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

South Woodstock Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for South Woodstock vacation rentals

Exterior

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 ￥30,343
￥41,755 total
includes taxes & fees
Sep 1 - Sep 2
Fat Sheep Farm & Cabins
Beach

2. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is ￥44,436
￥84,228 total
includes taxes & fees
Aug 16 - Aug 17
Cabin on the hill Ascutney Vt - 4 bedrooms
Interior

3. Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (18 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 ￥28,987
￥59,248 total
includes taxes & fees
Sep 1 - Sep 2
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Aerial view

4. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is ￥12,431
￥37,070 total
includes taxes & fees
Sep 1 - Sep 2
Mountain Green
TV, fireplace

5. 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.
TV

6. 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 ￥29,266
￥110,161 total
includes taxes & fees
Sep 3 - Sep 4
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
TV, fireplace, DVD player, books

7. 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 ￥10,703
￥54,402 total
includes taxes & fees
Aug 14 - Aug 15
Resort condo with mountain views, full kitchen, and free WiFi
Exterior

8. Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo

Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo
West Windsor
10.0 out of 10, Exceptional, (1 review)
"Yes, our stay was very nice! Beautiful cabin, very clean ! "
United States
Alicja
The price is ￥37,671
￥78,761 total
includes taxes & fees
Aug 19 - Aug 20
Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo
Interior

9. 103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (19 reviews)
"Would stay again!"
United States
Hannah M.
The price is ￥16,556
￥25,071 total
includes taxes & fees
Aug 23 - Aug 24
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Interior

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.4 out of 10, Exceptional, (15 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is ￥23,891
￥41,215 total
includes taxes & fees
Aug 23 - Aug 24
Addie's Place: A Quiet and Quirky Guesthouse
Exterior

11. Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441

Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Killington
8.0 out of 10, Very Good, (1 review)
Cozy Studio at Killington Center: Close to it all with pool, bus and discounted ski rentals. 441
Interior

12. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (48 reviews)
"We had a fantastic stay! Can’t wait to return for a summer or fall trip. Cabin was wonderful, clean and full of amenities. It is a plus having access to laundry services."
United States
John H.
The price is ￥30,268
￥60,882 total
includes taxes & fees
Aug 16 - Aug 17
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Interior

13. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is ￥35,836
￥96,862 total
includes taxes & fees
Aug 17 - Aug 18
Terrific 3-bedroom cottage with AC in charming Cavendish
Interior

14. Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is ￥29,815
￥52,116 total
includes taxes & fees
Aug 17 - Aug 18
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds

15. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is ￥11,874
￥42,406 total
includes taxes & fees
Aug 16 - Aug 17
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Dining

16. Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent location. Clean and easy."
United States
Todd I.
The price is ￥18,297
￥56,670 total
includes taxes & fees
Aug 18 - Aug 19
Killington resort: Walk to Mountain, Biking & Pool
TV, DVD player

17. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is ￥8,201
￥36,995 total
includes taxes & fees
Sep 9 - Sep 10
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Dining

18. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (9 reviews)
"Fantastic place to stay, beds were great. It was wonderful having two full baths. Would definitely recommend this gem again!"
United States
Dawn B.
The price is ￥18,686
￥56,664 total
includes taxes & fees
Aug 17 - Aug 18
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Interior

19. Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (63 reviews)
"Good place. Hosts were in touch and the hot tub was great. "
United States
Bethany S.
The price is ￥29,355
￥88,689 total
includes taxes & fees
Aug 31 - Sep 1
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Smart TV, fireplace, books

20. 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is ￥33,153
￥65,672 total
includes taxes & fees
Sep 13 - Sep 14
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Woodstock Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Was a great place to stay within walking distance of Quechee Gorge. An ideal location and very clean."
Samantha 1-night trip
Posted 5 hours ago
Align Inn Vermont

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 vacation rentals in South Woodstock?

Yes, we offer vacation rentals near well known points of interest in South Woodstock, or you can choose a more remote option if you're looking for relaxation. Our travelers 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 vacation rentals in South Woodstock?

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock: This vacation home rental outside of South Woodstock is located on a river and has an outdoor pool, a fireplace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in South Woodstock?

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

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 larger area, you’ll find VINS Nature Center and Woodstock Town Hall Theatre.

What’s a vacation rental in South Woodstock like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in South Woodstock. Vacation rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.