Middlebury Vacations

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Find the Best Middlebury Vacation Packages

Middlebury Hotel Deals

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 ₩192,731 per night from Aug 9 to Aug 10
₩192,731
₩221,641 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (2,209 reviews)
"Very clean, spacious room! Included mini fridge, safe, ironing board, hair dryer, and robe (!). There was in-room coffee and also large pots of drip coffee in the lobby. I would stay here again if I am ever in New Haven."

Reviewed on Jul 16, 2026

New Haven Hotel
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 ₩222,122 per night from Jul 19 to Jul 20
₩222,122
₩255,440 total
Jul 19 - Jul 20
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"Mattress was. Lumpy,ac noisy"

Reviewed on Jul 15, 2026

Trumbull Marriott Shelton
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 ₩169,230 per night from Jul 30 to Jul 31
₩169,230
₩194,614 total
Jul 30 - Jul 31
includes taxes & fees
8/10 Very Good! (1,712 reviews)
"Amazing"

Reviewed on Jul 16, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,088 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.
See properties

Frequently asked questions

How much does a Middlebury vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation packages and you could land some great off-season deals.
How many days is enough for Middlebury?
The ideal duration of your Middlebury vacation 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 vacation package to Middlebury?
From top attractions such as Middlebury Center Historic District and Quassy Amusement Park to its terrific golfing, a Middlebury vacation 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 vacation 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 vacation as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a customized vacation 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 vacation package to Middlebury?
If you have your Middlebury vacation 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 vacation in Middlebury.
  2. Plan your budget wisely: On top of the price of your accommodations, 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 accommodations and airfare: Once you've settled on your trip dates and duration, lock in the ideal Middlebury vacation 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.