Woodbury Vacation Packages
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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.
Top Woodbury Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Scranton Seahorse Inn
Madison Center
CA $1,409
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9/10 Wonderful! (245 reviews)
Excellent B&B. Great breakfast. Lovely area. Walk around to local stores and restaurants. And beach is nearby.
Reviewed on Aug 1, 2026
Madison Beach Hotel
Madison Center
CA $3,154
per person
Oct 15 - Oct 19
found 13 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9.4/10 Exceptional! (379 reviews)
The whole experience was fantastic. Very relaxed atmosphere.with a gorgeous beach view from the hotel room .
Reviewed on Aug 13, 2026
Head of Pond House
CA $1,783
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
10/10 Exceptional! (11 reviews)
My husband and I spent a weekend at this beautiful place and loved it! The house is super clean, well located and has a private feeling, with amazing views to a peaceful garden. Pauline’s customer service was great and really took care of us also letting us do a late check out. Strongly recommend you stay here during your trip to the Hamptons!
Reviewed on Jul 27, 2026
Ready to book your vacation to Woodbury?
Woodbury Hotel Deals
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
CA $133
CA $153 total
Sep 7 - Sep 8
includes taxes & fees
8.6/10 Excellent! (1,407 reviews)
"New hotel and well maintained. The front guy was t really helpful. We booked a room for 3 and we had only 2 bathroom set. When we called to get an extra one, he told us to come down to get an extra one… it would have been serviceable to bring it to room"
Reviewed on Aug 13, 2026
Ethan Allen Hotel
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
CA $134
CA $154 total
Aug 16 - Aug 17
includes taxes & fees
8/10 Very good! (1,390 reviews)
"Very clean and the staff was excellent."
Reviewed on Aug 13, 2026
Cambria Hotel New Haven University Area
20 Dwight Street New Haven CT
Fully refundable
CA $181
CA $208 total
Aug 16 - Aug 17
includes taxes & fees
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.
Stay near popular Woodbury attractions
Glebe House Museum and The Gertrude Jekyll Garden
10.0/10 (1 review)
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.
Flanders Nature Center
10.0/10 (2 reviews)
Explore the great outdoors at Flanders Nature Center, a lovely green space in Woodbury. Attend a sporting event in this family-friendly area.
Hollow Park
10.0/10 (2 reviews)
Explore the great outdoors at Hollow Park, a lovely green space in Woodbury. Attend a sporting event in this family-friendly area.
Pilgrim Mall Shopping Center
9.4/10 (3 reviews)
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.
Frequently asked questions
How much does a Woodbury vacation package cost?
You'll find cheap prices from CA $830 on Expedia for your Woodbury escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Woodbury costs.
What are the cheapest months to go to Woodbury?
The off-season is the best time to head to Woodbury if you're hoping to keep costs down. Another tip for finding cheap Woodbury vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Woodbury?
The ideal length for your Woodbury vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to visit all the leading sights and explore some hidden spots along the way.
Is it worth booking a vacation package to Woodbury?
It's no wonder a Woodbury vacation is on the must-do list of many travellers. Popular attractions like Pilgrim Mall Shopping Centre are just the beginning of things to keep you busy here.
How to find the best Woodbury package deals?
Landing a cheap Woodbury package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Woodbury package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Woodbury vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can customize your Woodbury escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Woodbury?
If you've got your Woodbury vacation dates locked in, book as soon as you can to snap up some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Woodbury?
- Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Woodbury.
- Set your budget: Consider expenses such as flights, food and transportation when working out how much to set aside for your trip to Woodbury. Then, select a property that matches your budget, whether that's a low-cost option or a deluxe retreat.
- Decide your trip length: Consider how long you'd like to spend exploring Woodbury. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
- Bundle your accommodations and airfare: Once you've nailed down your dates and duration, lock in the ideal Woodbury vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
