The Best Historic Hotels in Southern Vermont, VT from ￥38,275 in 2026

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

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Our top choices for Southern Vermont historic hotels

A red house with a covered porch and a chimney.

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.

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

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

Grafton

Eleanor D.

￥26,906

￥58,674 total

includes taxes & fees

Sep 30 - Oct 1

A large estate with a swimming pool, tennis court, and a spacious lawn.

An outdoor patio with wicker furniture, a glass table, and a grill area.

A large indoor swimming pool with a wooden interior, multiple windows, and seating areas.

A spacious living room with leather sofas, a coffee table with a fruit bowl, and a patterned rug.

2. The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!

Manchester

Jessica G.

￥213,665

￥337,149 total

includes taxes & fees

Oct 21 - Oct 22

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, comfortable seating, and a large window providing natural light.

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

3. Castle Hill Resort And Spa

Cavendish

Brandon

￥35,115

￥38,275 total

includes taxes & fees

Oct 21 - Oct 22

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

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

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

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

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

Hoosick Falls

Anita T.

￥29,771

￥62,558 total

includes taxes & fees

Sep 30 - Oct 1

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

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

5. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

￥36,244

￥76,019 total

includes taxes & fees

Oct 13 - Oct 14

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

A living room with a sofa, a coffee table, a TV, and a window with curtains.

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

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

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

Hancock

Kristina L.

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Top Southern Vermont Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Clean room good parking easy access"

The Manchester View

10/10 Excellent

"Very cool unique setting and property. The bed was like a cloud and very relaxing."

The Equinox Golf Resort And Spa

8/10 Good

"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."

Latchis Hotel

10/10 Excellent

"WE enjoyed the architecture of the whole complex - reception coffee lounge (Hot Drinks day and night as a compliment). Parking was right there. Center of town. The staff helped us when we needed to extend at the special rate. It attracts fun guests. It is a special place - not the run of the mill franchise. The linen is first class, nice thick towels. The room had a microwave and a refrig, plus the record player theme is another theme for folks who appreciate the vinyl era. Remember - Art Deco Era - not modern era."

The Putney Inn

8/10 Good

"The rooms are clean and the staff was helpful. The building and rooms were outdated but for the price it was a good stay. Not much at exit but available 20-30 minutes away."

Aspen At Manchester

10/10 Excellent

"Absolutely loved this property! Amazing location, super clean and spacious rooms! We loved being in close proximity to the town, which was soooooo amazingly pet friendly! We will definitely be back"

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Find Historic Hotels in Southern Vermont, VT

Change your mind

Treat yourself

Be picky

Check availability on Southern Vermont Historic Hotels

Our top choices for Southern Vermont historic hotels

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

2. The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!

3. Castle Hill Resort And Spa

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

5. A roomy remodeled retreat close to MassMoCA

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

Top Southern Vermont Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

The Manchester View

The Equinox Golf Resort And Spa

Latchis Hotel

The Putney Inn

Aspen At Manchester

Explore a world of travel with Expedia