Middlebury Packages (Flight + Hotel)

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Top hotels in Middlebury

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is ฿4,387 per night from 25 Aug to 26 Aug
฿4,387
฿5,045 total
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (845 reviews)
"Parking was great, although we paid for late check out and was charged an additional fee because we didn’t check out at 11:30. Also, housekeeping did a great job with providing a clean room-but did not know we had late check out and attempted to come into our room at 10:00am. At check out, the front ..."

Reviewed on 10 Aug 2025

Cambria Hotel New Haven University Area
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 ฿3,399 per night from 18 Aug to 19 Aug
฿3,399
฿3,909 total
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (1,265 reviews)
"Good place"

Reviewed on 9 Aug 2025

Best Western Executive Hotel Of New Haven - West Haven
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is ฿4,908 per night from 25 Aug to 26 Aug
฿4,908
฿5,644 total
25 Aug - 26 Aug
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Amazing stay, great view and comfortable accommodations. Only complaint is lower floors are subject to street noise which is out of the hotel’s control. Would 100% stay here again when returning to New Haven"

Reviewed on 12 Aug 2025

Omni New Haven Hotel at Yale
See all 954 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.

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.