South Woodstock Vacations from $804

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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.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $976, price is now $804 per person
$804
per person
May 5 - May 11
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Lebanon (LEB)
9/10 Wonderful! (806 reviews)
Very clean, spacious rooms, very apartment like. Everything we needed to have a great girls weekend the pool was enormous and very warm beautiful grounds. The kitchen had everything we needed to cook meals. The staff was wonderful during check-in. The room had everything we needed. Didn’t need to call them again.

Reviewed on Mar 11, 2026

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,240, price is now $989 per person
$989
per person
May 5 - May 11
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
9.2/10 Wonderful! (115 reviews)
Great stay! Very cozy and homey. Very yummy breakfast!

Reviewed on Feb 27, 2026

Treehouse Home in Ludlow

Treehouse Home in Ludlow

2 out of 5
Save 100% on your flight
Price was $4,139, price is now $3,310 per person
$3,310
per person
May 5 - May 11
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
No reviews
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,058, price is now $856 per person
$856
per person
May 5 - May 11
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.6/10 Excellent! (846 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,173, price is now $964 per person
$964
per person
May 5 - May 11
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

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South Woodstock Hotel Deals

Kedron Valley Inn

Kedron Valley Inn

3.5 out of 5
4778 South Road South Woodstock VT
$246 nightly
The price is $271 total per night from Mar 15 to Mar 16
$271 total
Mar 15 - Mar 16
Total with taxes and fees
9/10 Wonderful! (334 reviews)
Tv was unusable, very limited capabilities and remote was impossible to use.

Reviewed on Mar 6, 2026

Kedron Valley Inn
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $161 total per night from Apr 9 to Apr 10
$161 total
Apr 9 - Apr 10
Total with taxes and fees
7.4/10 Good! (1,001 reviews)
Great place! Close to the mountain and restaurants on access road.

Reviewed on Mar 12, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive White River Junction VT
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $133 total per night from Mar 22 to Mar 23
$133 total
Mar 22 - Mar 23
Total with taxes and fees
7/10 Good! (1,002 reviews)
Conditions of room was nice and roomy, temperature was perfect

Reviewed on Mar 11, 2026

White River Inn and Suites
See all 2,653 properties in South 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.

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 $804 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.