The Best Historic Hotels in Southern Vermont, VT from ￥33,066 in 2026 | Expedia

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

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Check availability on Southern Vermont Historic Hotels

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Sep 11 - Sep 13

Our top choices for Southern Vermont historic hotels

A red house with a covered porch and a chimney.

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.

A kitchen with white cabinets, a microwave, a stove, and a sink.

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

Grafton

United States

Eleanor D.

￥27,164

￥59,058 total

includes taxes & fees

Sep 8 - Sep 9

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

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.

A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

2. Castle Hill Resort And Spa

Cavendish

United States

Mirco

￥30,336

￥33,066 total

includes taxes & fees

Sep 8 - Sep 9

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 living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.

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.

￥30,056

￥63,513 total

includes taxes & fees

Sep 14 - Sep 15

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

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

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

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

Jennifer O.

￥36,592

￥77,463 total

includes taxes & fees

Sep 9 - Sep 10

Two Adirondack chairs and a fire pit in a grassy field with a forested hill in the background.

A laundry room with a washing machine, a table, and a blue bin.

A bedroom with a wooden floor, a white bed with a blue bedspread, a wooden wall paneling, a fireplace, and a nightstand with a lamp.

A living room with a sofa, a TV, a wooden cabinet, and a kitchen area in the background.

5. Entire Farmhouse with lots of open space 15 min north of Keene

Walpole

United States

Sean M.

￥60,615

￥75,154 total

includes taxes & fees

Sep 7 - Sep 8

A spacious living room with a checkered sofa, a grey sofa, and a patterned rug. There is a staircase leading to another level, and a dining area with a table and chairs.

A bedroom with a bed, a chair, a nightstand, a lamp, and a window.

A compact kitchen with white cabinets, a red refrigerator, a microwave, a kettle, and a sink.

A bedroom with a four-poster bed, two windows, a nightstand, and a lamp.

6. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole

United States

Kelly

￥49,561

￥61,421 total

includes taxes & fees

Sep 7 - Sep 8

A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

A snow-covered outdoor area with a fire pit, tables, and chairs, indicating a winter resort setting.

A two-story building with a swimming pool, outdoor seating, and a sign for 'John Harvard's Restaurant & Brewery'.

A spacious living area with a stone fireplace, comfortable seating, and a dining area.

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

Hancock

United States

Kristina L.

￥19,225

￥40,800 total

includes taxes & fees

Sep 9 - Sep 10

View all properties

Top Southern Vermont Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent

"The room was beautiful and clean with a great view. The breakfast was delicious and plentiful. I highly recommend the place."

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Conveniently located right off Rt. 91, with a restaurant located in the same parking lot and gas stations nearby."

Latchis Hotel

Latchis Hotel

10/10 Excellent

"Great place. Staff are very nice and helpful."

Colonial Motel

Colonial Motel

10/10 Excellent

"Staff was very helpful. A little seating area under some trees was a beautiful place to relax while the sun was setting."

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent

"Clean room and welcoming staff. Breakfast was well displayed."

The Putney Inn

The Putney Inn

10/10 Excellent

"It’s a motel. It’s clean and the staff is friendly. It’s definitely not fancy, but it gets the job done."

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