Middlebury Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Sleep Inn & Suites Niantic
Beechmont - Perfect for Family Retreat!
James Pharmacy Bed & Breakfast
Microtel Inn & Suites by Wyndham Uncasville Casino Area
Saybrook Point Resort & Marina

Ready to book your vacation to Middlebury?

 

Choose your dates

Middlebury Hotel Deals

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 CA $209 per night from Sep 7 to Sep 8
CA $209
CA $240 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"The best"

Reviewed on Aug. 27, 2025

Trumbull Marriott Shelton
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Sep 7 to Sep 8
CA $144
CA $165 total
Sep 7 - Sep 8
includes taxes & fees
Best Western Executive Hotel Of New Haven - West Haven
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 $197 per night from Sep 21 to Sep 22
CA $197
CA $226 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (1,013 reviews)
"Walkable to Yell. Good service. But no free internet"

Reviewed on Aug. 27, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.