Woodbury Vacations from $370

Book a Hotel + Flight or Car together to unlock savings

    deals illustration

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Holiday Inn Express Southington by IHG
Courtyard by Marriott Southington
HYATT house Hartford North/Windsor
Hilton Garden Inn Hartford North/Bradley Int'l Airport
Residence Inn by Marriott Southington
Don't see what you're looking for?
See all available trips from Boydton to Woodbury
View all trips

Discover the most popular places to visit in Woodbury

Woodbury Hotel Deals

Wyndham Southbury
Wyndham Southbury
3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Jul 27 to Jul 28
$107 total
Jul 27 - Jul 28
Total includes taxes and fees
8/10 Very Good! (1,010 reviews)
"The staff there was very helpful. The cleaning staff was excellent also. The rooms were beautiful. We loved the pool. Thank you to everyone."

Reviewed on Jul 10, 2025

Wyndham Southbury
The Blake Hotel
The Blake Hotel
4 out of 5
9 High Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $244 total per night from Aug 11 to Aug 12
$244 total
Aug 11 - Aug 12
Total includes taxes and fees
9.4/10 Exceptional! (1,012 reviews)
"Great hotel and in a good location. I liked that there was a small kitchen that included a small stove and kettle to make tea and even a microwave and dishwasher. My only complaint is that many of the TV channels didn't work for some reason, but I was able to log in to my Netflix account which worked ..."

Reviewed on Jul 9, 2025

The Blake Hotel
Cambria Hotel New Haven University Area
Cambria Hotel New Haven University Area
3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Jul 27 to Jul 28
$155 total
Jul 27 - Jul 28
Total includes taxes and fees
8.6/10 Excellent! (798 reviews)
"The hotel is beautiful and very clean. I didn't like so much that you had to pay $26 a night for parking."

Reviewed on Jul 9, 2025

Cambria Hotel New Haven University Area
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

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

More vacations you might like

Frequently asked questions

How much does a Woodbury vacation package cost?
You can grab a vacation package to this destination from $370 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.