Deals on vacations and trips to Middlebury

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Middlebury flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hot Tub Outdoor Living Game Room Coffee Bar

Hot Tub Outdoor Living Game Room Coffee Bar

2 out of 5
Price was $1,235, price is now $1,125 per person
$1,125
per person
Aug 14 - Aug 17
found 20 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to South Bend (SBN)
This vacation home includes free WiFi in public areas and barbecue grills.
Pool Hot Tub 5 min to ND Coffee Bar Games

Pool Hot Tub 5 min to ND Coffee Bar Games

2 out of 5
Price was $5,735, price is now $5,188 per person
$5,188
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
This vacation home includes free WiFi in public areas and barbecue grills.
La Quinta Inn & Suites by Wyndham South Bend

La Quinta Inn & Suites by Wyndham South Bend

3 out of 5
Price was $1,737, price is now $1,581 per person
$1,581
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.
Hyatt Place South Bend / Mishawaka

Hyatt Place South Bend / Mishawaka

3 out of 5
Price was $2,594, price is now $2,365 per person
$2,365
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.
Staybridge Suites Elkhart North by IHG

Staybridge Suites Elkhart North by IHG

3 out of 5
Price was $1,632, price is now $1,490 per person
$1,490
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Middlebury hotels deals

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

3.5 out of 5
240 Hwy 20 Middlebury IN
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $133 total per night
$133 total
Jun 28 - Jun 29
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. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
$126 nightly
The price is $141 total per night
$141 total
Jul 5 - Jul 6
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

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

Middlebury IN
$176 nightly
The price is $188 total per night
$188 total
Jul 2 - Jul 3
Total with taxes and fees
A garden is available at this cottage.
Kitchen
Free WiFi
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury IN
Get rates
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Van Buren Hotel

Van Buren Hotel

4 out of 5
1175 Van Buren Street Shipshewana IN
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $148 total per night
$148 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features an indoor pool and a gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Pool
Breakfast included
Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

2.5 out of 5
370 S Van Buren St Shipshewana IN
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $173 total per night
$173 total
Jun 28 - Jun 29
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. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.
Pool
Breakfast included
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See all available properties in Middlebury
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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

A calm lake with three white geese swimming near the shore, surrounded by rocks and trees.

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.

Stone Lake
A garden with a gazebo, stone steps, and a wooden fence.

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.

Krider Gardens

Hunter Lake

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

Hunter Lake

Frequently asked questions

How much are vacation packages to Middlebury?
With deals starting at just $1,125, 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.

Photos of local treasures

Browse Middlebury vacation photos for more inspiration

A log cabin with red shutters and a small porch.
A horse-drawn carriage with a covered wagon, parked on a dirt path with grass and trees in the background.
A black carriage with two horses tied to it, parked on a street.
A row of empty boats docked by a calm river, surrounded by trees with autumn foliage.
A Dutch County building with a covered walkway and red wagon wheels.