The Best Historic Hotels in Southern Vermont, VT from AED 822 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

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

Coffee/tea maker, fridge, microwave, oven

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

Grafton

Eleanor D.

AED 624

AED 1,358 total

includes taxes & fees

26 Aug - 27 Aug

Condo Hotel Room | Premium bedding, blackout drapes, iron/ironing board, WiFi (free)

Castle Queen Room | Premium bedding, blackout drapes, iron/ironing board, WiFi (free)

2. Castle Hill Resort And Spa

Cavendish

Mirco

AED 820

AED 894 total

includes taxes & fees

30 Aug - 31 Aug

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

Hoosick Falls

Anita T.

AED 691

AED 1,452 total

includes taxes & fees

21 Sep - 22 Sep

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

Walpole

Sean M.

AED 1,251

AED 1,544 total

includes taxes & fees

24 Aug - 25 Aug

5. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

AED 841

AED 1,781 total

includes taxes & fees

9 Sep - 10 Sep

Shower, eco-friendly toiletries, hair dryer

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

Walpole

Kelly

AED 1,023

AED 1,265 total

includes taxes & fees

24 Aug - 25 Aug

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

Hancock

Kristina L.

AED 354

AED 822 total

includes taxes & fees

24 Aug - 25 Aug

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Top Southern Vermont Hotel Reviews

The Manchester View

10/10 Excellent

"Was a great place to stay. Rooms and entire property was clean and well maintained. Definitely recommend this place for a nice relaxing night. Great views also"

Latchis Hotel

8/10 Good

"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the downside, my experience was not the best: When I arrived, the front desk lady said something like: "I'll be right with you". Two minutes later, she came to the front desk joking about having problems with her Emails. Not acceptable! You should pause your Email activity when someone is waiting in the lobby. My wife and I were looking forward to a drink at the hotel bar. The website indicated that the bar was open, and a note on the door confirmed. There was nobody there. Money and a lady's purse were spread out on the bar. We were told at the front desk that the people running the bar for them decided not to open that evening. Not acceptable. The next morning I took a lukewarm shower, as it took about ten minutes for the water to become warm enough, By then I was done and my feet were in about 5" of dirty water because the drain was clogged. We were also told that if we did not turn in our brass key, they would charge us $75 to replace it. When walked down to the lobby, there was a sign stating that front desk duty started at 9:00."

Hampton Inn Brattleboro

10/10 Excellent

"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"

Riverside Hotel, an Ascend Collection Hotel

8/10 Good

"Over all, pleasant stay. The balcony and balcony chairs need regular cleaning. Room and bathroom were fine. No coffee downstairs. Cheese and crackers, chips or candy available for sale at the desk or a vending machine would be nice."

Holiday Inn Express Hotel & Suites Brattleboro by IHG

8/10 Good

"Clean room, very nice front desk staff. Breakfast was good - nice variety and the coffee machine delivered great fresh coffee. It was worth paying the extra cost for this hotel vs the others in the area that seemed a bit sketchy."

The Equinox Golf Resort & Spa

10/10 Excellent

"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"The front desk staff were friendly and engaged, the room was clean. That’s all we needed."

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Stratton Vacations

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. Castle Hill Resort And Spa

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

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

5. A roomy remodeled retreat close to MassMoCA

6. 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

Top Southern Vermont Hotel Reviews

The Manchester View

Latchis Hotel

Hampton Inn Brattleboro

Riverside Hotel, an Ascend Collection Hotel

Holiday Inn Express Hotel & Suites Brattleboro by IHG

The Equinox Golf Resort & Spa

Comfort Inn & Suites Brattleboro I-91

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