Woodbury Vacations from $529

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Your Woodbury Vacation

Get ready to experience Woodbury in your own style with a custom Woodbury vacation package! Uncovering the best parts of this fascinating city is simpler with a base in a neighborhood such as Plymouth, which is great for nature, among plenty of other things. You'll want to go sightseeing during your trip to Woodbury. Don't miss big-name attractions such as Pilgrim Mall Shopping Center, Glebe House Museum and The Gertrude Jekyll Garden and Woodbury Ski Area. That dream Woodbury vacation is just clicks away. Search flights, hotels and more on Expedia for a getaway that's tailored to suit your travel style.

The Latest Woodbury Vacation Packages

Prices and availability subject to change. Additional terms may apply.
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Jun 1 - Jun 3
Roundtrip flight included
Washington (IAD) to New Haven (HVN)
8.4/10 Very Good! (969 reviews)
Loved the room other than no fan in the bathroom. Beds were excellent. Breakfast buffet was a welcome start to the morning although the staff running it didn't seem to want to be there. The front desk clerk who checked us in was awesome!

Reviewed on Apr 22, 2024

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Jun 1 - Jun 3
Roundtrip flight included
Washington (IAD) to New Haven (HVN)
8.8/10 Excellent! (999 reviews)
Your employees were amazing

Reviewed on Apr 22, 2024

Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Jun 1 - Jun 3
Roundtrip flight included
Washington (IAD) to New Haven (HVN)
8.4/10 Very Good! (472 reviews)
Overall the two room suite was perfect for our needs. However, the room need a bit of updating and a deep cleaning.

Reviewed on Apr 22, 2024

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
per person
Jun 1 - Jun 3
Roundtrip flight included
Washington (IAD) to New Haven (HVN)
8.8/10 Excellent! (444 reviews)
Love the executive suite for a quick getaway and soak in a hot tub . Staff are very attentive and friendly.

Reviewed on Apr 17, 2024

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
Jun 1 - Jun 3
Roundtrip flight included
Washington (IAD) to New Haven (HVN)
9/10 Wonderful! (1,003 reviews)
Would recommend anyone! Great service

Reviewed on Apr 22, 2024

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

Woodbury Hotel Deals

Holiday Inn Express Southington, an IHG Hotel
Holiday Inn Express Southington, an IHG Hotel
2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is $121 per night from Apr 28 to Apr 29
$121
$139 total
includes taxes & fees
Apr 28 - Apr 29
8.4/10 Very Good! (989 reviews)
Decent Stay
"As expected for a 2-star hotel, no frills, front desk was nice. Room wasn't cleaned after the first night, other than that no complaints."

Reviewed on Apr 22, 2024

Holiday Inn Express Southington, an IHG Hotel
Hilton Garden Inn Shelton
Hilton Garden Inn Shelton
3 out of 5
25 Old Stratford Rd, Shelton, CT
Fully refundableReserve now, pay when you stay
The price is $110 per night from May 6 to May 7
$110
$126 total
includes taxes & fees
May 6 - May 7
7.6/10 Good! (944 reviews)
"Everything was great"

Reviewed on Apr 23, 2024

Hilton Garden Inn Shelton
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
The price is $144 per night from May 26 to May 27
$144
$165 total
includes taxes & fees
May 26 - May 27
8.6/10 Excellent! (286 reviews)
"Stay was great."

Reviewed on Apr 23, 2024

Cambria Hotel New Haven University Area
See all 839 properties in Woodbury
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Woodbury vacation package cost?
Tailor make your Woodbury package from only $529. Choose from any combination of rental cars, flights and hotels to build the escape you’ve long been dreaming about. Don’t forget to add on a few activities!
How do I get a cheap travel package to Woodbury?
If you love landing a bargain, bundle your bookings into a Woodbury vacation package. Whether you’re searching for hotels, flights, rental cars or activities, you can book them all in one place. You’ll have lots of choice at your fingertips as well. Expedia has more than 550 air carriers and 1,000,000 hotel options across the globe to choose from. Fly with who you want, stay anywhere you like and save precious dollars — now that’s the perfect escape!
Where should I stay in Woodbury?
A trip to Woodbury wouldn’t be complete without checking out Glebe House Museum and The Gertrude Jekyll Garden, Woodbury Ski Area and Pilgrim Mall Shopping Center. Stay near these tourist attractions and make sightseeing simple.
What are the top hotels in Woodbury?
If it’s your very first time in Woodbury, reserve a room at The Milestone Inn or Large, Sunny 4 Bedroom Home And 1 Minute To Five Fabulous Restaurants. Both hotels offer friendly service and are favorites among many travelers.
How far in advance should I book my Woodbury vacation?
It can be hard to know when the best time is to book your Woodbury trip. But generally the earlier you book, the more affordable the prices. In some cases, you can secure your flights and hotels up to 12 months prior to your departure date. If you’re considering a last-minute getaway, no need to worry! There are fantastic deals announced on Expedia every single day.
What does an Expedia Woodbury travel package include?
Hotels, flights and a cool car for all your fun road trip adventures. Simply mix and match your favorite bundle and get access to great discounts. Once you’ve made your booking, add on a couple of experiences and tours and watch your savings stack up. When it comes to planning your Woodbury vacation, you’re the one in control!
What should I know before booking a Woodbury travel package?
Get ready to save with an Expedia travel package. Combine your airfares, rental cars and hotels and be rewarded with exciting discounts. You’re not limited to hotels, however. Book with us and take your pick of island villas, cozy city apartments and everything in between!
Can I choose my airline with a Woodbury Expedia vacation package?
Expedia offers access to more than 550 partner airlines globally, so you definitely can. Simply choose the airline you want and create your ideal Woodbury escape.
If I'm not able to travel, can I cancel my Woodbury vacation package?
Because we know life can be unpredictable, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to change or cancel it with no penalties. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

Discover the most popular places to visit in Woodbury

Image for Glebe House Museum and The Gertrude Jekyll Garden

Glebe House Museum and The Gertrude Jekyll Garden

Explore the great outdoors at Glebe House Museum and The Gertrude Jekyll Garden, a lovely green space in Woodbury. Attend a sporting event in this family-friendly area.

Glebe House Museum and The Gertrude Jekyll Garden
Image for Pilgrim Mall Shopping Center

Pilgrim Mall Shopping Center

You can browse for the perfect souvenirs at Pilgrim Mall Shopping Center during your trip to Woodbury. Attend a sporting event in this family-friendly area.

Pilgrim Mall Shopping Center
Image for Hollow Park

Hollow Park

Explore the great outdoors at Hollow Park, a lovely green space in Woodbury. Attend a sporting event in this family-friendly area.

Hollow Park

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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.