Middlebury Holidays

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Your Middlebury Holiday

With a reputation for its rich history and cultural experiences, Middlebury is a perfect getaway destination. Book one of our Middlebury holiday packages and discover all that this fascinating city has to offer. If taking in sights is on the to-do list during your trip to Middlebury, visit popular attractions like Quassy Amusement Park, Palace Theatre and Union Station Clocktower. No matter your travel plans or budget, putting together a tailored Middlebury holiday is a walk in the park with Expedia.

Middlebury Holiday

Middlebury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
7,000
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Quassy Amusement Park, Palace Theatre and Mount Southington Ski Area

Our pick of the best Middlebury Hotel Deals

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 AU$173 per night from 16 Nov to 17 Nov
AU$173
16 Nov - 17 Nov
includes taxes & fees
8.6/10 Excellent! (1,136 reviews)
"Nice place"

Reviewed on 18 Oct 2025

Holiday Inn Express Southington by IHG
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 AU$246 per night from 2 Nov to 3 Nov
AU$246
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Nice facility overall. A few minor issues in the room that were quickly corrected."

Reviewed on 16 Oct 2025

Trumbull Marriott Shelton
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 AU$296 per night from 1 Nov to 2 Nov
AU$296
1 Nov - 2 Nov
includes taxes & fees
8.4/10 Very Good! (1,021 reviews)
"Perfect overall"

Reviewed on 18 Oct 2025

Omni New Haven Hotel at Yale
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.

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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.