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
Sep 12 - Sep 13
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Sep 13 - Sep 14
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Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

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.
¥26,114
¥56,775 total
includes taxes & fees
Sep 22 - Sep 23
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Mirco
¥32,676
¥35,617 total
includes taxes & fees
Sep 14 - Sep 15
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.
¥28,894
¥60,886 total
includes taxes & fees
Sep 14 - Sep 15
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.
¥35,177
¥73,781 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.
¥60,255
¥73,710 total
includes taxes & fees
Sep 14 - Sep 15
Entire Farmhouse with lots of open space 15 min north of Keene

6. 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.
¥14,793
¥34,197 total
includes taxes & fees
Sep 15 - Sep 16
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

7. 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
¥55,212
¥65,406 total
includes taxes & fees
Sep 15 - Sep 16
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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Top Southern Vermont Hotel Reviews

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

8/10 Good
"Good location and good restaurant on the property. We enjoyed daily happy hour on the front porch sitting in the rocking chairs."
Oksana 2-night trip
Posted 2 hours ago
Kimpton Taconic Hotel by IHG
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

8/10 Good
"Pool wasn't accessible, only one ice machine. Good breakfast variety tho, cookies upon check in and fruit bars in the morning, that was a nice touch."
Janie 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Brattleboro I-91
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Wonderful place with people who care about your comfort!"
Cynthia 1-night trip
Posted 4 hours ago
The Palmer House Resort, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Great place for overnight stay"
Francesca 1-night trip
Posted 8 hours ago
Hampton Inn Brattleboro
The Manchester View

The Manchester View

10/10 Excellent
"Great place. Friendly, clean and serene. The breakfast was a cut above the typical continental fare and it was awesome to use the hot tub before driving into town for dinner. The only one thing that was tricky was the shower -- it's not well-designed so it's hard to stop water from spraying on to the floor. Other than that, no complaints!"
Alison 1-night trip
Posted 14 hours ago
The Manchester View
Aspen At Manchester

Aspen At Manchester

8/10 Good
"No interaction with the staff. They were invisible. The water stream in the shower was weak, but everything else was very good."
Izhar 2-night trip
Posted 1 day ago
Aspen At Manchester
Latchis Hotel

Latchis Hotel

8/10 Good
"This hotel is a great representation of a niche throw back. Record players in the room. Stacks of records in the hall to enjoy. The lobby is beautiful and they are attached to the movie theatre, which is old school and beautiful to witness. The hotel is in a TERRIBLE AREA and in fact Brattleboro, VT has an extremely large homeless and drug population. I truly feel for the business’ in the town. No foot traffic. We didn’t see one police vehicle at all. Multiple people told us to keep our wits about us if walking at night. The restaurants that we did visit have lovely people and are friendly but the places to see are not worth a visit to this sad town. It’s truly unfortunate too. You have this idea of small town in New England with shops and mom and pop places to eat and this had almost NONE of that."
Matthew 1-night trip
Posted 1 day ago
Latchis Hotel

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