Bear Mountain Quad Ski Lift
- Billings Farm and Museum
- Camp Plymouth State Park
- Cavendish Vacations
- Central Vermont Vacations
- Fire Tower
- Fletcher Farm School for the Arts and Crafts
- Fox Run Golf Course
- Gifford Woods State Park
- Green Mountain National Golf Course
- K-1 Express Gondola
- Killington Adventure Center
- Killington Golf Course
- Killington Peak
- Killington Resort
- Killington School for Tennis
- Killington Vacations
- Ludlow Vacations
- Mount Ascutney
- Mt Ascutney State Park
- Pico Mountain at Killington Ski Resort
- Quechee Gorge Bridge
- Quechee Ski Hill
- Visit Quechee
- Ramshead Express Lift
- Snowdon Triple Ski Lift
- Visit South Woodstock
- The Sustainable Farmer
- White River Junction Vacations
- Wilder Vacations
- Windsor Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
