Woodbury vacation rentals

We found 212 vacation rentals — enter your dates for availability

Discover a selection of 7 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:Apr 24 - May 1

Image gallery for Nature & Luxury @Lavender Lake Est (Kosher optional)

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Nature & Luxury @Lavender Lake Est (Kosher optional)

Roxbury

13% off
Price is $1,156
$8,094 for 7 nights
All fees included
Nature & Luxury @Lavender Lake Est (Kosher optional)

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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.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire reservation. Being the planner certainly has its perks. When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on eligible bookings. Sign up today and begin enjoying the savings.

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)
  • 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)
  • Lake Zoar (11.8 mi / 19 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 when booking a vacation rental?
When planning a vacation rental in Woodbury, Connecticut, the best area to consider is the quaint and picturesque downtown region. This charming neighborhood is known for its historic buildings and inclusive setting, making it a delightful spot to enjoy local shops, cafes, and restaurants. A stay here puts you within walking distance of attractions like the Woodbury Museum, where you can explore local history and culture, and the scenic Hollow Park, great for a leisurely stroll or a picnic.

Another appealing option is the area around the scenic Lake Quassapaug. This part of Woodbury offers a more serene setting, with vacation rentals often featuring beautiful views and easy access to outdoor activities. The lake itself is ideal for swimming, fishing, and enjoying nature, making it a great retreat for families or anyone looking to unwind.

In terms of available properties, both neighborhoods typically offer a variety of vacation rentals, ranging from cozy cabins to spacious homes, providing ample choices to suit different preferences and group sizes.
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 properties typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces like patios or gardens, making them ideal for families or larger groups. Additionally, there are several cottages that provide a charming and cozy atmosphere, often set in picturesque locations that offer a rustic feel. Condos and villas are also available, suiting travelers looking for a more upscale experience, with amenities such as pools, fitness centers, and modern furnishings.
Are there any family house rentals in Woodbury?
In Woodbury, Connecticut, there are several family-friendly vacation rentals available, making it an excellent choice for those traveling with children. The area is known for its picturesque landscapes and charming small-town atmosphere. Many homes feature spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy some fresh air. Amenities like Wi-Fi and laundry facilities are often included to enhance convenience during your stay.

Visitors can explore nearby attractions such as the scenic Lake Quassapaug, great for swimming and picnicking, or the historic town center, which offers quaint shops and local dining options. Additionally, the surrounding countryside provides opportunities for hiking and enjoying nature.
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, suiting travelers seeking relaxation and leisure. This charming town, known for its picturesque landscapes and rural charm, offers a variety of amenities in these rentals. Many properties come equipped with private pools, hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens for convenient meal preparation.

The surrounding neighborhoods provide a tranquil atmosphere, great for unwinding after a day of exploration. Visitors can enjoy local attractions such as parks, hiking trails, and historical sites, making it an ideal destination for both relaxation and outdoor activities.
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 for travelers looking to enjoy a comfortable stay with their furry companions. Many of these rentals feature amenities such as spacious yards, allowing pets to roam and play freely. Expect well-equipped kitchens, cozy living areas, and outdoor spaces like decks or patios where you can relax and unwind after a day of exploring.

Woodbury's picturesque surroundings provide a tranquil environment with access to parks and nature trails, ideal for pet owners. Nearby, the scenic Lake Quassapaug offers opportunities for outdoor activities, and the area is dotted with local shops and cafes that welcome pets, enhancing the overall experience for those traveling with animals.
Are there any remote work vacation rentals in Woodbury?
In Woodbury, Connecticut, there are several remote work vacation rentals available, making it a suitable destination for those looking to blend work and leisure. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi and dedicated workspaces, including desks and comfortable chairs, allowing for a productive environment.

The town is surrounded by picturesque landscapes and offers a serene atmosphere, ideal for unwinding after a day of work. Travelers can also explore local attractions, including beautiful parks and nature reserves, which provide opportunities for outdoor activities. 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 essential features that enhance the comfort and convenience of your stay. Most rentals come equipped with WiFi, allowing guests to stay connected during their visit. Kitchens are a common amenity, providing the flexibility to prepare meals and enjoy dining in a home-like setting. Many properties also offer patios, which are superb for relaxing outdoors and enjoying the scenic views of the Connecticut countryside. Additional amenities often include blenders for smoothies or other beverages, as well as coffee and tea makers for that morning boost.
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. This season is particularly popular among travelers seeking outdoor adventures, as the weather begins to warm up and the landscape comes alive with vibrant spring blooms. During these months, visitors can enjoy a variety of activities, from hiking the picturesque trails of the nearby Litchfield Hills to exploring the charming local shops and eateries in town.

In July, Woodbury experiences a lively atmosphere with many outdoor events and festivals, making it an ideal time for those who thrive on community activities and social engagements. The temperatures typically range from the mid-60s to the low 80s Fahrenheit, superb for exploring the scenic beauty of the area while enjoying the warmer weather.

For those looking for a more budget-friendly option, December can be an attractive choice. While this month marks the low season, it offers a unique charm with the holiday festivities and lovely winter landscapes. Visitors can revel in the serene beauty of Woodbury, which can be a wonderful time for cozy gatherings or a peaceful retreat.

Ultimately, your ideal time to visit Woodbury will depend on whether you prefer the vibrant energy of spring and summer or the tranquil beauty of winter.
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?
In Woodbury, visitors can explore a range of attractions that highlight the town's charm and natural beauty. The historic Main Street features quaint shops, antique stores, and cozy cafes, superb for leisurely strolls. Close by, the Woodbury Ski Area offers winter sports for outdoor enthusiasts seeking seasonal activities.

For nature lovers, the nearby Flanders Nature Center provides picturesque trails for hiking and birdwatching, showcasing the area's rich wildlife and scenic landscapes. The town also hosts events throughout the year, such as craft fairs and farmers' markets, which reflect the local culture and community spirit.

Additionally, the Woodbury Reservoir is a great spot for fishing and kayaking, offering a tranquil escape.
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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