Middlebury Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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 AED 434 per night from Apr 27 to Apr 28
AED 434
AED 499 total
includes taxes & fees
27 Apr - 28 Apr
8.8/10 Excellent! (1,497 reviews)
"Staff was friendly. Our stay was everything we expected."

Reviewed on 19 April 2025

New Haven Hotel
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is AED 320 per night from Apr 24 to Apr 25
AED 320
AED 367 total
includes taxes & fees
24 Apr - 25 Apr
8.6/10 Excellent! (1,003 reviews)
"I enjoyed my stay and the front desk personnel were very accommodating. I arrived early and they were able to get me in no issues. Then had an issue with the AC/Heating unit in the room and after realizing it would need a longer fix they moved me to a different room with no problems. My only issue ..."

Reviewed on 17 April 2025

Holiday Inn Express Southington by IHG
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 AED 496 per night from May 11 to May 12
AED 496
AED 571 total
includes taxes & fees
11 May - 12 May
8.8/10 Excellent! (702 reviews)
"Very close to campus"

Reviewed on 18 April 2025

Cambria Hotel New Haven University Area
See all 960 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 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 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.

Discover the most popular places to visit in Middlebury

Quassy Amusement Park

4.5/5(13 reviews)

Bring the kiddos to Quassy Amusement Park and have a fun-filled day at this theme park in Middlebury. Attend a sporting event in this family-friendly area.

Quassy Amusement Park