Photo by Brandon Miller

Hotels in Middlebury

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Check prices for these dates

Tonight
May 11 - May 12
Tomorrow
May 12 - May 13
Next weekend
May 16 - May 18
In two weeks
May 23 - May 25

Where to stay in Middlebury?

Wyndham Southbury
Lobby

Wyndham Southbury

3.0 star property
8.0 out of 10, Very Good, (1006)
$93 nightly
The price is $107
Jun 1 - Jun 2
Total includes taxes and fees
Wyndham Southbury
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.

Top landmarks in Middlebury

Quassy Amusement Park

Why not give yourself a treat with a trip to Quassy Amusement Park, one of the family attractions located 1.2 mi (1.9 km) from central Middlebury. If you have fun at Quassy Amusement Park, you'll love Glebe House Museum and The Gertrude Jekyll Garden, located nearby.

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Quassy Amusement Park

Learn more about Middlebury

Middlebury is well-known for its attractions such as Quassy Amusement Park and Lake Quassapaug.

See all hotels in Middlebury
Either off access road at the end of Old Waterbury Rd, or Umberfield Rd. Abandoned in the woods near I 84 and power lines overhead.
Photo by Brandon Miller
Open Photo by Brandon Miller
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What hotels do travelers like in Middlebury?
Guests like Courtyard by Marriott Waterbury Downtown and Wyndham Southbury.
Can I book refundable hotels in Middlebury?
If you need the flexibility to change your plans to Middlebury, most properties provide refundable* rates you can book. You can see these properties by searching our site and using the “fully refundable” filter to narrow down the results.
What will the weather in Middlebury be like during my vacation?
The warmest months in Middlebury are usually July and August with an average temp of 69°F. January and February are the chilliest months when the average temp is 32°F. The rainiest months are October and July.
Why should I book my Middlebury accommodation with Hotels.com?
There are plenty of reasons to book your Middlebury travel with us: our free cancellations on selected hotels* gives you the flexibility you’re looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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