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

South Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for South Woodstock holiday rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is HK$1,042
HK$1,564 total
includes taxes & fees
3 Nov - 4 Nov
Fat Sheep Farm & Cabins
A two-story house with a porch, surrounded by a well-maintained lawn and dense trees.

2. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is HK$942
HK$1,819 total
includes taxes & fees
8 Nov - 9 Nov
Bridgewater Living - Ben&Jerry Suite
A bedroom with two beds, a door, and a small table with a lamp.

3. Bridgewater Living - Ski VT Suite

Bridgewater Living - Ski VT Suite
Bridgewater
The price is HK$942
HK$1,811 total
includes taxes & fees
1 Nov - 2 Nov
Bridgewater Living - Ski VT Suite
A cozy living room with a sectional sofa, a fireplace, a flat-screen TV, and a bookshelf.

4. 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, (177 reviews)
"Clean, well maintained property. Perfect decor for a quaint Vermont town."
United States
Joann
The price is HK$1,436
HK$3,334 total
includes taxes & fees
25 Oct - 26 Oct
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

5. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is HK$1,774
HK$3,494 total
includes taxes & fees
30 Oct - 31 Oct
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A sunroom with wicker furniture, large windows, and string lights.

6. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (18 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is HK$1,177
HK$2,031 total
includes taxes & fees
28 Oct - 29 Oct
Addie's Place: A Quiet and Quirky Guesthouse
A spacious living room with a stone fireplace, wooden furniture, and large windows.

7. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is HK$1,442
HK$5,393 total
includes taxes & fees
8 Nov - 9 Nov
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

8. Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
The price is HK$577
HK$2,265 total
includes taxes & fees
13 Oct - 14 Oct
Welcoming condo near the slopes with free WiFi and full kitchen
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is HK$1,400
HK$4,471 total
includes taxes & fees
12 Oct - 13 Oct
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A picnic table and a fire pit by a lake with a forest in the background.

10. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is HK$1,169
HK$2,342 total
includes taxes & fees
15 Oct - 16 Oct
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

11. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (5 reviews)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is HK$917
HK$2,462 total
includes taxes & fees
12 Oct - 13 Oct
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

12. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (71 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is HK$1,040
HK$3,046 total
includes taxes & fees
12 Oct - 13 Oct
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
A living room with a fireplace, a sofa, a coffee table, and a television.

13. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is HK$733
HK$2,980 total
includes taxes & fees
21 Oct - 22 Oct
Resort condo with mountain views, full kitchen, and free WiFi
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

14. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (54 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
The price is HK$1,617
HK$3,268 total
includes taxes & fees
8 Nov - 9 Nov
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

15. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
The price is HK$1,059
HK$2,536 total
includes taxes & fees
15 Oct - 16 Oct
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
A compact kitchenette with a microwave, a small refrigerator, and a trash bin.

16. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was great"
United States
Nathan H.
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

17. Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards

Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
Cavendish
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
The price is HK$1,562
HK$3,195 total
includes taxes & fees
8 Nov - 9 Nov
Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

18. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is HK$1,229
HK$2,903 total
includes taxes & fees
12 Oct - 13 Oct
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A large indoor swimming pool with clear lanes, wooden beams, and seating areas.

19. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8

Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Hartford
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful and well appointed abode - super cozy!"
United States
Nina S.
The price is HK$2,331
HK$6,988 total
includes taxes & fees
28 Oct - 29 Oct
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

20. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
United States
John O.
The price is HK$1,182
HK$3,229 total
includes taxes & fees
12 Oct - 13 Oct
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
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

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"Friendly helpful staff. Clean"
Patricia 1-night trip
Posted 1 hour ago
Fireside Inn & Suites West Lebanon

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.

What are some of the best holiday rentals that South Woodstock has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of South Woodstock is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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. In the wider area, you’ll find Woodstock Town Hall Theatre and Billings Farm and Museum.

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.