Deals on vacations and trips to Middlebury

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Top Middlebury hotels deals

Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
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
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
$109 nightly
The price is $122 total per night
$122 total
Dec 14 - Dec 15
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
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

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

2 out of 5
Middlebury IN
$135 nightly
The price is $144 total per night
$144 total
Dec 14 - Dec 15
Total with taxes and fees
A garden is available at this cottage.
Kitchen
Free WiFi
The Wellington Cottage

The Wellington Cottage

3 out of 5
7420 N 1160 W Middlebury IN
$67 nightly
The price is $77 total per night
$77 total
Dec 22 - Dec 23
Total with taxes and fees
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. A 24-hour business center, a library, and a picnic area are also on offer.
Parking included
Free WiFi
HOT TUB | Beautiful Backyard Oasis|Newly Renovated

HOT TUB | Beautiful Backyard Oasis|Newly Renovated

Middlebury IN
$247 nightly
The price is $249 total per night
$249 total
Dec 15 - Dec 16
Total with taxes and fees
A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Middlebury IN
$310 nightly
The price is $331 total per night
$331 total
Dec 14 - Dec 15
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
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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

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

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.

Deutsch Kase Haus

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.

Meadow Valley Golf Club

Frequently asked questions

How much are vacation packages to Middlebury?
With deals starting at just , 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

Photo by Ann Sair
Photo by Ann Sair
Photo by Jw
Photo by Jw
Photo by Patrick Laughlin 
Photo by Patrick Laughlin 