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 5 - Sep 6
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Sep 18 - Sep 20

Our top choices for Southern Vermont historic hotels

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
¥26,537
¥57,170 total
includes taxes & fees
Sep 23 - Sep 24
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
¥30,350
¥33,082 total
includes taxes & fees
Sep 30 - Oct 1
Castle Hill Resort And Spa

3. 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.
¥29,362
¥61,700 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

4. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
¥35,747
¥75,151 total
includes taxes & fees
Sep 15 - Sep 16
A roomy remodeled retreat close to MassMoCA

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

Entire Farmhouse with lots of open space 15 min north of Keene
Walpole
United States
Sean M.
¥56,107
¥68,667 total
includes taxes & fees
Sep 8 - Sep 9
Entire Farmhouse with lots of open space 15 min north of Keene

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

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
United States
Kelly
¥45,875
¥56,210 total
includes taxes & fees
Sep 7 - Sep 8
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

7. 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.
¥17,579
¥38,312 total
includes taxes & fees
Sep 7 - Sep 8
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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Top Southern Vermont Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent
"This property checks all of the boxes. The views of surrounding mountains are among the best in the area. The rooms were recently updated and very comfortable. The location is just a small 1 mile drive to the village and great restaurants."
Scott 1-night trip
Posted 11 hours ago
The Manchester View
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

8/10 Good
"My room had candy on side table and needed to have phone cleaned. Older property has character but needs attention in rooms. Don't pay for valet parking basically the same as self parking. Upon check out they handed me the keys to get car. I think it was overpriced for what you get. Manchester is a cute town. Nothing in the room to make coffee and had to buy water no refrigerators as well"
Renata 1-night trip
Posted 1 day ago
Kimpton Taconic Hotel by IHG
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."
Ellen 1-night trip
Posted 3 days ago
Comfort Inn & Suites Brattleboro I-91
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."
Courtney 2-night trip
Posted 5 days ago
The Putney Inn

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