South Woodstock Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for South Woodstock holiday rentals

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, (18 reviews)
"It was an amazing experience! "
United States
Gruha
The price is AU$406
includes taxes & fees
18 May - 19 May
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (9 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is AU$425
includes taxes & fees
18 May - 19 May
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (10 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is AU$327
includes taxes & fees
26 May - 27 May
Addie's Place: A Quiet and Quirky Guesthouse

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
9.0 out of 10, Wonderful, (80 reviews)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
The price is AU$363
includes taxes & fees
18 May - 19 May
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is AU$271
includes taxes & fees
18 May - 19 May
Vermont Suite | 10 Min to Woodstock & Killington

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Location location location!"
United States
Britt H.
The price is AU$584
includes taxes & fees
18 May - 19 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

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
The price is AU$313
includes taxes & fees
18 May - 19 May
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is AU$264
includes taxes & fees
18 May - 19 May
Cozy Rutland Retreat

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.6 out of 10, Excellent, (37 reviews)
"Property was just as advertised. Shuttle to the mountain is only a short 2-3 ride. The spa area was amazing. "
United States
Quinten M.
The price is AU$388
includes taxes & fees
18 May - 19 May
Comfortable mountain gem with pool, mountain views, & indoor parking space

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 AU$337
includes taxes & fees
18 May - 19 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Killington Condo: Walk to Mountain, Pool & Hot Tub

Killington Condo: Walk to Mountain, Pool & Hot Tub
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent VRBO. Perfect location to the mountain. Condo was modern and clean and very comfortable. Would go back again!! "
United States
Sheri L.
The price is AU$475
includes taxes & fees
18 May - 19 May
Killington Condo: Walk to Mountain, Pool & Hot Tub

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, (46 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is AU$481
includes taxes & fees
19 May - 20 May
Resort condo with mountain views, full kitchen, and free WiFi

Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is AU$429
includes taxes & fees
18 May - 19 May
Killington condo 5 min to killington resort

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is AU$541
includes taxes & fees
18 May - 19 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AU$471
includes taxes & fees
18 May - 19 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is AU$344
includes taxes & fees
18 May - 19 May
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"This condo is a true ski-in, ski-out experience! Literally walked out the back door and skied to the lift. (A/B lifts) The kitchen was well appointed, the bed comfortable, and was perfectly set up for a ski vacation. The entire space had a comfortable, rustic vibe. Would definitely stay here again when returning to Okemo."
United States
Patricia D.
The price is AU$539
includes taxes & fees
18 May - 19 May
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

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)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is AU$385
includes taxes & fees
18 May - 19 May
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
The price is AU$427
includes taxes & fees
18 May - 19 May
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is AU$380
includes taxes & fees
20 May - 21 May
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Woodstock Hotel Reviews

Find out more about South Woodstock

Everything you need to know about South Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the South Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

South Woodstock holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A South Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Woodstock holiday rentals we have selected for you start as low as AU$327 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on South Woodstock rentals

At Expedia, we put the best South Woodstock holiday 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 holiday.

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 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?

Okemo Mountain Lodging by Vail Resorts: This holiday home rental outside South Woodstock is in the mountains and offers an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

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.