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Hotels in Middlebury

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Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Where to stay in Middlebury?

Lobby
Wyndham Southbury
Wyndham Southbury
3.0 star property
8.2 out of 10, Very Good, (1091)
The price is $93
$107 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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.
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Top neighborhoods in Middlebury

Middlebury Center Historic District

Middlebury's Middlebury Center Historic District neighborhood offers attractions including Lake Quassapaug.

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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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

Check out reviews of Middlebury hotels guests love

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

10/10 Excellent
"Very friendly staff"
Aleida 1-night trip
Posted 2 days ago
Holiday Inn Cheshire - Southington by IHG

Frequently asked questions

What hotels do travelers like in Middlebury?
Guests like Wyndham Southbury and Courtyard by Marriott Waterbury Downtown.
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.