Middlebury Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top hotels in Middlebury

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
The price is S$186 per night from 3 Dec to 4 Dec
S$186
3 Dec - 4 Dec
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Clean, easy check in, reasonable.

Reviewed on 12 Nov, 2025

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
The price is S$179 per night from 3 Dec to 4 Dec
S$179
3 Dec - 4 Dec
includes taxes & fees
8.8/10 Excellent! (538 reviews)
Clean room

Reviewed on 15 Nov, 2025

Courtyard Middlebury
Middlebury Sweets Motel

Middlebury Sweets Motel

2.5 out of 5
1395 Rt 7 South Middlebury VT
Fully refundableReserve now, pay when you stay
The price is S$156 per night from 3 Dec to 4 Dec
S$156
3 Dec - 4 Dec
includes taxes & fees
8.4/10 Very Good! (387 reviews)
Nice little room for a quick stay. We were in the Reese themed room. Thoughtful amenities, the dark makeup washcloth was a nice touch! Clean room and bathroom. Responsive front desk. Will stay again when visiting family in the area.

Reviewed on 2 Nov, 2025

Middlebury Sweets Motel
See all 945 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.