Destination guide

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.

Things to do

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)
  • 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)
  • Mohawk Mountain Ski Area (20.7 mi / 33.4 km)
Natural features

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:

  • Glebe House Museum and The Gertrude Jekyll Garden (0.4 mi / 0.7 km)
  • Southford Falls State Park (6.7 mi / 10.8 km)
  • Hop Brook Lake (7.4 mi / 11.9 km)
  • Lake Lillinonah (8 mi / 12.9 km)
  • Steep Rock Preserve (8 mi / 12.9 km)
  • Holy Land USA (9.2 mi / 14.9 km)
How to get there

Traveling to and around Woodbury

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 25.2 mi (40.5 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Oxford, CT (OXC-Waterbury - Oxford), which is 5.8 mi (9.4 km) away.

What are the top vacation rentals in or near Woodbury?

Whatever you're seeking in a vacation, you'll find a rental property in or around Woodbury that's perfect for you. Why not try these on for size?:

  • Around 17 miles from the center of Woodbury, it's hard to top "Waterfront Lake Home On Tranquil Harwinton Lake With Spectacular 180⁰ View". It has 2 bedrooms and a range of amenities including a nearby waterfront and heating.
  • "Charming Lakefront Cottage; Boat" also promises a memorable escape, offering 2 bedrooms, a TV, a fridge and more. It's around 35 miles from Woodbury.

For even more great options, use the search bar at the top of the page to find the perfect Woodbury vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Woodbury?

If you've been busier than a squirrel in a nut factory, you deserve a break for a few glorious days. Leave work early on Friday and make your way to one of these weekend getaways in or near Woodbury:

  • "New Updated 200 - Yr - Old Home W" is perfect for a weekend of enjoyment and rest. It features a range of amenities, such as a hair dryer and a TV, and is located roughly 3 miles to the south of Woodbury.
  • Otherwise, create memories with loved ones at "100% Roxbury Poshpadsct "tophet 3br" Ski", which is around 4 miles to the northwest of Woodbury. Take advantage of children's games, a restaurant dining guide and more here.

Can I find studio apartments for rent in and around Woodbury?

Studio apartments may be small, but they pack a mighty punch when it comes to location and convenience. Plonk your bags down at one of these sought-after studio apartments in or near Woodbury:

  • After a day filled with urban exploration, enjoy total comfort and privacy at "Tranquil Farmhouse Retreat". Heating and a fitness facility are among the amenities on offer here.
  • Another top rental is "Your Escape To The Hills". Don't let it's compact size fool you — this comfy apartment is loaded with useful amenities like a free nearby fitness center, WiFi and much more.

Can I find short term rentals in or near Woodbury?

Whether you're seeking a cabin for you and a pal or a house that'll fit the entire family, short-term rentals are easy to find in and around Woodbury. These properties make the perfect base for a short and sweet stay:

  • Within close reach of central Woodbury, "100% Roxbury Poshpadsct "tophet 3br" Ski" lays out the welcome mat for short-term guests. When you're not holed up in your comfortable digs, get out and discover the area's best sights.
  • Alternatively, spend a few relaxing nights at "100% Roxbury Poshpadsct "247 Painter" 1. 5hrs Nyc". This comfy, centrally located property will feel like your home away from home.

What are the best romantic weekend getaways in or near Woodbury?

Nothing says "I love you" like a romantic weekend trip. If you want to spend a couple of relaxing nights away with your sweetie, we've got some romantic getaways in and around Woodbury that will set your heart aflutter:

  • Sneak away on Friday for a few passionate nights at "Waterfront Lake Home On Tranquil Harwinton Lake With Spectacular 180⁰ View". Located approximately 17 miles from Woodbury, this place comes with lots of nice touches, like winery tours and a fireplace.
  • "Large, Sunny 4 Bedroom Home And 1 Minute To Five Fabulous Restaurants" is another popular option that's guaranteed to impress. It's around 3 miles from Woodbury and has winery tours and beauty services.

What are the best large group vacation rentals in or near Woodbury?

Big groups mean a whole lot of fun. They also mean finding a place that'll effortlessly fit your entire squad. Browse our large group vacation rentals in or around Woodbury and get your favorite people together under the same roof:

  • There's loads of space to sprawl out at "100% Roxbury Poshpadsct "moosehorn" 2hrsnyc". Around 6 miles west of Woodbury, this impressive retreat has 7 bedrooms sleeping up to 12 guests. Top amenities include a swimming pool and a fireplace.
  • Nothing's more important than being with the people you love, and "Long Meadow Manor, Heated Pool" is the ideal place to do that. Located around 7 miles to the north of Woodbury, as many as 12 people can stay in this vacation rental which has 4 bedrooms. A kitchen and a fireplace are among the numerous amenities on offer here.

What are the best houses for rent with a pool in or near Woodbury?

Nothing says fun times like a pool. Pump up your inflatable flamingo and check out these rental houses in or near Woodbury that feature this added bonus:

  • Say hello to "Charming Connecticut House Gateway To New England. In Foothills Of Berkshires", where your main priority will be enjoying the pool. Amenities such as free toiletries and childrens activities help make this retreat a guest favorite.
  • Spend leisurely days splashing about or just unwinding by the water at "Sun Filled Direct Lakefront 3 Bedroom House On Bantam Lake". This vacation rental is also a firm favorite and offers coffee and tea making facilities, a garden and more.

Not sure what to pack for your Woodbury getaway? This enticing destination has a humid continental climate. During the summer months, expect average temperatures of between 60 ºF and 80 ºF. Scroll through our range of Woodbury vacation rentals by using the search bar at the top of the page. Simply adjust the filters to get more ideas about where to stay.

What are the best large family vacation rentals in or near Woodbury?

Every family catch-up should be memorable. Whether you're organizing an action-packed escape with the kids or that long-overdue family reunion, Vrbo's large family vacation rentals in or near Woodbury offer a home away from home with enough space for everyone:

  • Get your nearest and dearest together at "Large, Sunny 4 Bedroom Home And 1 Minute To Five Fabulous Restaurants", which has 4 bedrooms that sleep up to 8 guests. This getaway is located 3 miles to the south of Woodbury and features amenities such as free toiletries and a TV.
  • "New Updated 200 - Yr - Old Home W" also offers the space you need to connect with the ones you love. This property is around 3 miles to the south of Woodbury, and accommodates as many as 8 guests in its 4 bedrooms. A garden and a dishwasher will help keep everyone comfortable and happy.

If you're eager to visit some family-friendly attractions around the area, you won't have to go far. Sharon Audubon Center, Mount Frissell and Laurel Lanes offer fun for young and old.

Can I find family cabin rentals in or near Woodbury?

Get away from the hustle and bustle and treat your loved ones to a different sort of vacation. Stay in one of these family cabins in or near Woodbury and get the camping experience — but with all the creature comforts you're used to!

  • "Secluded Cabin For The Perfect Weekend Escape" - Enjoy good times with your crew at this retreat, which is around 25 miles north of the center of Woodbury. Childrens activities and a garden are some of its family-friendly amenities.
  • "Cabin - Secluded Country Setting With Great Views" - Rally the troops and spend a few nights or more at this appealing property, which is around 25 miles to the northwest of Woodbury. You'll have access to a barbecue grill, a dishwasher and a good deal more.

For more options, use the search bar at the top of the page and adjust the filters to find the Woodbury vacation rental that's perfect for your needs.