Middlebury Vacation Packages
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Your Middlebury Vacation
You'll find plenty to like about Middlebury, from its rich history to its cultural experiences. When you're ready to say hello to this fascinating city, our Middlebury vacation packages are calling your name. A trip to Middlebury is a terrific opportunity to sightsee. Be sure to visit popular attractions like Quassy Amusement Park, Palace Theatre and Brass Mill Center. No matter your travel plans or budget, organizing your ultimate tailored Middlebury vacation is a breeze with Expedia.
Top Middlebury Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
CA $1,133
per person
Oct 16 - Oct 19
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
8/10 Very good! (1,009 reviews)
I visit cousins in Old Saybrook annually and Blue Pier Inn is my go to spot. It’s nothing fancy but it’s a good value and good location and I always get a good nights rest. It could use a little sprucing up but I hear the owners are doing some renovations.
Reviewed on Aug 15, 2026
The Scranton Seahorse Inn
Madison Center
CA $1,568
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9/10 Wonderful! (245 reviews)
Excellent B&B. Great breakfast. Lovely area. Walk around to local stores and restaurants. And beach is nearby.
Reviewed on Aug 1, 2026
Hampton Inn & Suites New Haven - South - West Haven
CA $1,186
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
8.4/10 Very good! (1,003 reviews)
I would recommend this hotel, very clean, updated rooms, staff helpful. Would definitely return i had no issues.
Reviewed on Aug 15, 2026
Madison Beach Hotel
Madison Center
CA $3,154
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to New Haven (HVN)
9.4/10 Exceptional! (379 reviews)
The whole experience was fantastic. Very relaxed atmosphere.with a gorgeous beach view from the hotel room .
Reviewed on Aug 13, 2026
Ready to book your vacation to Middlebury?
Stay near popular Middlebury attractions
Quassy Amusement Park
8.2/10 (21 reviews)
Bring the kiddos to Quassy Amusement Park and have a fun-filled day at this theme park in Middlebury. Attend a sporting event in this family-friendly area.
Frequently asked questions
How much does a Middlebury vacation package cost?
Offering great value package deals from CA $1,133 on Expedia, you'll be pleasantly surprised at how much a vacation to Middlebury costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Middlebury?
You can usually find lower rates and greater availability in January, February and March. Check out our cheap Middlebury vacation packages and you could get some great off-season deals.
How many days is enough for Middlebury?
Dedicate at least 2 days for your Middlebury vacation to enjoy everything that makes this destination special. Explore key areas, including Middlebury Centre Historic District and Oakville. Then tick off top sights like Lake Quassapaug and Southford Falls State Park. With a clever itinerary, you can keep busy with room for some relaxation too. Want to travel outside of Middlebury? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Middlebury?
Well known for its golfing and home to popular attractions like Middlebury Centre Historic District, a Middlebury vacation is sure to leave an impression. Another top sight to visit? Don't miss Quassy Amusement Park.
How to find the best Middlebury package deals?
Use Expedia's filter tool to help you find some of the best Middlebury package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Middlebury package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Middlebury vacation as a package?
You can enjoy significant savings on your next Middlebury escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Middlebury?
If you're considering a spur-of-the-moment Middlebury getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Middlebury?
- 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 go to Middlebury.
- Budget wisely: Besides the price of your hotel, you should consider other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may come up during your trip to Middlebury.
- Decide your trip length: Consider how long you'd like to spend discovering Middlebury. Plan your days so you can get to all the attractions and experiences 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 Middlebury vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
