Southbury Vacations from $650
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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
Save 100% on your flight
Price was $959, price is now $650 per person
$650
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean.
Reviewed on May 17, 2026
Madison Beach Hotel
Madison Center
Save 100% on your flight
Price was $3,257, price is now $2,353 per person
$2,353
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip flight included
Chicago (CHI) to New Haven (HVN)
9.4/10 Exceptional! (369 reviews)
Exceptionally clean and wonderful staff
Reviewed on May 10, 2026
Discover the most popular places to visit in Southbury
Shepaug Eagle Observation Area
You can learn about the history of Southbury with a trip to Shepaug Eagle Observation Area. Visit the spas in this culturally rich area, or simply enjoy its bars.
Southbury Hotel Deals
Wyndham Southbury
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from May 26 to May 27
$107 total
May 26 - May 27
Total with taxes and fees
8.2/10 Very Good! (1,192 reviews)
"Very old not clean."
Reviewed on May 18, 2026
Heritage Hotel, Golf & Conference Center
522 Heritage Road Southbury CT
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $163 total per night from May 20 to May 21
$163 total
May 20 - May 21
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
"Enjoyed my stay"
Reviewed on May 17, 2026
New Haven Hotel
229 George Street New Haven CT
$115 nightly
The price is $132 total per night from May 24 to May 25
$132 total
May 24 - May 25
Total with taxes and fees
9.2/10 Wonderful! (2,143 reviews)
"Would have given 5 stars but the lack of central air was an issue"
Reviewed on May 19, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
