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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,179, price is now CA $961 per person
CA $961
per person
Jun 22 - Jun 26
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (871 reviews)
Convenient parking behind the hotel, but not secure. Check in personnel were friendly and efficient. I had an economy room, which was a great price.

Reviewed on May 2, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,225, price is now CA $1,086 per person
CA $1,086
per person
Jun 22 - Jun 26
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (919 reviews)
The Shire is in a wonderful location and I would recommend for a short stay. They are in the midst of a renovation and the rooms and exterior are nice and well kept. My only issue was that the coffee bars were not well stocked all the time with the same variety and the ice machine was not well stocked as it ran out of water to produce ice during our 2 night stay. Otherwise, the place and location is wonderful.

Reviewed on Apr 19, 2026

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,087, price is now CA $982 per person
CA $982
per person
Jun 22 - Jun 26
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (267 reviews)
Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful

Reviewed on May 2, 2026

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was CA $2,368, price is now CA $2,182 per person
CA $2,182
per person
Jun 22 - Jun 26
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (572 reviews)
Our stay was absolutely wonderful! The Inn was very family friendly and they even gave my two year old daughter a stuffed moose! The staff was beyond friendly and very accommodating. They created such a beautiful atmosphere that all the patrons we ran into seemed so happy. We will definitely stay here again!

Reviewed on May 2, 2026

Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was CA $1,105, price is now CA $1,019 per person
CA $1,019
per person
Jun 22 - Jun 26
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.2/10 Very Good! (967 reviews)
Newly remodeled, enjoyed hot tub and very nice breakfast

Reviewed on Apr 30, 2026

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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 $447 per night from May 17 to May 18
CA $447
CA $552 total
May 17 - May 18
includes taxes & fees
9.4/10 Exceptional! (574 reviews)
Our stay was absolutely wonderful! The Inn was very family friendly and they even gave my two year old daughter a stuffed moose! The staff was beyond friendly and very accommodating. They created such a beautiful atmosphere that all the patrons we ran into seemed so happy. We will definitely stay ...

Reviewed on May 2, 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 $155 per night from May 25 to May 26
CA $155
CA $185 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (923 reviews)
Clean and easy and comfortable

Reviewed on Apr 30, 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 $225 per night from May 5 to May 6
CA $225
CA $297 total
May 5 - May 6
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
Breakfast was excellent

Reviewed on May 1, 2026

On The River Inn
See all 2,729 properties in Woodstock
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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Discover the most popular places to visit in Woodstock

Billings Farm and Museum, Woodstock Vermont USA

Billings Farm and Museum

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.

Billings Farm and Museum

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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.