Middlebury Holidays

Book a Hotel + Flight or Car together to unlock savings

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 3.304.932 ₫ per night from 13 Jul to 14 Jul
3.304.932 ₫
3.800.672 ₫ total
13 Jul - 14 Jul
includes taxes & fees
8.8/10 Excellent! (1,607 reviews)
"It was clean and kept up well"

Reviewed on 28 Jun 2025

New Haven Hotel
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
3 out of 5
400 Sargent Dr, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is 2.559.919 ₫ per night from 6 Jul to 7 Jul
2.559.919 ₫
2.943.907 ₫ total
6 Jul - 7 Jul
includes taxes & fees
5.8/10 (1,005 reviews)
"Good"

Reviewed on 27 Jun 2025

La Quinta Inn & Suites by Wyndham New Haven
Hyatt Place Milford / New Haven
Hyatt Place Milford / New Haven
3 out of 5
190 Old Gate Lane, Milford, CT
Fully refundableReserve now, pay when you stay
The price is 2.896.545 ₫ per night from 7 Jul to 8 Jul
2.896.545 ₫
3.331.027 ₫ total
7 Jul - 8 Jul
includes taxes & fees
8.6/10 Excellent! (1,034 reviews)
"Great place"

Reviewed on 26 Jun 2025

Hyatt Place Milford / New Haven
See all 958 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.

Popular places to visit

Quassy Amusement Park

4/5(1 review)

Bring the family to Quassy Amusement Park and enjoy this exciting theme park in Middlebury. Attend a sporting event in this family-friendly area.

Quassy Amusement Park