Middlebury Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Your Middlebury Holiday
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 holiday 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 Centre. No matter your travel plans or budget, organising your ultimate tailored Middlebury holiday is a breeze with Expedia.
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 |
Top hotels in Middlebury
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
£108
27 Sept - 28 Sept
includes taxes & fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
£78
20 Sept - 21 Sept
includes taxes & fees
8.6/10 Excellent! (1,452 reviews)
"Very clean hotel."
Reviewed on 14 Sept 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
£93
7 Oct - 8 Oct
includes taxes & fees
8.2/10 Very good! (1,847 reviews)
"Nice location for a quick overnight stay on a road trip. Hotel is right off the road. You could hear road noise but it wasn’t enough to keep me awake."
Reviewed on 14 Sept 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.
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.
Frequently asked questions
How much does a Middlebury travel package cost?
From just . Yes, you read that right. Our Middlebury packages are a great way to make your budget last longer. Bundle your preferred hotels, flights and rental car and discover this popular destination.
If I'm not able to travel, can I cancel my Middlebury travel package?
Yes you can, and we're here to help. You may be able to change or cancel your Middlebury travel package at no cost within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If your circumstances suddenly change, look up our Customer Service Portal for further information.
How do I get a cheap travel package to Middlebury?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got it all. Pick and choose the combination that suits you and see your savings pile up. Of course, a package deal is never one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 hotels around the globe, which lets you customize your Middlebury getaway.
Does Expedia offer Book Now, Pay Later Middlebury holidays?
Expedia has partnered with online lender Klarna to make your next trip easier on your bank balance. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to spend while you're away. Klarna has several payment plans to pick from, so you're sure to find one that suits your budget. Take a look at these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
- Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.
Where should I stay in Middlebury?
With so much to explore in Middlebury, it'd be convenient for you to book a room in a hotel near its attractions. Quassy Amusement Park, Hop Brook Lake and Lake Quassapaug are some good ones to add to your to-do list.
What are the top hotels in Middlebury?
Hilton Stamford Hotel & Executive Meeting Centre and Howard Johnson by Wyndham Mystic are two of the most sought-after properties in Middlebury. Why not take a look at the rates and amenities at each and then decide?
How far in advance should I book my Middlebury holiday?
Reserving your tickets early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to 12 months prior to departure dates. Usually, this is the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Middlebury are still known to appear just a few weeks before departure.
What does an Expedia Middlebury travel package include?
You can choose from a combination of rental cars, hotels and flights. Once you've made your booking, you can add activities and experiences. Want to pick your airfare class? That's also possible. The choice is yours when it comes to creating your ideal Middlebury getaway.
What should I know before booking a Middlebury travel package?
A travel package can be cheaper than separately booking everything you need for your adventure. For example, bundle your hotels, flights and rental cars and score big savings. Whatever your holiday goals are, there's bound to be a package that best suits your budget.
Can I choose my airline with a Middlebury Expedia travel package?
You can, and with more than 550 airlines to choose from around the world, you've got lots of choice. Search the available options and find out which airline best fits your needs and budget.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
