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Check availability on Middlebury Historic Hotels

Our top choices for Middlebury historic hotels

Exterior
Middlebury Inn

Middlebury Inn

Middlebury Inn
3.0 star property
Middlebury
9.0 out of 10, Wonderful, (1000)
"Perfect New England Inn right in the heart of town."
United States
LaTascha
The price is ₹11,254
₹12,380 total
includes taxes & fees
14 Dec - 15 Dec
Middlebury Inn
Standard Room, 1 Bedroom, Non Smoking (two full) | Free WiFi, bed sheets
Circle Court Motel

Circle Court Motel

Circle Court Motel
2.5 star property
Ticonderoga
8.6 out of 10, Excellent, (368)
"Staff was very friendly and helpful. definitely will stay here again"
United States
Dawn
The price is ₹8,000
₹9,040 total
includes taxes & fees
1 Jan - 2 Jan 2026
Circle Court Motel
Classic Room, 1 Queen Bed, Non Smoking | Desk, free WiFi, bed sheets
The Deers Head Inn

The Deers Head Inn

The Deers Head Inn
3.0 star property
Elizabethtown
8.8 out of 10, Excellent, (177)
"Charming inn built in 1808. The restaurant downstairs was great, too. "
United States
Pamela
The Deers Head Inn
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 Middlebury Hotel Reviews

Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Very comfortable bed. Clean room"
Josephine 2-night trip
Posted 7 days ago
Courtyard Middlebury

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Frequently asked questions

What should a history enthusiast expect from a trip to Middlebury?
You'll probably want to seek out the historical sites while you're staying in Middlebury. Why not absorb the local colour with a visit to the restaurants?
What's the best accommodation in Middlebury to learn about local history?
Based on our travel expertise, Middlebury Inn is a top historic hotel bookable on Expedia and it features a full-service spa. Halpin Covered Bridge is a short 10-minute drive away.
How many historical hotels are located in Middlebury?
In Middlebury, there are 26 hotels and other accommodation options bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical sites and other places to visit in Middlebury?
Landmarks like Halpin Covered Bridge and Pulp Mill Covered Bridge in Middlebury might be worth a visit. Cultural venues include Town Hall Theater, Henry Sheldon Museum of Vermont History and Kevin P. Mahaney '84 Center for the Arts. Additionally, you'll find Sugarbush Ski Resort in the area.
What is a historic hotel like in Middlebury?
By booking a historic hotel, guests can stay someplace that has an official historic designation. A palace, castle, stately home or even a lodge, pub or skyscraper can be identified as a historic hotel as long as it's of special interest. Traditional architecture and period features are typically found in the guestrooms or communal spaces of historic hotels in Middlebury, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
"Heritage hotel" is more common in Asia and Europe, while "historic hotel" is a term often used in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels are generally the most significant aspect. For a heritage hotel, mainly, it's cultural value along with how it shaped the community.
Do historic hotels in Middlebury have modern facilities?
Hotels have the safety features and modern conveniences you might expect, but every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities and the popular amenities found in most hotels will be available in a historic hotel. Rest assured that when you select a historic hotel in Middlebury, you won't be staying at a place that's uncomfortable or rundown.