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

Tonight
Oct 2 - Oct 3
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Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
￥26,763
￥58,362 total
includes taxes & fees
Oct 12 - Oct 13
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A large estate with a swimming pool, tennis court, and a spacious lawn.
A person sitting on a stone ledge outdoors with a scenic view in the background.
A large indoor swimming pool with a wooden interior, multiple windows, and seating areas.
An outdoor patio with wicker furniture, a glass table, and a grill area.

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

The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
Manchester
United States
Jessica G.
￥212,531
￥329,489 total
includes taxes & fees
Oct 21 - Oct 22
The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
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.

3. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
￥34,871
￥38,009 total
includes taxes & fees
Oct 21 - Oct 22
Castle Hill Resort And Spa
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A wooden deck with a grill, a table, and chairs.
A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.
A two-story house with a front porch, a small garden, and a mailbox.

4. 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
United States
Anita T.
￥29,613
￥62,226 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
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.
A two-story building with a swimming pool, outdoor seating, and a sign for 'John Harvard's Restaurant & Brewery'.

5. 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
United States
Kristina L.
￥18,806
￥40,069 total
includes taxes & fees
Oct 6 - Oct 7
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.
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.
A cozy room with a wooden bench, a small table, and a chair.

6. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
￥36,051
￥75,615 total
includes taxes & fees
Oct 14 - Oct 15
A roomy remodeled retreat close to MassMoCA
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Top Southern Vermont Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"The room was clean and spacious."
Wendy 1-night trip
Posted 4 hours ago
Hampton Inn Brattleboro
Colonial Motel

Colonial Motel

8/10 Good
"I love these kinds of motor lodges and I want them to keep improving and to succeed."
David 1-night trip
Posted 16 hours ago
Colonial Motel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent
"Very nice staff and enjoyed my stay."
Charlene 1-night trip
Posted 18 hours ago
Comfort Inn & Suites Brattleboro I-91
Aspen At Manchester

Aspen At Manchester

10/10 Excellent
"Modern, clean, easy access and parking and good location. Touchless check in was easy and efficient."
Joseph 1-night trip
Posted 2 days ago
Aspen At Manchester
The Putney Inn

The Putney Inn

10/10 Excellent
"Just needed the basics. Putney Inn delivered!"
Gregory 1-night trip
Posted 2 days ago
The Putney Inn
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

10/10 Excellent
"Our “go to” for an uber relaxing and comfortable getaway when we are seeking the amenities of an established hotel."
Deborah 1-night trip
Posted 2 days ago
The Equinox Golf Resort And Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"all was wonderful and well orchestrated"
Peter 3-night trip
Posted 5 days ago
Kimpton Taconic Hotel by IHG

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