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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Oct 3 - Oct 4
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Oct 9 - Oct 11
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Oct 16 - Oct 18

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.
¥26,835
¥58,519 total
includes taxes & fees
Oct 14 - Oct 15
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!

The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!
Manchester
United States
Jessica G.
¥213,098
¥338,573 total
includes taxes & fees
Oct 22 - Oct 23
The Privacy of a home & Perks of a Resort! Pool, Tennis, Views, Dogs, 6 baths!

3. Castle Hill Resort And Spa

Castle Hill Resort And Spa
Cavendish
United States
Brandon
¥34,831
¥37,966 total
includes taxes & fees
Oct 21 - Oct 22
Castle Hill Resort And Spa

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.
¥29,692
¥62,392 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

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.
¥17,048
¥37,733 total
includes taxes & fees
Oct 6 - Oct 7
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

6. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
¥36,148
¥75,994 total
includes taxes & fees
Oct 13 - Oct 14
A roomy remodeled retreat close to MassMoCA
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Top Southern Vermont Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent
"We arrived at the Manchester View in late September on a trip to see the beautiful change of colors. View is definitely what you get here. Surrounded by gorgeous rolling hills and mountains that were covered with green, yellow, red and orange leaves. We were celebrating our 40th anniversary and were upgraded to a suite room. Thank you! Room was very nice, clean and spacious. My only complaint was the door would stick when trying to open or close the door to the room. And, although the bath was updated and very nice, the finish work around the counter wasn't complete. There was a gap between the wall and counter the ends didn't match up to the wall. But that is just really a minor issue. They also have a continental breakfast with the basics and a nice kick off to start your day. The view, the staff and did I say the view?... We would definitely stay here again!"
Jim 2-night trip
Posted 8 hours ago
The Manchester View
Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"We stay here 2 or 3 times a year and know it well. The staff are always welcoming and helpful. On this visit, we found our original room to be noisy because of the ice machine (?), but the staff got us another room when asked. The room was spacious, quiet and comfortable. The hotel was unusually full, but very quiet. Breakfast is always good here and the coffee is excellent. (Vermont seems to be obsessed with coffee....) Having tried two or three other hotels in Brattleboro, we have settled on the Hampton Inn as our "go to" spot."
Thomas 1-night trip
Posted 10 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 2 days 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 2 days 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 3 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 3 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 3 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 6 days ago
Kimpton Taconic Hotel by IHG

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