
South Woodstock Holidays
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Top Flight + Hotel Deals in South Woodstock
Price found within the past 48 hours. Click for updated prices.

Greenbrier Inn
€653
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (686 reviews)
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on 3 Aug 2026



Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
€757
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on 26 Jun 2025

Pointe at Castle Hill Resort
€692
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
8.8/10 Excellent! (1,002 reviews)
I’m genuinely at a loss as to how this place has such high reviews. I would not stay here again or recommend it. I’ll give it two positives: it was clean (pretty much the only reason I gave it any stars) and it was cheap (reflective of the quality).
There are two properties, the Castle and the Pointe. I stayed at the Pointe, which is perhaps an entirely different experience. The room was essentially a rebranded 1992 Holiday Inn, complete with a strong smell of stale cigarettes and mildew.
By far, the biggest issue for me was the air conditioning. It was August, the room was stifling, and the AC barely blew warm air. A technician reset the condenser, which temporarily fixed it, but I later learned this is an ongoing issue. Around 1 a.m., I woke up sweating. The overnight employee reset it again and brought me a fan upon request. By 4 a.m., I was sweating again and the thermostat showed the room was 12 degrees warmer than the temp it was set at.
Other issues included: broken handicap door access, broken ice machine, broken refrigerator that spoiled my coffee creamer, a questionable toilet, a horribly sunken mattress, and no microwave. You have to give your food to them to take in the back, which is so unsanitary. I also found most staff rude, and I witnessed other guests commenting on this as well. Some advice, perhaps don't speak negatively about guests within earshot...
I have much more detail but limited characters. Suffice it to say though, I would not stay here again.
Reviewed on 1 Sept 2026
Top hotels in South Woodstock

Kedron Valley Inn
4778 South Road South Woodstock VT
€372
23 Sept - 24 Sept
includes taxes & 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 23 Aug 2026

Fireside Inn & Suites West Lebanon
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
€142
6 Sept - 7 Sept
includes taxes & fees

Align Inn Vermont
5817 Woodstock Rd Quechee VT
€109
13 Sept - 14 Sept
includes taxes & 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.
Frequently asked questions
How much does a South Woodstock holiday package cost?
You'll find cheap prices from €653 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 holiday to South Woodstock costs.
What are the cheapest months to go to South Woodstock?
To pick up cheap South Woodstock holiday packages, organise your getaway outside of busy periods such as school holidays. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for South Woodstock?
Typically, a handful of days is enough to see the main attractions during your South Woodstock holiday. However, if you'd like to have some time to rest or go on day tours, consider extending your trip.
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 personalise 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 holiday as a package?
You can enjoy significant savings on your next South Woodstock getaway by booking a tailored holiday package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday 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.
How to plan a trip to South Woodstock?
- Choose your travel dates: What you want to do in South Woodstock and your favourite season can help you decide when to get away.
- Plan your budget wisely: As well as the price of your stay, you'll need to consider other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to South Woodstock.
- Determine how many days away: Start by listing all the activities and attractions you'd like to experience in South Woodstock. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, lock in the ideal South Woodstock holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
