Woodstock Vacation Packages

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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.
Sinclair Inn Bed and Breakfast

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Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $712 per night from Jul 13 to Jul 14
CA $712
CA $845 total
Jul 13 - Jul 14
includes taxes & fees
9.4/10 Exceptional! (586 reviews)
"If you're looking for a very comfortable stay in the quaint and historic town of Woodstock VT and don't worry about the expense, then the Woodstock Inn is the place for you!"

Reviewed on Jun 16, 2026

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Jul 1 to Jul 2
CA $176
CA $209 total
Jul 1 - Jul 2
includes taxes & fees
8.8/10 Excellent! (938 reviews)
"Loved our summer stay here. We had a beautiful room with a balcony over the river. Loved the little touches of nooks with games and Starbucks Keurigs everywhere, the fire pits and cornhole by the river and the complementary use of bikes."

Reviewed on Jun 17, 2026

The Shire Woodstock
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $249 per night from Jul 9 to Jul 10
CA $249
CA $297 total
Jul 9 - Jul 10
includes taxes & fees
9.4/10 Exceptional! (1,012 reviews)
"This hotel was perfect for us. Two rooms next to each other for our family of 5. The beds were the most comfortable of all time. Toiletries were luxurious. Room was clean and comfortable. The pool, sauna and hot tub was perfect for our family. Breakfast was the best we’ve ever had at a hotel. Tasted ..."

Reviewed on Jun 17, 2026

On The River Inn
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.