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$194 per night from 27 Jul to 28 Jul
S$194
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
"Very nice property and within walking distance of restaurants and shops. Their restaurant was quite good with reasonably priced options and drinks. We sat outside on the deck, which was great. Room was very nice and bed was comfortable. Could use extra sleeping pillows. The bathroom could be upgraded ..."

Reviewed on 12 Jul, 2026

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$217 per night from 2 Aug to 3 Aug
S$217
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (581 reviews)
"Great convenient property. Clean and staff was pleasant."

Reviewed on 12 Jul, 2026

Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
The price is S$332 per night from 29 Jul to 30 Jul
S$332
29 Jul - 30 Jul
includes taxes & fees
9.6/10 Exceptional! (344 reviews)
"We stayed in one of the rooms in the Carriage House (as opposed to the Main House). It's by the road but wasn't too loud. The grounds are impeccably kept, with beautiful flowers and veggies growing everywhere. We enjoyed the buffet breakfast (shout-out to Linus for being the most friendly and welcoming ..."

Reviewed on 7 Jul, 2026

Swift House Inn
See all 982 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.

Stay near popular Middlebury attractions

Pulp Mill Covered Bridge

9.6/10 (20 reviews)
One of America's oldest double-barreled covered bridges, this 19th-century wooden marvel spans Otter Creek with its distinctive kingpost truss design. Photographers capture its charm against Vermont's seasonal backdrops.
See properties

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.
Is it worth booking a holiday package to Middlebury?
It's easy to see why a Middlebury holiday is on the to-do list of many travellers. Popular attractions like Henry Sheldon Museum of Vermont History are just the start of what you can explore here.
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.

Explore a world of travel with Expedia

* 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.