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 $986, price is now CA $795 per person
CA $795
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
8/10 Very Good! (1,004 reviews)
Friendly staff, clean room, nice location
Reviewed on Jun 3, 2026
Quality Inn Old Saybrook - Westbrook
Price was CA $836, price is now CA $785 per person
CA $785
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
7.8/10 Good! (1,002 reviews)
The room was very clean and quiet. The interior was modern and very well laid out. The breakfast was very good.
Reviewed on Jun 8, 2026
Super 8 by Wyndham Old Saybrook
Price was CA $994, price is now CA $945 per person
CA $945
per person
Jul 28 - Aug 3
just found
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (919 reviews)
This is exactly what I would expect from a super eight. It was clean safe comfortable bed. Also AC worked good bathroom was cleaned. They don’t have breakfast being served there, but that’s not an issue for me. It’s in a safe location. Very close to downtown old Saybrook that has a lot of beautiful restaurants and shopping for the value. I would stay here again.
Reviewed on Jun 7, 2026
Middlebury Hotel Deals
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jul 5 to Jul 6
CA $180
CA $207 total
Jul 5 - Jul 6
includes taxes & fees
9.2/10 Wonderful! (2,172 reviews)
"Everything was great"
Reviewed on Jun 9, 2026
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $214 per night from Jul 4 to Jul 5
CA $214
CA $246 total
Jul 4 - Jul 5
includes taxes & fees
8.6/10 Excellent! (1,025 reviews)
"Very nice place, conveniently situated to Yale."
Reviewed on Jun 3, 2026
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Jun 14 to Jun 15
CA $144
CA $166 total
Jun 14 - Jun 15
includes taxes & fees
8/10 Very Good! (1,649 reviews)
"I was satisfied with all the above no complaints... Will be returning soon"
Reviewed on Jun 8, 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.
