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.
Liberty Inn
Price was CA $947, price is now CA $887 per person
CA $887
per person
Jul 17 - Jul 19
found 6 hours ago
Roundtrip flight included
Vancouver (YVR) 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
Saybrook Point Resort & Marina
Old Saybrook Center
Price was CA $1,561, price is now CA $1,542 per person
CA $1,542
per person
Jul 17 - Jul 19
found 6 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
9.6/10 Exceptional! (1,001 reviews)
Everything was super clean and staff was friendly and helpful.
Reviewed on Apr 14, 2026
Middlebury Hotel Deals
New Haven Hotel
229 George Street New Haven CT
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! (2,120 reviews)
We weren’t happy that parking was $24 a day and that the only part of the breakfast that was free was the coffee. Otherwise, everything else was fine.
Reviewed on May 12, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
The price is CA $142 per night from May 25 to May 26
CA $142
CA $163 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (1,296 reviews)
Stayed for one night but it was great. Front desk staff was friendly, plenty of parking, bed and pillows were very comfy, room was super spacious, shower had great water pressure and water got very hot, AC in room got the room nice and cold to sleep comfy at night. Right near major highway for easy ...
Reviewed on May 13, 2026
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Jun 7 to Jun 8
CA $220
CA $253 total
Jun 7 - Jun 8
includes taxes & fees
8.6/10 Excellent! (1,019 reviews)
Hotel was very nice staff was excellent especially checking in very helpful friendly
Reviewed on May 11, 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.
