Discover a selection of 19 vacation rentals in Woodstock, VA 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 $108 per night, and houses and cabins 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

Why people love visiting friendly Woodstock

Experience the unique character of Woodstock with a stay in a vacation home rental. Travelers to this welcoming city praise the restaurants, shopping and hiking. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Things to do

Activities and attractions in Woodstock

Are you searching for top things to see and do while you're in the area? Venture out of your vacation home and experience everything that makes Woodstock a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Bryce Ski Resort (14.8 mi / 23.8 km)
  • The Garden Maze at Luray Caverns (15 mi / 24.1 km)
  • Yogi Bear's Jellystone Park (15.7 mi / 25.3 km)
  • Shenandoah Vineyards (3.8 mi / 6 km)
  • Cave Ridge Vineyard (9.8 mi / 15.8 km)
  • Mt Jackson Thrift & Gift (12 mi / 19.2 km)
Natural features

Exploring the natural landscape of Woodstock

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Woodstock is a great place to get outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Luray Caverns (15.1 mi / 24.3 km)
  • Massanutten Storybook Trail (10.6 mi / 17.1 km)
  • Shenandoah River State Park (11.1 mi / 17.9 km)
  • Shenandoah Caverns (14.5 mi / 23.3 km)
  • Skyline Caverns (15.6 mi / 25.1 km)
  • Front Royal Entrance Shenandoah National Park (16.9 mi / 27.2 km)
How to get there

How to get to and around Woodstock

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 47.7 mi (76.8 km) from the city center.

What are the top vacation rentals in or near Woodstock?

Whatever vacation experience you're seeking, you'll find a rental in or around Woodstock that's a match made in heaven. These are some of our favorites:

  • Around 12 miles from the center of Woodstock, you'll want to keep coming back to "Mountain Views~ 3 King Master Suites". It has 3 bedrooms and handy features including a washing machine and a garden.
  • Alternatively, unpack your bags at "Unique Massanutten Lodge, Hot Tub". Located around 35 miles from the heart of Woodstock, it has 5 bedrooms and comes with towels and an ice maker.

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?

For an unconventional experience, book one of Vrbo's tiny house rentals in Woodstock. A word of warning though — after you've stayed in a tiny house, the temptation to move into one of thes cute-as-a-button digs will be hard to resist!

  • Take a few days off to recharge at "New 2022 Charming, Comfortable Tiny Home With Great Views Of Farm". Located in Lagoa e Carvoeiro, a garden and an ice maker are just a couple of the amenities you can expect here.
  • Alternatively, book a weekend away at "Charming Tiny Home With Fire Pit On 25 Acre Historic Farm". Situated in Purcellville, this tiny gem comes with a hair dryer and a blender.

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

You can. From rustic hideaways to high-end escapes, you'll find a great range of log cabins to rent in or near Woodstock. If you're chasing adventure, here's where you can go:

  • "Log Cabin For Couples And Family In The Shenandoah Valley": Enjoy a week or so relaxing at this fabulous escape nestled in nature. Once you feel refreshed, enjoy cycling or mountain biking, which are some of the fun activities in this area.
  • "Highland Nest - Log Cabin - Stunning Mountain Views To National Forest": Spend your much needed break enjoying all the conveniences of this property. When it's time for some fresh air, hiking and biking and fishing are waiting for you.

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

Nothing tops a brief break to dust away the cobwebs. Pack your overnight bag and get comfy in one of these sought-after weekend getaways in and around Woodstock:

  • Located 25 miles to the south of the center of Woodstock, "Cabin - The Great Escape - Near Everything Yet Off The Beaten Path" is popular with nature buffs and adventurous types. Get out and discover nearby outdoor attractions, including Doyles River Falls and Back Home on the Farm. If you're up for some fun activities, try skiing or snowboarding.
  • Alternatively, enjoy a rejuvenating getaway at "Cabin - River Woods Retreat - Rustic Luxury In The Shenandoah Valley". Stay in and enjoy its creature comforts, or head out for some cross-country skiing and sledding. When it's time to discover more of the area, check out Yogi Bear's Jellystone Park and Elkwallow Picnic Area. This fantastic vacation rental is around 12 miles east of Woodstock.

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

Discover the culture of Woodstock from the comfort and privacy of a studio apartment. Whether you'd like to unwind on your own or have some fun with pals, we'll help you find the ideal studio apartment in or near Woodstock:

  • Make "Secluded, Cozy Cottage In The Shenandoah Valley" your home for a couple of days or more. This wonderful property comes with amenities including cable/satellite TV services and winery tours.
  • Alternatively, switch to vacation mode at "Solitude" Spectacular 1 Bedroom Cabin W", which comes with conveniences such as heating and a washing machine.

When it's time to step foot outside your studio apartment and explore, there's loads to keep you amused around Woodstock. Interested in culture? Organize a visit to Maier Museum of Art and J Fergeson Gallery.

Can I find short term rentals in or near Woodstock?

From modern studio apartments to huge vacation homes, Vrbo has your whirlwind escape sorted. Here are some of our top picks in and around Woodstock:

  • Within close reach of central Woodstock, "Mountain View 65 Acre Private Retreat Pool Hot Tub Wineries Charlottesville" welcomes short-term guests. When you're not enjoying your comfortable digs, get out and explore all the cool stuff around you.
  • Another great option is "Charming Cottage In Horse Country Near Blue Ridge". Round up your crew and enjoy a comfy stay close to the heart of Woodstock.

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

Forget chocolates and roses. Sometimes all you need is to escape for the weekend, just you and your sweetheart. At Vrbo, we've got romantic getaways in and around Woodstock that would make Cupid green with envy. Here are some to tempt you:

  • Located around 12 miles from Woodstock, "Mountain Views~ 3 King Master Suites" is the ideal place for lovestruck couples. Winery tours and a fireplace are among the many amenities here.
  • Another place where you can enjoy a few precious days together is "Stunning Family/friends Retreat". Located 30 miles from Woodstock, a fireplace and winery tours add to the ambiance here.

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

Big groups mean big fun. They also mean finding a place that'll comfortably fit your entire squad. Browse our large group vacation rentals in or around Woodstock and spend time with your favorite people under the one roof:

  • You'll have loads of space to move around at "Stunning Family/friends Retreat". Around 30 miles southeast of Woodstock, this welcoming property has 6 bedrooms sleeping up to 18 guests. Quality amenities include a garden and mountain views.
  • "Spotted Fawn Cabin - Serenity And Luxury Await You" is another awesome option. It's around 25 miles to the south of Woodstock, has 3 bedrooms and welcomes up to 12 guests. A kitchen and a fireplace are just a couple of things that'll help make your group getaway more comfortable.

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

Of all the amenities a vacation rental can have, a pool is without a doubt the most fun. Take a peek at these houses for rent with a pool in or near Woodstock and spend your days splashing about. Just don't forget your inflatable flamingo:

  • Pack your swim gear and get away with your gang to "Wow - Such A Delight Best Describes Your Experience At The Miller House". There are plenty of other great amenities here, including a living room and a dishwasher.
  • Spend leisurely vacation days splashing about or finding some peaceful moments by the water at "Spacious Log House At Bryce Resort On Blue Ridge Mountains". This property is another top pick and offers childrens activities, cable/satellite TV services and more.

Woodstock has a humid subtropical climate, with average summertime temperatures hovering between 55 ºF and 85 ºF. But you don't have to wait until summertime to visit. Take a look at the search bar at the top of the page and adjust the filters to find the perfect Woodstock vacation rental and organize your getaway for whenever you like.

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

No matter if your idea of the perfect escape is up in the mountains or near the beach, you'll enjoy it even more if you share it with loved ones. Consider one of these large family vacation rentals in or near Woodstock and bring the whole gang along:

  • Around 30 miles to the southeast of Woodstock, "Stunning Family/friends Retreat" has 6 bedrooms and can sleep up to 18 guests. It's equipped with a range of amenities, including a porch and a toaster.
  • "Studio - Budget - Shower - Garden View" also offers the space you need to connect with loved ones. This option is around 25 miles to the southwest of central Woodstock and accommodates 8 guests in its 3 bedrooms. A DVD player and a nearby laundromat will help keep everyone comfortable.

When it's time to get out and explore, there are lots of family-friendly attractions in the area to keep everyone entertained and happy. The Adventure Park at Sandy River Retreat, Amazement Square and AMF Lynchburg Lanes should be at the top of your list.