Trumbull Vacations from $289
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Your Trumbull Vacation
With all the details organized before you take off, our Trumbull vacation packages mean you can simply focus on having a great time. Whether you're staying in the neighborhood of Easton, which is good for hiking, or another area, this exciting city promises a wealth of discoveries. You'll want to go sightseeing during your trip to Trumbull. Swing by top attractions such as Sacred Heart University, Total Mortgage Arena and Hartford HealthCare Amphitheater. A few clicks is all it takes to put together the perfect Trumbull vacation on Expedia.
The Latest Trumbull Vacation Packages
- Pier Blue Inn Old Saybrook - Essex
Dec 11 - Dec 13Pier Blue Inn Old Saybrook - Essex + Flight
Saybrook Manor2 nights2.0 star property8.0/10 - Very good (1,009 reviews)Roundtrip • San Juan (SJU) - New Haven (HVN)SJU - BDL • Nonstop BDL - SJU • Nonstop$346$289found 1 day agoper traveler - Beechmont - Perfect for Family Retreat!
Jan 17 - Jan 19Beechmont - Perfect for Family Retreat! + Flight
North End2 nights5.0 star propertyRoundtrip • Tampa (TPA) - New Haven (HVN)TPA - LGA • Nonstop LGA - TPA • Nonstop - Landing Apartments New Haven Near Dixwell
Dec 30 - Jan 2Landing 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 • Miami (MIA) - New Haven (HVN)FLL - HVN • Nonstop HVN - FLL • Nonstop$1,142$971found 1 day agoper traveler - Heritage Hotel, Golf & Conference Center
Dec 30 - Jan 2Heritage Hotel, Golf & Conference Center + Flight
Southbury3 nights3.5 star property8.4/10 - Very good (1,002 reviews)Roundtrip • Miami (MIA) - New Haven (HVN)FLL - HVN • Nonstop HVN - FLL • Nonstop$742$635found 1 day agoper traveler - Landing Apartments Downtown New Haven
Dec 30 - Jan 2Landing Apartments Downtown New Haven + Flight
Downtown New Haven3 nights3.0 star propertyRoundtrip • Miami (MIA) - New Haven (HVN)FLL - HVN • Nonstop HVN - FLL • Nonstop$1,075$925found 1 day agoper traveler
Where to stay near Trumbull
Bridgeport
Discover Bridgeport, a vibrant city perfectly suited for families and weekend getaways who will appreciate its blend of outdoor activities and urban charm. With attractions like Fairfield University and the Total Mortgage Arena, as well as the historic Bridgeport Downtown South Historic District, there's something for everyone to enjoy. Located about 4 miles by car from Trumbull, Bridgeport serves as an ideal home base for your Connecticut adventure, making it a smart choice for your stay.
Milford
Experience the charm of Milford, an excellent hub for family travelers seeking a delightful mix of outdoor adventures and scenic beauty. With attractions like the beautiful Walnut Beach, the expansive Silver Sands State Park, and the historic Yale University nearby, Milford offers a rich variety of activities for all ages. Located about 8 miles by car from Trumbull, it's an ideal choice for a weekend getaway or a longer visit, making Milford a smart selection for your stay.
Fairfield
If you are a family traveler, look no further than Fairfield, which features a vibrant mix of city life and outdoor activities. You can enjoy the beautiful Jennings Beach, explore the academic atmosphere at Fairfield University, or catch an event at the Total Mortgage Arena. Located about 8 miles by car from Trumbull, Fairfield offers easy access to these attractions, making it a smart choice for your stay.
Stratford
Stratford stands out as a prime spot for family travelers and weekend getaway enthusiasts interested in a blend of outdoor and city experiences. With its inviting beaches and access to educational attractions like Yale and Fairfield Universities, visitors can enjoy both relaxation and culture. Just about 5 miles by car from Trumbull, Stratford offers easy transit to the Total Mortgage Arena for entertainment. Choosing Stratford for your stay ensures a diverse experience that caters to all ages.
Norwalk
Travelers visiting the area often choose Norwalk, especially those seeking a blend of city and outdoor experiences. With attractions like the historic South Norwalk, the beautiful Compo Beach, and the modern Fairfield University, this city offers a rich mix of education, leisure, and shopping. Located about 14 miles by car from Trumbull, Norwalk provides easy access for a weekend getaway or family vacation. Enjoying a stay here ensures a delightful experience with plenty to explore.
Trumbull Hotel Deals
"I kept smelling a light sulfur smell in my room. My theory was that the traps had just run dry and some smell was coming up from the drains, but those drains probably need to be bleached. The smell went away after I ran water in the sink and shower. Other than that, it was good."
Extended Stay America Suites Shelton Fairfield County
Extended Stay America Suites Shelton Fairfield County
Best Western Plus Fairfield Hotel
Best Western Plus Fairfield Hotel"Great hotel. Stayed here on the weekend we toured Fairfield University. Would definitely stay here in the future if my daughter is accepted. My top choice for the college she would go to so we shall see"
Find out more about Trumbull
Things to do near Trumbull
Trumbull offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal destination for a city-themed vacation. Visitors can enjoy educational tours, music concerts, and explore local resorts. For those seeking excitement, the area boasts adventure parks and a variety of outdoor activities that cater to all ages. Whether you're looking for relaxation or adventure, Trumbull has something for everyone.
Shopping
In Trumbull, you can enjoy shopping at Monroe Plaza Shopping Center, just 5 miles away, which offers a mix of entertainment and family-friendly options. If you're up for a drive, visit Westfield Connecticut Post Mall, 9 miles away, featuring a vibrant atmosphere, or the Westport Farmers Market, 11 miles away, for unique local finds.
Recreation
Explore the Hartford HealthCare Amphitheater for exciting sports events and a vibrant atmosphere. Enjoy the serene surroundings at Seaside Park, perfect for relaxation and wellness. For outdoor enthusiasts, Fairchild Wheeler Golf Course offers a beautiful setting for a round of golf amid nature.
Adventure
The Adventure Park at Discovery Museum offers thrilling ziplining and ropes courses, located 3 miles from Trumbull. For a unique experience, visit Blue Jay Orchards, 14 miles away, for apple picking and family fun. Wolfe Park Tennis Center, 5 miles away, is perfect for an energetic game of tennis.
Nightlife
Trumbull offers a cozy nightlife with local favorites like The Corner Pug for a relaxed drink and live music. For a more vibrant scene, check out Tashua Knolls, where you can enjoy dining and entertainment under the stars, creating a perfect end to your day.
Find the best attractions near Trumbull
Trumbull, Connecticut, is an ideal destination for city-themed, outdoor family vacations. Visitors can explore popular attractions such as beaches, historic colleges, and state parks, catering to those seeking cultural experiences and outdoor fun. Highlights include the Trumbull Mall and various local points of interest, making it easy to discover the charm of Trumbull while enjoying a mix of relaxation and adventure.
- Yale University: Located 15 miles from Trumbull, Yale University boasts stunning architecture and a rich history. Explore its beautiful campus, visit the Yale University Art Gallery, and soak in the vibrant cultural atmosphere that comes with one of the oldest institutions of higher learning in the U.S.
- Bridgeport Downtown South Historic District: Just 4 miles away, this charming historic district features beautifully preserved buildings and a lively arts scene. Stroll through its streets, enjoy local shops, and immerse yourself in the unique cultural vibes of this historic village.
- Total Mortgage Arena: Situated 5 miles from Trumbull, this entertainment venue hosts a variety of family-friendly events, including concerts and sports. Experience the excitement of live performances and enjoy a fun-filled atmosphere for all ages.
Best time to go to Trumbull
The best time to visit Trumbull can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Trumbull falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Trumbull falls in January, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Trumbull
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Trumbull.
- Consider traveling to Trumbull during the low season (January to March) 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.
Frequently Asked Questions
How much does a Trumbull vacation package cost?
You can snap up a vacation package to this popular destination from $289 on Expedia. But how much your vacation to Trumbull costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Trumbull?
September, October and December are the best times to look for cheap Trumbull vacation packages. Opting to travel in less busy periods means you can generally find better prices on flights and accommodations.
How many days is enough for Trumbull?
With a well-planned schedule, you can easily visit the main Trumbull attractions in a few days. But if you'd like to venture off the beaten track or go on day tours, think about booking your Trumbull vacation for longer.
How to find the best Trumbull package deals?
Use Expedia's filter tool to find some fabulous Trumbull package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Trumbull package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Trumbull vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Trumbull vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Trumbull?
If you have your Trumbull vacation dates locked in, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Trumbull?
- Choose when to get away: Check your calendar and get packing. Your preferred time of year and the available activities will also help you decide when to escape to Trumbull.
- Calculate your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Trumbull.
- Explore Trumbull using our trip planning tool: Gain insights into the top attractions and best hotels for your trip to Trumbull. You can also save your favorite locations, collaborate with your group and organize your plans in one place.
- Work out your trip length: Think about how long you want to spend discovering Trumbull. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Trumbull vacation package.
- Book activities and experiences in advance: Whether it's entrance to a major attraction or a day trip, you won't have to worry about missing out on the highlights of Trumbull. Find all the fun things to do in Trumbull with our dedicated activity guide.
Does Expedia offer Book Now, Pay Later Trumbull vacation packages?
If you're like us, you love discovering new places but are not a fan of the 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 break down the total cost of your Trumbull break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.