Middlebury Holidays

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Top hotels in Middlebury

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 €119 per night from 26 Jul to 27 Jul
€119
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (2,208 reviews)
"Management was very rude but the staff were great and helpful."

Reviewed on 29 Jun 2026

New Haven Hotel
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
The price is €116 per night from 12 Jul to 13 Jul
€116
12 Jul - 13 Jul
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"I came to CT because my brother passed away. • Upon arrival, my room was nearly 80 degrees. When I requested another room, I was told that was not possible. Maintenance eventually arrived and determined that the thermostat had simply been left on “heat” instead of “cool.” This should have been identified ..."

Reviewed on 30 Jun 2026

Hilton Garden Inn Milford
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
The price is €104 per night from 7 Jul to 8 Jul
€104
7 Jul - 8 Jul
includes taxes & fees
8/10 Very good! (1,689 reviews)
"Everything was fine, no complaints."

Reviewed on 30 Jun 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,096 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.

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.
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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.

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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.