South Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for South Woodstock holiday rentals

Interior

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 HK$1,233
HK$2,267 total
includes taxes & fees
19 May - 20 May
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Terrace/patio

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 HK$1,116
HK$2,425 total
includes taxes & fees
20 May - 21 May
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
1 bedroom, free WiFi, bed sheets

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 HK$1,042
HK$1,841 total
includes taxes & fees
26 May - 27 May
Addie's Place: A Quiet and Quirky Guesthouse
Property grounds

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 HK$619
HK$2,079 total
includes taxes & fees
31 May - 1 Jun
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
1 bedroom, iron/ironing board, WiFi, bed sheets

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 HK$619
HK$1,507 total
includes taxes & fees
19 May - 20 May
Vermont Suite | 10 Min to Woodstock & Killington
TV

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 HK$1,010
HK$3,330 total
includes taxes & fees
31 May - 1 Jun
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Property grounds

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 HK$415
HK$1,793 total
includes taxes & fees
31 May - 1 Jun
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Dining

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 HK$599
HK$1,469 total
includes taxes & fees
19 May - 20 May
Cozy Rutland Retreat
Property grounds

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 HK$493
HK$2,166 total
includes taxes & fees
19 May - 20 May
Comfortable mountain gem with pool, mountain views, & indoor parking space
Living area

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 HK$775
HK$1,894 total
includes taxes & fees
24 May - 25 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Dining

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 HK$896
HK$2,688 total
includes taxes & fees
19 May - 20 May
Killington Condo: Walk to Mountain, Pool & Hot Tub
Indoor pool

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 HK$579
HK$2,727 total
includes taxes & fees
19 May - 20 May
Resort condo with mountain views, full kitchen, and free WiFi
Living area

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 HK$698
HK$2,417 total
includes taxes & fees
19 May - 20 May
Killington condo 5 min to killington resort
Interior

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 HK$940
HK$3,006 total
includes taxes & fees
19 May - 20 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Interior

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 HK$1,057
HK$2,618 total
includes taxes & fees
19 May - 20 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Exterior

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 HK$744
HK$1,917 total
includes taxes & fees
19 May - 20 May
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Interior

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 HK$1,175
HK$3,035 total
includes taxes & fees
19 May - 20 May
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Smart TV, fireplace, books

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 HK$1,029
HK$2,199 total
includes taxes & fees
19 May - 20 May
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Exterior

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 HK$1,010
HK$2,432 total
includes taxes & fees
31 May - 1 Jun
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Fridge, microwave, oven, stovetop

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 HK$987
HK$2,133 total
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.
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Top South Woodstock Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

8/10 Good
"Great location, eat and drink on site. Relaxed atmosphere. "
Edward 1-night trip
Posted 2 hours ago
The Mountain Inn at Killington

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?

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.