Middlebury Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Middlebury Holiday

With a reputation for its rich history and cultural experiences, Middlebury is a perfect getaway destination. Book one of our Middlebury holiday packages and discover all that this fascinating city has to offer. If taking in sights is on the to-do list during your trip to Middlebury, visit popular attractions like Quassy Amusement Park, Palace Theatre and Union Station Clocktower. No matter your travel plans or budget, putting together a tailored Middlebury holiday is a walk in the park with Expedia.

Middlebury Holiday

Middlebury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
7,000
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Quassy Amusement Park, Palace Theatre and Mount Southington Ski Area

Our pick of the best Middlebury Hotel Deals

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
The price is AU$263 per night from 19 Aug to 20 Aug
AU$263
19 Aug - 20 Aug
includes taxes & fees
8/10 Very good! (1,000 reviews)
"The rooms were incredibly clean and very large. The staff (all the staff) were amazing. Will be staying there again."

Reviewed on 4 Aug 2026

Trumbull Marriott Shelton
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 16 Aug to 17 Aug
AU$150
16 Aug - 17 Aug
includes taxes & fees
Holiday Inn Express Southington by IHG
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 31 Aug to 1 Sept
AU$225
31 Aug - 1 Sept
includes taxes & fees
New Haven Hotel
See all 1,100 properties in Middlebury
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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Middlebury attractions

Quassy Amusement Park

8.2/10 (21 reviews)
This century-old Connecticut park balances nostalgia with modern thrills, featuring the award-winning Wooden Warrior coaster and lakeside beach. Rent a waterpark cabana for a premium experience during hot summer days.
See properties

Frequently asked questions

How much does a Middlebury holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday to Middlebury costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Middlebury?
You can usually find lower rates and better availability in January, February and March. Explore our cheap Middlebury holiday packages and you could land some great off-season deals.
How many days is enough for Middlebury?
The ideal duration of your Middlebury holiday depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to check out all the leading sights and discover some hidden treasures along the way.
Is it worth booking a holiday package to Middlebury?
From top attractions such as Middlebury Centre Historic District and Quassy Amusement Park to its terrific golfing, a Middlebury holiday delivers big on experiences. With so much to do and see, it's time to find out for yourself why Middlebury is such a good holiday destination.
How to find the best Middlebury package deals?
Landing a cheap Middlebury package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Middlebury package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Middlebury holiday as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Middlebury?
If you have your Middlebury holiday dates finalized, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Middlebury?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the type of activities on offer will also help you decide when to holiday in Middlebury.
  2. Plan your budget wisely: On top of the price of your accommodation, you should factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Middlebury.
  3. Work out your trip length: Think about how long you'd like to spend exploring Middlebury. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: Once you've settled on your trip dates and duration, lock in the ideal Middlebury holiday package for you.

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