A rural landscape with rolling hills, a winding dirt road, and a cluster of red barns.

Holiday Homes in South Woodstock

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for South Woodstock holiday homes

A large house with a fire pit and outdoor seating.

1. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is NZ$1,050
includes taxes & fees
20 Oct - 21 Oct
Beautiful 3-bedroom house with AC in charming Bridgewater
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

2. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is NZ$501
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

3. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is NZ$499
includes taxes & fees
1 Oct - 2 Oct
CozyDen - AC, Bike to Mountain, Porch!
A spacious living area with a wooden ceiling, a fireplace, and a television mounted on the wall.

4. RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
Plymouth
8.8 out of 10, Excellent, (3 reviews)
"Everything about the property was beautiful and relaxing. We loved our stay .... We did however run into one issue, while we were enjoying the property, someone claiming to be there to service the hot tub decided to let themselves in with the lock code unannounced while we were undressed and stood there listening to us and only when the dog ran down there did he announce himself. Not sure if simple sent them or if they showed up on their own accord but boy did we get quite the scare and hope...
United States
Adam S.
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

5. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is NZ$908
includes taxes & fees
27 Sept - 28 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A modern living room with a dark gray sectional sofa, a white armchair, a wooden coffee table, and a spiral staircase.

6. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is NZ$1,763
includes taxes & fees
5 Oct - 6 Oct
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

7. 180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck
Hartford
9.0 out of 10, Wonderful, (8 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is NZ$959
includes taxes & fees
28 Sept - 29 Sept
180-degree panoramic views of Vermont's mountains from the living room and Deck
A wooden cabin with a covered porch and a garage, surrounded by a forested hillside.

8. Stunning Views, 10 Mins from Woodstock

Stunning Views, 10 Mins from Woodstock
Pomfret
The price is NZ$1,475
includes taxes & fees
8 Oct - 9 Oct
Stunning Views, 10 Mins from Woodstock
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

9. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is NZ$413
includes taxes & fees
29 Sept - 30 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A cozy living room with a fireplace, comfortable seating, and a television.

10. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is NZ$718
includes taxes & fees
28 Sept - 29 Sept
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

11. New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (19 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is NZ$1,041
includes taxes & fees
27 Sept - 28 Sept
New Ludlow Village Home with Stunning Okemo Mountain View

12. Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Killington
10.0 out of 10, Exceptional, (1 review)
"Beautiful home made for a perfect holiday weekend"
United States
Gregg Z.
The price is NZ$1,075
includes taxes & fees
27 Sept - 28 Sept
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

13. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is NZ$1,026
includes taxes & fees
27 Sept - 28 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A dining table set with plates, glasses, and a vase with a plant.

14. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is NZ$335
includes taxes & fees
25 Oct - 26 Oct
Cozy Rutland Retreat
A two-story house with a deck, surrounded by dense forest.

15. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (5 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is NZ$1,724
includes taxes & fees
27 Sept - 28 Sept
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A cozy living room with a fireplace, a television, and a view of a snowy deck.

16. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (59 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is NZ$1,878
includes taxes & fees
27 Sept - 28 Sept
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

17. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is NZ$1,026
includes taxes & fees
27 Sept - 28 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A cabin with a deck, a hot tub, and a fire pit area.

18. New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Killington
The price is NZ$1,515
includes taxes & fees
27 Sept - 28 Sept
New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

19. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.0 out of 10, Wonderful, (8 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is NZ$835
includes taxes & fees
27 Sept - 28 Sept
large ski ranch hot tub close to killington pets ok
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

20. The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is NZ$1,290
includes taxes & fees
28 Sept - 29 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
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

Align Inn Vermont

Align Inn Vermont

8/10 Good
"Breakfast was a typical contenital breakfast. Waffles were also available."
Mark 1-night trip
Posted 10 hours ago
Align Inn Vermont

Find out more about South Woodstock

South Woodstock Holiday Homes information

Number of reviews
145
Accommodation
841 Holiday Homes
Lowest Price
NZ$335
Highest Price
NZ$1,878