Woodbury holiday lettings

We found 216 holiday rentals — enter your dates for availability

Discover a selection of 9 homes and other holiday rentals in Woodbury that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or just with your pet, you'll find the amenities that you need and want, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Woodbury

Showing deals for:14 Nov - 21 Nov

Image gallery for Fabulous year round waterfront retreat on Lake Waramaug

The house in peak Fall colors!
10 out of 10 rating
Exceptional
(6 reviews)

Fabulous year round waterfront retreat on Lake Waramaug

New Preston, CT

8% off
Price is £6,272
£896 per night
includes taxes & fees
Fabulous year round waterfront retreat on Lake Waramaug

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Woodbury

Find out more about Woodbury

Historical Woodbury will entice you

Enjoy the history and other features of Woodbury. This walkable city is known for its hiking, skiing and coffee shops. With a holiday 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 looking for top things to see and do in the area? Venture out of your holiday home and check out everything that makes Woodbury a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Sunset Meadow Vineyards (17.2 mi / 27.7 km)

Exploring the natural landscape of Woodbury

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

  • Lake Lillinonah (8 mi / 12.9 km)
  • Steep Rock Preserve (8 mi / 12.9 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)
  • White Memorial Conservation Center (12.4 mi / 20 km)

Travelling to and around Woodbury

The nearest airport is in Oxford, CT (OXC-Waterbury - Oxford), located 5.8 mi (9.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to 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 holiday rental?
When considering a holiday rental in Woodbury, Connecticut, the area around Main Street is particularly appealing. This charming neighbourhood offers a quaint, small-town atmosphere and is conveniently situated near several local attractions. Visitors can explore the historic Woodbury Museum, which showcases the town's rich heritage, or take a leisurely stroll through the picturesque parks that dot the landscape.

Another wonderful option is the area surrounding the scenic Hollow Park. This neighbourhood is known for its beautiful outdoor spaces and is a great choice for families and nature enthusiasts alike. The park features walking trails, picnic areas, and a lovely pond, making it an ideal spot for relaxation and recreation. There are numerous properties available in both of these areas, providing a variety of choices to suit different preferences and budgets.
How much does it cost to rent a holiday home in Woodbury?
Prices for holiday 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 holiday 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 holiday rental accomodation in Woodbury?
In Woodbury, holiday houses are the most popular rental option, with several available throughout the area. These homes typically feature spacious interiors, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as decks or patios, superb for enjoying the serene surroundings. Additionally, cottages are also a common choice, offering a quaint and charming atmosphere, often with unique architectural details and a cosy feel. Condominiums are available as well, providing modern amenities and convenient access to local attractions.
Are there any family house rentals in Woodbury?
In Woodbury, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for groups seeking a memorable getaway. This charming town is known for its picturesque landscapes and outdoor activities, with options ranging from spacious homes to cozy cottages.

Many of these properties come equipped with amenities such as full kitchens, allowing families to prepare meals together, as well as comfortable living rooms for relaxation after a day of exploring. Outdoor spaces often feature gardens or patios, superb for children to play or for family barbecues.
Can I rent a holiday home with a pool or hot tub in Woodbury?
In Woodbury, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque town, known for its scenic landscapes and charming rural atmosphere, offers a variety of options for travellers seeking a relaxing getaway. Many of these properties come equipped with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying sunny days and warm evenings. Inside, guests can expect modern amenities such as fully equipped kitchens, comfortable living spaces, and often additional features like fireplaces and game rooms.
Can I find long-stay holiday rentals in Woodbury?
A long-stay holiday rental in Woodbury is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Woodbury?
In Woodbury, Connecticut, there are several pet-friendly house rentals available, providing a comfortable and welcoming environment for both travellers and their furry companions. Many of these holiday homes come equipped with convenient amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.
Are there any remote work holiday rentals in Woodbury?
In Woodbury, Connecticut, there are several holiday rentals that cater to remote work needs. Many of these properties provide essential amenities such as Wi-Fi, dedicated desk spaces, and comfortable chairs to create an efficient workspace. Travellers can expect to find well-equipped homes that combine the comforts of modern living with a tranquil setting, ideal for focusing on work while enjoying a peaceful environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Woodbury holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Woodbury with parking available—perfect for families or travellers 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 holiday rental amenities typically include a range of conveniences to enhance guests' comfort. Most rentals come equipped with kitchens, allowing travellers to prepare their own meals with ease. Essential cookware, dishware, and utensils are also commonly provided, making it simple to dine in. Additionally, free Wi-Fi is available in many properties, ensuring guests can stay connected during their stay. Refrigerators are standard in these rentals, offering space for food and drinks, while stovetops are often included for cooking.
When is the best time to visit Woodbury for a holiday rental?
July is the most popular month to visit Woodbury, as families flock to the area to enjoy the warm weather and a variety of outdoor activities. This peak season runs from March to May, when the region blossoms with vibrant flora and offers numerous recreational opportunities, including hiking trails and scenic parks superb for picnics and exploration.

During July, visitors can expect pleasant temperatures, often reaching the high 20s Celsius, making it ideal for enjoying Woodbury's charming countryside and local attractions. The area's picturesque settings serve as a fantastic backdrop for outdoor events, farmers' markets, and community festivals that frequently take place during this lively season.

If you're looking for a more budget-friendly option, consider visiting in December. During this time, this month provides a unique opportunity to experience the festive spirit of the holiday season in a picturesque New England setting. Winter activities, such as snowshoeing or simply enjoying the serene landscape, can be quite enchanting.
How early should I book a Woodbury holiday rental?
Book your Woodbury holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Woodbury home rental booking on Vrbo?
To find Woodbury holiday 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Woodbury holiday 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.

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