Discover a selection of 22 vacation rentals in Woodstock, VT 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 WiFi and swimming pools. Prices start at $150 per night, and houses and condos are popular options for a stay in Woodstock. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Woodstock
Destination guide

Just a little bit different than that other Woodstock

Like much of Vermont, this Woodstock is certainly earthy and crunchy, but it's not quite as boho as the Woodstock you're thinking of. Instead of daisy chains and peace signs, Vermont's version features a backdrop of mountains and rivers that could be from a painting. Skiing and hiking are the main activities here, but Woodstock manages to cater to both luxury travelers, and those looking for a quaint escape. Opt for a Woodstock vacation rental that feels like a true home away from home, and by the end you might be daring yourself to leave.

Things to do

Where ski bunnies and nature nerds converge

Woodstock is an easy drive from Killington Resort, which offers some of the best skiing in the region. Indoor sports lovers, however, might prefer the Union Arena Community Center, which features a state-of-the-art ice skating rink (plus loads of other events and performances). Head to the VINS Nature Center for the planetarium, nature camps, and bird rehabilitation, and then take your newfound knowledge out into the wild at a nearby state or national park. If you can't get enough of the local history and culture, make sure the galleries and specialty museums all make it on your list, too.


Any chance 80s ski style is making a comeback?

In Vermont, you're never too far from a ski resort, so pack for your Woodstock vacation rental with fresh pow in mind. Or, should you visit when the temps are more mellow, plan for hiking, biking, and camping through the mountains. Birdlovers can happily spy on their feathered friends in the wild, or at the local wildlife rehabilition center. The insanely charming town center also features a local community center with festivals, performances, and sporting events, as well as plenty of shops, galleries, and restaurants to suit your fancy. Most importantly, don't miss the bar scene, perfect for apres-ski festivities.


Here, Woodstock is in season every season

For most travelers, Woodstock, like much of Vermont, is strictly a winter destination. But think outside the seasonal box! Winter might be the obvious time to head deep into ski country, but there are perks to the area all year long. Enjoy the wildflowers that pop up in spring, or spend a summer day exploring life on the lake or in the river. Visitors in fall should pick a Woodstock vacation rental in the woods for optimal leaf-peeping -- just don't forget your camera!

Natural features

In Woodstock, an uphill climb is a good thing

With so much to do outdoors, nature lovers will find it impossible to pick exactly what to see. From walks in the forest, spotting deer on the ground and hawks in the sky, to getting up close at the local wildlife refuge center, there's much to learn in Woodstock. If animals don't strike your fancy, then perhaps picking wildflowers, walking along the creek, or floating around the lake or down the river will be more your speed? Speaking of speed, downhill skiiers can spend a full day on ski runs and still be ready for more.

How to get there

How to get to and around Woodstock

The nearest airport is in Springfield, VT (VSF-Hartness State), located 19.4 mi (31.3 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Lebanon, NH (LEB-Lebanon Municipal), which is 10.5 mi (16.9 km) away.

What are the top vacation rentals in or near Woodstock?

The heart wants what it wants, and right now that's to get away. It's time to pack your suitcase and zip off to one of these top vacation rentals in or near Woodstock:

  • "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations" is a favorite with guests. Around 9 miles from Woodstock, it has 1 bedroom and plenty of useful amenities, including nearby birdwatching activities and a nearby hospital.
  • "Vermont Hillside Cottage With Great View" is another top pick, offering 2 bedrooms, children's toys, a stair gate and more. It's around 25 miles from Woodstock.

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

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

Punching far above its weight when it comes to charm and ingenuity, a tiny house vacation rental in Woodstock delivers big adventure. Disconnect all your gadgets and turn your focus to Mother Nature at one of these fun-sized escapes:

  • Unwind and get back to basics at "Custom - Built Tiny House In Forest Near Quechee". Located in Hartland, a fridge and a firepit are a couple of amenities on offer here.
  • Alternatively, book a weekend at "Cozy Tiny Home On Black River - Walk To Town". Situated in Wendtorf, this tiny abode comes with a nearby waterfront and a boat.

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

Select a lovely log cabin from the many scattered in or around Woodstock and you'll soon be inside your wooden sanctuary, wine in hand, relaxing next to a roaring fire. But adventure is just outside your front door too. These cabins promise a great mix of comfort and fun:

  • "Log Cabin Retreat On 40 Acres": This is an ideal base to try out some of the exciting outdoor activities on offer in the area, including mountain biking and hiking and biking.
  • "Cozy And Bright Log Cabin Just 8 Minutes From Okemo Mountain": After a busy day of trying out some local activities, such as snowmobiling and fishing, recharge your batteries at this cozy getaway.

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

We all deserve some "me time" every once in a while. If you're longing for a couple of uninterrupted mornings in bed with a good book and a steaming coffee, there's no shortage of fabulous weekend getaways in and near Woodstock. Here are two of our favorites:

  • "It's Foliage Season" is perfect for a couple of days of relaxation and fun. It comes with useful amenities, such as optional ski privileges and a fridge, and is located about 1 mile to the southwest of Woodstock.
  • Or, fling a few clothes in your suitcase and set out for "Quiet Vermont Winter Getaway". This top-rated getaway is around 9 miles west of Woodstock and features towels and a balcony.

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

Studio apartments are a simple yet stylish pick, ideally suited for one or two guests. Spend your days getting acquainted with your new surroundings and your nights kicking back in your comfy hideaway. These getaways in or near Woodstock are guaranteed to please:

  • Enjoy some time out on your own or take a few buddies along to "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations". You'll have plenty of amenities to make your stay comfortable, including pet-friendly services and internet services.
  • Another cool property is "It's Foliage Season". Don't be fooled by its modest size — this comfortable apartment is loaded with handy amenities like a boat, optional golf privileges and plenty more.

Can I find short term rentals in or near Woodstock?

Whether you need a cottage for you and a friend or a villa with space for the whole family, there's no shortage of short-term rentals in and around Woodstock. These retreats make the perfect base for a whirlwind visit:

  • For a wonderful night or two away, it's hard to beat "Cancellation Special 60% Off - Fabulous Log Home". It's near the center of Woodstock, along with countless things to see and do.
  • "Private And Affordable Country Living In Beautiful South Woodstock" is also ideally located. Put your feet up here and find out why lots of guests rate this property as one of their favorites.

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

Nothing says "I love you" like a romantic weekend trip. If you're eager to spend a couple of relaxing nights away with your other half, we've got some romantic getaways in and around Woodstock that will get your heart racing:

  • Put on some mellow music and chill together at "Savage Hart Farm Is A Small Sheep Farm With Guest Accommodations". Around 9 miles from Woodstock, this property has all you need for a romantic getaway, including winery tours and a restaurant dining guide.
  • "Vermont Hillside Cottage With Great View" is another retreat that's guaranteed to impress. It's about 25 miles from Woodstock and has a fireplace and air conditioning.

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

Take a look at these large group vacation rentals in or near Woodstock and forget about leaving anyone off your invite list:

  • A wide array of amenities including a kitchen and mountain views make "Quiet Vermont Winter Getaway" a favorite with groups. This expansive getaway has 4 bedrooms and sleeps up to 12 people. From the center of Woodstock, it's around 9 miles away to the west.
  • Invite as many as 12 of your best friends to "Cancellation Special 60% Off - Fabulous Log Home" and fill the place with laughter and love. This option has 6 bedrooms and is around 19 miles to the southwest of central Woodstock. It's crammed with features to keep a large group comfortable and content, including a fireplace and a kitchen.

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

Of all the conveniences a vacation rental can have, a pool delivers the most fun. Have a look at these houses for rent with a pool in or near Woodstock and spend your days splashing about. Just remember to take your inflatable unicorn:

  • Round up your crew and enjoy a memorable stay at "Romantic Guest House Hideaway". There's plenty to love about this escape apart from its pool, such as a nearby laundromat and a kitchen.
  • "Relax At The Vineyard House In Beautiful Woodstock" is the kind of place you go to get away from everything and enjoy your surroundings, starting with its awesome pool. A toaster and a kitchen are also on hand to make your visit as comfy as possible.

Woodstock has a humid continental climate, with average summertime temperatures hovering between 50 ºF and 75 ºF. But there's no need to wait until summer to visit! Take a look at the search bar at the top of the page and adjust the filters to find the ideal Woodstock vacation rental and plan your escape for whenever you like.

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

Whether you're traveling with the immediate family or you're bringing all your relatives along, family vacations spell fun. These large rentals in and around Woodstock have space for everybody — as well as everything you need to keep them happy:

  • About 9 miles west of Woodstock, "Quiet Vermont Winter Getaway" has 4 bedrooms and sleeps up to 12 guests. Some amenities here include towels and a DVD player.
  • "Cancellation Special 60% Off - Fabulous Log Home", around 19 miles to the southwest of central Woodstock, is also ideal for family gatherings. As many as 12 of your nearest and dearest can fit into this popular rental which features 6 bedrooms, a nearby laundromat, a stereo and more.

When you're ready to go sightseeing, there are lots of family-friendly attractions nearby to add to your to-do list. Buttermilk Falls is an excellent place to start.