Middlebury Holidays

Photo by David Alpert

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Top hotels in Middlebury

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is S$190 per night from 2 Nov to 3 Nov
S$190
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
"A lovely"

Reviewed on 27 Sept, 2025

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is S$165 per night from 2 Nov to 3 Nov
S$165
2 Nov - 3 Nov
includes taxes & fees
8.8/10 Excellent! (524 reviews)
"Daily or at least every other day housekeeping service would have been appreciated."

Reviewed on 14 Aug, 2025

Courtyard Middlebury
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street, Brandon, VT
The price is S$158 per night from 19 Oct to 20 Oct
S$158
19 Oct - 20 Oct
includes taxes & fees
8.6/10 Excellent! (525 reviews)
"Very lovely gem that has become a new favorite! Fun to live like previous generations!!!"

Reviewed on 27 Sept, 2025

Brandon Inn
See all 947 properties in Middlebury
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.

Popular places to visit

Halpin Covered Bridge

Learn about the local history of Middlebury when you take a trip to Halpin Covered Bridge. Stroll along the riverfront or visit the cathedral while you're in the area.

Halpin Covered Bridge

Holy Cow Inc.

You can browse the exhibits at Holy Cow Inc., a museum with a storied past, during your holiday in Middlebury. Wander the riverfront or discover the area's waterfalls.

Holy Cow Inc.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.