South Woodstock Vacations from $530

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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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $671, price is now $530 per person
$530
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.6/10 Excellent! (936 reviews)

The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $1,453, price is now $1,052 per person
$1,052
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.8/10 Excellent! (967 reviews)
It would be great to have a coffee maker in the room

Reviewed on Jul 31, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $852, price is now $670 per person
$670
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
9/10 Wonderful! (858 reviews)

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $4,578, price is now $3,666 per person
$3,666
per person
Sep 20 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

Chalet 239

Chalet 239

2 out of 5
Price was $664, price is now $536 per person
$536
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
9.4/10 Exceptional! (133 reviews)
The room was small. But very new, modern and clean. I’d stay again.

Reviewed on Aug 1, 2026

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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
$337 nightly
The price is $371 total per night from Aug 4 to Aug 5
$371 total
Aug 4 - Aug 5
Total with taxes and fees
Kedron Valley Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundable
$125 nightly
The price is $138 total per night from Aug 9 to Aug 10
$138 total
Aug 9 - Aug 10
Total with taxes and fees
Comfort Inn Rutland - Killington
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $173 total per night from Aug 2 to Aug 3
$173 total
Aug 2 - Aug 3
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
"A very nice over night place to stay on our way to Maine. Clean, comfortable and reasonable. Plenty of shopping nearby and just off the highway."

Reviewed on Aug 1, 2026

Fireside Inn & Suites West Lebanon
See all 2,595 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 $530 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.