Middlebury Vacations from ￥176,713

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The Latest Middlebury Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eastern Inn & Suites

Eastern Inn & Suites

2 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Burlington (BTV)
8.4/10 Very Good! (1,000 reviews)
No continental breakfast

Reviewed on Nov 15, 2024

The Village of Loon Mountain by VRI Americas

The Village of Loon Mountain by VRI Americas

3 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Burlington (BTV)
8.6/10 Excellent! (481 reviews)
Clean , convenient, location .. friendly staff

Reviewed on Nov 30, 2024

Sunset Hill House

Sunset Hill House

4 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Burlington (BTV)
8.8/10 Excellent! (996 reviews)
Clean, cozy and beautiful

Reviewed on Dec 8, 2024

InnSeason Resorts Pollard Brook

InnSeason Resorts Pollard Brook

3 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Burlington (BTV)
9.4/10 Exceptional! (739 reviews)
Everything was great! The room, staff, activities, amenities, and surrounding area were wonderful! We'd definitely stay here again!

Reviewed on Dec 2, 2024

Mountain View Grand Resort & Spa

Mountain View Grand Resort & Spa

4 out of 5
per person
Feb 24 - Mar 3
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Burlington (BTV)
9/10 Wonderful! (1,000 reviews)
Beautiful views. Very clean. Very friendly and helpful staff. Excellent massage by Cassandra at the spa. Learned a lot from Jessica, the farmer, at the barn. MVG would be a great place for a knitting or weaving workshop and to learn more about the wool, etc. Might be nice to have their yarn in the gift shop. By magic ( or hard working staff who came in at 3:30-4:00 am) Christmas decorations were all in place the day after Thanksgiving (when we had a delicious buffet).Also meals at the restaurant were very good and my partner said he had the best pizza he’d ever eaten. My only complaint was that our room was rather small with only one chair (2 of us) compared to our friends who by luck had a corner room which was larger ( same price). Other than that it was a very enjoyable stay.

Reviewed on Nov 30, 2024

Find the Best Middlebury Vacation Packages

Middlebury Hotel Deals

Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is ￥21,383 per night from Jan 1 to Jan 2
￥21,383
￥23,521 total
includes taxes & fees
Jan 1 - Jan 2, 2025
8.8/10 Excellent! (1,003 reviews)
"Very charming inn. Excellent restaurant. Check-in staff exceptionally friendly and helpful."

Reviewed on Dec 21, 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 ￥21,727 per night from Dec 23 to Dec 24
￥21,727
￥23,900 total
includes taxes & fees
Dec 23 - Dec 24
8.8/10 Excellent! (479 reviews)
Comfortable and Welcoming!
"Great facility managed by very friendly people! Really appreciated the guest laundry facilities."

Reviewed on Dec 15, 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 Jul 6, 2024

Get rates
Waybury Inn
See all 879 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 vacation package cost?
Offering excellent value package deals from ￥176,713 on Expedia, you’ll be surprised at how little a vacation 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 vacation package, consider traveling 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 vacation, a handful of days will be enough to tour the best spots. Be sure to check out Town Hall Theater — 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 vacation package as soon as possible.
Is it cheaper to book a Middlebury vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can customize 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 vacation 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 accommodations: Once you’ve settled on your trip dates and duration, book the ideal Middlebury vacation package for you.

Discover the most popular places to visit in Middlebury

Middlebury College

4.5/5(108 reviews)

Enjoy the collegiate vibe when you visit Middlebury College, during your trip to Middlebury. Stroll along the riverfront or visit the cathedral while you're in the area.

Middlebury College
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.