Middlebury Holidays from NZ$1,325
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The Latest Middlebury Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Anchorage Inn
NZ$1,325
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
San Diego (SAN) to Burlington (BTV)
6.6/10 (1,440 reviews)
Room was clean but run down. Definitely outdated.
Did not use the pool, but it looked clean and nice.
Great location. Easy to park and walk to restaurants/shopping.
Reviewed on 13 Aug 2026
Middlebury Holiday
Our pick of the best Middlebury Hotel Deals
Middlebury Inn
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
NZ$286
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Was disappointed how clean the bathroom was. There was hair and a hairpin on the floor with some other debris and the inside of the toilet did not look clean. Some of the bathroom looked renovated but the toilet was old."
Reviewed on 11 Aug 2026
Courtyard Middlebury
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
NZ$269
30 Aug - 31 Aug
includes taxes & fees
Swift House Inn
57 North Pleasant Street Middlebury VT
NZ$404
31 Aug - 1 Sept
includes taxes & fees
9.6/10 Exceptional! (352 reviews)
"Beautiful grounds. Wonderful breakfast. Helpful staff."
Reviewed on 12 Aug 2026
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
Otter Creek Brewing
9.2/10 (38 reviews)
This pioneering Vermont brewery has crafted innovative beers since 1991, including their signature Copper Ale. Tour the facility and sample fresh brews in their tasting room while enjoying local food pairings.
Middlebury College
9.6/10 (285 reviews)
Founded in 1800, Middlebury College offers a stunning campus where historic architecture meets the Green Mountains of Vermont. Explore the Old Chapel in this prestigious liberal arts setting.
UVM Morgan Horse Farm
9.4/10 (13 reviews)
This historic breeding facility preserves America's first native horse breed with guided tours through scenic barns. Meet Morgan horses up close during the May-October visiting season.
Henry Sheldon Museum of Vermont History
8.0/10 (1 review)
America's oldest community-based museum houses Vermont treasures in the historic 1829 Judd-Harris House. Explore period rooms with authentic 19th-century furniture and rotating exhibits in the Walter Cerf Gallery.
Kevin P. Mahaney '84 Center for the Arts
10.0/10 (10 reviews)
This cultural cornerstone houses Middlebury College's art museum, theatres, and a stunning recital hall. Visitors can immerse themselves in diverse exhibitions and performances by both local and international artists.
Cornwall Swamp Wildlife Management Area
Explore the great outdoors at Cornwall Swamp Wildlife Management Area, a lovely green space in Cornwall.
Halpin Covered Bridge
9.4/10 (19 reviews)
Vermont's highest covered bridge stands 41 feet above the Muddy Branch, showcasing 19th-century craftsmanship. Photographers capture its wooden architecture against seasonal backdrops of vibrant foliage or lush greenery.
Holy Cow Inc.
9.2/10 (5 reviews)
This whimsical Vermont boutique showcases Woody Jackson's iconic cow-themed art across clothing and gifts. Browse locally crafted bovine treasures in a charming setting that captures the essence of rural New England.
Frequently asked questions
How much does a Middlebury holiday package cost?
Offering excellent value package deals from NZ$1,325 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?
- 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.
- 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.
- 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.
- Bundle your airfare and accommodation: Once you've settled on your trip dates and duration, book the ideal Middlebury holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
