Discover a selection of 500 vacation rentals in South Woodstock that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $131 per night, and houses and condos are popular options for a stay in South Woodstock. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — South Woodstock
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Destination guide

Travel to friendly South Woodstock

Experience the unique character of South Woodstock with a stay in a vacation home rental. Travelers like the bars, restaurants and horseback riding in this welcoming and romantic city. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Things to do

Activities and attractions in and around South Woodstock

Are you hoping to find things to do in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes South Woodstock a one-of-a-kind vacation spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Okemo Mountain Resort (14.6 mi / 23.5 km)
  • Suicide Six Ski Area (6.7 mi / 10.7 km)
  • Sugarbush Farm (7.6 mi / 12.2 km)
  • Quechee State Park (7.9 mi / 12.7 km)
  • Upper Valley Aquatic Center (10.8 mi / 17.4 km)
  • Fox Run Golf Course (13.4 mi / 21.5 km)
Natural features

Exploring the natural landscape of South Woodstock

Whether you're an outdoor enthusiast or just want to take in the scenery, South Woodstock is a great place to spend some time outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Quechee State Park (7.9 mi / 12.7 km)
  • Quechee Gorge Bridge (7.9 mi / 12.8 km)
  • Mt Ascutney State Park (9.5 mi / 15.3 km)
  • Buttermilk Falls (13.3 mi / 21.5 km)
  • Killington Peak (14.7 mi / 23.6 km)
  • Gifford Woods State Park (15.8 mi / 25.4 km)
How to get there

Transportation options to and around South Woodstock

The nearest airport is in Lebanon, NH (LEB-Lebanon Municipal), located 11.9 mi (19.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 20.8 mi (33.5 km) away.

What are the top vacation rentals in or near South Woodstock?

Whether you're searching for a cozy retreat for you and your sweetie or someplace spacious to fit family and friends, you'll find some top vacation rentals in and around South Woodstock. Here are a couple to get you inspired:

  • "Cabin - Cozy Loft For Two With Hot Tub" is a hit with guests. Around 30 miles from South Woodstock, it has 1 bedroom and plenty of handy amenities, including high-speed internet services and a firepit.
  • Alternatively, make yourself comfy at "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations". Located around 13 miles from the heart of South Woodstock, it has 1 bedroom and features a nearby hospital and a dryer.

For even more great options, use the search bar at the top of the page to find the perfect South Woodstock vacation rental for you.

What are the best tiny house vacation rentals in or near South Woodstock?

You need only set foot into one of Vrbo's tiny house vacation rentals in South Woodstock to discover that awesome things really do come in little packages. Expertly designed to maximize every spare inch of space, these pint-sized digs deliver a big vacation experience:

  • Get set for a simpler way of living at "Custom - Built Tiny House In Forest Near Quechee". Amenities at this hideaway in Hartland include a boat and a blender.
  • Alternatively, book a weekend away at "Cheerful Tiny Home Cabin Near Hiking". Located in Townshend, this little abode comes with a hair dryer and a washing machine.

Can I find log cabins to rent in or near South Woodstock?

Choose a stunning log cabin from the many scattered in or around South Woodstock and you'll soon be inside your wooden sanctuary, drink in hand, reclining in front of a crackling fire. But adventure will be right there on your doorstep too. These cabins offer a great mix of comfort and fun:

  • "Cozy Family - Friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities": Enjoy a week or so unwinding and relaxing at this awesome vacation home nestled in nature. Once you're feeling revitalized, enjoy cycling or hiking and biking, which are some of the fun things to do in this region.
  • "Private And Artistic Log Cabin": After a fun day of trying out some popular local pastimes, such as snowmobiling and fishing, return home to this unique getaway.

What are the top-rated vacation rentals for weekend getaways in or near South Woodstock?

Weekends were made for having fun. Choose one of these weekend getaways in and near South Woodstock and make the most of all the incredible things to do nearby:

  • Enjoy a change of scenery at "Grafton Village Haven", which is around 25 miles to the south of South Woodstock. There's lots of adventure and nature to keep you occupied here. Do some sledding and basketball or just wander around the sights of Mount Snow and Sunrise Express Ski Lift.
  • "Cozy Family - Friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities" is another dream escape to consider. Around 30 miles west of South Woodstock, use it as a base to try some hiking and biking or golf. VINS Nature Center and Stratton Mountain Summit Gondola should also be on your must-do list if you stay here.

Can I find studio apartments for rent in and around South Woodstock?

Typically small in size, economical and well located, it's not difficult to fall for the charms of a studio apartment. Escape to one of these vacation rentals and get to know South Woodstock up close:

  • Unpack your bags at "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations". Amenities including golf and a barbecue grill will help you feel at home here.
  • Another inviting choice is "Grafton Village Haven". Take advantage of an iron and ironing board, a microwave oven and other convenient amenities during your vacation.

When you're ready to walk out of your studio apartment and do some sightseeing, there's lots to entertain you around South Woodstock. Love cultural attractions? Don't miss Mad River Glass Gallery and Green Mountain Cultural Center.

Can I find short term rentals in or near South Woodstock?

From time to time, you've just got to get away from it all, even if it's only for two or three days. Enjoy the ideal combination of relaxation and sightseeing at one of these short-term rentals in or around South Woodstock:

  • If you'd like to be close to the action, "Charming Vermont Home On 7 Acres W" will be just the ticket. It's within reach of the center of South Woodstock and a convenient base to discover sights like The Governor's House and Noyes House Museum.
  • "Beautiful Lodge With Furnished Deck And Views" is another fabulous option. We suggest adding Tea at the Governor's House and Ryder Brook Golf Course to your itinerary when it's time to sightsee.

What are the best romantic weekend getaways in or near South Woodstock?

Nothing says "I love you" quite like a romantic weekend escape. If you're longing to spend a couple of nights away with your sweetie, we've got some romantic getaways in and around South Woodstock that will set your hearts aflutter:

  • Around 13 miles from South Woodstock, "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations" is a perfect place for adoring couples. Winery tours and shopping facilities are some of the amenities here.
  • Alternatively, spend a few magical days sipping on bubbly and canoodling at "Vermont Hillside Cottage With Great View", around 20 miles from South Woodstock. A fireplace and outdoor furniture will help ramp up the romance.

What are the best large group vacation rentals in or near South Woodstock?

Share your stay and multiply the fun. Whether you're organizing an epic escape with friends or a big family gathering, you'll have your pick of large group vacation rentals in and around South Woodstock:

  • You'll have plenty of room to spread out at "Quiet Vermont Winter Getaway". Around 7 miles west of South Woodstock, this impressive property has 4 bedrooms and sleeps up to 12 guests. Quality amenities include a kitchen and mountain views.
  • Invite as many as 12 of your closest friends to "Cancellation Special 60% Off - Fabulous Log Home" and fill its spaces with laughter and love. This popular option has 6 bedrooms and is around 15 miles to the southwest of central South Woodstock. It's crammed with features to keep large groups occupied, such as a garden and a fireplace.

What are the best houses for rent with a pool in or near South Woodstock?

Nothing screams good times like a pool. Pump up your inflatable doughnut and browse these houses in or near South Woodstock that feature this added perk:

  • Treat your loved ones to a memorable stay at "Relax At The Vineyard House In Beautiful Woodstock". There's plenty to love about this retreat apart from its pool, such as a kitchen and a dishwasher.
  • Alternatively, spend your break at "Nana's House". Along with an invigorating pool, make use of a TV and free toiletries.

Unsure how to pack for your South Woodstock getaway? This appealing destination has a humid continental climate. In the summer months, expect average temperatures of between 50 ºF and 75 ºF. Check out our range of South Woodstock vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near South Woodstock?

Every catch-up with the family should be one to remember. Whether you're organizing a break with the kids or a party with relatives, Vrbo's large family vacation rentals in or near South Woodstock offer a home away from home with enough space for everyone:

  • Sleeping up to 8 guests in 3 bedrooms, "Holiday Apartment Le Chalmieu For 1" is the perfect place to hang out with the family. This popular retreat is 30 miles to the west of South Woodstock and has amenities that include a separate dining area and coffee and tea making facilities.
  • "Sunrise 3bedroom - 2 Story Remodeled Condo" also offers the space you need to live it up with loved ones. This rental is around 12 miles to the west of central South Woodstock and accommodates 8 guests in its 3 bedrooms. A toaster and skiing facilities will help keep everyone comfortable.

When you're ready to leave the house and explore, there are loads of family-friendly attractions nearby to keep everyone entertained. Pump House Indoor Waterpark, Ben and Jerry's Factory and Jay Peak Pump House should be on your agenda.