The Bennington County Court House with a white facade, green shutters, and a gold dome.

Southern Vermont Hotel Guide - Historic Hotels in Southern Vermont, Vermont

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Southern Vermont Historic Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Southern Vermont historic hotels

A red house with a covered porch and a chimney.

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (174 reviews)
"We had such a great time! Those is a well taken care of, clean, cozy property. We would absolutely visit again!!"
United States
Kathy H.
The price is €322
includes taxes & fees
18 Nov - 19 Nov
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A large stone building with a steep roof, surrounded by dense forest and hills.

2. Castle Hill Resort And Spa

Castle Hill Resort And Spa
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (127 reviews)
"I promise, especially if you’re staying in the condo buildings you will love it"
United States
Brandon
The price is €263
includes taxes & fees
1 Nov - 2 Nov
Castle Hill Resort And Spa
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

3. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (117 reviews)
"enjoyed our week at this property"
United States
cory p.
The price is €353
includes taxes & fees
29 Oct - 30 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

4. Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is €460
includes taxes & fees
15 Nov - 16 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
A cozy living room with a fireplace, a black leather sofa, and a television mounted above it.

5. 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is €360
includes taxes & fees
15 Nov - 16 Nov
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

6. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is €206
includes taxes & fees
29 Oct - 30 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A kitchen with white cabinets, a wooden dining table, and pendant lights.

7. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is €424
includes taxes & fees
29 Oct - 30 Oct
A roomy remodeled retreat close to MassMoCA
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.
View all properties

Top Southern Vermont Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good
"The room was clean and the staff was knowledgeable about the area especially for dining. The facilities are a bit older, but the breakfast was solid, especially the bacon."
Annica 1-night trip
Posted 2 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Explore a world of travel with Expedia