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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for South Woodstock holiday homes

A large house with a fire pit and outdoor seating.

1. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
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 €497
includes taxes & fees
28 Oct - 29 Oct
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

2. Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
Hartford
10.0 out of 10, Exceptional, (175 reviews)
"Clean, well maintained property. Perfect decor for a quaint Vermont town."
United States
Joann
The price is €389
includes taxes & fees
25 Oct - 26 Oct
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A compact kitchen with a refrigerator, stove, microwave, and sink.

3. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

4. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

5. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is €321
includes taxes & fees
18 Oct - 19 Oct
Luxury Condo Tucked in the Heart of Killington
A golf course with sand bunkers and a forested area.

6. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

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

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

8. CozyDen- Location, Fireplace, Ski Off/ Shuttle On

CozyDen- Location, Fireplace, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
CozyDen- Location, Fireplace, Ski Off/ Shuttle On
A hot tub surrounded by snow, with lounge chairs and string lights.

9. Fall Getaway Near Killington with Hot Tub

Fall Getaway Near Killington with Hot Tub
Bridgewater
Fall Getaway Near Killington with Hot Tub
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

10. 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 €206
includes taxes & fees
1 Nov - 2 Nov
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

11. 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.
180-degree panoramic views of Vermont's mountains from the living room and Deck
A dining table set with plates, glasses, and a vase with a plant.

12. 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
Cozy Rutland Retreat
Living area

13. 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.
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

14. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!
Clarendon
9.2 out of 10, Wonderful, (5 reviews)
"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "
United States
Ahmad H.
Killington Retreat | Deck-Fire Pit-Mountain Views!
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A spacious living area with a wooden ceiling, a fireplace, and a television mounted on the wall.

16. 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 living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

17. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

18. 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 €509
includes taxes & fees
18 Oct - 19 Oct
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A cozy living room with a fireplace, a television, and a view of a snowy deck.

19. 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.
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A cabin with a deck and a stone chimney.

20. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is €1,537
includes taxes & fees
5 Oct - 6 Oct
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
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

Six South St Hotel

Six South St Hotel

10/10 Excellent
"Excellent location and pristine rooms. Highly recommend."
Kristen 3-night trip
Posted 2 hours ago
Six South St Hotel

Find out more about South Woodstock

South Woodstock Holiday Homes information

Number of reviews
384
Accommodation
849 Holiday Homes
Lowest Price
€206
Highest Price
€1,537