Search Holiday Rentals in South Woodstock

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for South Woodstock holiday rentals

House, 6 Bedrooms | Private kitchen
Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
2.0 star property
Killington
Breakaway House by Killington Vacation Rentals
Indoor pool
Mountain Green

Mountain Green

Mountain Green
2.0 star property
Killington
6.8 out of 10, (16)
"Great communication from Jeff."
United States
Dennis
The price is ฿7,396
฿9,922 total
includes taxes & fees
12 Jan - 13 Jan 2026
Mountain Green
Condo, 1 Bedroom | Exterior
Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
The price is ฿6,566
฿13,139 total
includes taxes & fees
21 Jan - 22 Jan 2026
Killington Ski Resort VT Vacation Condos
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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Top South Woodstock Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Very good 👍 "
Alex 2-night trip
Posted 19 hours ago
Pointe at Castle Hill Resort

Find out more about South Woodstock

Search for holiday rentals in South Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in South Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in South Woodstock
  • Use the map to find apartments and other holiday homes in the South Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Woodstock while they last

Look no further and take a look at our great range of rental properties in South Woodstock!

Frequently asked questions

Can I find holiday rentals in South Woodstock?

Yes, there are holiday rentals close to the most popular sights in South Woodstock, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say South Woodstock has a good selection of restaurants. Make sure you have time to check out the bars while you're in the area.

How many holiday rentals are there in South Woodstock?

Choose from 5 Expedia holiday rentals in South Woodstock for a memorable holiday.

What’s there to see and do in South Woodstock?

While exploring the area, visit family-friendly sights like Sugarbush Farm, or get outside and enjoy nature at Marsh-Billings-Rockefeller National Historical Park. Other popular places to visit in the area include Killington Resort and Okemo Mountain Resort.

What’s a holiday rental in South Woodstock like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in South Woodstock. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.