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

South Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for South Woodstock vacation 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
$177 nightly
The price is $193
Nov 5 - Nov 6
Total with taxes and fees
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.
$184 nightly
The price is $206
Nov 3 - Nov 4
Total with taxes and fees
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
$183 nightly
The price is $205
Nov 3 - Nov 4
Total with taxes and fees
Bridgewater Living - Ski VT Suite
A large house with a fire pit and outdoor seating.

4. 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, (3 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.
$472 nightly
The price is $529
Nov 3 - Nov 4
Total with taxes and fees
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.

5. 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, (179 reviews)
"Clean, well maintained property. Perfect decor for a quaint Vermont town."
United States
Joann
$379 nightly
The price is $428
Oct 25 - Oct 26
Total with taxes and fees
Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock
A wooden cabin with large windows, a door, and a small porch with Adirondack chairs.

6. 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, (55 reviews)
"The cabins are amazing, everything you need for a great weekend! I will be back for sure!"
United States
Joe C.
$377 nightly
The price is $406
Nov 9 - Nov 10
Total with taxes and fees
Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit
A sunroom with wicker furniture, large windows, and string lights.

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (19 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
$206 nightly
The price is $233
Oct 27 - Oct 28
Total with taxes and fees
Addie's Place: A Quiet and Quirky Guesthouse
A spacious living room with a stone fireplace, wooden furniture, and large windows.

8. 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.
$618 nightly
The price is $692
Oct 31 - Nov 1
Total with taxes and fees
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.

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

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
$256 nightly
The price is $290
Oct 19 - Oct 20
Total with taxes and fees
Welcoming condo near the slopes with free WiFi and full kitchen
A compact kitchen with a refrigerator, stove, microwave, and sink.

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

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
$511 nightly
The price is $572
Oct 19 - Oct 20
Total with taxes and fees
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A residential area with houses, a swimming pool, and a mountain backdrop.

11. 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, (5 reviews)
"Place was great"
United States
Nathan H.
$229 nightly
The price is $259
Oct 19 - Oct 20
Total with taxes and fees
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.

12. 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.
$377 nightly
The price is $406
Nov 9 - Nov 10
Total with taxes and fees
Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards
A cozy cabin interior with a TV displaying 'NETFLIX', a fireplace, wooden walls, a window with a forest view, and a comfortable seating area.

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

Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
Cavendish
10.0 out of 10, Exceptional, (29 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
$378 nightly
The price is $407
Nov 11 - Nov 12
Total with taxes and fees
Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub
A modern living room with a stone fireplace, a flat-screen TV mounted above it, wooden flooring, and a kitchen area in the background.

14. Modern Killington Farmhouse Condo: Close to it all! 412

Modern Killington Farmhouse Condo: Close to it all! 412
Killington
10.0 out of 10, Exceptional, (61 reviews)
"Fantastic spot for hitting mountains as a family. Incredibly clean, convenience, and comfortable. Couldn’t be better! EV charging on site was the icing on the cake "
United States
Tyler L.
$331 nightly
The price is $374
Oct 19 - Oct 20
Total with taxes and fees
Modern Killington Farmhouse Condo: Close to it all! 412
A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

15. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Killington
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Host was responsive to questions. Great stay overall."
United States
Riley T.
$327 nightly
The price is $369
Oct 19 - Oct 20
Total with taxes and fees
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
A modern loft bedroom with a sloped ceiling, a fireplace, a large TV, and a balcony with a scenic view.

16. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
$284 nightly
The price is $321
Oct 19 - Oct 20
Total with taxes and fees
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
A living room with a fireplace, a sofa, a coffee table, and a television.

17. 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.
$336 nightly
The price is $380
Oct 19 - Oct 20
Total with taxes and fees
Resort condo with mountain views, full kitchen, and free WiFi
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

18. 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)
"Great property, clean and close to the slope"
United States
tiliger01
$205 nightly
The price is $232
Oct 19 - Oct 20
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

19. 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.
$261 nightly
The price is $295
Oct 21 - Oct 22
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

20. 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)
"Great condo! We enjoyed our stay! "
United States
Frank M.
$329 nightly
The price is $372
Oct 19 - Oct 20
Total with taxes and fees
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. 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

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

10/10 Excellent
"Wonderful place to stay. The hotel is clean and well maintained. It was decorated beautifully and the room was spacious and very nice."
Julie 1-night trip
Posted 1 hour ago
Fireside Inn & Suites West Lebanon

Find out more about South Woodstock

Everything you need to know about South Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Woodstock. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $193 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Woodstock rentals

At Expedia, we put the best South Woodstock vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Woodstock vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental outside of South Woodstock is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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 Woodstock Town Hall Theatre and Billings Farm and Museum.

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.