Middlebury Vacations from $355

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Your Middlebury Vacation

Our vacation packages to Middlebury let you customize your own adventure. Tailor your journey to your interests and needs and make the most of your time in this fabulous city. You'll want to do some exploring during your trip to Middlebury. Make time for major attractions such as Middlebury College, National Museum of the Morgan Horse and UVM Morgan Horse Farm. A couple of clicks is all it takes to build the perfect Middlebury vacation on Expedia.

The Latest Middlebury vacation packages

Price found within the past 48 hours. Click for updated prices.
Swanson Inn of Vermont

Swanson Inn of Vermont

3 out of 5
Price was $508, price is now $355 per person
$355
per person
Nov 7 - Nov 10
found 1 hour ago
Roundtrip flight included
Tampa (TPA) to Burlington (BTV)
9.6/10 Exceptional! (154 reviews)
A mixed bag. Nice views of brook, woods & mountain. Frank was very helpful! The room was comfortable but the door was broken. No pancakes or waffles; just a lousy continental breakfast & bad coffee.

Reviewed on Jul 21, 2025

Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Price was $489, price is now $363 per person
$363
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
7.6/10 Good! (1,004 reviews)
It was friendly. Other guests were nice. Bed and pillows were great. Ac was great too. Breakfast was minimal ( no decaf coffee). Some things were old and should be updated. Wifi and Tv did not work in the 2rooms we had. No cold water in one.

Reviewed on Jul 13, 2025

The Village of Loon Mountain

The Village of Loon Mountain

3 out of 5
Price was $805, price is now $621 per person
$621
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Burlington (BTV)
8.6/10 Excellent! (528 reviews)
There were many activities right on the property, multiple pools, tennis courts, playground, grills, outdoor games. Great for families.

Reviewed on Aug 19, 2025

Eagle Mountain House & Golf Club

Eagle Mountain House & Golf Club

3.5 out of 5
Price was $587, price is now $454 per person
$454
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
8.8/10 Excellent! (1,003 reviews)
This hotel is like going back in time. The staff is superb. If you are looking for modern amenities, maybe shop around. But if you want the true experience of a grand hotel, this is the best. History and Leisure, views from the verandah. Every night was magical. Can't wait to come back.

Reviewed on Aug 25, 2025

Valcour Inn & Boathouse

Valcour Inn & Boathouse

3 out of 5
Price was $1,356, price is now $1,050 per person
$1,050
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Burlington (BTV)
8.8/10 Excellent! (114 reviews)
Nice quiet get away place. Beautiful porch that opens from your room to sit and enjoy a sunset or start the day with coffee and a sunrise looking out over the lake. Rooms are good size and comfortable. Amenities were available as needed. Highly recommend!

Reviewed on Jul 29, 2025

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Discover the most popular places to visit in Middlebury

Northern Vermont showing drinks or beverages

Otter Creek Brewing

Learn about the local history of Middlebury with a stop at Otter Creek Brewing. While you're here, you can savor the top-notch restaurants.

Otter Creek Brewing

Middlebury College

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

UVM Morgan Horse Farm

Learn about the local history of Weybridge when you take a trip to UVM Morgan Horse Farm. While you're here, you can savor the top-notch restaurants.

UVM Morgan Horse Farm

Middlebury Hotel Deals

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
$172 nightly
The price is $189 total per night from Sep 23 to Sep 24
$189 total
Sep 23 - Sep 24
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
"This is a beautiful old in, very well maintained. Friendly welcoming staff."

Reviewed on Aug 25, 2025

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
$143 nightly
The price is $157 total per night from Sep 7 to Sep 8
$157 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (523 reviews)
"Daily or at least every other day housekeeping service would have been appreciated."

Reviewed on Aug 14, 2025

Courtyard Middlebury
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street, Brandon, VT
$143 nightly
The price is $158 total per night from Aug 27 to Aug 28
$158 total
Aug 27 - Aug 28
Total with taxes and fees
8.6/10 Excellent! (507 reviews)
"A very old historic hotel. Has the oldest elevator in VT. Charming. Nice gardens. Guest can not use elevator and all rooms are upstairs. so if you have any mobility issues its a problem."

Reviewed on Aug 22, 2025

Brandon Inn
See all 917 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.

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Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals from $355 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 snag a cheap Middlebury vacation package, consider traveling in September, October and December. You'll generally find better rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Middlebury?
Generally, a few days is ideal for a Middlebury vacation. With a carefully crafted itinerary, you can go to all the main sights such as Town Hall Theater, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Middlebury?
Middlebury is a good vacation destination with attractions like UVM Morgan Horse Farm among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Middlebury vacation promises fun for everyone.
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.
Does Expedia offer Book Now, Pay Later Middlebury vacation packages?
Jet off on your ideal getaway to Middlebury with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up cheap deals before they sell out.

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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.