Woodbury vacation rentals

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Discover a selection of 9 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.

Holiday rentals with weekly discounts - Woodbury

Showing deals for:Aug 14 - Aug 21

Image gallery for Litchfield County Four Season Country Paradise

Front entrance with gate for privacy
9.4 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)

Litchfield County Four Season Country Paradise

Roxbury

9% off
Price is $1,369
$9,581 for 7 nights
All fees included
Litchfield County Four Season Country Paradise

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Find out more about Woodbury

Why visit Woodbury

  • Outdoor Adventures: Woodbury is a haven for outdoor enthusiasts with its beautiful state parks, lakes, and urban parks.
  • Charming Neighborhoods: Explore vibrant downtown areas and the picturesque Litchfield Hills for a quaint experience.
  • Family-Friendly Activities: Enjoy a range of activities suitable for all ages, making it perfect for family vacations.
  • Cultural Experiences: Immerse yourself in local history and the welcoming atmosphere of the community.
  • Variety of Accommodations: Choose from luxury homes, cozy cottages, and modern apartments for a comfortable stay.

Popular types of accommodation in Woodbury

Planning a getaway to Woodbury? Discover the perfect place to stay with our selection of popular accommodations, including houses, cozy cottages, and modern apartments. Whether you're looking for a townhouse rental in Woodbury, CT, or nearby options, we have you covered. Don’t forget to check out the local Woodbury Library for a glimpse of the community's charm. Your ideal vacation rental awaits.

  • Houses: The top choice for travelers in Woodbury, offering spacious and comfortable living for families, groups, or couples seeking a homey atmosphere.
  • Cottages: A charming retreat option, perfect for those wanting a cozy, rustic experience surrounded by nature.
  • Apartments: A convenient option for solo travelers or couples, providing easy access to local amenities.
  • Villas: Luxurious accommodations that offer upscale living and stunning views for a memorable getaway.
  • Cabins: A popular choice for nature lovers, providing a peaceful escape in a woodland setting.**

Top attractions in and around Woodbury

Woodbury, Connecticut, is perfect for outdoor enthusiasts and couples seeking a scenic getaway. With a variety of attractions including state parks, lakes, and urban parks, visitors can enjoy family-friendly activities and cultural experiences. Whether you're exploring the natural beauty or immersing yourself in the local culture, Woodbury offers something special for every traveler looking to unwind and connect with nature.

  • Quassy Amusement Park: A family-friendly amusement park featuring thrilling rides, water attractions, and classic arcade games, Quassy is perfect for a fun-filled day. Enjoy the outdoor adventure atmosphere with attractions suitable for all ages, making it an ideal place for families and friends.
  • Candlewood Lake: This stunning lake offers beautiful beaches and picturesque scenery, perfect for swimming, picnicking, or simply relaxing by the water. Enjoy romantic sunsets and outdoor activities in a tranquil setting that invites you to unwind and connect with nature.
  • Glebe House Museum and The Gertrude Jekyll Garden: Explore rich local history at this charming museum, showcasing period furnishings and artifacts. The beautifully landscaped garden, designed by renowned horticulturist Gertrude Jekyll, offers a serene experience, perfect for culture enthusiasts and garden lovers alike.

Things to do recommended for couples

For a romantic getaway in Woodbury, consider hitting the slopes at Woodbury Ski Area for some winter fun. Savor exquisite wines at Hopkins Vineyard, just 13 miles away, or enjoy a playful round at The Cave mini-golf, also 13 miles from town. Perfect for couples.

Things to do recommended for families

Your family will love exploring Kettletown State Park for relaxation and outdoor fun, or enjoying thrilling games at Crystal Bees. Don't miss Hubbard Park for a peaceful day in nature, all within a short drive from Woodbury.

Things to do recommended for groups

In Woodbury, groups can enjoy shopping at the Pilgrim Mall Shopping Center, explore the Elephant's Trunk Flea Market nearby, and catch a show at the Palace Theatre for a mix of culture and entertainment. It's a perfect blend of local vibes for an unforgettable experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Woodbury

If you're traveling with a group, family, or pets, or if you're seeking extended stays, it's important to prioritize your filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Woodbury with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, Vrbo allows you to filter for all these options and many more.
  • Traveling to Woodbury with young kids: Traveling with small children can present its own set of challenges. It's important to prioritize their comfort and safety, along with providing age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Woodbury: For many, a family vacation feels incomplete without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Woodbury: If you're in search of vacation rentals that offer special rates for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Woodbury

Woodbury, Connecticut, offers a delightful blend of outdoor adventures and romantic scenery, perfect for travelers seeking family-friendly experiences. Explore the charming neighborhoods, including vibrant downtown areas and the picturesque Litchfield Hills. With options for luxury homes and cozy apartments, you'll find the ideal spot to unwind. Whether you’re indulging in local history or enjoying the friendly atmosphere, Woodbury promises a memorable getaway filled with unique vibes and beautiful surroundings.

  • Waterbury: Located 9 miles from Woodbury, Waterbury is a vibrant city known for its family-friendly atmosphere and outdoor adventures. Visitors can enjoy a range of activities, from exploring local amusement parks to relaxing at resorts. Highlights include popular landmarks such as a large event conference venue, a thrilling theme park, and a fun-filled waterpark. With its rich history and diverse attractions, Waterbury offers something for everyone, making it an ideal spot for a day trip or weekend getaway.
  • Southbury: Just 5 miles from Woodbury, Southbury is a charming city that caters to families, couples, and outdoor enthusiasts alike. Known for its picturesque lakes and scenic parks, Southbury provides ample opportunities for recreation and relaxation. Visitors can explore various attractions, including amusement parks and water parks, as well as the local event conference venue and theme park. The romantic ambiance and friendly community make Southbury a delightful destination to unwind and appreciate nature.
  • Middlebury: Only 4 miles away from Woodbury, Middlebury is a quaint city that combines outdoor fun with family adventures. Known for its recreational areas and beautiful lakes, this destination is perfect for those who love spending time in nature. Visitors can indulge in exciting activities at the local amusement park and water park, or simply enjoy the peaceful surroundings. Middlebury's close proximity to Woodbury makes it an excellent choice for a quick escape filled with adventure and charm.

Best time to go to Woodbury

If you're planning a trip to Woodbury, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and July, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.2°F (-2.1°C)Light RainMostly SunnyModerately LowSlightly Low
February29.8°F (-1.2°C)Light RainMostly CloudyModerately LowAverage
March37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly Low
April48.4°F (9.1°C)Light RainMostly SunnyModerately HighSlightly Low
May59.0°F (15.0°C)Light RainMostly SunnyModerately HighAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.9°F (23.3°C)Light RainMostly SunnyModerately HighSlightly High
August72.1°F (22.3°C)Light RainMostly SunnyAverageSlightly High
September65.1°F (18.4°C)Light RainMostly SunnyAverageAverage
October54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December34.3°F (1.3°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often yield significant savings. To help you discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you plan your travels seamlessly. Here, you can create new trips, refine your existing plans, and manage your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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)
  • Mount Southington Ski Area (14.9 mi / 24 km)
  • Lake Compounce (16 mi / 25.8 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:

  • Steep Rock Preserve (8 mi / 12.9 km)
  • Holy Land USA (9.2 mi / 14.9 km)
  • Beacon Falls Town Recreation Field (9.8 mi / 15.8 km)
  • Mount Tom State Park (10.9 mi / 17.6 km)
  • Bantam Lake (11.1 mi / 17.8 km)
  • Candlewood Lake (13 mi / 20.9 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 best area to stay in Woodbury, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in Woodbury, Connecticut, the best area to stay in is the charming downtown neighborhood. This area is known for its picturesque landscape and quaint atmosphere, making it a delightful spot for visitors. You'll find a variety of properties to choose from, ensuring there's something to suit your taste and budget.

Staying in downtown Woodbury gives you easy access to some of the town's top attractions. One highlight is the historic Woodbury Village, where you can explore unique shops and local boutiques that reflect the town's character. Additionally, the nearby Hollow Park offers beautiful walking trails and scenic picnic spots, superb for enjoying the outdoors.
How much does it cost to rent a vacation home in Woodbury?
Prices for vacation rentals in Woodbury vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Woodbury to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Woodbury vacation house rentals?
You can find great discounts on house rentals in Woodbury on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Woodbury?
In Woodbury, vacation houses are the most popular type of rental, with several available throughout the area. These homes typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Additionally, cottages and cabins are also quite common, offering a quaint and rustic charm. Many of these properties are situated near scenic spots, allowing guests to enjoy the natural beauty of Woodbury.
Are there any family house rentals in Woodbury?
In Woodbury, Connecticut, there are several family-friendly house rentals available. This charming town features spacious homes that cater well to families, often providing amenities like full kitchens, comfortable living rooms, and large backyards for outdoor play. Many properties also include conveniences such as Wi-Fi and laundry facilities, ensuring a pleasant stay for all ages.

Visitors can explore the nearby Woodbury Common Premium Outlets for shopping or take advantage of the many parks and recreational areas in the vicinity. The scenic beauty of the Litchfield Hills offers a superb backdrop for outdoor activities like hiking and biking.
Can I rent a vacation home with a pool or hot tub in Woodbury?
In Woodbury, Connecticut, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers looking to relax and enjoy their stay. This picturesque town is known for its scenic landscapes and charming rural atmosphere, providing a peaceful backdrop for a getaway. Expect amenities such as private pools, hot tubs, and outdoor spaces great for entertaining or unwinding after a day of exploring. Many properties also come equipped with full kitchens and comfortable living areas, ensuring a convenient and enjoyable experience for guests.
Can I find long-stay vacation rentals in Woodbury?
A long-stay vacation rental in Woodbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Woodbury?
In Woodbury, Connecticut, there are several pet-friendly house rentals available that cater to travelers with furry companions. Many of these properties offer spacious layouts with amenities such as fully equipped kitchens, laundry facilities, and outdoor areas where pets can play and relax.

The town is surrounded by beautiful natural scenery, including hiking trails and parks that are superb for outdoor activities with pets. Nearby, the Woodbury Town Park provides open spaces and walking paths, making it an ideal location for pet owners to enjoy leisurely strolls. Additionally, the charming rural atmosphere of Woodbury allows for a peaceful retreat while still being accessible to local shops and restaurants. See all pet-friendly rentals in Woodbury.
Are there any remote work vacation rentals in Woodbury?
In Woodbury, Connecticut, there are several vacation rentals that cater to remote work needs. Many properties in the area come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable desk chairs, making them suitable for those looking to balance work and leisure. The serene surroundings of Woodbury provide a peaceful environment for productivity, while also allowing for easy exploration of local parks and scenic spots. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Woodbury vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Woodbury with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Woodbury?
In Woodbury, popular vacation rental amenities include kitchens, fireplaces, and outdoor spaces such as decks or patios. Many properties offer a homey atmosphere, allowing travelers to prepare their own meals and enjoy cozy evenings by the fire. Additionally, some rentals feature dedicated workspaces or desks, making them suitable for remote work or study.
When is the best time to visit Woodbury for a vacation rental?
The best time to visit Woodbury for a vacation rental is during the peak season from March to May, when the area comes alive with vibrant spring blooms and outdoor activities. As temperatures rise from the low 40s to mid-70s Fahrenheit, this season offers a superb climate for enjoying scenic hikes and exploring the charming town.

In May, particularly, visitors can revel in the beauty of the surrounding landscapes, including the picturesque parks and trails that showcase the region's natural splendor. This month is ideal for outdoor enthusiasts looking to engage in activities like biking and hiking, while also experiencing local festivals and events that celebrate the arrival of spring.

For travelers seeking a more budget-friendly option, December presents a unique opportunity. While it is considered the low season, the holiday decorations and cozy atmosphere create a delightful backdrop for winter getaways. Visitors can enjoy local shops, festive events, and the warmth of a quaint B&B, all while avoiding the summer crowds.
How early should I book a Woodbury vacation rental?
Book your Woodbury vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woodbury, Connecticut, United States of America?
In Woodbury, Connecticut, visitors can explore a variety of attractions that highlight the area's rich history and natural beauty. The historic Main Street, lined with charming shops and cafes, is a great place to start, offering unique local goods and a taste of the town's character. The Woodbury Historical Society provides insights into the town's past, showcasing artifacts and hosting events throughout the year.

Outdoor enthusiasts will appreciate the scenic landscapes in the area, particularly at the nearby Flanders Nature Center, which features trails for hiking and opportunities for birdwatching. For those interested in arts and culture, the Woodbury Ballet is a local gem, often presenting performances and community events.

Additionally, the town is close to the picturesque Lake Quassapaug, where visitors can enjoy seasonal activities like swimming, fishing, and picnicking.
Can I change or cancel my Woodbury home rental booking on Vrbo?
To find Woodbury vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Woodbury vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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