Southbury Vacation Packages

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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.

Top Southbury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was CA $814, price is now CA $678 per person
CA $678
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
9.2/10 Wonderful! (2,191 reviews)
Easy check-in and helpful staff. Only there over night as family member in Yale Hospital. Paring easy as was check out. Needs more charging ports.

Reviewed on Jul 3, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,373, price is now CA $1,112 per person
CA $1,112
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was CA $942, price is now CA $806 per person
CA $806
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.

Reviewed on Jun 2, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $802, price is now CA $690 per person
CA $690
per person
Aug 28 - Aug 30
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
While the staff were very friendly and helpful. The property itself was like strolling back into 1980. It was not at all what I was expecting to find upon my arrival. Things were clean enough, but very outdated. I will say that the bed was actually very comfortable. The impression I gathered from the website was that of abotuque bed and breakfast, which was not at all the case.

Reviewed on Jul 3, 2026

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was CA $858, price is now CA $740 per person
CA $740
per person
Aug 24 - Aug 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8.6/10 Excellent! (1,316 reviews)
It was smell in the bathroom

Reviewed on Jul 4, 2026

Ready to book your vacation to Southbury?

 

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Southbury Hotel Deals

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 12 to Jul 13
CA $155
CA $178 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (1,250 reviews)
"The hotel overall was fine. Breakfast took an hour and it wasn’t crowded. One server who was the hostess, bus person and server with one cook. The hotel room was also fine, however the remote for the TV didn’t work so it took a little bit to get it fixed. Staff was friendly and helpful."

Reviewed on Jul 4, 2026

Wyndham Southbury
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Jul 5 to Jul 6
CA $176
CA $227 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (1,002 reviews)
"Very nice experience except the elevators were scary and a bit outdated but very nice and lovely great amenities affordable price"

Reviewed on Jul 4, 2026

Heritage Hotel, Golf & Conference Center
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 $143 per night from Jul 5 to Jul 6
CA $143
CA $164 total
Jul 5 - Jul 6
includes taxes & fees
8/10 Very good! (1,278 reviews)
"The staff was excellent. Abby at the front desk was super helpful and pleasant. When we had a small problem Bill in maintenance came by right away and fixed it. The property is a little dated but it is maintained and clean."

Reviewed on Jul 4, 2026

Ethan Allen Hotel
See all 1,360 properties in Southbury
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.
All Inclusive Vacations
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Stay near popular Southbury attractions

Shepaug Eagle Observation Area

7.8/10 (10 reviews)
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.
See properties

Frequently asked questions

How much does a Southbury vacation package cost?
You can snap up a vacation package to this top destination from CA $678 on Expedia. However, how much your vacation to Southbury costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Southbury?
January, March and April are great times to search for cheap Southbury vacation packages. Opting to travel in quieter periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Southbury?
With a well-organized schedule, you can easily hit the top Southbury sights in a handful of days. But if you'd like to discover lesser-known spots or go on day tours, consider booking your Southbury vacation for longer.
How to find the best Southbury package deals?
Begin your search for a Southbury package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Southbury package deal straight away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Southbury escape off to a flying start.
Is it cheaper to book a Southbury vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Southbury vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Southbury?
If you have your Southbury travel dates finalized, book early to bag some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Southbury?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Southbury.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Southbury.
  3. Decide your trip length: Think about how much time you want to spend discovering Southbury. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Southbury vacation package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.