South Woodstock Vacations from $564
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Your South Woodstock Vacation
When you book a vacation package to South Woodstock, you can relax and enjoy your getaway knowing your travel plans are under control. Discover the wonders of this amazing city while staying in a neighborhood like West Bridgewater, which is good for skiing. You'll want to do a little exploring during your trip to South Woodstock. Don't miss famous attractions like Billings Farm and Museum, Marsh-Billings-Rockefeller National Historical Park and Woodstock Town Hall Theatre. That dream South Woodstock vacation is a few clicks away. Explore accommodations, flights and more on Expedia for a getaway that's tailored to suit your travel style.
The Latest South Woodstock vacation packages
Price found within the past 48 hours. Click for updated prices.
Castle Hill Resort And Spa
$613
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
9/10 Wonderful! (124 reviews)
We stayed in a two bedroom condo that was fabulous. It was very clean. It had a fireplace and anything we needed was available. One thing that was upsetting is that there was a wedding Saturday night at the castle so we were unable to have dinner there and then they were closed on Sunday so both nights of our stay we could not have dinner at the castle, which we were actually looking forward to. We had a great time regardless of that, we ended up having dinner at Murdock which was sooooo good highly recommend. We didn't use the pool because it was a little chilly, but it looked great. Would go back again especially for ski season.
Reviewed on Sep 15, 2026
Vikings Villages Resort
$824
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
10/10 Exceptional! (232 reviews)
Wonderful experience. Beautiful and unique. Deco was lovely. Very quiet place to relax and enjoy the stay. We enjoyed the scenery. Nice set up. Had a fireplace and we did not use it since there was no need to. Kitchen had all the amenities. We did not have to clean up after the stay. It will be a perfect place to have an event!
Reviewed on Sep 17, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
$712
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Springfield (VSF)
8.6/10 Excellent! (889 reviews)
Well maintained
Less equipped with amenities in bathroom
Reviewed on Sep 18, 2026
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View all tripsSouth Woodstock Hotel Deals
Kedron Valley Inn
4778 South Road South Woodstock VT
$410 nightly
$451 total
Sep 20 - Sep 21
Total with taxes and fees
9/10 Wonderful! (340 reviews)
"We love staying at Kedron Valley Inn for horse shows and when in the Woodstock area. The inn is in a bucolic area. Everything is always clean and ready and easy to access. We had a peaceful stay. Food at the restaurant and country store is great."
Reviewed on Aug 23, 2026
Align Inn Vermont
5817 Woodstock Rd Quechee VT
$221 nightly
$243 total
Sep 20 - Sep 21
Total with taxes and fees
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$156 nightly
$172 total
Oct 18 - Oct 19
Total with taxes and 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.
Find the Best South Woodstock Vacation Packages
South Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Lebanon Municipal Airport (LEB) |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Mt Ascutney State Park, Saskadena Six Ski Area and Harpoon Brewery |
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Frequently asked questions
How much does a South Woodstock vacation package cost?
You'll find cheap prices from $564 on Expedia for your South Woodstock break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to South Woodstock costs.
What are the cheapest months to go to South Woodstock?
You can typically find lower prices and better availability in May, September and October. Check out our cheap South Woodstock vacation packages and you could get some great off-season discounts.
How many days is enough for South Woodstock?
Typically, a handful of days is enough to go to the top attractions during your South Woodstock vacation. However, if you want to have time to relax or go on day trips, consider extending your itinerary.
How to find the best South Woodstock package deals?
Landing a cheap South Woodstock package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical South Woodstock package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a South Woodstock vacation as a package?
You can enjoy significant savings on your next South Woodstock getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to South Woodstock?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu South Woodstock getaway.
Does Expedia offer Book Now, Pay Later South Woodstock vacation packages?
If you're like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your South Woodstock vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
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- Quechee Vacations
- Calvin Coolidge Historic Site
- Green Mountain Sugar House
- Marsh-Billings-Rockefeller National Historical Park
- Visit West Woodstock
- American Precision Museum
- Reading Vacations
- Saskadena Six Ski Area
- Sugarbush Farm
- Skyeship Express Gondola Stage I
- Green Mountain Rock Climbing Center
- Quechee Ski Hill
- Simon Pearce Mill
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- Old Constitution House
- The Strong House Spa
- Wilderness Trails
- Route 4 Glassblowing Studio
- Visit Woodstock
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- Killington Resort
- Killington Vacations
- Visit South Woodstock
- Killington Golf Course
- Camp Plymouth State Park
- Fox Run Golf Course
- Visit Quechee
- Quechee Gorge Bridge
- K-1 Express Gondola
- Vins Nature Center
- Billings Farm and Museum
- Mt Ascutney State Park
- Quechee Gorge Village
- Calvin Coolidge Homestead
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
