Photo by George Sykes

Search Holiday Rentals in South Woodstock

Save an average of 15% on thousands of properties with Expedia Rewards

Become a member for free and get more than just a booking discount. Members also earn points towards their next trip.

Search over 2.9 million properties and 550 airlines worldwide.

Top Holiday Rentals in South Woodstock

Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (29)
"Two families stayed for a ski trip to okemo. Proximity to the mountain was a big plus for us. The cabin is cozy."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
1 bedroom, free WiFi, bed sheets
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (9)
"This is an adorable spot! Super quiet, the treehouse is very unique, and moments away from downtown Woodstock. We’ll be back!"
The price is £151
per night
6 May - 7 May
Treehouse at Wise Pines- SoBo
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (173)
"Very clean and all accommodations Definitely good to go!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Fridge, microwave, oven, stovetop
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
9.8 out of 10, Exceptional, (15)
"Great location to restaurant and ski mountain"
The price is £234
per night
3 May - 4 May
Two cozy tiny homes with a private hot tub, large deck, grill, AC - dog friendly
Smart TV, fireplace, books
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (57)
"This was a great stay. The condo was located in a quiet safe area in Quechee. Very clean, easy checkin process and it had all the amenities and fully stocked. The host was extremely responsive and easy to deal with. I would highly recommend staying here. Chris"
Beautifully renovated with fireplace and coffee bar
Exterior
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (156)
"Communication with owners was amazing. Heather was a great respondent and communicator. We were able to get three generations under one roof for a quiet and relaxing family getaway. We shared old stories around the fireplace and played cards late into the night (which is ten thirty pm, for us). Both my father and sister commented, at separate times, that the location was relaxing and peaceful. The pictures represent the property correctly. This was my first experience with VRBO and I am...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Fridge, microwave, oven, stovetop
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
9.4 out of 10, Exceptional, (27)
"Loved everything about it. Will look to book again"
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views
Property grounds
Comfortable mountain gem with pool, mountain views, & indoor parking space
8.4 out of 10, Very good, (16)
"Quick to killington Snowshed lodge. Easy load and unloading (sliding door backs up to street). This is a first floor unit. Fireplace use is not permitted which is not accurately reflected in the listing. I didn’t check out the pool or hot tub. Plenty of space in this unit for my group. Overall a good choice for a short ski trip."
The price is £244
per night
5 May - 6 May
Comfortable mountain gem with pool, mountain views, & indoor parking space
Fridge, oven, stovetop, coffee/tea maker
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
8.6 out of 10, Excellent, (7)
"The home is charming, immaculate and amidst woods with no neighbors in eye or earshot. It is on a dirt road, so an awd vehicle is a good idea. A stream runs along the driveway. The Ottauquechee River is across the road. The bathroom is on the first floor, and bedrooms on the second floor. The smoke detector goes off if you saute on the stove. I recommend learning how to turn off a wired in smoke detector. You should open the kitchen window when you saute, because most of the smoke detectors...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Indoor pool, outdoor pool
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
10.0 out of 10, Exceptional, (151)
"Property has a great layout and the location was perfect. Would definitely book again."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
Killington Center Inn & Suites by Killington VR - Studios
Exterior
Amazing Mountain Condo - Right across the street to Killington Resort
9.8 out of 10, Exceptional, (165)
"Great location and very clean. You can walk to Snowshed or Ramshead Lodges. Nathan was great and very communicative. I would highly recommend."
Amazing Mountain Condo - Right across the street to Killington Resort
Exterior
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
9.4 out of 10, Exceptional, (56)
"We came into town to see our friend play a two night show at Pickle Barrel. The place was perfect. Check in info was thorough and easy. Kim was great. She was responsive to communications and very accommodating. Would definitely stay here or one of her other properties again!"
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
Property grounds
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Exterior
Cozy Studio for 4 - Walk to Mountain w/ Balcony
8.8 out of 10, Excellent, (11)
"This property is located in the Mountain Green complex, which is ideal for mountain access without needing your car. The bed was comfortable, there were plenty of Pillows and towels for us to use. Kitchen is well equipped and the appliances worked well. One of the chairs on the terrace was broken, though. We definitely recommend this property."
The price is £156
per night
5 May - 6 May
Cozy Studio for 4 - Walk to Mountain w/ Balcony
Fridge, microwave, oven, stovetop
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
8.4 out of 10, Very good, (27)
"I was nervous reading about issues in other reviews, but we didn’t have a single problem. Both showers had plenty of hot water, access was a breeze, hot tub worked great and it was clean and comfortable. I had 9 people with us - teens and adults. The layout made it possible for us all to hang out as we wanted. Kitchen had a big pot for pasta and a griddle which made breakfasts easy. Great location made it easy for the kids to pop back for lunch. We had one little issue with the alarm when the...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
2 bedrooms, iron/ironing board, Internet, bed sheets
Two-level vacation rental with mountain view, pellet stove, W/D & full kitchen
8.8 out of 10, Excellent, (15)
"The property was clean, spacious and had lots of natural light. It was very close (driving distance) to all we wanted to explore. It would have been nice to have more instruction on the heating systems and pellet stove. We read the stove manual, determined it needs cleaned (badly) so cleaned it after we unplugged the vacuum (it was totally clogged and full). I could not get on the review link for vacasa. King bedroom door lock doesn't work properly, and I had to buy more toilet tissue. "
Two-level vacation rental with mountain view, pellet stove, W/D & full kitchen
6 bedrooms, WiFi, bed sheets
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, (69)
"This was our second stay at the condo. Can’t beat the convenience of ski in ski out and coming home for lunch. The owner, Ralph, is very quick at getting back with any questions. Highly recommend!"
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
Don't see what you're looking for?
See all available properties in South Woodstock
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.

South Woodstock Holiday Rental Travel Info

Number of holiday rentals
5
Popular accommodation
South Woodstock private holiday homes
Known landmarks
Suicide Six Ski Area, Quechee State Park and Harpoon Brewery
International airports
Springfield, VT (VSF-Hartness State) and Lebanon, NH (LEB-Lebanon Municipal)

Other types of properties in South Woodstock you may be interested in

Indoor pool
Comfort Inn Trolley Square
2.5 star property
8.0 out of 10, Very good, (1003)
"No USB"
The price is £108
per night
7 May - 8 May
Comfort Inn Trolley Square
Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, (1001)
"Friendly"
The price is £119
per night
19 May - 20 May
Killington Mountain Lodge, Tapestry Collection by Hilton
Indoor pool
White River Inn and Suites
2.5 star property
7.2 out of 10, Good, (1001)
"The woman at the front desk was friendly and knowledgeable."
The price is £116
per night
5 May - 6 May
White River Inn and Suites
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.

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, apart-hotels, 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 favorite 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 depends 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 £151 per night. Entering your travel dates in the search wizard you might find 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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of South Woodstock is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in South Woodstock?

Choose from 4 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 Billings Farm and Museum and Harpoon Brewery.

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.

Recent reviews of South Woodstock properties
Expedia verified reviews

Hotel Coolidge

Hotel Coolidge

5/5 Excellent
"The location is very convenient. The staffs are very nice and helpful. The train arrived/departured several times during the night, if you are a light sleeper, that may be a problem."
A verified traveller stayed at Hotel Coolidge
Posted 2 days ago
Hotel Coolidge