Middlebury Holidays

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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$204 per night from 1 Jan to 2 Jan
S$204
includes taxes & fees
1 Jan - 2 Jan,2025
8.8/10 Excellent! (1,001 reviews)
"The property was ensconced in the center of Middlebury in a historic building but our accommodations in the annex were comfortable and modern. So easy to walk around the corner and enter the warmth and coziness of the hotel and dine in the beautiful dining room which was decorated for Christmas. ..."

Reviewed on 17 Dec,2024

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$207 per night from 23 Dec to 24 Dec
S$207
includes taxes & fees
23 Dec - 24 Dec
8.8/10 Excellent! (479 reviews)
Comfortable and Welcoming!
"Great facility managed by very friendly people! Really appreciated the guest laundry facilities."

Reviewed on 15 Dec,2024

Courtyard Middlebury
Waybury Inn
Waybury Inn
3.5 out of 5
457 East Main Street, Middlebury, VT
9.2/10 Wonderful! (69 reviews)
"Online it says it has an EV charging station but it doesn't. But not too much of a setback otherwise the place was very cute and hospitable! Great Vermont charm!"

Reviewed on 6 Jul,2024

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Waybury Inn
See all 875 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.

Frequently asked questions

How much does a Middlebury holiday package cost?
Offering excellent value package deals on Expedia, you’ll be surprised at how little a holiday to Middlebury costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Middlebury?
If you’re hoping to book a cheap Middlebury holiday package, consider travelling in January, March and November. You’ll typically find better rates on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Middlebury?
When planning your Middlebury holiday, a handful of days will be enough to tour the best spots. Be sure to check out Town Hall Theatre — it’s one of the top attractions in this destination. If you want more adventure, think about basing yourself here and going on some tours from Middlebury.
How to find the best Middlebury package deals?
Use Expedia’s handy filters to find some great Middlebury package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your adventure for midweek, or search for Middlebury package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to lock in your holiday package as soon as possible.
Is it cheaper to book a Middlebury holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can customise your Middlebury getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Middlebury?
If you have your Middlebury travel dates locked in, book as early as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Middlebury?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the activities on offer will also help you decide when to escape to Middlebury.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Middlebury.
  3. Work out your trip length: Consider how long you want to spend exploring Middlebury. Plan your days so you can get to all the attractions and experiences you’re interested in at a leisurely pace.
  4. Bundle your airfare and accommodation: Once you’ve settled on your trip dates and duration, book the ideal Middlebury holiday package for you.

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.