Woodbury Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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.

Top Woodbury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.2/10 Very Good! (1,001 reviews)
Clean, professional

Reviewed on Jul. 21, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (1,047 reviews)
I see lot of bugs in the room

Reviewed on Aug. 2, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (827 reviews)
Very near Yale university. The hotel is very clean and the hotel staff were kind and helpful. I got a work out in their nice fitness room. I enjoyed my stay before making my self into NYC.

Reviewed on Aug. 2, 2025

Comfort Inn Naugatuck-Shelton, CT

Comfort Inn Naugatuck-Shelton, CT

2.5 out of 5
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
7.8/10 Good! (692 reviews)
The staff was friendly and the room was bigger then I thought it would be. Had a nice stay. No complaints.

Reviewed on Jul. 25, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.6/10 Excellent! (550 reviews)
Had a great stay and the employees were top notch

Reviewed on Aug. 1, 2025

Ready to book your vacation to Woodbury?

 

Choose your dates

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 refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 18 to Aug 19
CA $186
CA $214 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (835 reviews)
"Very near Yale university. The hotel is very clean and the hotel staff were kind and helpful. I got a work out in their nice fitness room. I enjoyed my stay before making my self into NYC."

Reviewed on Aug. 2, 2025

Cambria Hotel New Haven University Area
The Blake Hotel

The Blake Hotel

4 out of 5
9 High Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $288 per night from Aug 10 to Aug 11
CA $288
CA $331 total
Aug 10 - Aug 11
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"We LOVE visiting the Blake. It’s always our go to when we need a stay-cation. It’s so close to amazing restaurants and night life, always so clean, the rooms are beautiful and it’s such a great boutique hotel. Can’t wait to come back!"

Reviewed on Aug. 2, 2025

The Blake Hotel
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Aug 11 to Aug 12
CA $128
CA $147 total
Aug 11 - Aug 12
includes taxes & fees
8/10 Very Good! (1,010 reviews)
"The lady staff member who checked us in was WONDERFUL! She went above and beyond! Male next night was not as nice or welcoming but everyone else was. Place is gorgeous, pool water is warm and heavenly. That male staff member on 2nd night made us feel like criminals for staying in water at 10:01pm! ..."

Reviewed on Jul. 30, 2025

Wyndham Southbury
See all 840 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Woodbury

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

Frequently asked questions

How much does a Woodbury vacation package cost?
You'll find cheap prices from CA $600 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.