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

South Woodstock Vacation Rentals

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Dates

November 2026

December 2026

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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

Windsor

Brenda

$168 nightly

Nov 18 - Nov 19

Total with taxes and fees

A large house with a fire pit and outdoor seating.

2. Bridgewater Living - Ben&Jerry Suite

Bridgewater

Sylvia F.

$175 nightly

Nov 11 - Nov 12

Total with taxes and fees

3. Bridgewater Living - Ski VT Suite

Bridgewater

$174 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Bridgewater

Lisa G.

$441 nightly

Nov 11 - Nov 12

Total with taxes and fees

A cabin interior with a wooden staircase, a kitchen with modern appliances, and large windows offering a forest view.

5. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails

Cavendish

Joe C.

$375 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

6. Cozy Village Condo-Okemo Shuttle

Ludlow

walter s.

$221 nightly

Nov 11 - Nov 12

Total with taxes and fees

A sunroom with wicker furniture, large windows, and string lights.

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

Hartford

Victor R.

$218 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden cabin interior with a staircase, a sofa, and a table.

8. Adventure Cabin Hot Tub Sauna Trails Game Area

Cavendish

Katherine B.

$375 nightly

Nov 11 - Nov 12

Total with taxes and fees

A covered porch with wicker furniture, a table, and chairs.

9. Renovated Vermont Retreat with mountain views near Okemo & Killington for 6

Cavendish

Mark G.

$512 nightly

Nov 11 - Nov 12

Total with taxes and fees

A cabin interior with a wooden staircase, kitchen area, and large windows offering a forest view.

10. Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes

Cavendish

Kristen A.

$375 nightly

Nov 11 - Nov 12

Total with taxes and fees

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

Killington

Carla M.

$239 nightly

Nov 11 - Nov 12

Total with taxes and fees

A residential area with houses, a swimming pool, and a mountain backdrop.

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

Killington

Nathan H.

$241 nightly

Nov 11 - Nov 12

Total with taxes and fees

A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

13. Mountain Green ground-floor condo with private yard off the patio

Killington

$260 nightly

Nov 14 - Nov 15

Total with taxes and fees

An aerial view of a residential area with houses, a swimming pool, and a parking lot.

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

Killington

Asad B.

$246 nightly

Nov 11 - Nov 12

Total with taxes and fees

A red house with a gravel driveway and lush greenery.

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

Plymouth

$555 nightly

Nov 11 - Nov 12

Total with taxes and fees

A living room with a sofa, a bench, a fireplace, a TV, and a large window.

16. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Clock Tower Base Area

tiliger01

$206 nightly

Nov 14 - Nov 15

Total with taxes and fees

A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

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

Killington

Marcus G.

$233 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern cabin with a deck, surrounded by a forest.

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

Hartford

Nina S.

$762 nightly

Nov 11 - Nov 12

Total with taxes and fees

A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

19. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Killington

Kathleen M.

$430 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern loft bedroom with a sloped ceiling, a fireplace, a large TV, and a balcony with a scenic view.

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

Killington

Mike B.

$324 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Find vacation rentals that suit your style

Top South Woodstock Hotel Reviews

A two-story house with a front porch, a central entrance, and a garden with various plants and flowers.

Kedron Valley Inn

South Woodstock

10/10 Excellent

Anonymous traveler

A bathroom with a walk-in shower, a toilet with a grab bar, and a towel rack.

Sleep Woodstock Motel

Woodstock

10/10 Excellent

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

On The River Inn

West Woodstock

10/10 Excellent

Ayleen

Fat Sheep Farm & Cabins

Windsor

10/10 Excellent

Brenda

A spacious room with a large bed, a sofa, and a chair, featuring large windows and a view of greenery outside.

Lincoln Inn & Gallery

Woodstock

10/10 Excellent

Jennifer

A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

Woodstock Inn & Resort

Woodstock

10/10 Excellent

Anonymous traveler

A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

10/10 Excellent

Jamie

A rustic interior with a bar area, wooden beams, a fireplace, and a dining table with chairs.

The Quechee Inn at Marshland Farm

Quechee

10/10 Excellent

Teddy

A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

Mountain Meadows Lodge

Killington

10/10 Excellent

Timothy

Snowed Inn

Killington

10/10 Excellent

Tammy

Après Inn Killington

Killington

10/10 Excellent

Anonymous traveler

A multi-story hotel with a covered entrance, columns, and a well-lit facade.

Holiday Inn Express Hotel & Suites White River Junction by IHG

White River Junction

10/10 Excellent

Kristina

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

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 $183 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.