Middlebury Vacations from $596
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
The Inn at Round Barn Farm
$808
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Burlington (BTV)
9.4/10 Exceptional! (196 reviews)
We had a comfortable and amazing stay. The innkeeper was extremely knowledgeable and made wonderful suggestions to make our stay exactly what we wanted .
Breakfast was delicious and varied each day and included fresh local ingredients.
The grounds were stunning and well cared for. And we were lucky to see the bittern one morning !!
We highly recommend a stay at this beautiful B and B !
Reviewed on Jul 30, 2026
Club Wyndham Smugglers’ Notch Vermont
$1,321
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
8.4/10 Very Good! (225 reviews)
The rooms were clean and spacious. The kitchen was well stocked. The shuttle to Lot 6 was nice. The map was useless for finding things. Too many things were closed on Monday.
Reviewed on Aug 25, 2026
The Essex Resort & Spa
$1,367
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
9/10 Wonderful! (1,001 reviews)
We had a wonderful stay! Both pools were amazing, and the staff was super nice and welcoming. A big plus was the citronella they spray early morning —there were noticeably fewer bugs at night, which made sitting outside much more enjoyable. We would definitely come back!
Reviewed on Aug 25, 2026
Hilton Garden Inn Burlington Downtown
Downtown Burlington
$1,738
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
8.8/10 Excellent! (1,003 reviews)
Great location but front desk staffing was minimal at best. Waited
Reviewed on Aug 22, 2026
Don't see what you're looking for?
See all available trips from Singapore to Middlebury
View all tripsStay 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.
Vermont Folklife Center
9.6/10 (4 reviews)
Enjoy an outing to Vermont Folklife Center during your stay in Middlebury. While you're here, you can savor the top-notch restaurants.
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, theaters, and a stunning recital hall. Visitors can immerse themselves in diverse exhibitions and performances by both local and international artists.
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.
Middlebury Falls
Commune with nature and explore the great outdoors at Middlebury Falls during your travels in Middlebury. You can enjoy the restaurants while in the area.
Middlebury Hotel Deals
Middlebury Inn
14 Court Square Middlebury VT
$162 nightly
$178 total
Aug 30 - Aug 31
Total with taxes and fees
Courtyard Middlebury
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
$159 nightly
$175 total
Aug 30 - Aug 31
Total with taxes and fees
Swift House Inn
57 North Pleasant Street Middlebury VT
$229 nightly
$252 total
Aug 31 - Sep 1
Total with taxes and fees
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.
Find the Best Middlebury Vacation Packages
Middlebury Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 6,600 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Branbury State Park, Otter Creek Brewing and Lincoln Peak Vineyard |
More vacations you might like
Frequently asked questions
How much does a Middlebury vacation package cost?
Offering excellent value package deals from $596 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.
Explore a world of travel with Expedia
- Hotels with a Pool in Middlebury
- Burlington Hotels
- Pet-Friendly Hotels in Middlebury
- B&B in Middlebury
- Extended Stay Hotels in Middlebury - Warren
- Cottages in Middlebury
- Chalets in Middlebury
- B&B in Middlebury - Warren
- Hotels with Free Parking in Middlebury
- Treehouses in Middlebury
- Resorts & Hotels with Spas in Middlebury
- Motels in Middlebury
- Hilton Hotels in Middlebury
- Hotels with an Outdoor Pool in Middlebury
- Resorts in Middlebury
- Beach Hotels in Middlebury
- Hotels near Sugarbush Ski Resort
- Historic Hotels in Middlebury - Warren
- Vacation Homes in Middlebury
- Stowe Hotels
- Hotels near Otter Creek Brewing
- Hotels with Free Breakfast in Middlebury
- Cabin Rentals in Addison County
- Relais & Chateaux Hotels in Middlebury - Warren
- Accor Hotels in Middlebury
- Condo Rentals in Middlebury
- Killington Hotels
- Hotels with Hot Tubs in Middlebury
- Villas in Middlebury - Warren
- Hotels with an Indoor Pool in Middlebury
- Hostels in Middlebury
- 3 Star Hotels in Middlebury
- Inns in Middlebury
- Extended Stay Hotels in Middlebury
- Cheap Hotels in Middlebury
- 5 Star Hotels in Middlebury
- Rv Parks in Middlebury
- Marriott Hotels & Resorts in Middlebury
- Middlebury Hotels
- Hotels with Laundry Facilities in Middlebury
- Golf Hotels in Middlebury
- Apartments in Middlebury
- Hotels near Henry Sheldon Museum of Vermont History
- Luxury Hotels in Middlebury
- 4 Star Hotels in Middlebury
- Cabin Rentals in Middlebury
- Chalets in Middlebury - Warren
- Cabin Rentals in Vermont
- Hotels near Middlebury College
- Flights to Middlebury
- Flights to Vermont
- Flights from Burlington Intl.
- Flights from Boston (BOS) to Burlington (BTV)
- Flights from Chicago (ORD) to Burlington (BTV)
- Flights from Middlebury
- Flights to Middlebury - Warren
- Flights from New York (JFK) to Burlington (BTV)
- Flights to Burlington
- Flights from New York (NYC) to Burlington (BTV)
- Neshobe River Winery
- Middlebury College
- Judith Reilly Gallery
- Vergennes Falls Park
- Danforth Pewter
- Warren Kimble Gallery & Studio
- Uvm Morgan Horse Farm
- Visit Middlebury - Warren
- Vergennes Opera House
- Moss Glen Falls
- Slide Brook Express Quad Ski Lift
- Addison Vacations
- Gate House Quad Ski Lift
- Visit Middlebury
- Robert Frost Wayside Trail
- National Museum of the Morgan Horse
- New Haven Vacations
- Killington Resort
- Castle Rock Double Ski Lift
- Pulp Mill Covered Bridge
- Texas Falls Recreation Area
- North Lynx Triple Ski Lift
- Bristol Vacations
- Kevin P. Mahaney '84 Center for the Arts
- Sugarbush Ski Resort
- Henry Sheldon Museum of Vermont History
- Vermont Vacations
- Chimney Point State Historic Site
- Button Bay State Park
- Bulwagga Books & Gallery
- Holy Cow Inc.
- Brandon Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
