Middlebury Vacation Packages

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Your Middlebury Vacation

You'll find plenty to like about Middlebury, from its rich history to its cultural experiences. When you're ready to say hello to this fascinating city, our Middlebury vacation packages are calling your name. A trip to Middlebury is a terrific opportunity to sightsee. Be sure to visit popular attractions like Quassy Amusement Park, Palace Theatre and Brass Mill Center. No matter your travel plans or budget, organizing your ultimate tailored Middlebury vacation is a breeze with Expedia.

Top Middlebury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartments South End Stratford
Pier Blue Inn Old Saybrook - Essex
Liberty Inn
Quality Inn Old Saybrook - Westbrook
Westbrook Inn B&B

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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 CA $174 per night from May 25 to May 26
CA $174
CA $200 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (2,128 reviews)
I arrived in the 9p hour after a long day at work and it was a relief to get quickly checked in, easily park my car, and head to my room. The room was immaculate and the temperature was just right. Slept like a log, woke up to a fantastic shower, easy checkout and back on the road. A terrific way ...

Reviewed on May 15, 2026

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 refundableReserve now, pay when you stay
The price is CA $143 per night from May 25 to May 26
CA $143
CA $164 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (1,298 reviews)
Very comfortable beds, easy location, and pleasant employees. Breakfast was better than most, but still continental. Recommend it.

Reviewed on May 15, 2026

Holiday Inn Express Southington by IHG
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 CA $221 per night from Jun 7 to Jun 8
CA $221
CA $254 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Good

Reviewed on May 15, 2026

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.