South Woodstock Vacations from $601

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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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $699, price is now $601 per person
$601
per person
Oct 11 - Oct 14
found 21 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (503 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.

Reviewed on Aug 23, 2025

Mt Green Quick Walk to Lift Pool Sauna hot tub

Mt Green Quick Walk to Lift Pool Sauna hot tub

2 out of 5
Price was $1,500, price is now $1,272 per person
$1,272
per person
Dec 4 - Dec 7
found 7 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rutland (RUT)
No reviews
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,184, price is now $1,008 per person
$1,008
per person
Dec 4 - Dec 7
found 7 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rutland (RUT)
9.2/10 Wonderful! (880 reviews)
The inn was nice and clean, the included breakfast satisfactory. The pool needed cleaning, lots of bugs. My only complaint is the mattresses were too soft and old. If you tend to sleep on the she, you may roll off.

Reviewed on Sep 5, 2025

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

Rent An Inn! Takeover The Birch Ridge W/ Your Group. Mountain Lodge: 11 Rooms, Bar, Fireplace. 28ppl 11 Bedroom Home

2 out of 5
Save 100% on your flight
Price was $7,525, price is now $6,476 per person
$6,476
per person
Dec 4 - Dec 7
found 7 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rutland (RUT)
No reviews
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $914, price is now $789 per person
$789
per person
Dec 4 - Dec 7
found 7 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
Heather was very hospitable and friendly.

Reviewed on Sep 7, 2025

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South Woodstock Hotel Deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $138 total per night from Sep 11 to Sep 12
$138 total
Sep 11 - Sep 12
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
$169 nightly
The price is $184 total per night from Sep 14 to Sep 15
$184 total
Sep 14 - Sep 15
Total with taxes and fees
Fireside Inn & Suites West Lebanon
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$639 nightly
The price is $703 total per night from Sep 14 to Sep 15
$703 total
Sep 14 - Sep 15
Total with taxes and fees
Woodstock Inn & Resort
See all 2,515 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.

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Frequently asked questions

How much does a South Woodstock vacation package cost?
You'll find cheap prices from $601 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

Explore a world of travel with Expedia

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