Book the Best HISTORIC Hotels in Southern Vermont in 2026 | Expedia.ca

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

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

Tonight

Oct 17 - Oct 18

Tomorrow

Oct 18 - Oct 19

Next weekend

Oct 23 - Oct 25

In two weeks

Our top choices for Southern Vermont historic hotels

A red house with a covered porch and a chimney.

A kitchen with a wooden table and chairs, a microwave, and cabinets.

Two single beds with wooden frames and striped bedding, a small wooden nightstand with a lamp, and a window with a view of greenery.

A living room with a wood-burning stove, a blue armchair, and a bookshelf.

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

Grafton

United States

Eleanor D.

CA $240

CA $518 total

includes taxes & fees

Oct 19 - Oct 20

A large stone building with a steep roof, surrounded by dense forest and hills.

A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.

A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.

A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.

2. Castle Hill Resort And Spa

Cavendish

United States

Brandon

CA $316

CA $344 total

includes taxes & fees

Oct 27 - Oct 28

A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.

A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.

A wooden deck with a grill, a table, and chairs.

A two-story house with a front porch, a small garden, and a mailbox.

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

Hoosick Falls

United States

Anita T.

CA $266

CA $562 total

includes taxes & fees

Oct 20 - Oct 21

A kitchen with white cabinets, a wooden dining table, and pendant lights.

A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.

A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.

A room with a wooden bench, a table, and a door with glass panels.

4. A roomy remodeled retreat close to MassMoCA

North Adams

United States

Diane

CA $324

CA $686 total

includes taxes & fees

Oct 19 - Oct 20

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A living room with a flat-screen TV, a sofa, a coffee table, and a lamp.

A compact kitchen with white cabinets, a dishwasher, and a countertop with various appliances.

A two-story house with a porch, a white picket fence, and a tree in front.

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

Ludlow

United States

Tina l.

CA $328

CA $734 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Top Southern Vermont Hotel Reviews

Aspen At Manchester

Aspen At Manchester

10/10 Excellent

"It was very modern looking well renovated properties a hole, and we were very well taken care of throughout our one night there."

Colonial Motel

Colonial Motel

10/10 Excellent

"Value for money. Clean and conveniently located. Friendly staff."

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT

10/10 Excellent

"Old, but clean, friendly, everything worked. Good size TV, microwave and fridge."

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent

"Good"

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good

"Clean room. Breakfast good for quick bite and coffee was good"

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent

"Great place my wife and I enjoyed our stay."

Explore a world of travel with Expedia

Book Historic Hotels in Southern Vermont on Expedia.com