
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.

Sleep Inn & Suites Niantic
Price was CA $1,234, price is now CA $1,075 per person
CA $1,075
per person
Nov 8 - Nov 15
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
8.4/10 Very Good! (1,003 reviews)
stayed 2 nights. no complaints. kids appreciated the pool
Reviewed on Aug. 26, 2025


James Pharmacy Bed & Breakfast
Old Saybrook Center
Price was CA $2,346, price is now CA $1,911 per person
CA $1,911
per person
Nov 8 - Nov 15
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(
Reviewed on May 1, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area
Price was CA $1,634, price is now CA $1,356 per person
CA $1,356
per person
Nov 8 - Nov 15
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
8.8/10 Excellent! (1,742 reviews)
We were in the non smoking room. The hallway and areas around the property smelled like weed. Accessible room was far from the entrance. Staff referred to website rather than answering questions. Night staff on the cell phone each time I went to get coffee (coffee in the lobby).
Reviewed on Aug. 29, 2025

Saybrook Point Resort & Marina
Old Saybrook Center
Price was CA $2,579, price is now CA $2,207 per person
CA $2,207
per person
Nov 8 - Nov 15
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
9.4/10 Exceptional! (1,006 reviews)
Great place couldn’t even take my financeé away from the pool even if god asked her to leave
Reviewed on Aug. 29, 2025
Middlebury Hotel Deals

Trumbull Marriott Shelton
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

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 Sep 7 to Sep 8
CA $144
CA $165 total
Sep 7 - Sep 8
includes taxes & fees

Omni New Haven Hotel at Yale
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
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.