Woodbridge Vacations from $528
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The Latest Woodbridge Vacation Packages
- Pier Blue Inn Old Saybrook - Essex
Sep 24 - Sep 28Pier Blue Inn Old Saybrook - Essex + Flight
Saybrook Manor4 nights2.0 star property8.0/10 - Very Good (1,002 reviews)Roundtrip • Fort Lauderdale (FLL) - New Haven (HVN)FLL - LGA • Nonstop LGA - FLL • Nonstop$687$528found 1 day agoper traveler - Landing Apartments New Haven Near Dixwell
Aug 27 - Aug 30Landing Apartments New Haven Near Dixwell + Flight
Newhallville3 nights3.0 star property2.0/10 - (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 May 25, 2026Roundtrip • Chicago (CHI) - New Haven (HVN)ORD - HVN • Nonstop HVN - ORD • Nonstop - Hyatus Luxury Residences City Crossing
Aug 27 - Aug 30Hyatus Luxury Residences City Crossing + Flight
The Hill3 nights4.0 star property9.2/10 - Wonderful (32 reviews)"the room and amenities are well maintained, clean and convenient, the customer service is awesome , answering requests fast and responsive."Reviewed July 5, 2026Roundtrip • Chicago (CHI) - New Haven (HVN)ORD - HVN • Nonstop HVN - ORD • Nonstop - Luxury Furnished Apartments by Hyatus Downtown at Yale
Aug 27 - Aug 30Luxury Furnished Apartments by Hyatus Downtown at Yale + Flight
The Hill3 nights3.5 star property9.6/10 - Exceptional (85 reviews)"I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!"Reviewed July 6, 2026Roundtrip • Chicago (CHI) - New Haven (HVN)ORD - HVN • Nonstop HVN - ORD • Nonstop - Graduate by Hilton New Haven
Sep 17 - Sep 20Graduate by Hilton New Haven + Flight
Downtown New Haven3 nights4.0 star property9.2/10 - Wonderful (1,002 reviews)"-"Reviewed July 17, 2026Roundtrip • Tampa (TPA) - New Haven (HVN)TPA - HVN • Nonstop HVN - TPA • Nonstop
Woodbridge Hotel Deals
Best Western Executive Hotel Of New Haven - West Haven
Best Western Executive Hotel Of New Haven - West Haven
Courtyard by Marriott New Haven Orange-Milford
Courtyard by Marriott New Haven Orange-Milford
Hampton Inn & Suites New Haven - South - West Haven
Hampton Inn & Suites New Haven - South - West Haven
Residence Inn by Marriott New Haven Hamden
Residence Inn by Marriott New Haven Hamden
Hampton Inn & Suites By Hilton North Haven
Hampton Inn & Suites By Hilton North HavenFrequently Asked Questions
How much does a Woodbridge vacation package cost?
Offering great value package deals from $528 on Expedia, you'll be thrilled with how little a vacation to Woodbridge costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Woodbridge?
You're likely to find lower prices and better availability in December, January and February. Browse our cheap Woodbridge vacation packages and you could get some great off-season discounts.
How many days is enough for Woodbridge?
The ideal duration of your Woodbridge vacation depends on what you'd like to see and do. Usually, a few days to a week will give you plenty of time to tick off all the main attractions and discover some hidden gems along the way.
Is it worth booking a vacation package to Woodbridge?
Whether you're planning to discover attractions like Tradition Golf Club at Oak Lane and Beverly Kaye Gallery, or want to experience its top-notch nature and hiking, a Woodbridge vacation is sure to exceed your expectations. Book your getaway with Expedia and find out why Woodbridge is such a good vacation destination.
How to find the best Woodbridge package deals?
Bagging a cheap Woodbridge package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Woodbridge package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Woodbridge vacation as a package?
You can enjoy significant savings on your Woodbridge getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Woodbridge?
Secure amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Woodbridge escape.
Does Expedia offer Book Now, Pay Later Woodbridge vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Woodbridge trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
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Things to do in and around Woodbridge
Woodbridge, Connecticut, is perfect for family vacations with outdoor adventures and cultural experiences. Enjoy educational attractions, local theater performances, and recreational areas. Explore nearby destinations for day trips or engage in various outdoor activities for an exciting Woodbridge adventure. Whether you're looking to relax or explore, there's something for everyone in this charming town.
Shopping
For a delightful shopping experience in Woodbridge, visit the Ansonia Mall Shopping Center and Acme Mall Shopping Center, both 4 miles away, offering a variety of shops and family-friendly vibes. If you're up for a drive, check out the Westfield Connecticut Post Mall, located 8 miles away, for even more options.
Recreation
Experience the vibrant culture and entertainment at the Shubert Theater, just 5 miles from Woodbridge. Enjoy a round of golf amid beautiful outdoor scenery at Tradition Golf Club. For tennis enthusiasts, the Cullman-Heyman Tennis Center, located 4 miles away, offers a fantastic sports atmosphere.
Adventure
Experience the whimsical Lighthouse Point Carousel, located 9 miles from Woodbridge, perfect for family fun. For thrill-seekers, The Adventure Park at Discovery Museum, 15 miles away, offers an exhilarating zipline ropes course. Enjoy water sports and adventure at Waterski Connecticut, only 6 miles from Woodbridge.
Nightlife
In Woodbridge, Connecticut, enjoy a cozy nightlife atmosphere with local bars and restaurants offering live music and craft cocktails. Explore the vibrant scene at nearby New Haven, just a short drive away, where you’ll find lively pubs, dance venues, and cultural hotspots for a memorable night out.
Find the best attractions near Woodbridge
Woodbridge, Connecticut, offers a delightful mix of outdoor activities, cultural experiences, and family-friendly attractions. Visitors can explore historic college campuses, enjoy nearby beaches, and visit national and state parks, making it an ideal destination for those seeking adventure and relaxation. Whether you're looking to immerse yourself in local culture or simply enjoy nature, Woodbridge has something to offer for every traveler.
- Yale University: Immerse yourself in the rich history and culture of Yale University, a prestigious institution renowned for its stunning architecture and vibrant campus life. Explore the iconic libraries, museums, and galleries that showcase an impressive collection of art and historical artifacts, making it a must-visit for culture enthusiasts.
- Yale Bowl: Experience the thrill of live sports at the historic Yale Bowl, where tradition meets excitement. This iconic stadium hosts a variety of events, including football games that embody the spirit of college athletics, offering a unique blend of sports and cultural vibes.
- Wooster Square: Discover the charm of Wooster Square, a picturesque piazza known for its beautiful cherry blossoms and vibrant community. Enjoy local eateries, artisanal shops, and seasonal events that reflect the lively city atmosphere, making it a perfect spot to relax and soak in the culture.
Best time to go to Woodbridge
The best time to visit Woodbridge can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Woodbridge falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Woodbridge falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain.
Tips to save on your trip to Woodbridge
- Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
- Consider traveling to Woodbridge during the low season (December to February) for more affordable options.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.