The Best Historic Hotels in Southern Vermont, VT from ￥38,505 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 a wooden table and chairs, a microwave, and cabinets.

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

Grafton

United States

Eleanor D.

￥27,215

￥59,348 total

includes taxes & fees

Sep 1 - Sep 2

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

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

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.

2. Castle Hill Resort And Spa

Cavendish

United States

Mirco

￥35,326

￥38,505 total

includes taxes & fees

Sep 2 - Sep 3

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

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

Hoosick Falls

United States

Anita T.

￥30,113

￥63,633 total

includes taxes & fees

Sep 8 - Sep 9

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 cozy room with a wooden bench, a small table, and a chair.

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.

￥36,661

￥77,609 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 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.

A wooden dining table with chairs, a brick wall, and a kitchen with green cabinets and a dishwasher.

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

Walpole

United States

Sean M.

￥54,514

￥67,659 total

includes taxes & fees

Sep 1 - Sep 2

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

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

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

￥47,047

￥58,341 total

includes taxes & fees

Sep 2 - Sep 3

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, surrounded by buildings and a ski lift in the background.

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

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

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

Hancock

United States

Kristina L.

View all properties

Top Southern Vermont Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent

"I really have no complaints whatsoever! I would’ve loved a pancake conveyor belt to go with the breakfast but the waffle irons did the trick just the same."

The Manchester View

The Manchester View

10/10 Excellent

"I will definitely stay here again. The location of the property is beautiful. Staff is great and helpful"

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"Nice room and property. With was down."

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent

"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Thanks"

The Putney Inn

The Putney Inn

8/10 Good

"Outward appearance was deceiving. The room was very nice and appeared to be newly remodeled."

Colonial Motel

Colonial Motel

8/10 Good

"X"

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