Woodbury holiday homes, CT, USA: holiday houses & more

Discover a selection of 8 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:18 Jul - 25 Jul

5,100 Sq. Ft. Swiss Chalet-sixteen beautiful, private acres-Perfect for Holidays

Exceptional

(9 reviews)

Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

Watertown, CT

8% off

NZ$2,440 per night

includes taxes & fees

Exceptional

(11 reviews)

Waterfront modern cottage. Great getaway- summer retreat under 2 hours from NYC!

Bethlehem, CT

7% off

NZ$646 per night

includes taxes & fees

Exceptional

(20 reviews)

Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!

Roxbury, CT

12% off

NZ$363 per night

includes taxes & fees

Wonderful

(5 reviews)

The Overlook near South Farms in Litchfield County is Hospitality, integrated.

Morris, CT

8% off

NZ$416 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Woodbury

Climbing roses and wisteria frame the covered porch.

Large, Sunny 4 Bedroom Home Sleeps 8 and 1 minute to Five Fabulous Restaurants

Sleeps 8 · 4 bedrooms · 2+ bathrooms

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, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

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)
Lake Compounce (16 mi / 25.8 km)
Connecticut Valley Winery (20.6 mi / 33.2 km)
Mohawk Mountain Ski Area (20.7 mi / 33.4 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:

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)

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 most popular type of holiday home accommodation in Woodbury?

Houses are the most popular kind of holiday home in Woodbury, according to our data. Even if you have a different idea about what you want, Bookabach has properties in many shapes and sizes. Look over our options to find your perfect match.

How much does it cost to rent a holiday home in Woodbury?

Length of stay, property type and season are some things that can affect the price of a holiday home. Simply click on your dates of travel to find your dream escape. From homey country cottages to plush villas, all Bookabach holiday homes offer unbeatable value.

How much does it cost to rent a beach house in Woodbury?

When you travel and the style and size of the property will help determine the cost of your beachside stay. Type in your Woodbury travel dates to see your options on Bookabach. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use our filters to select the features and amenities you want in your home.

Are there pet-friendly holiday homes in Woodbury?

With eight holiday homes that allow pets, your furry friend can join in the fun on your Woodbury holiday. Use the filter tool to browse our pet-friendly holiday homes and find a stay that’ll set tails wagging on Bookabach.

Can I rent a house with a pool in Woodbury?

Add a whole other level of fun to your adventure by booking your family into one of the two houses with a private pool in Woodbury. Use our search filter to find properties with pools on Bookabach, then spend leisurely days playing and splashing in a swimming pool that’s all yours.

What are popular home amenities in Woodbury?

When it comes to home amenities that guests are searching for in Woodbury, a fireplace, a firepit and a swimming pool rank the highest. With Bookabach holiday homes, you’ll enjoy options to match your taste and style, whether you’re holidaying with family, friends or even pets.

Are there large group holiday homes in Woodbury?

Take your pick of six Bookabach holiday properties in Woodbury that can accommodate a group of five or more guests. You’ll enjoy all the room and privacy you need to have fun with your nearest and dearest — and nobody else.

Are there holiday homes in Woodbury that welcome kids?

Gather your whole crew for an adventure in Woodbury at one of our eight family-friendly properties. A lot of these stays feature conveniences that are ideal for getaways with the kids, including laundry facilities, living rooms and entertainment units. Just check the “Properties good for families” filter box and select your favourite.

What are the top attractions for families in Woodbury?

Treat the kids to a day out at these top family-friendly attractions in Woodbury:

Pilgrim Mall Shopping Centre
Woodbury Ski Area

Are there holiday homes with WiFi in Woodbury?

You’ll find four holiday homes with WiFi in Woodbury. If you want to disconnect from daily life on your trip, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Bookabach.

How can I find holiday homes with air conditioning in Woodbury?

You’ll have a choice of eight Bookabach holiday homes with air conditioning in Woodbury providing that gentle, cool breeze and extra touch of comfort. Simply enter your chosen travel dates and then take advantage of our filters to find properties with air conditioning.

How old do you have to be to rent a holiday home in Woodbury?

The minimum age allowed can vary across properties on Bookabach, so be sure to look at the rules of the holiday home in Woodbury you’re considering. But normally, it’s 16, 18 or 21.

How long can I rent a holiday home in Woodbury for?

The length of time you can rent a holiday home in Woodbury differs according to the property. Just enter your desired travel dates to view a list of options offering extended stays. With tons of amenities such as washing machines and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to get a terrific place to call your home away from home in Woodbury.