Middlebury Vacations from $493
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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.
The Latest Middlebury vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG
Price was $581, price is now $493 per person
$493
per person
Oct 17 - Oct 21
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,083 reviews)
Good location, close to the exits. Great breakfast, comfortable beds.
Reviewed on Sep 14, 2025
Mayflower Inn & Spa, Auberge Resorts Collection
Save 100% on your flight
Price was $4,494, price is now $3,294 per person
$3,294
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (53 reviews)
Incredible place - will definitely return.
Reviewed on Aug 19, 2024
Courtyard by Marriott Southington
Save 100% on your flight
Price was $697, price is now $543 per person
$543
per person
Oct 17 - Oct 21
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (432 reviews)
The rooms were clean and the area was nice as well. Would stay again.
Reviewed on Sep 1, 2025
Residence Inn by Marriott Southington
Price was $619, price is now $495 per person
$495
per person
Oct 17 - Oct 21
found 4 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (563 reviews)
Landscaping terrible overgrown never been cut. The outside building needs to be repainted inside the room that I stayed in room one06 first floor has cracked tiles in the bathroom. The kitchen needs re-renovating the bathroom. The bathroom tub needs to be replaced fungus on the grout. The rugs throughout the whole entire room needs to be replaced. The sofa is ripped the kitchen table and chairs are about 20 years old need to be replaced.
Reviewed on Sep 14, 2025
Discover the most popular places to visit in Middlebury
Quassy Amusement Park
Bring the kiddos to Quassy Amusement Park and have a fun-filled day at this theme park in Middlebury. Attend a sporting event in this family-friendly area.
Middlebury Hotel Deals
New Haven Hotel
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $170 total per night from Sep 28 to Sep 29
$170 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (1,760 reviews)
"Friendliest staff!"
Reviewed on Sep 10, 2025
Trumbull Marriott Shelton
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $180 total per night from Sep 21 to Sep 22
$180 total
Sep 21 - Sep 22
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"I have stayed at this Marriot before a couple years back and within that time I feel some disrepair has fallen on the property. The landscaping, cleanliness, as well as staff has always been more than adequate. However I found the condition of the parking lot and the main entrance are in dire need ..."
Reviewed on Sep 7, 2025
Omni New Haven Hotel at Yale
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $183 total per night from Oct 5 to Oct 6
$183 total
Oct 5 - Oct 6
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
"Beautiful building nice people, outstanding location"
Reviewed on Sep 9, 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.
