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.
Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
Price was CA $850, price is now CA $684 per person
CA $684
per person
Jun 29 - Jul 3
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
If you can look beyond the immediate exterior and sense of disrepair (it's not...), then you can enjoy the stay here. While there is no swimming pool, the property is well positioned to the coast and local beaches.
They were doing some road construction immediately outside the property and on the route to the shore roads, this should be wrapped up fairly quickly.
Restaurants were close enough to walk to, we recommend Luigi's for their calamari, whether it be for seafood or pizza. There is even a store selling fresh produce right down the street.
Enjoyed our stay and would definitely stay here again in the future if the opportunity presents itself.
Reviewed on May 15, 2026
Liberty Inn
Price was CA $966, price is now CA $873 per person
CA $873
per person
Aug 8 - Aug 13
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New Haven (HVN)
7.6/10 Good! (646 reviews)
This hotel is nearly on 95. Super busy traffic noise all night. I would not stay here again.
Reviewed on May 11, 2026
Westbrook Inn B&B
Westbrook Center
Price was CA $1,268, price is now CA $1,209 per person
CA $1,209
per person
Jun 29 - Jul 3
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.8/10 Exceptional! (191 reviews)
Staff kind and helpful. Very clean both inside and out! Will visit again.
Reviewed on Apr 28, 2026
Middlebury Hotel Deals
New Haven Hotel
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
Holiday Inn Express Southington by IHG
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
Omni New Haven Hotel at Yale
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
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.
