Southbury Vacations from $664
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Your Southbury Vacation
Reserve a Southbury vacation package and get ready to experience all this city has to offer. Think about staying in the neighborhood of Washington, which is good for nature, history and views. Quassy Amusement Park, Lake Lillinonah and Southford Falls State Park are just a few of the sights you'll want to check out during your trip to Southbury. A few clicks is all it takes to craft the ultimate Southbury vacation on Expedia.
The Latest Southbury vacation packages
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
$664
per person
Nov 19 - Nov 25
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8/10 Very Good! (1,009 reviews)
My room smelled like urine and the lobby smelled like a wet dog. Bathroom was dim and dingy, ironing board stained, A/C vents were full of dust and didn’t work well. TV didn’t work either. How they can charge $150 for a room here is appalling. The front sign is the only thing nice about the property- do not let the pictures fool you, the rooms are gross.
Reviewed on Aug 28, 2026
Landing Apartments New Haven Near Dixwell
Newhallville
$872
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Hyatus Luxury Residences City Crossing
The Hill
$1,171
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (34 reviews)
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Stay near popular Southbury attractions
George C. Waldo State Park
8.8/10 (3 reviews)
This secluded Connecticut park descends 140 feet through mixed forest to the shores of Lake Lillinonah. Explore historic stone walls while hiking, mountain biking, or horseback riding along its serene trails.
Shepaug Eagle Observation Area
7.8/10 (10 reviews)
Witness majestic bald eagles fishing and soaring at this winter wildlife hotspot along the Housatonic River. Reserve your free spot and bring binoculars for an unforgettable morning of eagle watching.
Vicinanza Studios & Gallery
This vibrant gallery showcases diverse works from local and regional artists in an intimate setting. Engage directly with creators during interactive workshops and cultural events that foster artistic exploration.
Southbury Hotel Deals
Wyndham Southbury
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
$93 nightly
$107 total
Sep 20 - Sep 21
Total with taxes and fees
8.2/10 Very Good! (1,289 reviews)
"Ok"
Reviewed on Aug 31, 2026
Heritage Hotel, Golf & Conference Center
522 Heritage Road Southbury CT
Fully refundableReserve now, pay when you stay
$140 nightly
$161 total
Sep 8 - Sep 9
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
"Thank you"
Reviewed on Aug 30, 2026
Trumbull Marriott Shelton
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
$149 nightly
$171 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (1,008 reviews)
"Website said there was a hot tub but there wasn’t one. Otherwise it was a good experience."
Reviewed on Aug 30, 2026
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.
Find the Best Southbury Vacation Packages
Southbury Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 19,800 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Southford Falls State Park, Shepaug Eagle Observation Area and Osborndale State Park |
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Frequently asked questions
How much does a Southbury vacation package cost?
You'll find cheap prices from $664 on Expedia for your Southbury getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Southbury costs.
What are the cheapest months to go to Southbury?
You're likely to find lower prices and better availability in November, December and January. Browse our cheap Southbury vacation packages and you could land some excellent off-season deals.
How many days is enough for Southbury?
The ideal duration of your Southbury vacation depends on what you'd like to see. Typically, a handful of days to a week will give you plenty of time to go to all the top attractions and explore some hidden spots along the way.
How to find the best Southbury package deals?
Start your search for a Southbury package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Southbury package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Southbury getaway off to a flying start.
Is it cheaper to book a Southbury vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Southbury trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Southbury?
Score incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Southbury adventure.
Does Expedia offer Book Now, Pay Later Southbury vacation packages?
Your Southbury break is meant to be an escape from your busy life, not a reason for money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
