Middlebury Vacation Packages 2026 from $631

Middlebury flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Vermont Suites

$631

per person

Apr 29 - May 6

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Burlington (BTV)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Blind Tiger Burlington

South End

Save 100% on your flight

$1,000

per person

Apr 29 - May 6

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Burlington (BTV)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden and a fireplace in the lobby are also provided.

Smugglers' Notch Resort Private Suites

Save 100% on your flight

$955

per person

Apr 29 - May 6

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Burlington (BTV)

Ski-in/ski-out access, a water park, and 8 outdoor pools are all featured at this smoke-free condo. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities.

DoubleTree by Hilton Burlington Vermont

$780

per person

Apr 29 - May 6

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Burlington (BTV)

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Valcour Inn & Boathouse

Save 100% on your flight

$979

per person

Apr 29 - May 6

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Burlington (BTV)

This guesthouse features free WiFi in public areas, wedding services, and free self parking. Enjoy the free continental breakfast each morning. A garden and a communal living room are also provided.

Top Middlebury hotels deals

Middlebury Inn

14 Court Square Middlebury VT

Free Cancellation

Reserve now, pay when you stay

$154 nightly

$169 total

Mar 1 - Mar 2

Total with taxes and fees

A full-service spa, a gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A business center, a terrace, and a lobby fireplace are also on offer.

Spa

Parking included

Courtyard Middlebury

309 Court Street Middlebury VT

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$157 total

Mar 16 - Mar 17

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, a coffee shop, and a garden are also offered.

Parking included

Free WiFi

Swift House Inn

57 North Pleasant Street Middlebury VT

$199 nightly

$219 total

Mar 9 - Mar 10

Total with taxes and fees

This hotel features a restaurant, a sauna, and a bar/lounge. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A garden, a lobby fireplace, and a library are also on offer.

Breakfast included

Pet friendly

Middlebury Sweets Motel

1395 Rt 7 South Middlebury VT

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$132 total

Mar 1 - Mar 2

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli, a picnic area, and express check-in are also on offer.

Pet friendly

Parking included

White Horse Lodge

999 German Flats Rd Waitsfield VT

$155 nightly

$169 total

Mar 29 - Mar 30

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A library, express check-in, and express check-out are also on offer.

Parking included

Free WiFi

Lake Bomoseen Lodge

2551 Vermont 30N Bomoseen VT

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$158 total

Mar 4 - Mar 5

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.

On private beach

Pool

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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.

Popular places to visit

Otter Creek Brewing

4.5/5(11 reviews)

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.

Pulp Mill Covered Bridge

Find out about the history of Weybridge when you spend time at Pulp Mill Covered Bridge. While you're here, you can savor the top-notch restaurants.

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.

Frequently asked questions

How much are vacation packages to Middlebury?

Travelocity has package deals to Middlebury, including flights and hotels, starting from an impressive $631. With the money you save, you could purchase some cool tours or maybe add on a few extra nights to your exciting adventure.

How long should my Middlebury vacation be?

Most travelers lock in their hotel for 2 nights in Middlebury. But that doesn't necessarily mean you have to follow in their footsteps. How long you stay all depends on how much you want to see on your vacation. If you want to familiarize yourself with every corner of this impressive place, consider booking another night or two (or even an extra week!).

Where can I get the best vacation package deals for Middlebury?

There are terrific Middlebury package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties around the world? Keep this in mind when you're ready to cross another destination off your must-visit list.

Why should I purchase my Middlebury vacation bundle with Travelocity?

From our 24/7 customer support to our range of exciting destinations, we are dedicated to giving you the vacation of a lifetime. All you'll have to do is to click and book — our Price Match Guarantee will ensure you get the lowest price.

Can I save money on my Middlebury car rental if I combine it with hotels and flights?

With a Middlebury vacation package, you can combine your flight, car and hotel bookings and save loads. When you're ready to uncover the best of this awesome part of the world, why not start with Notre Dame Basilica? This top attraction is 100 mi from Middlebury. With your own rental car, you'll be there before you know it.

Which airport is best for Middlebury?

Many visitors choose to fly into Burlington Intl. Airport (BTV), 30 mi north of downtown Middlebury. Others prefer Lebanon Municipal Airport (LEB) (50 mi away from central Middlebury) or Adirondack Regional Airport (SLK) (55 mi away from central Middlebury).

What is there to do in Middlebury?

You'll sense a certain magic as you stroll the streets of Middlebury. Otter Creek Brewing and Henry Sheldon Museum of Vermont History are just two renowned sights that entice visitors to this wonderful city, so add them to your to-do list.

Where should I stay when visiting Middlebury?

Many visitors check in to the Middlebury Inn. It's sure to be a great base for your Middlebury escape.