Woodbury vacation rentals

We found 215 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in Woodbury that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Woodbury

Showing deals for:Aug 22 - Aug 29
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Historic Woodbury will entice you

Enjoy the history and other features of Woodbury. This walkable city is known for its hiking, skiing and coffeehouses. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Woodbury

Are you hoping to discover attractions to visit in the city? Venture out of your vacation home and experience everything that makes Woodbury a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Quassy Amusement Park (3.3 mi / 5.3 km)
  • The Christmas Shop (6.3 mi / 10.2 km)
  • Hopkins Vineyard (13.4 mi / 21.5 km)
  • Lake Compounce (16 mi / 25.8 km)
  • Richter Park Golf Course (18.4 mi / 29.6 km)
  • Connecticut Valley Winery (20.6 mi / 33.2 km)

Exploring the natural landscape of Woodbury

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

  • Hop Brook Lake (7.4 mi / 11.9 km)
  • Lake Lillinonah (8 mi / 12.9 km)
  • Steep Rock Preserve (8 mi / 12.9 km)
  • Bantam Lake (11.1 mi / 17.8 km)
  • Lake Zoar (11.8 mi / 19 km)
  • White Memorial Conservation Center (12.4 mi / 20 km)

Traveling to and around Woodbury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 5.8 mi (9.4 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Danbury, CT (DXR-Danbury Municipal), which is 18.6 mi (30 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Woodbury?
The most popular types of vacation rentals in Woodbury are cottages. Ready for more choices? Vrbo has many options to match our guests’ unique requirements, so you’ll see vacation homes in loads of shapes and sizes. The perfect home away from home is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in Woodbury?
Length of stay, property type and time of year are some of the things that can influence the price of a vacation home. Simply add your travel dates to find your perfect fit. From comfy cabins to plush villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Woodbury?
Prices for beach houses in Woodbury will vary depending on the size and type of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use the filters to tailor your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Woodbury?
Pack up a suitcase for your pooch because Woodbury has eight vacation homes that open their doors to pets. Let your furriest friend enjoy the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates and destination, then check the “Pets allowed” filter box.
Can I rent a house with a pool in Woodbury?
Add another level of fun to your getaway by staying in one of the two houses with a private pool in Woodbury. Use our search filter to find properties with pools on Vrbo, then spend your downtime splashing about in a swimming pool that’s exclusively for you.
What are popular rental amenities in Woodbury?
A swimming pool, a firepit and a fireplace are the most popular rental amenities in Woodbury. Whether you plan to travel solo, with your better half or as a family group, Vrbo can help you find a vacation home that fits your style with all the options you need.
Are there large group vacation rentals in Woodbury?
Take your pick of seven Vrbo vacation rentals in Woodbury that can host five or more people. You’ll get all the privacy and room you need to spend time with the people you’re vacationing with — and no one else.
Are there vacation rentals in Woodbury that welcome kids?
Bring the whole family together for a fun-filled adventure in Woodbury at one of our eight family-friendly vacation homes. Many of these stays offer amenities that are ideally suited to getaways with the little ones, including kitchens, bunk beds and private pools. Simply check the “Properties good for families” filter and choose your favorite option.
What are the top attractions for families in Woodbury?
You’ll find loads of fun things to see and do with the family in Woodbury, including:

  • Woodbury Ski Area
  • Pilgrim Mall Shopping Center
  • Glebe House Museum and The Gertrude Jekyll Garden

Are there vacation rentals with WiFi in Woodbury?
Woodbury has four vacation rentals with WiFi, so you can stay connected during your trip. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to sending emails, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Woodbury?
Woodbury has eight vacation rentals where you’ll be able to unwind in air-conditioned comfort. To book a property on Vrbo that comes with this perk, enter your preferred travel dates and use the handy filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Woodbury?
The age limit can vary across properties on Vrbo, so double-check the rules of the vacation rental in Woodbury you’re interested in. But typically, it’s 16, 18 or 21.
How long can I rent a vacation rental in Woodbury for?
The amount of time you can book a Woodbury vacation rental for is down to the property. Just enter your preferred travel dates to view available options offering extended stays. They come with the things you need to make your extended trip more convenient and enjoyable, like kitchens and air conditioning. Some vacation homes may also offer discounted weekly or monthly prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Woodbury?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to find some fabulous bargains and discounts on Vrbo. From weekend trips to extended vacations, we’ve got the perfect space for your next Woodbury escape.

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