Woodstock Vacations

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Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is AED 1,172 per night from Jan 19 to Jan 20
AED 1,172
AED 1,450 total
19 Jan - 20 Jan
includes taxes & fees
9.2/10 Wonderful! (559 reviews)
Luxurious and friendly resort! Loved it

Reviewed on 18 December 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
The price is AED 457 per night from Jan 25 to Jan 26
AED 457
AED 543 total
25 Jan - 26 Jan
includes taxes & fees
8.6/10 Excellent! (897 reviews)
Room was clean, a little tired Great view of river and Billings Farm

Reviewed on 5 January 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 AED 871 per night from Feb 12 to Feb 13
AED 871
AED 1,092 total
12 Feb - 13 Feb
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Wonderful stay at this beautiful inn. Couldn’t fault it. The only downside is that the bar and restaurant isn’t open every evening. When it was open, it was excellent - top quality food and brilliant staff.

Reviewed on 3 January 2026

On The River Inn
See all 2,689 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.

Discover the most popular places to visit in Woodstock

The house

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
When visiting Woodstock, Vermont, one not-to-miss outdoor attraction is the Marsh - Billings - Rockefeller National Historical Park, the first National Park in Vermont. The site is full of ambient trails with different atmospheres, whether you want to summit a mountain, run through a field or picnic on a lovely lake. Here you see The Pogue, a 14-acre

Marsh-Billings-Rockefeller National Historical Park

Explore the lovely green spaces of Marsh-Billings-Rockefeller National Historical Park and enjoy the ski slopes in Woodstock. Stroll along the riverfront or discover the mountain views in this quaint area.

Marsh-Billings-Rockefeller National Historical Park

Saskadena Six Ski Area

Hit the slopes in Woodstock with a visit to Saskadena Six Ski Area. Wander the riverfront in this quaint area.

Saskadena Six Ski Area

Frequently asked questions

How do I find cheap flights to Woodstock that have flexible change policies?
Search for your affordable flights to Woodstock, then check the "No change fee" box directly under the "Flexible change policies" filter. It's that simple. We know that travel plans change and flexibility is essential, so you can book with confidence with Expedia.
Which airlines fly to Woodstock?
You can fly into a range of airports in or near Woodstock with Cape Air. It runs 182 monthly services to this area, including 121 to Lebanon Municipal Airport (LEB). Rutland Southern Vermont Regional Airport (RUT) a better alternative for you? Cape Air conducts 60 flights a month here.
How can I find cheap tickets to Woodstock?
In the last seven days, was the lowest price for a flight to Woodstock. If you want to save even more, book ahead of time and be flexible with your dates. Search for your airfare to Woodstock, then compare prices for nearby days by clicking on the "flexible dates" link above.
How much is a flight to Woodstock?
In the last seven days, round-trip flights to Woodstock sold for as low as and reached a maximum of . For one-way fares taking off from (), the lowest amount paid during this same period was only .
What are the most popular airports to fly into in Woodstock?
When you've decided where you're going first in Woodstock, take your pick of these well-known airports:

  • Lebanon Municipal Airport (LEB) - 121 flights per month.
  • Rutland Southern Vermont Regional Airport (RUT) - 60 flights per month.

When is the cheapest time to fly to Woodstock?
If you'd prefer to spend your cash enjoying the delights of Woodstock rather than on your journey there, depart early in the week. The most cost-effective day to travel is usually Tuesday, with Monday coming in second. With many folks traveling over the weekend, Saturday tends to have the highest fares.
How much is a plane ticket to Woodstock?
Seats to Woodstock ranged from to in the last seven days. Generally, the sooner you book the better the deal.
What months are the cheapest to book a flight to Woodstock?
February is the best month to reserve a seat for your Woodstock vacation. Airfares are at their most expensive throughout the month of December, so avoid this time if you can.