Middlebury Vacation Packages 2026 from $516

Middlebury flight + hotel vacation packages

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

Sunset Dunes Vacation Villas

$516

per person

May 28 - May 31

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to South Bend (SBN)

This villa features laundry facilities. Take advantage of the free self parking.

The Inn at Saint Mary's

$1,037

per person

Jun 30 - Jul 5

found 1 hour ago

Roundtrip non-stop flight included

Los Angeles (LAX) to South Bend (SBN)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.

La Quinta Inn & Suites by Wyndham South Bend

$843

per person

Jun 30 - Jul 5

found 1 hour ago

Roundtrip non-stop flight included

Los Angeles (LAX) to South Bend (SBN)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Morris Inn

$1,422

per person

Jun 30 - Jul 5

found 1 hour ago

Roundtrip non-stop flight included

Los Angeles (LAX) to South Bend (SBN)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Self parking, a business center, and a terrace are also offered.

Hot Tub The Strong Retreat Fire Pit 3BR

$1,724

per person

Jun 30 - Jul 5

found 1 hour ago

Roundtrip non-stop flight included

Los Angeles (LAX) to South Bend (SBN)

This vacation home includes free WiFi in public areas and barbecue grills.

Top Middlebury hotels deals

Essenhaus Inn & Conference Center

240 Hwy 20 Middlebury IN

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$144 total

Apr 27 - Apr 28

Total with 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

Hampton Inn & Suites Middlebury

105 Crystal Heights Blvd Middlebury IN

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$141 total

May 10 - May 11

Total with 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

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

Middlebury IN

$135 nightly

$144 total

Apr 27 - Apr 28

Total with taxes and fees

A garden is available at this cottage.

Kitchen

Free WiFi

Lemon Hill Amish Guest House. . . an Amish themed, whole house experience.

Middlebury IN

$240 nightly

$257 total

Apr 27 - Apr 28

Total with taxes and fees

This farm stay features a garden, laundry facilities, and barbecue grills.

Free WiFi

Air conditioning

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Middlebury IN

Get rates

This vacation home featured laundry facilities and barbecue grills.

Kitchen

Washer

Farmstead Inn & Conference Center

370 S Van Buren St Shipshewana IN

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$151 total

Apr 27 - Apr 28

Total with taxes and fees

This hotel features an indoor pool and a gym. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Guests will appreciate free perks like free self parking and WiFi in public areas.

Pool

Parking 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.

A trail on a sunny day in the Krider World’s Fair Garden in Middlebury, Indiana.

Krider Gardens

After visiting Krider Gardens, make a plan to see the other sights and activities 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.

Frequently asked questions

How much are vacation packages to Middlebury?

With deals starting at just $516, 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.