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Check availability on Middlebury Historic Hotels

Our top choices for Middlebury historic hotels

Standard Room, 1 Double Bed | Premium bedding, individually decorated, blackout drapes

Middlebury Inn

Middlebury Inn
3.0 star property
Middlebury
9.0 out of 10, Wonderful, (1,000 reviews)
"Beautiful old hotel. Staff was very helpful. We enjoyed a delicious brunch."
United States
Mary
The price is AED 509
AED 560 total
includes taxes & fees
20 May - 21 May
Middlebury Inn
2 bedrooms, travel crib, WiFi, bed sheets

Go Skiing or Hiking from an Enchanting, Light-Filled Home

Go Skiing or Hiking from an Enchanting, Light-Filled Home
Waitsfield
9.8 out of 10, Exceptional, (46 reviews)
"Excellent Location ! "
United States
Luke A.
The price is AED 564
AED 1,216 total
includes taxes & fees
19 May - 20 May
Go Skiing or Hiking from an Enchanting, Light-Filled Home
Smart TV

1830 Enchanting, Light-Filled Farmhouse Apartment

1830 Enchanting, Light-Filled Farmhouse Apartment
Waitsfield
9.8 out of 10, Exceptional, (39 reviews)
"We skied at Sugarbush. The location was great. Very nice place to stay!"
United States
Laurie K.
The price is AED 596
AED 1,264 total
includes taxes & fees
19 May - 20 May
1830 Enchanting, Light-Filled Farmhouse Apartment
Smart TV, fireplace, DVD player, books

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Ripton
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful place. Lots to do around the cabin and in the area. The hosts are very helpful. The cabin has everything you could want for a great stay. "
United States
Susan
The price is AED 940
AED 1,285 total
includes taxes & fees
26 May - 27 May
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns
Exterior

Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is AED 940
AED 1,269 total
includes taxes & fees
17 May - 18 May
Adorable cabin with screened porch and private fire pit
Interior

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Ripton
9.4 out of 10, Exceptional, (12 reviews)
"Our group booked this place for a ski trip to sugarbush. A remote area, but the cabin was very cool and our host were the best. The warm cinnamon twists in the morning were a big hit and the hot tub was perfect after a day of skiing. Would definitely look into booking this in the summer/fall. "
United States
John H.
The price is AED 940
AED 1,269 total
includes taxes & fees
17 May - 18 May
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest
Exterior

Cozy and pristine timberframe cabin

Cozy and pristine timberframe cabin
Ripton
10.0 out of 10, Exceptional, (4 reviews)
"It is a gorgeous property with lots of fun amenities...perfect for a winter getaway"
United States
Karen H.
The price is AED 940
AED 1,269 total
includes taxes & fees
17 May - 18 May
Cozy and pristine timberframe cabin
Exterior

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Ripton
10.0 out of 10, Exceptional, (12 reviews)
"Excellent facilities enjoyed staying there very much"
United States
Linda
The price is AED 853
AED 1,161 total
includes taxes & fees
28 May - 29 May
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch
Exterior

Inviting timber frame cabin in Vermont's Green Mountains

Inviting timber frame cabin in Vermont's Green Mountains
Ripton
10.0 out of 10, Exceptional, (7 reviews)
"This is a very special place. Close to Middleburyyetfar away. "
United States
Jim P.
The price is AED 940
AED 1,269 total
includes taxes & fees
17 May - 18 May
Inviting timber frame cabin in Vermont's Green Mountains
Exterior

Immaculate mountain cabin with awe inspiring sunrise and mountain views

Immaculate mountain cabin with awe inspiring sunrise and mountain views
Ripton
10.0 out of 10, Exceptional, (3 reviews)
"Our cabin was lovely—artfully built, well-stocked, perfectly clean, and very comfortable. We awoke to silence and a beautiful view of the mountains from our screened porch. We are already planning our return!"
United States
Sara S.
Immaculate mountain cabin with awe inspiring sunrise and mountain views
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

8/10 Good
"I booked this, on 4/13/26, for an overnight stay, before my daughter’s college tour at Middlebury College. I was pleasantly impressed with the Courtyard Middlebury. We arrived the evening before, just needing a place to sleep. The staff at the front desk was very nice. There are not much amenities, but they did have a fitness room, which was all that I needed. It is across from a plaza with stores and restaurants, so it was convenient. I would definitely recommend it. "
Melissa 1-night trip
Posted 2 days ago
Courtyard Middlebury

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Frequently asked questions

What should I expect on my historical trip to Middlebury?
You're already probably planning a visit to places with historical relevance during your trip to Middlebury. Why not absorb the local color with a visit to the restaurants?
What's the best accommodation in Middlebury to absorb the local history?
Based on our travel expertise, Middlebury Inn is a top historic hotel bookable on Expedia and it features a full-service spa. Pulp Mill Covered Bridge is a short 3-minute drive away.
How many historical hotels will I find in Middlebury?
In Middlebury, there are 25 hotels and other accommodations bookable on Expedia though you won't find many designated historic hotels.
What are the most important 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 Henry Sheldon Museum of Vermont History, Kevin P. Mahaney '84 Center for the Arts, and National Museum of the Morgan Horse. A couple of additional sights to add to your agenda are UVM Morgan Horse Farm and Green Mountain National Forest.
What is a historic hotel like in Middlebury?
Guests who book a historic hotel can stay in a place that has an officially recognized national historic designation. A castle, a palace or even a pub or an old police station can be identified as a historic hotel as long as it's of special interest. Traditional architecture and period features are typically preserved in the public spaces and guestrooms of historic hotels in Middlebury, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels tend to be what's most important. For a heritage hotel, it's mainly the cultural value along with how it shaped the community.
Do historic hotels in Middlebury have modern facilities?
Hotels include modern conveniences and safety features you might expect, but every effort is made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found at a contemporary hotel will be available in a historic hotel. When you choose a historic hotel in Middlebury, don't worry that you'll be staying at a place that's uncomfortable or rundown.