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.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was CA $1,033, price is now CA $947 per person
CA $947
per person
Jan 1 - Jan 4
found 21 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.4/10 Very good! (895 reviews)
This inn has a lot of potential but unfortunately it was extremely dirty. The room smelled so bad that I could hardly breathe and there was a thick layer of dirt on the walls and baseboards. The bed made a loud creaking noise with any subtle move. I felt so dirty when I left there. We were supposed to leave at 10am and I made my husband get up and drive home at 6am because I couldn't stand to be there any longer. I should have done more research about the property before I stayed but I used to live in Cheshire and it is such a nice town that it really just didn't cross my mind that a place so dirty would be there. The lady who checked me in was very nice and friendly but besides that I have nothing positive to say about my stay.

Reviewed on Nov 13, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,068, price is now CA $1,588 per person
CA $1,588
per person
Dec 20 - Dec 23
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
No reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was CA $1,276, price is now CA $1,095 per person
CA $1,095
per person
Jan 1 - Jan 4
found 21 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.8/10 Excellent! (1,000 reviews)

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was CA $1,256, price is now CA $1,101 per person
CA $1,101
per person
Jan 1 - Jan 4
found 21 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,368, price is now CA $1,263 per person
CA $1,263
per person
Dec 24 - Dec 26
found 21 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Ready to book your vacation to Woodbury?

 

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Woodbury Hotel Deals

Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Nov 15 to Nov 16
CA $156
CA $179 total
Nov 15 - Nov 16
includes taxes & fees
8/10 Very good! (1,557 reviews)
"Parking was good. Check-in was slow as there was only one person at the desk. The restaurant was not open as advertised but the bar was open. The food choices were limited, but delicious. The bartender was a great server as well. The place is clean, just showing its age. The TV remote did not work, ..."

Reviewed on Nov 14, 2026

Ethan Allen Hotel
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Dec 6 to Dec 7
CA $138
CA $159 total
Dec 6 - Dec 7
includes taxes & fees
Best Western Danbury/Bethel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Fully refundable
The price is CA $176 per night from Dec 13 to Dec 14
CA $176
CA $202 total
Dec 13 - Dec 14
includes taxes & fees
Cambria Hotel New Haven University Area
See all 918 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.
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Stay near popular Woodbury attractions

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.
See properties

Frequently asked questions

How much does a Woodbury vacation package cost?
You'll find cheap prices from CA $947 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.