Middlebury Holidays

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Top Flight + Hotel Deals in Middlebury

Price found within the past 48 hours. Click for updated prices.
Club Wyndham Smugglers’ Notch Vermont

Club Wyndham Smugglers’ Notch Vermont

3.5 out of 5
Price was €801, price is now €657 per person
€657
per person
2 Oct - 4 Oct
found 18 hours ago
Return direct flight included
New York (NYC) to Burlington (BTV)
8.4/10 Very good! (223 reviews)

Field Guide Lodge

Field Guide Lodge

3.5 out of 5
Price was €1,134, price is now €858 per person
€858
per person
2 Oct - 4 Oct
found 18 hours ago
Return direct flight included
New York (NYC) to Burlington (BTV)
9/10 Wonderful! (1,008 reviews)
This place is a hidden gem. The hotel has spacious and clean rooms. Our air conditioning worked just great ( in fact it got so cool at night that we had to shut the ac off in the morning). The location is perfect right next to downtown and near all recreational activities. However, the experience is nothing without helpful staff. Which brings us to Zane. What an amazing person! A credit to the organisation. Zane is kind, charming, helpful, no, not just helpful but goes out of the way to make guests feel valued and appreciated. He truly is the best advertisement and ambassador for the Lodge.

Reviewed on 11 Jul 2026

Outbound Stowe

Outbound Stowe

3.5 out of 5
Price was €918, price is now €729 per person
€729
per person
2 Oct - 4 Oct
found 18 hours ago
Return direct flight included
New York (NYC) to Burlington (BTV)
9/10 Wonderful! (351 reviews)
very good hotel with a great pool! definitely recommend and will come back.

Reviewed on 10 Jul 2026

Hilton Garden Inn Burlington Downtown

Hilton Garden Inn Burlington Downtown

3 out of 5
Downtown Burlington
Price was €1,059, price is now €888 per person
€888
per person
2 Oct - 4 Oct
found 18 hours ago
Return direct flight included
New York (NYC) to Burlington (BTV)
8.8/10 Excellent! (1,004 reviews)
Very convenient location and beautiful lobby. Staff were very accommodating when I arrived late at night with a moving truck.

Reviewed on 8 Jul 2026

Hampton Inn Colchester

Hampton Inn Colchester

3 out of 5
Price was €815, price is now €695 per person
€695
per person
2 Oct - 4 Oct
found 18 hours ago
Return direct flight included
New York (NYC) to Burlington (BTV)
8.8/10 Excellent! (1,396 reviews)
Great breakfast. Comfortable rooms

Reviewed on 10 Jul 2026

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 €131 per night from 27 Jul to 28 Jul
€131
27 Jul - 28 Jul
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"The annex provided modern conveniences alongside the old world charm"

Reviewed on 11 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 €147 per night from 29 Jul to 30 Jul
€147
29 Jul - 30 Jul
includes taxes & fees
9/10 Wonderful! (580 reviews)
"This was a great hotel. I would definitely stay there again. Highly recommended."

Reviewed on 9 Jul 2026

Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
The price is €216 per night from 14 Jul to 15 Jul
€216
14 Jul - 15 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 983 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 from €657 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.

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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.