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South Woodstock Vacation Rentals

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Vacation Rentals in South Woodstock

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, 32 reviews
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, 32 reviews
"Lovely property and great location to outdoor activities."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, 176 reviews
"This property was beautiful and literally had everything we needed to cook family meals including spices and all necessary pots/pans. I was impressed by how much this hike had available form our convenience. My only issue is that the home is advertised as a 2 bedroom but it is a loft space with 3 beds and no doors. We were not expecting this but made it work. Other than that this place is a slice of heaven!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, 157 reviews
"The place is beautiful and the stay was fantastic. It is up a couple mile hill/road from the center of town, just long enough to make you feel you are out of the hustle. The property presents very well. The rooms are large for private space with 2 common rooms that are just as large for group time. The one suggestion would be to add a check in book of information, including necessary passwords (WIFI) and local attractions/restaurants. We had much of this in the interaction with the host through...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, 60 reviews
"This is a sweet convo with lovely views from all windows. There is a porch off the kitchen where you can sit and hear birds. Fragrant lilac as you come up the stairs to the door. Wanda was very easy to work with, friendly and available. We thoroughly enjoyed the coffee bar, and in all, had a wonderful stay."
Beautifully renovated with fireplace and coffee bar
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, 58 reviews
"Awesome house. Great location. I would stay there again for sure!"
Lakefront home with amazing views, fireplace, firepit, & gas grill
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, 144 reviews
"Really enjoyed our stay! The view of the lake from the living room was so peaceful and pretty. The flowers were just starting to bloom, which added a nice splash of color to the view. The house is fully equipped with everything you need both inside and out. There were kayaks available (as well as a canoe) and we were out on the lake a couple times. The lake is long enough to really experience a very scenic paddle. There is also a little country store down a ways a bit where you can stop and get...
Idyllic Lakefront House Suited Two Families
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.0 out of 10, Wonderful, 9 reviews
"Beautiful, quiet location next to river with spectacular views of covered bridge & VT landscapes! Clean, cozy, bright, rustic home in wonderful rural Woodstock area. Home is conveniently close to most highways & the center of town. The spacious rooms have mix of period & contemporary furniture, adding to the charm. Had great outdoor deck & river view was certainly a big plus! A few deck chairs would have made that even better! The kitchen had all necessary items for nice stay, loved...
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
10.0 out of 10, Exceptional, 12 reviews
"Nothing but positive things to say about the house. Would stay there again."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
TRAILSIDE, Huge, Newly Renovated, 6 bedroom condo ski-on ski-off, sleeps 18
9.6 out of 10, Exceptional, 69 reviews
"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
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, 1 review
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
The price is CA $145
CA $462 total
includes taxes & fees
Jun 22 - Jun 23
Killington Center Inn & Suites by Killington VR - Studios
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, 29 reviews
"We had a great stay here! Looked just like the pictures. We especially loved the hot tub. Would love to come back."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
9.6 out of 10, Exceptional, 4 reviews
"Really enjoyed our stay. Beautiful location and truly relaxing"
Dog-friendly, lakefront home with large yard, firepit, canoe, and fireplace
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
10.0 out of 10, Exceptional, 116 reviews
"Great place to stay for an early spring ski trip and eclipse viewing (we drove north after checking out). Clean, cozy place and pet friendly for our small dog. Located on a quiet dirt road but close to Ludlow town center and Okemo for skiing. Not too far from Killington either (which is where we went to ski). Minor issue for me was the bed was a bit too soft for my liking but otherwise, great place and would consider again in future."
Cozy Chalet,Lake Pauline, Lake Rescue,and 2 miles to Okemo Mt
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, 189 reviews
"Our family enjoyed the dock and decks most of all, and my children spent as much time as they could playing in the water. The cottage is small but fit our family of four nicely. It had everything we needed for our 4-night getaway!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
8.8 out of 10, Excellent, 38 reviews
"Great location within just a few miles of Killington base made our spring skiing getaway nice. The unit was as advertised clean with a comfortable king size bed, adequate room, and convenient parking. We especially like the privacy, nestled up top in this community off the access road. The icing on the cake for us was an excellent pool, a lab pool, and hot tub that we made grade use of enjoy your stay, will be back again!"
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, 10 reviews
"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 CA $226
CA $278 total
includes taxes & fees
Jun 23 - Jun 24
Treehouse at Wise Pines- SoBo
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
9.8 out of 10, Exceptional, 107 reviews
"Clean home close to downtown. Responsive owner. Highly recommended"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
8.0 out of 10, Very good, 14 reviews
"We enjoyed our stay. It is a beautiful property. The only complaint I have is the TV did not have any good channels. No news channels not cable etc.."
Lovely wooded home with deck, enclosed porch, & fireplace - dog-friendly
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
9.6 out of 10, Exceptional, 53 reviews
"Everything was great, good location close to Killington and the house had everything we needed!"
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
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 Vacation Rental Travel Info

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

White River Inn and Suites
2.5 star property
7.2 out of 10, Good, 1,001 reviews
"Staff was nice and accomodating."
The price is CA $220
CA $242 total
includes taxes & fees
Jun 25 - Jun 26
White River Inn and Suites
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, 1,002 reviews
"Nice buffet "
The price is CA $192
CA $211 total
includes taxes & fees
Jun 30 - Jul 1
Killington Mountain Lodge, Tapestry Collection by Hilton
Hotel Coolidge
3.0 star property
8.2 out of 10, Very good, 1,002 reviews
"The property is historic with a ton of character. The room was extra large, quiet, clean, and had a lot of windows. I sleep well both nights. I enjoy the history and character. "
The price is CA $204
CA $225 total
includes taxes & fees
Jun 25 - Jun 26
Hotel Coolidge
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 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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of South Woodstock vacation rentals we have selected for you start as low as CA $145 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 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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This vacation home rental outside of South Woodstock is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in South Woodstock?

Choose from 4 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 Billings Farm and Museum and Harpoon Brewery.

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.

Recent reviews of South Woodstock properties
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