Middlebury Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Middlebury

Hampton Inn & Suites Middlebury
Hampton Inn & Suites Middlebury
2.5 out of 5
105 Crystal Heights Blvd, Middlebury, IN
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 24 Nov to 25 Nov
S$149
includes taxes & fees
24 Nov - 25 Nov
8.4/10 Very Good! (1,000 reviews)
"The hotel was comfortable and clean. Staff was very friendly & helpful. Would recommend…"

Reviewed on 15 Nov,2024

Hampton Inn & Suites Middlebury
Essenhaus Inn & Conference Center
Essenhaus Inn & Conference Center
3.5 out of 5
240 Hwy 20, Middlebury, IN
Fully refundableReserve now, pay when you stay
The price is S$179 per night from 1 Dec to 2 Dec
S$179
includes taxes & fees
1 Dec - 2 Dec
9.6/10 Exceptional! (1,001 reviews)
"Always awesome."

Reviewed on 20 Nov,2024

Essenhaus Inn & Conference Center
Blue Gate Garden Inn
Blue Gate Garden Inn
2.5 out of 5
800 South Van Buren Street, Shipshewana, IN
Fully refundableReserve now, pay when you stay
The price is S$195 per night from 1 Dec to 2 Dec
S$195
includes taxes & fees
1 Dec - 2 Dec
9.4/10 Exceptional! (1,245 reviews)
"Room was fresh and clean, staff friendly and helpful. Breakfast buffet was excellent!"

Reviewed on 18 Nov,2024

Blue Gate Garden Inn
See all 504 properties in Middlebury
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.

Frequently asked questions

How much does a Middlebury holiday package cost?
Tailor make your Middlebury holiday package from as little as . Choose from any combination of flights, hotels and rental cars to build the getaway you’ve been dreaming of. Remember to add on one or two experiences!
How do I get a cheap travel package to Middlebury?
Browse and lock in everything in one place with our Middlebury holiday packages. We have incredible bargains on flights, hotels and more that’ll keep your credit card happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotels throughout the world to choose from, you have countless opportunities to mix and match as you like.
Where should I stay in Middlebury?
There’s plenty to do in Middlebury, so spend your evenings near its top sights and treat yourself to more time sightseeing. Deutsch Kase Haus is one spot to put on your to-do list.
What are the top hotels in Middlebury?
Farm Country|amish Country|newly Renovated and Essenhaus Inn & Conference Centre are among the most popular properties in Middlebury. Why not check out the amenities and facilities at each and then make up your mind?
How far in advance should I book my Middlebury holiday?
While prices fluctuate, we generally recommend booking your flight as soon as possible. Many international fares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you might still get lucky. Low prices to Middlebury sometimes occur only weeks before departure.
What does an Expedia Middlebury travel package include?
That’s up to you. You can select from a variety of Middlebury packages, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car and a flight. Once you’ve made your booking, you can add on the fun stuff like experiences and tours. Whatever your perfect Middlebury escape looks like, you’re sure to save!
What should I know before booking a Middlebury travel package?
So many places to visit, so many things to see. With a travel package, you’ll be able to check more of them off your list. Bundle your hotels, rental cars and flights and enjoy big savings.
Can I choose my airline with a Middlebury Expedia holiday package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply choose the airline you want and put together your ideal Middlebury trip.
If I'm not able to travel, can I cancel my Middlebury holiday package?
If your holiday plans in Middlebury have changed, it’s good to know that it’s possible to cancel your booking. If you made your booking less than 24 hours ago, you may be able to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may charge a cancellation fee. For more details, check our Customer Service Portal.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.