Middlebury Vacation Packages 2025/2026 from $604

Middlebury flight + hotel vacation packages

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

Doubletree Hotel South Bend

Downtown South Bend

Save 100% on your flight

$604

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to South Bend (SBN)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. You'll appreciate the free area shuttle, self parking, and 24-hour business center.

Brand New Luxury Townhouse Steps To Notre Dame Fire Place Fire pit 1418

Wooded Estates

Save 100% on your flight

$5,986

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to South Bend (SBN)

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Mid Century Modern With Modern Touches 10 min Walk to Notre Dame 1831

Save 100% on your flight

$2,618

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to South Bend (SBN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

10 min Walk to ND Stadium 1820

Save 100% on your flight

$2,618

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to South Bend (SBN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.

Modern Home Just Mins to Notre Dame 52723

Save 100% on your flight

$1,905

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to South Bend (SBN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

Top Middlebury hotels deals

Hampton Inn & Suites Middlebury

105 Crystal Heights Blvd, Middlebury, IN

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$118 total

Sep 14 - Sep 15

Total includes taxes and fees

This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a snack bar/deli are also on offer.

Pool

Hot Tub

Essenhaus Inn & Conference Center

240 Hwy 20, Middlebury, IN

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$133 total

Aug 24 - Aug 25

Total includes taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

$135 nightly

$144 total

Aug 28 - Aug 29

Total includes taxes and fees

A garden is available at this cottage.

Kitchen

Free WiFi

Charming 1-Bedroom Bed & Breakfast-upon request- in Middlebury

$147 nightly

$157 total

Aug 22 - Aug 23

Total includes taxes and fees

This bed & breakfast features barbecue grills.

Parking available

Travelodge by Wyndham Elkhart

115 Northpointe Blvd, Elkhart, IN

Free Cancellation

Reserve now, pay when you stay

$62 nightly

$69 total

Sep 1 - Sep 2

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Pet friendly

Parking included

Van Buren Hotel

1175 Van Buren Street, Shipshewana, IN

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$143 total

Aug 24 - Aug 25

Total includes taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 3 conference rooms, along with free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

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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

Stone Lake

Commune with nature and explore the great outdoors at Stone Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.

Deutsch Kase Haus

Enjoy an outing to Deutsch Kase Haus during your stay in Middlebury. While in this relaxing area, find time to visit its shops.

Meadow Valley Golf Club

Enjoy a round of golf in Middlebury at Meadow Valley Golf Club. While in this family-friendly area, you can enjoy the restaurants.

Frequently asked questions

How much are vacation packages to Middlebury?

With deals starting at just $604, hotel and flight packages are a superb way to stretch your travel budget. Watch out Middlebury — here you come!

How long should my Middlebury vacation be?

Most sightseers vacation in Middlebury for approximately 2 nights. That being said, travel is all about discovering hidden gems and losing yourself in the moment — why not book a few extra nights so you can do just that?

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

With at least 400 airline partners and 1,000,000 properties across the globe, it's hard to top Travelocity. Browse our comprehensive range and pick up the best Middlebury package deal. Isn't it amazing when planning a trip is that easy?

Why should I book my Middlebury vacation package with Travelocity?

Travel is all about making fantastic new memories and leaving all your worries behind — which is why we provide you with a professional team of customer service experts available 24/7 should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our terrific range of vacation packages. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.

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

With a Middlebury vacation package, you can bundle your flight, hotel and car bookings and save a whole lot. If you're eager to uncover the best of this fantastic destination, why not start with Wrigley Field? This well-known attraction is 100 mi from Middlebury. With your own wheels, you'll be there in a flash.

Which airport is best for Middlebury?

There's a very good chance you'll land at South Bend Intl. Airport (SBN), situated 30 mi west of downtown Middlebury. Fort Wayne Intl. Airport (FWA) (55 mi away from central Middlebury) and Kalamazoo-Battle Creek Intl. Airport (AZO) (40 mi away from central Middlebury) are other choices.

What is there to do in Middlebury?

Deutsch Kase Haus should be toward the top of your travel itinerary. After you've crossed off this leading attraction, simply stroll the streets of Middlebury and find out what makes this vibrant place tick.

Where should I stay when visiting Middlebury?

If you're searching for someplace comfortable to lay your head, have a look at the Hampton Inn & Suites Middlebury. It's the top choice for many travelers.