Woodbury Vacations from $319

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Your Woodbury Vacation

When a city getaway is calling, answer it with a Woodbury vacation package. The neighborhood of Washington, which is great for nature, history and views, makes a wonderful base for your adventures. Glebe House Museum and The Gertrude Jekyll Garden, Woodbury Ski Area and Pilgrim Mall Shopping Center are just a few of the many sights worth visiting during your trip to Woodbury. Don't delay exploring this city any longer. Your perfect Woodbury vacation is a few quick clicks away with Expedia.

The Latest Woodbury vacation packages

Price found within the past 48 hours. Click for updated prices.
The Surfside Hotel
Beechmont - Perfect for Family Retreat!
Comfort Inn Naugatuck-Shelton, CT
Quality Suites Stratford
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
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Woodbury Hotel Deals

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Fully refundable
$103 nightly
The price is $119 total per night from Feb 15 to Feb 16
$119 total
Feb 15 - Feb 16
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Friendly & helpful staff & bartenders

Reviewed on Jan 16, 2026

Cambria Hotel New Haven University Area
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$86 nightly
The price is $99 total per night from Feb 7 to Feb 8
$99 total
Feb 7 - Feb 8
Total with taxes and fees
8.6/10 Excellent! (1,207 reviews)
The room was drafty around the heating unit. Additionally, this hotel, like most newly built hotels, uses an automatic thermostat for the heat and cool. When the thermostat is set and it gets a little too warm in the room, and you turn it down a couple degrees the AC kicks on rather than just allowing ...

Reviewed on Jan 14, 2026

Holiday Inn Express Southington by IHG
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $179 total per night from Jan 24 to Jan 25
$179 total
Jan 24 - Jan 25
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
A wonderful surprise in Danbury! One minor complaint- the sleeping pillows were all very firm, a variety of pillows would be amazing.

Reviewed on Jan 17, 2026

Hotel Zero Degrees Danbury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Woodbury Vacation Packages

Things to do in and around Woodbury

Woodbury, Connecticut, is perfect for outdoor enthusiasts and romantic getaways, offering stunning scenery and a variety of activities. Visitors can explore recreational areas, enjoy shopping at local centers and malls, and take advantage of guided tours to discover the region's charm. Whether you’re seeking adventure or relaxation, Woodbury has something for everyone.

Shopping

Woodbury offers a delightful shopping experience at Pilgrim Mall Shopping Center, featuring a mix of entertainment and family-friendly vibes. If you're up for a drive, check out Brass Mill Center, 10 miles away, and the Elephant's Trunk Flea Market, located 11 miles away, both offering unique finds.

Recreation

Experience the charm of the Palace Theatre, offering a blend of culture and entertainment just 9 miles from Woodbury. For relaxation, Kettletown State Park, located 8 miles away, provides serene trails and tranquil views. Enjoy family fun at The Cave mini-golf, situated 13 miles from Woodbury.

Adventure

At Woodbury Ski Area, experience thrilling skiing and snowboarding on diverse slopes, perfect for all skill levels. Nearby, Blue Jay Orchards offers a fun-filled day of apple picking and farm activities, while the Big Cathedral Trail invites you to explore stunning outdoor scenery through invigorating hikes.

Nightlife

Experience a cozy evening in Woodbury with a visit to the charming 4-Hour Brew Tour for craft beer lovers. For a relaxed vibe, enjoy live music at the Woodbury Brewery, or unwind with friends at the local taverns offering a warm, inviting atmosphere.

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

Find the best attractions in and around Woodbury

Woodbury, Connecticut, is an ideal destination for outdoor enthusiasts and those seeking romantic getaways. Surrounded by beautiful scenery, visitors can explore various attractions, including national parks, lakes, and urban parks. These points of interest cater to families and cultural experiences, making Woodbury a perfect spot for travelers looking to enjoy nature and create lasting memories with loved ones.

  • Quassy Amusement Park: Experience a day of family fun at Quassy Amusement Park, located just 3 miles from Woodbury. With thrilling rides, games, and beautiful outdoor spaces, it's the perfect spot for adventure seekers of all ages.
  • Candlewood Lake: Enjoy the serene beauty of Candlewood Lake, situated 13 miles away. This picturesque lake offers stunning scenery, beach access, and a romantic atmosphere, making it ideal for relaxation and outdoor activities.
  • Glebe House Museum and The Gertrude Jekyll Garden: Explore the rich culture of Woodbury at the Glebe House Museum and its exquisite gardens. This local gem showcases a blend of history and horticultural beauty, perfect for history buffs and garden enthusiasts alike.

Best time to go to Woodbury

The best time to visit Woodbury is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

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

Tips to save on your trip to Woodbury

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Woodbury.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Woodbury.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Woodbury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
9,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Lovers Leap State Park, Woodbury Ski Area and Elephants Trunk Flea Market

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Frequently asked questions

How much does a Woodbury vacation package cost?
You can grab a vacation package to this destination from $319 on Expedia. However, how much your vacation to Woodbury costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Woodbury?
November, December and January are the best times to look for cheap Woodbury vacation packages. Opting to travel in quieter months means you can generally find reduced prices on accommodations and flights.
How many days is enough for Woodbury?
With a well-organized schedule, you can easily hit the main Woodbury attractions in a handful of days. But if you prefer to discover hidden gems or go on day tours, think about booking your Woodbury vacation for longer.
How to find the best Woodbury package deals?
Landing a cheap Woodbury package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Woodbury package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Woodbury vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still get the freedom to create a tailored Woodbury vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Woodbury?
Enjoy incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Woodbury escape.
Does Expedia offer Book Now, Pay Later Woodbury vacation packages?
Your Woodbury getaway should be a relaxing escape from your daily routine, not a source of money worries. So to allow you that extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.