South Woodstock Vacations from $665
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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.
Deerfield Valley Inn
$665
per person
Oct 6 - Oct 11
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
9.4/10 Exceptional! (132 reviews)
We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay.
Reviewed on Aug 17, 2026
The Landgrove
$964
per person
Oct 10 - Oct 15
found 20 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
8/10 Very Good! (5 reviews)
Lots to like about this Inn: Accurate web descriptions including of their many tasty breakfast options; Very clean, Comfortable mattress with quality linens, Great bath products, Hot showers, Individual temp controls for room, Tasty tap water, Pretty landscaping. Every staff member is very pleasant – shout out to Audrey. Other things to expect: Bring a sleep mask if sensitive to light, no cell service nearby but inn offers unsecured Wi-Fi; stairs to 2nd flr rooms are shallow & steep-typical for age of building; and its easy to take country walks on the road.
Reviewed on Sep 1, 2026
The Shire Woodstock
$2,569
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
8.8/10 Excellent! (985 reviews)
Great Location. great views of the river, lawn and firepits for relaxing. Rooms recently redone and well done.
Reviewed on Sep 1, 2026
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Kedron Valley Inn
4778 South Road South Woodstock VT
$384 nightly
$422 total
Sep 9 - Sep 10
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
Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
$147 nightly
$159 total
Sep 6 - Sep 7
Total with taxes and fees
Align Inn Vermont
5817 Woodstock Rd Quechee VT
$132 nightly
$145 total
Sep 10 - Sep 11
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 $665 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.
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- Quechee Vacations
- Calvin Coolidge Historic Site
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- Marsh-Billings-Rockefeller National Historical Park
- Visit West Woodstock
- American Precision Museum
- Reading Vacations
- Saskadena Six Ski Area
- Sugarbush Farm
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- Killington Golf Course
- Camp Plymouth State Park
- Fox Run Golf Course
- Visit Quechee
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- 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.
